Some personal news:
I took a new role in January, working on frontier AI in Google DeepMind. Some of my writing will likely shift toward AI tools and roles, which I suspect will be interesting to most of you. I am still getting clarity on what I can/will write about, but hopefully this post gives you a taste of what’s top of mind for me, which is: AI models, AI careers, and life+careers in a post-AGI world.

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↓ Let’s dive in to what’s top of mind: Superintelligence and Human Data (ScaleAI)

Q: What is happening with Meta Superintelligence and ScaleAI? I heard there are $100M job offers flying around that people are crazy enough to actually turn down. What is superintelligence anyway? How do I get one of those offers?

Blockbuster “investments.” Zuck collecting AI CEOs. $10M to $100M job offers that people are apparently insane enough to turn down. Tech news is wild this week.

Lots of you have reached out to ask me what is this insanity, and below are Coach Erika’s loose thoughts:

• Mark Z is feeling mega FOMO after the flop that was the Llama 4 model launch.

• Nobody wants to work at Meta, but everyone loves 💸 MONEY 💸 — and with their mega offers, AI researcher compensation now rivals Saudi Prince annual yacht allowances.

• Mark Z is collecting AI CEOs to staff his superintelligence play — lots of big egos, big paychecks, and big responsibilities — this is going to be interesting 👀🍿

• Meta “bought” ScaleAI without “buying” ScaleAI. At a time when pretty much everything about American corporate regulation is a free-for-all, so they will probably get by with this odd deal. But ScaleAI’s customer’s aren’t buying it, and contracts are being pulled (and placed elsewhere…blue sky opportunity for human data vendors).

• SurgeAI, ScaleAI’s top competitor in the human data space, is probably about to fundraise. What happens with their fundraise will hint at the future of human in the loop data suppliers.

• It’s a fabulous time to be a chip maker, an AI researcher, and a human data supplier.

The full breakdown is for paid subscribers only, and it includes my predictions for what is likely to happen next in the ScaleAI/human data world, and what’s coming for AI compensation and careers:

Read more

For me, the end of the year is a time for reflection and a time to recharge for the year to come. For those of you in an active job search, I encourage you to take time to write down 3-5 gains from your job search, even if it’s ongoing. These gains can be anything. Some ideas:

• social joy from reconnecting with old colleagues and networking

• respinning your resume into something that makes you feel more competent and powerful

• taking those first steps to apply (especially if you did a lot of prep to get there!)

• getting recruiter calls and phone screens and knowing that means you have candidate-market fit

Last year, I wrote an article about my annual reflection process. Substack rated it a must-read, and you might find that approach particularly useful if your year was bumpy.

For those planning a job search in 2025, I encourage you to use the holidays to recharge and reinforce your sense of belonging and ability. Get your batteries charged and set your expectations for a more challenging job search, especially if the last time you searched for a job was prior to mid-2022.

Today’s post is a shortened version of an AMA I did last week for an online community. The information I shared is useful for all tech workers, so I wanted to share it more broadly. I simplified some of the questions to make it easier for you to read and digest.

In each answer, I link to one or two relevant TCW articles to enable deeper exploration if the question interests you. By linking to other writings, I hope this AMA will also serve as a compendium of articles that you can use now or in the future to unlock a new role with ease and confidence.

This is my last post before Christmas, and I want to also take a moment to express my gratitude to each of you for giving me 5,000+ reasons to sit behind this keyboard and clank-clank-clank out what I know about tech careers. You are the reason I write, and I thank you for investing in yourself and taking the time to read. Without you, there would be no reason for me to Whisper 🤫

If you have someone in your world who is job searching now or planning to in 2025, consider gifting them a one-year paid subscription to The Career Whispers so they don’t have to do it the hard way. Many readers who come in from gift subscriptions say it was the most useful gift of the year.

Let’s dive in ↓

AMA with Coach Erika December 2024

I’m Coach Erika. Since 2020, I've coached 280+ tech job seekers on how to write a door-opening resume, woo recruiters and hiring managers, impress interviewers, and land and negotiate job offers in Big Tech and rocket ship startups.

In my 15 years in tech, I’ve built and scaled unicorn startups, raised over $3B in venture capital, taken 2 startups public, and grown organizations from ~30 to 2000+. I’m passionate about helping people unlock career-catapulting roles because doing so for myself paved the way to a fulfilling and fruitful career.

Since 2020, I’ve become the most sought-after job search coach in tech, partly because of my high client success rate (93%+). My advice is timely and relevant because I am a tech worker, too. I know exactly what the candidate experience feels like because I’ve been there myself – as both a candidate and an interviewer. In the last 10 years, I’ve interviewed over 1100+ people, and hired 75+ people into my own teams.

Ask me anything about job searching, career shifts, interview prep, negotiating an offer, resume advice, or growing and thriving in tech roles!

PS: If you’re job searching in 2025, consider joining an upcoming cohort of my Lenny-recommended 4.9 ⭐️ Teeing up your Tech Job Search workshop. Apply here.

Q: From your experience, what questions should candidates ask more often at initial interviews but don't?

A: Candidates often forget that they are supposed to be interviewing the company as much as they are being interviewed by the company.

You always want to pass an interview, of course. But if you can coach yourself to ask tough questions to the interviewer (and get past the idea that this will make you seem bossy or demanding), you can go beyond passing the interview and impress them instead. When you impress interviewers, it makes them more enthusiastic about working with you. This means faster, better offers and an easier compensation negotiation process.

The best way to impress interviewers is to establish that you have two goals in an initial interview:

(1) pass the interview, and move on to the next round
(2) collect information that will help you decide if you want the role

Once you clarify your goals, it's time to do some research into the company, the role, the product, the team you're interviewing with. To impress interviewers and get more information out of them, you need to ask "high-signal questions" — these are questions that get you critical information and also signal to interviewers that you have done your homework.

Some categories of questions I think every candidate should ask:

- industry dynamics
- company and team strategy
- competitive landscape
- team goals and contribution to company strategy
- goals the interviewer has for the role
- manager's leadership (only if you are interviewing with the manager or someone who reports to them. Skip these questions in recruiter screens, as recruiters often won't have a lot of insights on this front, and other questions will get you more useful signal).

If you are curious about this approach, you can read more about the impact of asking high-signal questions and learn how to formulate them yourself here:

As a bonus, here’s another article with questions to ask in recruiter screens:

Q: I think my experience may be a little too "all over the place" for recruiters, as I'm having trouble getting past the ATS for interviews. I've sent tons of applications into the void and am feeling really stressed. Advice?

A: Varied experience that all adds to your dimensionality and will make you more competent in the role, which is great! We just need to get you through the door.

When it comes to job searching, employers just want to find the right person to fit the role gap they have. They need to know that you have expertise in that specific area.

I've written about the importance of focusing your job search on a Niche of One and then adapting your resume and LinkedIn to advertise your expertise. The worst approach you can take in any job market is to leave it up to the ATS or recruiter to figure out how to leverage you.

Here’s my step by step guide to defining your Niche of One and injecting it into your resume and LinkedIn for a more focused and productive job search:

And here’s a 4-hour job search plan that will keep you focused and sane in your job search:

Q: I am not into tech but I have always been interested in pivoting into tech. I am based in Europe. What advice do you have for me?

A: Industry changes are always tricky, especially trying to shift into tech right now as things are downturned in most US tech companies due to the end of the long zero percent interest rate period, amongst other factors.

Some good news is that many large US tech companies are expanding geographically to get access to different talent, lower cost geos, and expanding their footprint in parts of the world where they have growing user bases. You can see this in particular in Ukraine, Poland, Romania, but also in Finland any many other European countries, along with India, Mexico, Brazil, Canada and other countries around the world.

If you want to make a pivot into the tech industry, the easiest way will always be to leverage your existing skill set. In your case, since you have revenue-focused experience, you would look for companies hiring roles in revenue operations or finance and key in on those roles that would value your prior experience in purchase and sales channel data analysis and/or sales strategy.

My best strategies for making career pivots in tech in the current job climate: https://thecareerwhispers.substack.com/p/avoid-the-sunk-cost-fallacy-and-make

Q: For 6 years I’ve been consulting with startups on building MVPs. I really want to move in-house to scale products. In this market it seems people want to only hire those who have equivalent experience with their domain and scale. How might I position myself to break into larger organizations? Should I do that, or focus on the startup space aligned with my recent experience?

A: The best way in is always the door that is right in front of you. From what I am reading, you are an expert at zero-to-one product design and launch (MVP) but not as experienced with scaling products and growth engineering. My advice would be to pick the company you've worked with to design and launch their MVP. Pick the one you believe has the highest chance of scaling up as large as you want, and see if they have a role for you. This is usually the fastest way to your end goal. Get the experience scaling, then roofshot over to a larger organization when you have learned how to scale.

If you want to go straight into larger organizations, you are right that they are currently in the mode of hiring for expertise over potential; this is in part because of market conditions. There are usually smaller pockets within larger organizations that have more nascent products and want to find people who are scrappier, more entrepreneurial, and more familiar with current/relevant early scale approaches. Find those pockets and network, network, network into interviews.

ps: articles I’ve written that may help you navigate this career shift:

Q: What advice do you have for an unemployed senior IC (individual contributor) who wants to move into people management roles?

A: It’s extraordinarily hard to convince a new employer in this market (or any market) to take a big risk by offering a level-up title or scope. My advice to anyone trying to break into management roles for the first time is to do it from within a company. If you are unemployed, land the IC role first and then earn your way into a manager role. It's almost always the fastest way into management.

It’s also usually the fastest way to pivot roles, for what it’s worth. I can’t count how many former recruiting coordinators I’ve seen pivot internally into analytics, data science, engineering, growth, and other roles. Those same, talented individuals would have never even made it through an ATS filter. They were smart to pivot internally.

Q: I’m a Sr. PM trying to land something in this tough market. I’m seeing orgs flattening and fewer roles posted these days, which combined with the AI wave, makes me think I need to change my approach. Would becoming a founder help me land bigger titles with higher impact should I choose to go back to a corporate job in the future?

A: As a former founder myself, all I can say is that being a founder takes all of your time, energy, your soul, even your bone marrow. I would only go into a founder journey if you feel absolutely called to it. That said, I personally love hiring former founders and PMs who have founded a side hustle and built something independently from scratch. Pragmatic entrepreneurship maps nicely into internal PM roles.

Q: There have been widespread layoffs in the industry and I’m looking to pivot to tech from advertising/media, but it’s such a tough market. There are already qualified candidates that have tech experience. What are your tips for a door-opening resume or a way to stand out from the crowd?

A: You have a popular concern, given how many others asked similar questions!

Two ways to help your resume stand out:

(1) Map your past experience to the roles you are targeting. Do the hard work for them, and show that you already have the skills for the role. Make it clear that there is no risk to hiring you even though you aren’t a veteran of the industry.
(2) Be very direct (and focused). In the first three lines of your resume, call out the specific role you desire, the company type, and the industry. Be opinionated.

Please check out my other responses in this AMA to get additional tips on role and industry pivots and mapping your skills into new roles. Also, check out these articles I wrote for people facing similar situations to yours:

Actionable tips for making career pivots in the current job climate:

Niche of One Job Searching

Resume optimization

Translating resumes to LinkedIn

Q: What do CEOs/executive recruiters look for in Head of Products/VP of Products in startups? I want to reverse engineer the skillset and focus on the right upskilling.

A: Here's how I would approach this:

(1) find 30 job descriptions for roles you're interested in, throw them into a single doc, upload to your favorite LLM and ask it to look for patterns and keywords. That will give you a rough sense of what skills you may need to emphasize/develop/shore up.

(2) find a headhunter who specializes in this role and level, and ask them. It might take time to find one who will talk to you, but the conversation would be gold.

(3) acknowledge that this role is very senior, and the more senior you get, the less "templatized" the role tends to be. Head of Product at one company could be completely focused on growth engineering. At another company, they could be an ML expert crunching data all day. At another company, they might be implementing tools like JIRA and processes for performance management, hiring, and roadmap planning for the PM org. It really is all over the map, especially as you look at smaller companies.

This process will probably lead you to look at job descriptions for Head of PM / VP of Product roles that you actually like, at companies you actually want to work for. And then use that to drive your development goals and roadmap 🚀

Q: I currently work in Big Tech and have had a strong career path (IC to manager in 3 years). I’m trying to find a role that will allow me to relocate to Switzerland. Job searching so far has been a frustrating, with no results. I've shifted my CV, networked, but nothing materializes. I think it’s because jobs like my current one don’t really exist in Switzerland. What would be your advice to get noticed by recruiters in a different job market / geo?

A: Any time you are trying to make one big shift, your top goal is localization. You need to map your value proposition onto the new team / product / market, so that friends, companies, and recruiters look at your resume / CV / LinkedIn profile and go, "aha! I know exactly what role they fit in my organization!"

Some actionable and tactical tips:

1. BIG congrats on the high velocity career! Make sure it shows on LinkedIn and in your CV. Having that connecting line showing a promotion is a big deal.

2. Consider if your short duration as a manager is a problem. Most companies want to promote from within for first-time managers, since they know the person and their subject matter expertise. If you haven't been a manager longer than 2-3 years but are looking for manager roles, you might consider looking for IC roles instead and build back to manager roles.

3. Map, map, map. You say roles like yours don't exist in Switzerland, but I find this hard to believe. It's more likely that they exist but are called something else. Find out what jobs encapsulate the skills, expertise, and job responsibilities you currently have, and then switch the CV and LinkedIn to use the local nomenclature. Reset your job alerts, and network with people using the local title.

I hope this helps unlock your search!

ps: some additional thoughts I've shared on debugging a job search:

Q: I had to resign from my last role because I burned out from full-time work + caregiving. With a 1+ year career gap, I'm eager to land something new. I recently learned about "returnships" for people with gaps due to caregiving or other reasons. What are your thoughts about these programs? Are they worth it, and how can I best position myself for one?

A: I’m not super familiar with returnship programs, but I have seen many people go from bootcamps into apprenticeship programs with great success. The biggest challenge with these programs is that there are often a high volume of applicants, so it can (counterintuitively) become more competitive than just going after regular full time roles.

The teams that run these programs tend to be isolated from the rest of the recruiting team, too, so when you apply to the returnship program or apprenticeship program, do not expect the right hand to talk to the left hand within the company. You can view your candidacy for each role as effectively independent.

Given that your gap is relatively small (less than 3 years), my recommendation is a dual-path approach: apply for returnship programs and in parallel apply for full time roles where you feel qualified and interested.

There are also fast tracks if you are able and willing to work for free for a while to bolster your portfolio and show more recent, relevant work experience. Some tips for speeding up a job search here:

🎉 That’s a wrap! I hope this helps you navigate your career and thrive. Got a question to add to the AMA? Use the comments below.

Leave a comment

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Become a paid subscriber to support my writing and get access to every post, across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

Guess what? This newsletter is an educational resource and can probably be expensed through your manager or your company's L&D budget. Here is a template I wrote for you to use when asking your manager. For subscription details, see the About page.

ps: You can also check out coacherika.co for free resources, resume help, and various coaching options, including my very popular (Lenny Rachitsky recommended) TUYJS Workshop. Follow me on Substack, YouTube, and LinkedIn to stay in touch. Subscribe to this newsletter to receive uncommon tech career advice and experimentation ideas 💛

This topic came to mind as I’ve been coaching a few folks who are keen to pivot their careers but who are also aware that the tech job market is challenging right now. I’ve written about the fastest path to an offer, but what about when you’re OK taking the slower path to change things up?

Today’s post is about how to frame a career pivot mentally, plus the tactics to actually make it happen (even in a difficult job market). It’s a two-part post. The first part (how to frame a career pivot) comes from a fellow Substack writer , a Deloitte engineering lead who writes The Level Up Ladder on Substack. The second part (with actionable tactics to make a career pivot in this market) is from me, Coach Erika.

I met Leo on X (then Twitter) a couple of years ago when I first signed up for Twitter to whisper my career tips into the universe. Leo’s post about sunk costs (with fantastic examples of late-career pivoters who did very well post-pivot) was exactly what I think many TCW readers need to see as they consider “staying in role” or “trying something new” in the next phase of their career.

I hope you enjoy this two-part post and consider signing up for Leo’s newsletter The Level Up Ladder if you enjoy his writing!

With that context, here’s Leo’s original post ↓

It’s never too late to start anew

There is a concept in economics called “sunk costs”. From a rational perspective, decision-making should be based on future costs and benefits, not on past expenditures that cannot be recovered.

Psychologists Daniel Kahneman and Amos Tsversky spent their lives studying how human decision-making often deviates from rational economic models. The “sunk cost fallacy” emerged as a prime example of this deviation.

Here’s an example of it:

Imagine you're halfway through a movie at the theater, and you're not enjoying it at all. The plot is confusing, the acting is poor, and you're bored. However, you paid $15 for the ticket and already invested an hour of your time, so you decide to stay until the end, thinking, "I've already spent money and time on this, I might as well see it through." This is the sunk cost fallacy in action. The rational decision would be to leave and spend your remaining time doing something you enjoy, as the money and time already spent cannot be recovered whether you stay or go. By staying, you're only losing more of your valuable time.

Why do humans have this fallacy?

1. Loss Aversion: Humans have a stronger preference for avoiding losses than acquiring equivalent gains. This makes the prospect of "wasting" past investments particularly aversive.

2. Commitment and Consistency: As described by psychologist Robert Cialdini, people have a strong desire to appear consistent in their behavior. Abandoning a path we've committed to can feel like a threat to our self-image.

3. Status Quo Bias: There's a general tendency to prefer the current state of affairs, even when change might be beneficial. This inertia can make career changes particularly daunting.

4. Escalation of Commitment: As described by organizational behavior researcher Barry Staw, individuals often increase their investment in a failing course of action to justify prior decisions.

What does it mean for your career?

Easy; this fallacy will prevent us from changing careers or even our jobs. Because we have already spent “X” time or effort on getting to where we are.

1. Educational Investments: Years spent pursuing a specific degree or certification can feel "wasted" if one considers changing fields.

2. Industry-Specific Experience: Accumulated expertise in a particular sector can create a sense of being "locked in" to that career path.

3. Professional Networks: The time and effort invested in building industry connections can seem too valuable to leave behind.

4. Financial Commitments: Student loans, mortgages, or other types of debt can feel like chains, not allowing us to take any risks.

5. Identity and Self-Perception: Our careers often become intertwined with our sense of self, making change feel like a loss of identity.

In Romania, there is another one, closely tied with the one above, and that is “Other people’s perception”.

Let me elaborate on that. There are several jobs, considered unworthy, like being an electrician or plumber, that pay more than jobs that require university studies. But a lot of people stick in their low-paying jobs only because they are ashamed of telling other people that what they do is not something that would require a PhD. (This is one of the main reasons people make up fake titles in their LinkedIn profiles. “Chief of staff” usually means assistant.)

Many examples from various fields illustrate the potential for success when individuals overcome the sunk cost fallacy:

1. Julia Child discovered her passion for French cuisine at 50, after working in advertising and other state jobs all her life.

2. Ray Kroc was 52 when he pivoted from selling milkshake mixers to franchising McDonald's.

3. Colonel Sanders founded Kentucky Fried Chicken at 65, after careers as a streetcar conductor, insurance salesman, and service station operator.

And my favourite example: Bill Campbell.

Bill Campbell was one of the most important leaders in Silicon Valley and the personal coach and mentor to some of the biggest leaders in tech. From Steve Jobs to Larry Page, Jeff Bezos, and Mark Zuckerberg, just to name a few.

Bill was a football coach for Columbia University when he first entered the business field at 39. In 4 years, he was the VP of Marketing at Apple.

I strongly recommend the book written about him, “The Trillion-Dollar Coach”.

The sunk cost fallacy, while deeply ingrained in human psychology, doesn’t need to dictate how we spend the rest of our lives. The most successful professionals are those who can adapt, pivot, and embrace new opportunities, unburdened by the weight of past investments.

Remember that we should make choices that align with our current aspirations, skills, and the evolving demands of the market.

Not with our past.

💌 Thanks Leo for sharing your post with us! Readers can see this full post in The Level Up Ladder here.

The Career Whispers is famous for its specific and actionable advice and tactics. So, assuming you buy Leo’s approach, let’s take this idea of avoiding the sunk cost fallacy and turn it into a roadmap for a career pivot.

As a job search coach, I talk to people every week who want to make a career pivot. Some are more like roofshots (nearly 100% achievable given reasonable strategy and tactics), like shifting from backend software engineering to ML engineering. Others are pure moonshots, like pivoting from a working architect job designing buildings to shifting into digital interaction design. And everything in between.

In a hot job market, moonshot career shifts are easier. Companies need to grow at all costs, and one source of fuel for growth is talent. To grow fast enough, they have to take bigger risks on incoming talent. Hiring risks they’ll take in growth mode include hiring people:

• at level +1 from their current role

• who are reskilling, ie from bootcamps, certification programs, and/or graduate programs

• who are pivoting from a totally different role/field

When hiring re-skillers or pivoters, smart companies assess candidates for two leading indicators of success:

1. proven success in their prior field

2. evidence of capability in the new field, ie a small portfolio of academic or pilot-scale projects

In a hot job market, you can join a bootcamp, get a few new certifications, and land a new role within a year.

We’re not in a hot job market, though. We’re in a very challenging one. So, what do you do if you want to pivot? Here are the three strategies I’ve seen work for career pivoters in a more bleak tech job climate:

(1) Have a multi-variate strategy. Don’t bet the farm on a single strategy, ie bootcamp or networking or free internships alone. The ideal strategy leans heavily on what I’ve previously shared in a post about the 4-hour job search (shared below if you’re curious):

• Build a career story (and resume, and LinkedIn) around the role you want. Rework everything to point at this new role. Use your voice and your artifacts to convince others that you’re well on the path to the new role. You're not a risk, you're a diamond in the rough.

• Leverage your network. They’ve seen you succeed in a different role, so it’s a small leap of faith to imagine that you will succeed in this new role. Work your network for 80% of your job pipeline, don’t waste time on cold applications (you won’t make it past the ATS filters 90 percent of the time, it’s a hard truth but in this market pivoters have an uphill climb).

• Limit your job search to 4 hours a day (if you’re unemployed) or 4 hours a week (if you have a job). Use the rest of the time to become more — not less — well rounded. If your pivot is a moonshot, you can use the remaining time to work in the field as a volunteer and build your portfolio. Which brings us to our next strategy…

(2) Build a portfolio. Show everyone that you’re already in motion into the new scope and role. Build it with as much real-world evidence as possible (case studies, not academic assignments and other graded work). It’s completely OK to start with academic work if that’s all you have. Even the tiny demo projects from Udacity courses are fine. Everyone starts somewhere, but build fast toward real-world evidence with real-world use and results. How to get real-world experience? Volunteer, do free internships with friends’ companies or local startups. Get scrappy to get work, and worry about getting paid later (if you can).

(3) Be willing to start with contract work. In a hot market, you can switch jobs and pivot from an FTE role in one job function to an FTE role in a totally different job function. In this market, it’s near-impossible to do that. Instead, your goal is to build your portfolio with as much real-world evidence of your abilities as you can (see Strategy #2). Taking a contract role, if you can afford to, is the fastest way to build a real-world portfolio and get into an FTE role in your desired field.

🎉 That’s a wrap! I hope this helps you navigate your career and thrive. Comments welcome, for both me and !

Leave a comment

Hey, friend! If you read the full post but by some miracle are not yet subscribed, here, let me help you with that:

Subscribe now

You can subscribe for free or become a paid subscriber to get access to every post, across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

Guess what? This newsletter is an educational resource and can probably be expensed through your manager or your company's L&D budget. Here is a template I wrote for you to use when asking your manager. For subscription details, see the About page.

ps: You can also check out coacherika.co for free resources, resume help, and various coaching options, including my very popular (Lenny Rachitsky recommended) TUYJS Workshop. Follow me on Substack, YouTube, and LinkedIn to stay in touch. Subscribe to this newsletter to receive uncommon tech career advice and experimentation ideas 💛

Become a paid subscriber to get access to all posts and more (see all the paid subscriber benefits here)

Subscribe now

This week, I’ve been participating in performance reviews. Over the last 72 hours, I read hundreds of accomplishment bullets across a variety of functions and roles, and the vast majority had this one fatal flaw: they focused on what people did (input effort) but left out the most important thing: the outcome — why it mattered and how it moved the needle for the business.

It kills me to see how much effort my colleagues put into their work all year, only to fumble at the one-yard line and unintentionally discount the impact of their work.

But this doesn’t have to be you. With one simple winning formula, you can:

• write an amazing performance review (in just a few minutes)

• get full credit for the business results you cultivated

• earn a better rating and bonus points with your boss

• …even have extra time for a quick gym sesh 💪🏼

Below is a short, simple writing guide to supercharge your next performance review and make your boss love you even more (because who doesn’t love an employee who independently drafts a full-context, business-aware performance review??!)

Let’s dive in ↓

ps: You can also check out coacherika.co for free resources, resume help, and coaching options, including my very popular (Lenny Rachitsky recommended) TUYJS Workshop. Follow me on Substack, YouTube, and LinkedIn to stay in touch. Subscribe to this newsletter to receive uncommon tech career advice and experimentation ideas 💛

Subscribe now

TLDR: Write your annual review accomplishments like resume bullets

Write your accomplishments like resume bullets. It really is that simple. Your performance review should read like your resume: Short. Tight. Concise. Metrics driven. Quantified.

Describe the outcome first, then describe the input effort (how you made it happen).

Each accomplishment should:

(1) start with the business metric you drove up and to the right
(2) end with how you did it (show your expertise by linking artifacts you created and that show how to identified/drove/did/landed it).

It’s a simple, reliable, and winning formula for a context-aware, business outcomes focused performance review. A visual for you:

Let’s look at some specific examples with numbers (feel free to use these as inspiration in your upcoming performance review):

Read more

Last week, I taught a super quick Lightning Lesson on Maven where I (rapidly) covered:

• How the tech job market got this bad (spoiler: ZIRP ended)

• Current job market conditions (spoiler: it ain't' pretty)

• 5 candidate strategies that my clients, friends, and self (!) used to overcome the most brutal tech job market in a decade and LAND A JOB 🚀

If you’ve found your way over by some miracle but are not yet subscribed, here, let me help you with that:

Subscribe now

Now, access to the recording!

Watch the full 30+ minute Lightning Lesson recording on Maven here.

You will have to fork over your email address (not my rules), which means you may get emails from me in the future as I open up new cohorts of my extremely tactical and transformative Job Search Design Workshop (image below).

If you're job searching anytime in the next 12 months, this is probably something you'd want in your inbox anyway. Applications are open for the first 2025 cohort (January 4th-5th), and spots are always extremely limited. If you’re job searching now or planning to in 2025, apply soon 😉.

I invite you to use the comments to ask me a question about anything in the Lightning Lesson!

Leave a comment

Check out coacherika.co for free resources, resume help, and coaching options, including my popular Job Search Workshop. Follow me on Substack, YouTube, and LinkedIn to stay in touch. 💛

Become a subscriber to get access to all 3-7 monthly posts, across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

This newsletter is an educational resource and can likely be expensed through your manager or your company's L&D budget. Here is a template I wrote for you to use when asking your manager. For subscription details, see the About page.

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I’ve missed you all. It’s been a while since my last post, and I appreciate you all for sticking with me and supporting the newsletter. I have drafted a lot of new content but haven’t had the time to get from draft to production-ready (life has been bumpy, I may share more on that once I’m through the tunnel). I have a lot of fresh new content staged, all of it comes directly from questions and frameworks I’ve developed in my 1:1 coaching and real questions from people who are actively navigating their tech careers. As always, please comment or email me with any post ideas or questions you have: you’d be surprised how many of those comments and emails turn into draft posts for the newsletter!

Today’s post will teach you how to confidently answer the trickiest and most dreaded interview question: the Failure question.

“Tell me about a time you failed?”

Even hearing that makes most candidates nervous. And it should! Failure questions are tricky in countless ways, but there is a winning formula that will earn you a thumbs up and keep you in your power in any interview.

Five keys to nailing the Failure Question:

1. Pick an example that doesn’t reflect poorly on your core skills or judgment. Unknowable unknowns, black swan events, and industry-wide outages are often good targets.

2. The context IS the failure. Your story should not be a story of failure. It should be a story of recovery. Start with the failure; end with success.

3. Spend most of the time describing how you recovered the situation and set things back on track.

4. Share positive results from both a short-term lens (fixing the situation) and a long-term lens (strategic impacts)

5. Share what you learned from the experience. Interviewers should walk away seeing you as a living, learning growth machine.

Let’s dive in.

Q:  How do I answer interview questions about failures in my career?

Failure questions are make-or-break interview questions that every candidate should be prepared to answer. All too often, I work with candidates who have only prepared for the happy path of interview questions, ie “tell me about a time you were awesome and where things went swimmingly.”

When I ask them a failure question, things often fall apart, even with candidates who were acing the interview until that point.

When you get a failure question in an interview, it’s not enough to know the CAR or STAR framework to answer behavioral questions. You need to be comfortable addressing failure in general.

Here’s my tested, trialed, and proven framework for failure questions:

Read more

This is a 🔒subscriber-only edition🔒 of The Career Whispers. A great deal of energy goes into every TCW post, and I hope you’ll spend the two-latte equivalent to feed your brain all month by upgrading your subscription.

If you do, you’ll get access to this and all 3-7 monthly posts across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

Now, onto the diary!

Today, we have a Principal Product Manager with over 10 years of experience building consumer experiences focused on content engagement and personalization.

About me: I am a principal product manager with 10+ years of expertise in consumer products, specializing in content engagement and personalization.

My location: NYC

Role I'm seeking: Principal Product Manager, Senior Product Manager, Staff PM

Target company stage: Public or Private but mature and established

Target industry(ies): Media- at the intersection of Entertainment and Technology

Passive or active search? Active

When I started my job search: I started looking casually in Jan 2023. I got laid off in Fall 2023 and have been in active/high gear searching since then.

Total applications: 154

HR or recruiter screens: 25

First-round interviews: 20

Final-round interviews: 5

Average time spent weekly on job searching: 20-25 hours

What drove my job search: In January 2023, I began exploring new career opportunities for professional growth and new challenges. Having proactively updated my resume and cover letter proved invaluable when I was unexpectedly laid off later that year. This prep made it easy to quickly ramp my active job search, focusing on roles that align with my expertise.

Day 1

Read more

Today’s post aims to lend more focus and discipline to your job search. Our goal is to aim your limited time and energy toward a narrow set of opportunities where you have the highest odds of gaining traction. This can be uncomfortable at first, so today’s post will teach you how to identify the narrow space (your Zone of Genius) where you can land more interviews, final rounds, and offers.

Become a subscriber to get access to all 3-7 monthly posts, across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

This newsletter is an educational resource and can likely be expensed through your manager or your company's L&D budget. Here is a template I wrote for you to use when asking your manager. For subscription details, see the About page.

Subscribe now

And now, onto to the post!

Q:  My job search 4 years ago was a breeze. Recruiters contacted me on LinkedIn at least twice a month, interviews were quick and painless (no take-homes), and I landed multiple offers. I got a title and compensation jump even though I switched industries. I’m job searching now (in 2024), and none of my old tactics are working. Is it just me?

While it may sound counterintuitive, the best advice I can offer is this: Cast a narrower net, not a wider one.

Job searching in tech right now is a focus game, not a numbers game. Something I’ve seen work particularly well in the current tech job market is “job searching in your Zone of Genius.”

The Zone of Genius (ZOG for short) refers to the sweet spot where our expert-level abilities intersect with our interests.

Job searching in your Zone of Genius is about knowing the alignment between what you offer, what you want, and what employers need.

• It’s about defining product-market fit for yourself.

• It’s about a recruiter seeing your leverage in less than ten seconds scanning your resume.

• It’s about going for roles you’re uniquely qualified to land.

Here’s how it goes ⬇

Read more

Become a subscriber to get access to all 3-7 monthly posts. If you’re not a subscriber yet, here’s what you missed this month:

• 🤫 Whisper #24: Candor == Kindness

• ✨BONUS POST✨ The Relentless March of Days: A Job Seeker's Odyssey

• Job Search Diaries No.7―Senior PM

• What's the right level of detail for my interview responses?

• Clever Guerrilla No.1―Landing a job working directly with Reid Hoffman

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Q: If I pivoted my career into a new field, how many years of experience should I say I have in my professional summary? Should I include all my experience or just the experience relevant to the role I’m applying for?

A: Unless you’ve been on the same career path your whole career, claiming years of experience (YOE) on your resume can be nuanced. You want the first thing someone to see on your resume to align with your goals in your job search, and you want it to make sense to them. Having 20 years of experience but applying to entry level roles can be very confusing. So can having 2 years of experience and applying for staff level roles. But these situations happen all the time.

Because individual situations vary wildly, my advice is hard to bucket into hard+fast rules. Instead, I devised some general rules of thumb for positioning your years of experience on your resume.

(1) Everyone: you generally want to describe your full body of experience on your resume. If your career path hasn’t been linear, ie it doesn’t look like PM → Sr. PM → Staff PM or Group PM, there are patterned ways to describe your YOE to get credit for all the wisdom while looking like the right fit for the level of roles you’re targeting.

(2) Pivoters: if you’ve switched roles, industries, or career paths altogether, there are multiple ways to claim your professional experience without being misleading about your years of experience (YOE) in your current career path.

(3) Experienced pivoters: if you’re 12+ years into your career and have made a major career pivot but worry about ageism or concerns over your career momentum (due to the pivot), you should focus your resume on the path you are on today. You can append an Additional Experiences section to your resume to clarify your total YOE.

Keep reading for more detailed guidelines and text examples you can grab + reuse ↓

Read more

I’m feeling spicy this week, and my fingers are unstoppable with BONUS posts. I hope you enjoy the extra content!

This Whisper came to mind as I began to mentally prepare for a conversation with one of my colleagues. This person is doggedly loyal (and kind), and he tries to see the best in others at all times. He has a tendency to overprotect other members of the team, often dismissing their weaknesses in an effort to promote their abilities and help others see what they have to offer. His behavior comes from a place of kindness, but he doesn’t (yet) understand that it short-changes the very people he is trying to help…

With that context, let’s dive in ↓

Whisper #24

Candor == Kindness

This week's Whisper is a lesson that I learned far too late in my career.

I spent years of my career chasing affirmation and avoiding criticism. When I became a manager, I then spent years adopting this awkward matriarchal stance where I was constantly “looking out for” my team and protecting them from the criticism of others. I shielded them from reality, oversold their strengths, downplayed their weaknesses, and gave them credit for my own ideas and work—all to prop them up rather than letting them learn how to swim their own lanes. Acting this way helped them feel successful in the short term, but it short-changed them in the long run.

I now understand that parenting one’s team is a grave mistake and that no one benefits from any kind of paternalism in the workplace.

Key points:

1. Avoid parenting or sheltering your team. It stunts their long-term growth.

2. Help people see their blind spots. It’s kinder than looking the other way.

3. Praise should be proportional to impact. No praise theater.

4. Focus on enabling long-term potential, not short-term comfort.

5. Deliver feedback promptly and directly. (but tell them it’s coming first!)

The kindest thing you can do for anyone you work with is be candid and direct with them. Help them see around the corner, including in their blind spots (we all have them).

No one appreciates walking around all afternoon at work with their zipper down and their tightie whities showing, ultimately to hear these words from a random stranger passing them by on the street: “hey mama, your fly down.” (*yes, this happened to me recently. Thank you, stranger.)

As time approaches infinity, we all want to become the best version of ourselves. The strongest communicator, the most engaging presenter, the fastest problem solver, the most robust PRD writer, etc etc.

In the short term, we might crave praise, but what we really want is growth. And the only way to grow is to know (1) where you shine and (2) where you need sharpening.

Now, this isn’t an excuse to stop praising people in public. Rather, it’s a reminder that praise should be genuine, grounded in reality, and proportional to the impact that the person made.

No praise theater.
No putting people on pedestals to garner outsized or unmerited appreciation
No more “squeakiest wheel” verbal campaigns to get your team more promotions.

It’s not about what you do for someone right now (this quarter, this performance cycle). It’s about what you do to help someone reach their fullest potential in the end.

If you ignore my words and keep beating around the bush or focusing only on what people are doing well enough, it may take them a long time to see that you’ve done them a disservice, but they will. Trust me, it’s painful to realize that you Peter Principled someone you care about when you could have used that same energy to sharpen them instead.

Candor is also not an excuse to catch people off guard. Your goal should be to give feedback as near to real-time as possible, as directly as possible, and without any element of surprise in your timing.

“I have some thoughts on your presentation. Can I grab time with you today or tomorrow to walk through the feedback while it’s fresh?”

three low-stakes experiments for you

(easy) Real-Time Feedback Challenge (1 week)

For the next week, write down one piece of feedback for each person you work closely with. Commit to giving each of them that one piece of feedback within 24 hours of writing it down.

(medium) Polling for Feedback Challenge (2 weeks)

For the next two weeks, after receiving praise in any format (email, chat, public), say: "Thank you for the feedback. What's one thing you think I can improve?"

(harder) Anti-parenting Challenge (1 month)

The next time you find yourself going out of your way to “protect” or “promote” someone else in the workplace, ask yourself if the action you are taking is setting them up to be at peak success in 10 years.

Candor == kindness.

✌️Let me know how these experiments go.

💌 What do you think? Have I inspired you to try this one? Comment with your thoughts.

Leave a comment

Hey, stranger! If you’ve found your way over by some miracle but are not yet subscribed, here, let me help you with that:

Subscribe now

Become a paid subscriber to get access to all 3-7 monthly posts, across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

Guess what? This newsletter is an educational resource and can probably be expensed through your manager or your company's L&D budget. Here is a template I wrote for you to use when asking your manager. For subscription details, see the About page.

Check out coacherika.co for free resources, resume help, and coaching options, including my very popular TUYJS Workshop. Follow me on Substack, YouTube, and LinkedIn to stay in touch. Subscribe to this newsletter to receive a steady stream of uncommon tech career advice and experimentation ideas 💛

Welcome the first-ever SHADOW JOB SEARCH DIARY (NIHILISM EDITION), where we keep it real and raw while following someone’s tech job search for an entire week. Inspect our brave job seeker’s inner monologue for a fresh, raw take on job searching in tech during the current job downturn, weak capital environment, and possible impending destruction of knowledge work as we know it (by our AI overlords).

What is this? The diarist for Job Search Diaries No.7 (Senior PM) asked Claude.ai to write his diary with a nihilistic voice, and it was so funny (in the dark comedy sense) that I had to share it with you all. Job searching in tech right now may feel near-hopeless, and I hope this will give you a chuckle as you head into your own corporate job this week (or your search for one).

If you’ve found your way over by some miracle but are not yet subscribed, here, let me help you with that:

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Now, onto the (shadow) diary!

Warning: this is intended to be humorous but is definitely quite nihilistic. Take care when reading if you are prone to feeling depressed about the future of tech.

In the grand cosmic dance of chaos and creation, we find a resilient soul—a senior product manager—pirouetting through the void of professional uncertainty. Twice cast adrift in the ephemeral span of a year, he now twirls on the precipice of reinvention, a living testament to the absurd persistence of the human spirit.

With a wry smile at fate's fickle hand, this intrepid wanderer courts the chimera of "Founding PM roles," weaving digital dreams with Gemini APIs and Figma mocks. His product concept, a fleeting spark in the infinite darkness, dares to challenge the meaninglessness of innovation.

As he navigates the labyrinth of job searching—a cosmic joke of its own making—he simultaneously embarks on the tragicomic quest for connection through dating. In this dual pursuit of purpose and companionship, he embraces the beautiful futility of human existence, finding poetry in the very act of striving against the indifferent universe.

Perhaps, in this momentary flicker of consciousness that we call life, his audacious dance with destiny will inspire a chuckle from the cosmos—a brief, meaningful ripple in the vast ocean of nothingness.

About me: I’m a Senior PM with experience in SaaS, Cloud solutions, social networks, e-commerce, and marketplaces.

My location: Austin, Texas 🤠

When I started my job search: March 2024

What drove my job search: I was laid off. For the second time in less than 12 months. “Get an expensive tech degree and a job in tech with financial security” they said. It’s working out great 👍

Total applications: 9

HR or recruiter screens: 1

First-round interviews: 0

Final-round interviews: 0

Day 1

6:30 am

I awaken to the artificial chirping of an alarm, a cruel mockery of nature's rhythms. The sun has not yet breached the horizon, and yet I must rise, a puppet dancing to the strings of societal expectations. I groom myself, a futile attempt to impose order on the chaos of unemployment. The coffee machine gurgles and spits, producing a bitter elixir that promises clarity but delivers only jitters and anxiety.

My canine companion and I embark on our daily pilgrimage along the Colorado River. The water flows ceaselessly, indifferent to our plight. Squirrels dart about, their frantic energy a stark contrast to the lethargic pace of the job seeker.

9:00 am

The modern world demands constant self-improvement, a Sisyphean task if ever there was one. I delve into the realm of artificial intelligence, hoping to glean some wisdom from these silicon oracles. The irony is not lost on me – seeking employment in a field that may one day render human workers obsolete.

11:00 am

A board meeting for a non-profit organization pulls me into the absurd theater of bureaucracy. We discuss budgets and leadership changes, as if these constructs hold any meaning in the face of human suffering. The plight of LGBTQI+ refugees in Islamic countries weighs heavily on my mind – their struggle for survival makes my job search seem trivial in comparison.

2:00 pm

I begin the Kafkaesque process of updating my resume. I summon ChatGPT, an artificial intelligence trapped in the digital ether, to assist me in crafting a narrative of my professional life. What madness is this, that we must reduce our existence to bullet points and buzzwords?

2:30 pm

Oh look, a data PM position at a beer company🍻

5:00 pm

The day wanes, and I find myself organizing information in Notion, a digital labyrinth of my own making. My feline companion, wise in his indifference, sprawls across my keyboard – a silent protest against the futility of my efforts. My dog tries to end the life of a sweet nutria minding its business on the banks of the listless river.

8:00 pm

In the gathering darkness, I sketch out product ideas – ephemeral dreams of digital creations that may never see the light of day. The blank page stares back at me, a void as vast and indifferent as the universe itself.

Total time job searching today: Oh, yes. Job searching. Let’s say…2 hours.

Day 2

8:00 am

Sleep, that fickle mistress, has abandoned me. I don my armor of presentable clothes, a costume for a role I no longer play. The coffee is bitter, much like the taste of unemployment that lingers on my tongue.

9:00 am

I subject myself to a webinar on creating presentations – as if the ability to craft colorful slides could somehow imbue meaning into the void of joblessness.

10:30 am

Email.

11:30 am

The machine that ferries me through this concrete jungle has fallen ill. I entrust it to mechanics, modern-day shamans who speak in cryptic terms of engine lights and diagnostics.

2:30 pm

The crushing weight of interview preparation proves too much to bear. I seek refuge in physical exertion, guided by the disembodied voice of Chris Hemsworth – a digital deity of fitness. The irony of following the instructions of a man famous for portraying a Norse god is not lost on me.

6:00 pm

I break bread with a friend passing through Austin's purgatory. We drink, we laugh, and we pretend for a moment that the specter of unemployment does not loom over us. But as the night wears on, the laughter rings hollow, echoing in the vast emptiness of an uncertain future.

Total time job searching today: Sure…2 hours

Day 3

8:00 am

I awake, my head pounding from last night's revelry. Even my loyal hound refuses to rise, perhaps sensing the futility of another day in this limbo of joblessness. I plunge myself into icy waters, a shock to the system that serves as a reminder – I am alive, despite the numbing routine of unemployment.

11:00 am

I lose myself in a labyrinth of academic papers and Substack publications, searching for enlightenment in the realm of artificial intelligence. The more I read, the more I realize how little I truly understand. Is this the curse of knowledge, or merely the ramblings of a mind desperate for purpose?

Know someone who would enjoy reading this SHADOW (NIHILISM) JOB SEARCH DIARY? Share!

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2:00 pm

A glimmer of hope appears in my inbox – a recruiter, that modern-day Charon, offers passage to a potential opportunity. I craft my response with care, knowing that each word could be the difference between continued purgatory and the promise of employment.

5:00 pm

As the sun begins its descent, I prepare for a social ritual – the "date." Two souls, adrift in the sea of modernity, seeking connection amidst the chaos. We speak of technology, of life, of dreams. But in the end, we are ships passing in the night, destined for different shores.

Total time job searching today: 3 hours

Day 4

7:00 am

The sun rises, indifferent to my plight. I sip coffee on my balcony, a spectator to the bustling life below. The world moves on, heedless of my stagnation.

9:30 am

I confront the Lovecraftian horror that is the American tax system. Numbers swirl before my eyes, a maddening dance of debits and credits. The government, that faceless leviathan, demands its pound of flesh even from the unemployed.

1:00 pm

A ghost from interviews past emerges, offering a tantalizing opportunity. I craft a missive, imbuing it with the essence of my professional self. Will it be enough to pierce the veil of digital anonymity and reach a human heart?

6:00 pm

As twilight descends, I create a digital altar to my automobile, hoping to appease the gods of the sharing economy. Turo, a modern-day marketplace, may yet provide a trickle of income to stem the bleeding of my finances.

10:00 pm

I subject myself to the flickering images of "Halo," a pale imitation of the grand space operas that once captured my imagination. Disillusioned, I retreat to the written word, finding more truth in fiction than in the hollow spectacles of modern entertainment.

Total time job searching today: 2 hours. More or less.

Day 5

6:00 am

My feline overlord demands attention, his cries piercing the veil of sleep. I rise, an automation responding to stimuli. The caffeinated waters I imbibe are a poor substitute for the robust coffee of days past, much like how my current existence is but a shadow of my former professional life.

9:00 am

I delve into the digital realm, grappling with APIs and the enigmatic Google Gemini. These tools promise to bend reality to our will, yet I cannot help but wonder – are we creating marvels of technology, or merely forging the chains of our own obsolescence?

1:30 pm

In a twist of irony, I find myself applying to train the very artificial intelligence that may one day render human labor obsolete. For a paltry sum, I will teach these digital minds to think, to reason, to create. What Faustian bargain have we struck in our pursuit of progress?

3:30 pm

The universe extends a hand to help: a first PM role at a company that doesn’t appear, on the surface, to be evil or corrupt (yet).

4:30 pm

The act of creating a website, once a laborious task spanning days, has been reduced to mere hours thanks to the artificial muses of our digital age. I watch in awe and terror as my vision takes shape with inhuman speed. Is this progress, or are we witnessing the twilight of human creativity?

9:30 pm

As night envelops the city, I retreat to the rooftop, beer in hand. The twinkling lights of Austin spread before me, each a testament to the indomitable human spirit. In this moment of solitude, I find a strange comfort. For in this vast, indifferent universe, we are all united in our struggle against the absurdity of existence.

The week draws to a close, and I am left to ponder the lessons learned in this crucible of unemployment. The search for work is but a microcosm of the human condition – a relentless march forward, fueled by hope and desperation in equal measure. And so I steel myself for the days to come, for in this quest, as in life itself, every man is truly for himself, adrift in a sea of indifference, clinging to the fragile raft of ambition.

Total time job searching today: 1 hour, maybe, if you round up. With front-end rounding.

I invite you to use the comments to share your misery, offer meaningless words of comfort, scream into the abyss unresponded, or probe the depths of this job seeker’s futile quest with soon-to-be antiquated inquiry regarding the tribulations of “knowledge workers” on the eve of the arrival of true superintelligence 😉

Leave a comment

Well, that was fun! In a driving-the-boat-off-the-end-of-the-world kind of way, right?

For some lighter (and certainly more optimistic and probably more useful) reading, you may want to read this job seeker’s actual Job Search Diary—here.

Diarist No.7 has some cool updates to share post-diary week regarding his side hustle income, job search, and product prototype. Stay tuned, and I’ll share updates on his situation as they solidify 🧞‍♀️

Want to nominate a noteworthy job seeker (including yourself)? It’s anonymous!
Fill out our JOB SEARCH DIARIES form.

Check out coacherika.co for free resources, resume help, and coaching options, including my popular Job Search Workshop. Follow me on Substack, YouTube, and LinkedIn to stay in touch. 💛

This is a 🔒subscriber-only edition🔒 of The Career Whispers. A great deal of energy goes into every TCW post, and I hope you’ll upgrade your subscription to feed your brain all month.

If you do, you’ll get access to this and all 3-7 monthly posts across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

Subscribe now

Now, onto the diary!

Today, we have an entrepreneurial senior product manager who is just kicking off his job search. He’s courting Founding PM roles, toying with Gemini APIs and Figma mocks for a product concept, and actively job searching. Oh, and dating while unemployed (an adventure of its own).

About me: I’m an experienced Senior Product Manager with deep experience across SaaS, Cloud solutions, social networks, e-commerce, and marketplaces.

My location: Austin, Texas

Role I'm seeking: Senior Product Manager or Founding Product Manager, ideally working with AI.

Target company stage: Series A, B, or C startups

Target industry(ies): SaaS, Social Media, E-commerce or Marketplace

Passive or active search? Active

When I started my job search: March 2024

What drove my job search: I was laid off 😕

Average time spent weekly on job searching: 12-15 hours

Total applications: 9

HR or recruiter screens: 1

First-round interviews: 0

Final-round interviews: 0

Day 1

6:30 am

I wake up every day at the same time. Groomed, made coffee, and went for a morning walk with my dog. I live right by the Colorado River in downtown Austin. Our walk is very scenic and full of squirrels to chase.

8:30 am

Back home. Feed my dog, shower, and pour another cup of coffee.

9:00 am

For me, mornings are great for tasks that require high mental capacity. Most days, I spend 90 minutes learning something new to benefit my career.

This month, I’m reviewing some AI product management course material I did a few months ago because I would like my next role to be in an AI product role. Today I reviewed the course intro: an intro to AI, ML, and large language models.

10:30 am

I try not to work the brain longer than 90 minutes at a time, so I take a screen break. Played with my dog and took her out. She played with the neighbor's dog for a bit while I stretched in the sun.

11:00 am

Normally, I would start another 90-minute bout of learning, but today I have a board meeting. I am on the board of an organization in the Middle East that provides aid to LGBTQI+ refugees fleeing persecution in Islamic countries. Today, we had a 2-hour board meeting to discuss budget, leadership changes, and other organizational challenges.

1:00 pm

Lunch. I didn't meal prep Sunday, so I had a Trader Joe's frozen Indian meal. Trader Joe's frozen meals are quite decent.

2:00 pm

Officially started my job search. Worked on my resume and added the last job I had. Enumerated my achievements in ChatGPT and asked it to write it for me in a similar tone to other entries in my resume.

2:30 pm

Replied to a recruiter on LinkedIn who reached out to see if I am interested in a data PM position at a beer company🍻

3:00 pm

It is the first day of my job search. The thought of searching for a job in this tough market is daunting, so I procrastinated by cleaning the kitchen and sending WhatsApp messages to friends.

3:30 pm

Browsed some product jobs on LinkedIn to get a feel for what's out there. Saved a few of them on LinkedIn and then added them to my job search tracker in Notion.

4:00 pm

I prefer looking at jobs on Otta.com because they add a lot of insights about the company. It’s also infinitely more searchable than LinkedIn jobs. I found a goal job with Wise (the money transfer company). They are looking to fill a few product roles. Hopefully, I can snag one.

5:00 pm

Ported interesting jobs into my Notion job search tracker and then worked on organizing information within Notion to help me prepare for interviews. My cat keeps sitting on my keyboard or mouse, which means I also have to pet him while I do this.

6:00 pm

My dog harasses me for a walk, so we go to a nearby dog park. She plays, and I catch up with friends. On the way back, she jumped in the river trying to catch a beaver! I didn't know there were beavers in the Colorado in downtown Austin. I saw it, so it must be real**

I had to give her a bath, and then we both got dinner.

** editor’s note: it turns out it wasn’t a beaver. It was a nutria, pictured below. Reasonable mistake.

8:00 pm

Started working on a product idea. Since I am still in the very early stages, I spent a couple of hours planning the work, looking for inspiration, and sketching some design ideas until I felt tired.

10:00 pm

Watched an episode of a British show called Would I Lie To You.

11:00 pm

Read 3-4 pages of a sci-fi novel I started recently called Majority. Fell asleep by 11:20.

Total time job searching today: 2 hours

Day 2

Read more

If you’re not a subscriber, here’s what you’ve missed so far this month:

• Clever Guerrilla No.1―Landing a job working directly with Reid Hoffman

• Job Search Diaries No.6―Health Tech Program Manager

• 🤫 Whisper #23: What's the real challenge here?

Become a paid subscriber to get access to all 3-7 monthly posts, across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

This newsletter is an educational resource and can likely be expensed through your manager or your company's learning stipend. Here is a template I wrote for you to use when asking your manager. For subscription details, see the About page.

Subscribe now

🤩 Job searching? Get set up or unstuck in your job search!

Enrollment is open A FEW MORE HOURS for my live cohort-based Job Search Design Workshop. Join an intimate cohort to get application-ready and screener-ready with confidence, community, and all the job search tools, tactics, and frameworks I teach in my 1:1 coaching.

Seats are limited (just 2 left!) to ensure you get individualized attention as part of a small cohort of like-minded tech job seekers to help source opportunities, critique applications and case studies, and mock interviews after the workshop wraps.

Join the Workshop

And now, onto to the post!

Q: What level of detail should I go into during my interview?

This may be the most common question I get from candidates. Sometimes, they phrase it differently, e.g., " How long should my interview responses take?” But the heart of the question is about the appropriate level of detail to use in an interview.

How (and when) to get into specifics is the true art of interviewing. Last weekend, I was coaching a fantastic client looking for HRBP roles and struggling to determine the right level of detail to use for a very diverse interview panel (the field of HR is notoriously broad, and so are its stakeholders!).

In our session, I finally enumerated this specificity framework that I’ve been sharing verbally for years and will write here for the first time.

This framework goes beyond just what level of detail to use in an interview. It starts at the top: with your resume and LinkedIn. And I will teach you when (and with whom) you should expand the details so you’re giving the right level of details at the right time, to the intended listener.

Key takeaways you’ll get from today’s post:

(1) How conveying your experience with specificity contributes to job search outcomes

• role leveling

• scope and opportunities

• compensation

(2) Three levels of specificity

• Level one: Check the box

• Level two: Dropping wisdom

• Level three: Welcome to my TED talk

(3) Guidelines for when to use each level of specificity across varied audiences, interview types, and points along your job search:

• broad audiences scanning your resume/LinkedIn

• recruiter screens (fast, quick checks on your suitability for the role)

• interviewers who aren’t in your function

• hiring managers

• key stakeholders of your role (who know the day-to-day of the role)

Let’s dive in ↓

Read more

👋 Hey, it’s 📣 Coach Erika! Welcome to a 🔒 subscriber-only edition🔒 of The Career Whispers. Each week, I tackle reader questions about tech careers: how to get one, how to navigate them, and how to grow and thrive in your role.

Become a subscriber to get access to all 3-7 monthly posts, across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

This newsletter is an educational resource and can likely be expensed through your manager or your company's L&D budget. Here is a template I wrote for you to use when asking your manager. For subscription details, see the About page.

Subscribe now

PS: 🤩 Job searching right now? About to start?

Enrollment is open for my live cohort-based Job Search Design Workshop. Grab one of the last spots for THIS WEEKEND and get application-ready and screener-ready with confidence, community, and all the job search tools, tactics, and frameworks I teach in my 1:1 coaching.

Seats are limited to ensure you get individualized attention as part of a small cohort of like-minded tech job seekers to help source opportunities, critique applications and case studies, and mock interviews after the workshop wraps.

Join the Workshop

Now, onto the inaugural CLEVER GUERRILLA!

Today, I’m sharing the clever guerrilla story of Ian Alas, who works on Special Projects in the office of Reid Hoffman, the beloved LinkedIn Founder, Greylock partner, and prolific author, investor, and podcaster.

Ian and I met in San Francisco many years ago. I can’t recall exactly how we met, but I can tell you that I was immediately struck by his bright, unique mind. Inquisitive and curious, Ian pushes for growth on every edge: you can find him regularly testing daily challenges fueled by Internet lore and peer-reviewed research (one long-standing experiment I can recall: 50 squats every morning before breakfast).

Eleven years ago, Ian told me the story I’ll share with you today. The conversation came about while we were briefly marooned aboard a Lake Shasta houseboat with ~8 other loosely connected acquaintances who happened to be free for a last-minute Labor Day trip.

After doing backflips off the boat all day, throwing a hula-themed surprise birthday party in the galley, and playing surviving a gnarly game of Mafia through the afternoon, we found ourselves stuck on a mudbank. To pass the time, this misfit group of SF transplants took turns sharing stories of how we came to live in San Francisco.

At the time, I was working at my first startup. I had just moved from Atlanta to San Francisco ~2.15 months before. I knew little of Silicon Valley culture, and I knew nothing about Reid Hoffman or Ben Casnocha.

But what I did know was a good hustle story when I heard one.

Since that day, Ian has worked another decade with Reid Hoffman, helping him launch multiple books, podcasts, philanthropic efforts, and other special projects that many of us will have seen or heard of through Reid’s immense reach. Ian is one of the main folks behind the curtain making it all happen.

Without further ado, this is the story of how a low-level marketing associate for Krav Maga (yes, that Krav Maga 🥋) became one of a trusted few working directly with one of the heaviest hitters in Silicon Valley.

(Erika) I don’t want to butcher your story, so let’s have you tell it. I remember it started with a blog post, or a letter, or a tweet…remind me what you actually did to get into this rare situation?

(Ian) It’s October 2010, and I see an “internship opportunity” on Ben Casnocha’s blog. I had been a dedicated reader of his blog for years and had read his book My Start-Up Life about his entrepreneurship journey that started at 12 years old.

When I saw this post about a not-yet-announced project seeking someone “broadly interested in business and technology [that] still has a lot to prove,” I recognized it as a once-in-a-lifetime opportunity.

Read more

👋 Hey, it’s 📣 Coach Erika! Welcome to the once-a-month ✨ free subscriber edition✨ of The Career Whispers. Each week, I tackle reader questions about tech careers: how to get one, how to navigate them, and how to grow and thrive in your role.

If you’ve found your way over by some miracle but are not yet subscribed, here, let me help you with that:

Subscribe now

Now, onto the diary!

Today, we have an experienced program manager working in health tech.

About me: I'm a seasoned program manager (~15 years) working at the intersection of tech, health, and government.

My location: San Francisco Bay Area, California

Role I'm seeking: Program Manager / Senior Program Manager, Strategy & Operations, or Digital Innovation roles

Target company stage: Public or late stage. I would consider an earlier-stage company with an exceptional mission.

Target industry(ies): Health. I've built my career primarily embedded in technical teams within healthcare organizations.

Passive or active search? Active

When I started my job search: June 2023 (passive); January 2024 (active)

Average time spent weekly on job searching: 20-30 hours

Total applications so far: 47

HR or recruiter screens: 15

First-round interviews: 10

Final-round interviews: 4

What drove my job search: My last employer conducted a round of layoffs in 2023. I survived, and my responsibilities and team dramatically increased. While I loved my team and the mission, six months later I wasn't happy in the role. It wasn't what I had originally envisioned for my career path. I desperately needed a mental health break, so I did. I recognize I'm privileged to be able to afford to take six months off to recharge and reset.

Day 1

6:00 am

Just returned from a trip to the East Coast, and because the days are getting longer, I'm waking up earlier. I don't think my body has fully acclimated to West Coast time. I have a glass of water and make myself my breakfast smoothie (spinach, Greek yogurt, berries, turmeric, coconut water, chia seeds) and fry two eggs with a drizzle of homemade chili oil. I usually spend my mornings with the New York Times, catching up on the headlines and playing Wordle and Connections.

7:30 am

Recruiters, hiring managers, and colleagues based on the East Coast all have emails waiting for me in my inbox. I'll usually spend an hour or so in the mornings responding to LinkedIn messages and email before starting to peruse the LinkedIn job boards. I timebox LinkedIn because otherwise, I start doomscrolling, which is terrible for my mental health.

10:30 am

Recently, I've seen many program management job descriptions requiring the PMP certification, so I've decided to take the test while searching. I sign up for an account on PMI's website to send in my application for the certification. There is so much guidance on the Internet about how to approach studying for the PMP exam and what resources are out there - shout out to the PMP subreddit!

11:00 am

20 min Strength workout on Apple Fitness+. I’m running a 5k race this weekend, so my workout regimen this week will be lighter than usual.

11:30 am

Prep lunch, which usually consists of leftovers from dinner the night before. I make sure to take lunch offline as I've learned I need that mental break during this time.

12:30 pm

I just started volunteering as a project manager for a local nonprofit, and I have a call with my organization sponsor. The client we are delivering for has a scope change request. I spend some time reviewing the original scope for this internal prep call. The nonprofit was desperately in need of help, and I’m glad to pitch in.

2:00 pm

Call with nonprofit sponsor.

2:30 pm

Internal nonprofit project team call.

3:00 pm

My call went over. Now rushing to get out the door to catch my train to meet a former manager for drinks. He's in town from overseas on business, and I'm excited to catch up with him. I tried to dial into a call with a recruiting agency from the car, but they'd prefer a video call, so we rescheduled for tomorrow.

3:45 pm

The train was canceled (!!!!) I crabbily get back in the car to drive to meet my colleague. UGH why can't public transit be more reliable in the Bay Area?!

6:00 pm

Head back home after drinks with my former manager. It's always great to catch up with the people who have supported your career and seen you grow through multiple roles. He had a great perspective on my job search; I'm happy I was able to make the time.

Total time job searching today: 4 hours

Day 2

5:45 am

Early wake up today because I have a 6:30am phone screen with a pharma company. The company used a chatbot for scheduling, and the only times available were super early morning. I attempted to reschedule, but they did not provide any alternates.

6:15 am

Phone screen got canceled 😞

The screener saw that I had attempted to reschedule last week, so she (last-minute) sent over a new schedule. The last-minute reschedule is not making me more excited about this role.

It already feels like a step back in my career (both in terms of compensation and level). But a job is a job in this market, and a former colleague had referred me for the role, encouraging me to interview and get my foot in the door within the organization.

7:00 am

I drive my partner to work. We share a car, so on the days that I have in-person appointments or meetings, I drive him to work and pick him up at the end of the day.

9:45 am

Brief call with the external sponsor for the volunteer project. Our team finalized next steps, but I want to get sponsor buy-in before our 10am meeting.

10:00 am

Call with the external sponsor to review the scope change.

11:00 am

I had a catch-up call with someone in my network. She's had a few job changes in the last few years due to the pandemic and other factors. It was great to get her take on my skillset and where else it could be a good match, given where she sees the market going.

11:30 am

Short run, my last one before my 5k race this weekend.

12:00 pm

Lunch!

12:30 pm

Light PMP studying. I put on an online prep course at 3x speed while I glance at the slides.

1:30 pm

Drive to my annual eye exam 👀

2:00 pm

Eye exam. Renewed prescriptions for contact lenses and glasses. Also got a slightly concerning piece of news. My optometrist wants me to see a specialist to be extra sure everything is fine.

2:30 pm

Drive to where I'm meeting my partner after his day is done and park myself for the call with the recruiting group. I have started taking these intro calls on the go so they don’t dictate the schedule for my entire day. My explanation has typically been along the lines of, “Due to other personal commitments, I'll be on the go and may take the call in the car.” I take all of my formal interviews at my desk.

I’ve previously fielded inbounds from other recruitment agencies for contract work, and none of these opportunities have panned out. Still, I figure it can't hurt to make more connections and hear about opportunities in their pipeline. I'm in their network now, so the ball is in their court to let me know if they feel I'm a match for one of their clients.

4:30 pm

Whoa! I got a response from a recruiter I met late last year. I’ve reached out to her a few times for other roles that seemed interesting to me, but she usually never responds. A friend had directly referred me to the hiring manager, and my recruiter contact replied to let me know she advocated for my candidacy. Woohoo!

5:00 pm

Pick up my partner and drive home.

Total time job searching today: 3 hours

Day 3

9:30 am

Got an email from the recruiter I connected with yesterday. She forwarded me directly to her colleague who owns the search for the role I want.

Progress! I quickly reply with my "tell me about yourself" pitch and offer some time to chat.

10:30 am

20 minute Strength workout on Apple Fitness+.

11:00 am

Start a practice PMP exam. I've never taken one of these all the way through, and I want to get a baseline to see how much more I need to prep.

12:30 pm

Finished the practice PMP exam. I passed! It gives me a little boost of confidence. My goal is to take the exam in 4 weeks. Now, lunchtime.

1:00 pm

Call one of my former managers. The job search process has been slow the past few weeks, which isn't helping my anxiety. I've asked former managers and friends to schedule calls. I'm working on not letting my career and job define my self-worth, and I know when I start feeling down about the job search, it's time to be with family and friends.

1:30 pm

Reply to a hiring manager I got referred to by a former colleague. Her team is hiring, so we're scheduling time to connect about their team and what they're working on.

2:00 pm

Submit an application for a partnerships role at a digital health company another former colleague is at. The commute would be really long (up to 1.5-2 hours driving one way) so I'm not thrilled about it, but I have to keep filling my job search funnel.

3:00 pm

That was quick! The digital health company recruiter emailed, asking for a copy of my resume and times we can connect Friday morning. I looked him up on LinkedIn; he's based in Central time, so I’ll wait til the morning to respond to him so I’m at the top of his inbox tomorrow.

5:00 pm

Finish my homework for my weekly evening French class. I've been learning French for years now, and this weekly commitment ensures that I keep exercising the muscle.

Total time job searching today: 4 hours

Day 4

9:00 am

Walk around the neighborhood.

11:00 am

Strange recruiter screen with the big pharma company from earlier in the week. It was obvious she was reading from a script. I think I did well enough to get to the next stage, though. She said she'll “send my notes to the hiring manager, who will make the final call” and the next step would be a talent acquisition person (so who was this?) Okay...

11:30 am

Sent a note via LinkedIn to my former colleague who referred me for the big pharma role, letting him know how it went. We shared some anecdotes about how strange the interview processes and job requirements have been since the last time we were both on the job market. He's been going to bat for me on another role, and I appreciate how much of a champion he's been for me.

12:00 pm

Call with a local shop owner looking for part-time help. It went well! I love her mission. I hadn't expected the job search to take this long, so I started looking for part-time work as a way to meet some new people, sharpen my skills, and do something completely out of my comfort zone.

2:00 pm

Send in two more applications to another company. I did not have a direct referral, so I don’t expect to hear back.

2:30 pm

Internal volunteer project team call.

3:00 pm

Wrapping up my day with some PMP studying.

Total time job searching today: 3 hours

Day 5

9:00 am

Prepped for the recruiter call for the digital health partnerships role by checking out the team's website and reviewing the job description.

Got another canned rejection email from a company with a similar digital health partnerships role. I’m not surprised. I reached out to someone in my network for a referral, but he never got back to me. You need referrals in this market.

9:30 am

Great recruiter call! I leveraged Coach Erika's best questions to ask a recruiter which have been super helpful throughout this process. The best part: he mentioned that my resume was "very marketable." I was really happy to get that feedback. Maybe a breakthrough, finally?

10:00 am

Break to power wash one of the external walls of the house. We've been dealing with a minor ant infestation, and while it isn't a big problem yet, I like to nip these things in the bud.

10:30 am

PMP studying. Reviewing my practice exam and taking notes on the questions I missed.

11:00 am

Reply to one of my former colleagues who reached out asking for a connection to a company she's interested in. I believe in paying it forward and enjoy the thought of sending some positivity into the universe.

11:30 am

Lunch

12:30 pm

Prep for volunteer project team call with our external partner.

1:00 pm

Volunteer project team call. External partner expressed how thankful he is that we've been able to meet a major project milestone. I'm happy that I was able to help them turn this project around. It's been meaningful and nourishing work while I continue looking for my next full-time gig.

2:00 pm

Cleaning up project notes to send to our full project team.

3:00 pm

Wrapping up my week. Driving to pick up my race bib for the 5k run tomorrow! 🏃‍♀️

Total time job searching today: 2 hours

What I learned this week

Pursuing the PMP, while costly, has actually been helpful. It's making me review different project management frameworks so that I can be that much more confident interviewing at different companies.

What I’ll adjust for next week

I've realized that if I spend too much time on LinkedIn, it isn't productive and often puts me in a negative headspace. Staying busy with volunteering and exploring part-time work while studying for my PMP is making me feel like I am making progress. I keep having to remind myself that this is a marathon, not a sprint (like other Job Search Diarists have mentioned) and that the right opportunity is out there for me.

Tell us more

How would you describe your job search strategy? What's working? What needs adjustment? What's working: focusing on roles that speak to my super powers: organizing teams, connecting technical and operational teams for delivery, and underscoring my extensive experience across the healthcare domain.

When I was passively looking last year, I entertained leads for Technical Program Manager roles, but I got limited traction. The feedback was that I lacked the technical background, and with the market saturated with talented TPM candidates, I abandoned that pursuit.

How many hours a week do you spend on your job search? Can you break this into rough buckets? 20-25 hours a week:

• Sourcing opportunities (5 hrs)

• Interview prep (5 hrs)

• Upskilling (10 hrs)

How much of your time do you spend sharpening your skills? How do you do this? One observation I've made is that many job postings for Program Managers in tech are now asking for the PMP certification. This wasn't the case before, so I'm spending this time studying to finally get my certification. I also help run my homeowner's association and have been volunteering project management work for nonprofits in the area.

What is the best part about job searching? Getting back in touch with so many colleagues in my network. For the most part, they've been so supportive, offering to make connections and referrals. It's been great to hear what everyone's been up to personally and professionally.

What’s the worst part? Ghosting by recruiters and hiring managers. And the fact that processes are taking weeks longer than before makes you feel like you have no momentum.

What are your current favorite job search tools, and how are you using them?

• LinkedIn for job postings. (not sure I would call it my favorite; it's more a necessity)

• Perplexity AI for interview prep and first drafts for messages, cover letters, and other job search communications.

• Google Sheets for tracking my job search funnel

• Slack to engage with former colleagues of mine (ex-Alphabet)

What's one tool or service you couldn't imagine living without in this job search? Perplexity. It's helped me plan and prep for interviews by doing company research, and give me first drafts of LinkedIn connection request messages and cover letters in the job search.

What's one thing you regret spending time on while job searching? Constantly refreshing my inbox for post-interview updates and doomscrolling social media posts by career coaches and recruiter influencers. Some have been helpful, others are not.

Advice for other job seekers in tech? Have a set of people in your life to serve as your "kitchen counter Board of Directors.” These should be people who know your professional capabilities and accomplishments and can provide a sounding board for when you are feeling discouraged about your search. It's been so beneficial for me to lean on my mentors, many of whom are former managers, to remind me:

• I am capable

• I am hireable

• the right opportunity is out there for me

Anything else you would like to add? I've been taking steps to get some part-time work completely outside of my current career trajectory. Two of the things I miss about work are (1) knowing that there was inbound cash flow and (2) having some structure to my week. Part-time work feels like a low-risk way to address both.

I invite you to use the comments to share your thoughts, cheer on this job seeker, or ask a clarifying question. Please be thoughtful in any comments directed at the job seeker. I reserve the right to delete anything I deem unkind. Thank you 🙏

Leave a comment

Want to nominate a noteworthy job seeker (including yourself)? It’s anonymous!
Fill out our JOB SEARCH DIARIES form.

Check out coacherika.co for free resources, resume help, and coaching options, including my popular Job Search Workshop. Follow me on Substack, YouTube, and LinkedIn to stay in touch. 💛

Become a subscriber to get access to all 3-7 monthly posts, across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

This newsletter is an educational resource and can likely be expensed through your manager or your company's L&D budget. Here is a template I wrote for you to use when asking your manager. For subscription details, see the About page.

Subscribe now

Let’s dive in ↓

Whisper #23

What's the real challenge here?

Read more

👋 Hey, it’s 📣 Coach Erika! Here with a quick, important update. This post is a 🔒 subscriber-only edition🔒 of The Career Whispers. You’re going to see a lot more of these in the future.

Moving forward, free subscribers will get ONE free post per month, and the rest of TCW will be reserved for paid subscribers. Free subscribers still get previews for most posts, but they’ll encounter the paywall earlier in each post and more frequently (in all but one post per month).

A great deal of research, energy, and expertise goes into every post on The Career Whispers, and I hope you’ll spend the two-latte equivalent to feed your brain and upgrade your subscription.

If you do, you’ll get access to all 3-7 monthly posts, across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

Subscribe now

Now, onto the diary!

Today, we have a Bay Area PM Director who went from Big Tech to startups later in his career because of the Green Card wait game. Now, he’s looking to explore the middle ground in late-stage startups (pre-IPO and early Public).

About me: I am passionate about building products that make a difference in users’ lives. I spent the last 13+ years crafting successful products in the payments, e-commerce, marketplace, and monetization domains.

My location: Bay Area, California

Role I'm seeking: Director of Product or Senior Manager of Product (depending on the company size and role scope)

Target company stage: Public / Late-Stage / Pre-IPO

Target industry(ies): E-Commerce, Payments, FinTech

Passive or active search? Active

When I started my job search: February 2024

Number of applications so far: 20+

Number of HR or recruiter screens: 8

Number of first-round interviews: 6

Number of final-round interviews: 3

Average time spent weekly on job searching: 20-30 hours

What drove my job search: After working at a big company for 10+ years (while earning my green card), I wanted to join a product-led (PLG) pre-IPO company, and I did. In January, the company pivoted to a sales-led growth model, which didn’t align with my interests. I decided to leave and take a short break after 13+ years of continuous work.

A note: I wanted to move to a smaller company earlier in my career, but I chose to wait an insanely long time to get a green card. If I had moved companies before I got a green card, I would have had to restart the process, opening myself to unnecessary risks like the new company going out of business, laying off (which impacts filing green cards), facing unnecessary audit risks, and visa stamping uncertainty because of smaller companies.

Day 1

7:00 am

Woke up at 7 am (it’s usually the same time every weekday). Started the uphill task of getting my kids ready for school. Coffee. Breakfast. Pack Lunch. School Drop.

9:00 am

Last week, I provided my availability for a second round interview with a large e-commerce company for Sr. Manager, PM role. Today, the recruiter sent the calendar invites (Wed, Thurs, and Fri this week). Spent some time to confirm interviews, move around meetings on my calendar, and get organized for the week.

10:30 am

Some reading on Medium (for fun), The Career Whispers (for interview prep), and Lenny's post on representing business as an equation (for PM skill sharpening).

11:30 am

I've always wanted to try my hand at entrepreneurship, so decided to explore an idea that I had nursed for some time: building an iOS app for home gardeners. Decided to use OpenAI, so I got started.

12:00 pm

Lunch

12:30 pm

An expertise network reached out and wanted to invite me to share some expertise in a paid interview. Worked on scheduling that. I learned that once accepted, my profile would be available to all of their client companies to book interviews to glean from my knowledge.

1:30 pm

LinkedIn job search. My strategy: reach out to network for the roles where I have a connection; blind apply when I don’t know anyone in a target firm.

4:00 pm

Gym group workout - functional strength and isometric strength movements combined with high-energy circuit training

5:00 pm

Kids pick up, dinner, and wind down. My partner and I want to ensure we eat home-cooked meals with the kids. So a decent amount of time every evening is spent making fresh food (Italian today). We hope this will help our children make healthy choices.

9:00 pm

Handle some complaints about how the younger or older one is not sharing. Wind down with some silent me time. I reflect on the day, taking care of payments/renewals/etc, and plan for the day ahead. I note down learnings from my networking and recruiter interactions. I refer to these before key interviews.

Total time job searching today: 3.5 hrs

Day 2

7:00 am

Read more

☢️ Hey! Quick, important update.

Moving forward, free subscribers will get ONE free post per month, and the rest of TCW will be reserved for paid subscribers. Free readers will still get previews for most posts, but you’ll run into the paywall earlier in the post, and much more frequently.

A great deal of research and expertise goes into every post on The Career Whispers, and I hope you’ll spend the two-latte equivalent to feed your brain and upgrade your subscription. If you do, you’ll get access to all 3-7 monthly TCW posts, covering topics across these thoughtfully crafted career experimentation series:

• JOB SEARCH DIARIES

• THE WEEKLY WHISPER

• DEBUGGING YOUR JOB SEARCH

• MVIP (MINIMUM VIABLE INTERVIEW PREP)

• CLEVER GUERRILLA

• BONUS EDITIONS and more (see all the paid subscriber benefits here)

Subscribe now

Let’s dive in ↓

Whisper #22

Logging your learning

I have a 6 month-old baby who learns simple things at an extraordinary pace.

An example is this recent milestone: learning to pass objects from one hand to another 🫱🧸🫲

Another example was when he learned how to balance his body while seated and reaching forward to grab a toy.

Both times, my spouse and I delighted at the new competency and showered our baby with congratulations. We love celebrating every win, every new competency, and every new learning as we see it happening.

I thought to myself, “Wouldn’t it be great if we gave ourselves as much credit for learning small things?”

This thought set me out to try this new experiment: logging my small-win daily learnings.

I grabbed a white steno pad and a pen, and I started logging what I learned each day.

Some days it’s a whole 8x11 page; other days, it’s two bullets with concepts strung together with arrows, ie: IMG → MIPI → NoC→ DRAM

At the end of each week, during my weekly winddown, I review all the learning logs.

Skimming the logs reinforces the learning and commits it to memory, and it makes me feel incredible to celebrate my cognitive evolution 🎉

a low-stakes experiment for you

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A great deal of research and expertise goes into every post on The Career Whispers, and I hope you’ll spend the two-latte equivalent to feed your brain and upgrade your subscription. If you do, you’ll get access to this and all 3-7 monthly TCW posts, across these thoughtfully crafted career experimentation series:

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Let’s dive in ↓

Whisper #21

The best mental health ROI of your life: 5 steps to avoid a toxic employer.

I work with people who have been searching high and low for a new job for months, to no avail. It can be tempting to take the first offer that comes, even if you saw a red flag or two in the job description or during the interview process.

There’s a quick and easy way to get perspective from someone who’s been on the ground (and isn’t trying to actively recruit you for the company).

It takes 5 minutes to start, and less than 20 minutes total.

I promise you this will get you the kind of intel you can’t get from anyone who is currently working there.

And if you manage to discover a lurking landmine and avoid a toxic job, this will be the best mental health ROI of your life (because therapy ain’t cheap!)

a low-stakes experiment for you

1. Open LinkedIn and search for the company name

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Eep! I’m returning to work this month, after parental leave for the birth of my first child. The nerves are real. 😬

In honor of my return to the working world, this bonus post is a resource guide and a love letter to soon-to-be parents. This post features all of the conception, pregnancy, and post-partum products that, looking back, I couldn’t do without.

Not a parent or parent-to-be? No worries, this post doesn’t replace your regularly scheduled weekly tech career advice!

ps: If you’ve found your way over by some miracle but are not yet subscribed, here, let me help you with that:

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Let’s dive in!

I recently became a parent, and as any first-time parent can attest: it’s a lot 😳

• New (tiny, helpless, and in my case—colicky, 24/7 screaming 😱) person

• New lingo (pre-eclampsia, meconium, toco numbers, combo feeding)

• New ways to use your body (conception, carrying, delivery, feeding)

…and new products to (hopefully) make everything a tad bit easier.

As much as my new baby brought me joy, it was also overwhelming to learn so many new skills, all at once, with the urgency of a screaming baby. And doing it all without sleep. Or food. Or showers. (no judgment)

Adding to my overwhelm was that I prefer to buy something once and be done. I don’t love shopping, and the idea of buying a bunch of stuff, trying it out, and sending back or giving away stuff I don’t like is just so wasteful on so many levels.

I generally prefer to buy items from friends’ personal attestations and from lists I can trust. When it came to items to buy for my baby, I found ‘s post with the best and worst baby items quite helpful.

But what about me? There’s nothing in that list (or any list I could find) to help ME with conception, pregnancy, or postpartum.

Today’s post offers the list I wish I had a year ago as I started my parenting journey. It’s designed as an essentials-only, greatest hits list of items that I found helpful on my journey into parenthood. I include items from these six phases:

1. Pre-conception

2. Conception

3. Pregnancy (up to week 35ish)

4. Pre-partum and Delivery (the last 4 weeks before birth, plus the main event)

5. Postpartum (until where I am today: 5 months pp)

6. Newborn: a couple of super handy and “lifesaver” baby items I didn’t see on other lists but couldn’t imagine life without.

Let’s dive in ↓

Pre-conception

In this phase: Priming your mind to become a parent, plus giving extra nutrients for your eggs and sperm.

Vitamins

Given my “advanced maternal age,” friends told me to read the book It Starts With the Egg by Rebecca Fett. I did not read it 🙄. Instead, I skimmed Reddit and peer-reviewed papers to decide which prenatal vitamins to take (and when to start).

Emily Oster has a great post about why most vitamins are basically useless, except folic acid and iron for pregnant women and vitamin D for breastfed babies. My research led me to a similar conclusion, but my husband loves his vitamins (he claims to ti feel superhuman most days since starting this ritual).

The true benefit of pre-conception vitamins: giving us a sense of control over a process that is nowhere near as easy as we were told in middle school 🤭

For me and my husband, peace of mind was worth the cost (and the daily chore).

Item #1: Mom vitamins

I hate taking pills, so I knew I needed something easy. I started taking prenatals 4+ months before trying to conceive because egg cycles are four months long. I’m still taking them now, 5 months post-partum, even though I don’t need to. I just like the way they taste 🤤

What I take: Vita Fusion Prenatals (gummies, raspberry lemonade flavor)

Item #2: Dad vitamins

Husband started taking his vitamins 2+ months before trying to conceive because sperm cycles are ~two months long. He claims immediate, visceral health benefits—and while he’s not lifting cars to save kittens, I can attest that he has enjoyed taking all of these for the last year+.

• Multivitamin containing 20mg Zinc, Folic Acid (positively associated with fertility in men), Vitamin C 120-500mg

• CoQ10 (ubiquinol form, 100-300mg daily)

• Vitamin C gummies 120-500mg (daily recommendation from NIH)

• Vitamin E 100 IU/day

• Vitamin A 5000 IU/day

Conception

Item #3: Flo Cycle Tracking ($40ish/year)

Learn 👏 your 👏 cycle, ladies! I love this app so much that I’m always happy to pay for the Premium version and renew it every year, even when I’m not using the app daily (like right now). They have great conception content and tracking tools and even better pregnancy content. If you’re TTC (trying to conceive), get this app or one like it.

Item #4: Ovulation Test Strips (Easy@Home) ($20)

Even if you think you know your cycle. Even if you’re sure you know exactly when you ovulate. Yes, sperm can live for 5 days in the reproductive tract, but the reality is that the conception numbers are slim if you don’t make things happen on the right day. Knowing the right day instantly doubles your chance of getting pregnant.

Use the strips! It’s easy.

Data below if you need more convincing about why day-level precision matters.

Item #5: Fancy candle (Diptyque $120) and a *certain kind of* Spotify playlist

❤️🎵🕯️🔥

*BONUS* One thing we didn’t find very useful for Conception:

1. kindbody. Most doctors recommend trying for at least 6 months before getting fertility testing, and as we got closer to that timeline, we wanted to start some non-invasive testing. kindbody is a well-funded health startup that advertises helping women and men with fertility services. We had the worst experience at every step of the journey: getting appointments, billing, test results, appointment follow-ups, and generally having the sense that anyone was running the company to ensure we were getting the services we were paying for. Luckily, we got pregnant on our own during the shuffle. I hope there are better services out there, please comment if you know of one so I can recommend it to readers.

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Pregnancy

From day 0 til week 35ish

Item #6: Cheap pregnancy tests (Easy@Home) ($20)

If you’re a double-checker like me, you’ll want to test if you’re pregnant 2-3 times a day, for multiple days, to convince yourself that omg, yes, it finally happened. Go with a bulk option to avoid buying 15 boxes of individual tests at $20 each. I used the tests that came with the ovulation strips test kit, and they worked great. The $20 box comes with 20 pregnancy tests in case your OCD is full flare like mine was.

Item #7: Smallshow Ruched Dresses (Short $20; Long $35) and Layerable Loose Jumpsuits ($30)

These dresses and jumpsuits were a dream: affordable, soft, flattering, and available in many colors and patterns. I hate clothing shopping, and I love that I only had to buy one item to confirm the fit and then I could buy five in different patterns. Arrived in two days. What more could you ask for?

I wore one of the blue floral full-length dresses to a wedding and my baby shower, and it was gorgeous.

The leopard print jumpsuit is surprisingly chic (and softer than the single-color versions 🤷🏻‍♀️).

Item #8: Tall maternity underwear ($35)

Love love love these. At first, they were huge, then I humbly “grew into them.” Coverage plus comfort 👍

Item #9: Omron BP Cuff ($42)

I got very swollen for the last 10+ weeks of pregnancy, so taking my BP every day kept fears of pre-eclampsia at bay. Plus, I got it reimbursed using my FSA.

Item #10: Kizik Sneakers (~$120-$150)

My feet grew a half size in the third trimester since I was so.so.so.swollen 🐡. Reddit told me that people who stand all day (ie nurses) love these shoes, and with ~50+ extra pregnancy pounds, I was grateful for the joint relief. These offered extra cushion and support, plus no need to bend over my big belly to tie laces. 10 months later, I still love these shoes (I got the Athens, but I’ve been eyeing the Londons, too). They have become a daily driver. Word to the wise: don’t get the white ones (they won’t stay white long).

Item #11: Tums Chewy Bites ($9)

Medicinal perfection! I had so much acid reflux and indigestion. Tums Chewy Bites became a 7th food group for me. Don’t suffer with the chalky stuff! Get these instead. Husband pops them for fun because they taste like candy.

Item #12: Anti-stretch mark remedies: Hatch belly oil ($64) and Palmer’s massage cream ($14)

I used both oil and lotion because I was freaked out about getting stretch marks. Turns out I did anyway; it’s really all genetics. But it still made me feel good to know I did my best. Plus, the Hatch belly oil smells incredible and made me feel less frumpy.

Item #13: Smokeless moxibustion sticks ($20)

Baby was breech for a while, and I tried acupuncture and all the spinning babies exercises, but he stayed put. The acupuncturist recommended moxibustion, so my husband and I gave it a try (it’s a two-person sport). While we’re pretty sure the baby just flipped on his own (most babies do), we really enjoyed the forced togetherness time and meditative energy that moxibustion requires. Those moments were some of our favorites.

*BONUS* 4 things I didn’t find very useful during Pregnancy:

1. prenatal massage. Honestly I was just so busy I didn’t make time.

2. belly bands. Meh. I didn’t feel a huge lift, the velcro caught on everything, and the band made me hot and sweaty.

3. belly sleeves/jean extenders (to extend the usable time for wearing your pre-pregnancy jeans). Slipped and slid and generally felt annoying.

4. ginger chews, lemonheads, vitamin B6. Nothing calmed my nausea. It was outrageously bad, and eventually I had to take prescription medication to make it through the day. My advice: if you’re not functioning well (or vomiting more than 3x/day), tell your doctor. There are meds that will squelch the nausea⎯though be warned, they will make you extremely drowsy, as in you can’t operate a car or use an iron without potential danger to yourself or others.

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Pre-partum & Delivery

The 3-4 weeks leading up to birth.

Item #14: Chiropractor visit ($85)

I had a lot of pinching pain in my sacrum throughout my pregnancy, plus my baby was late so I read about using the Webster Technique to go into labor. One visit and I had immediate, massive relief in my sacrum pain (though I did not go into labor, sadly).

Item #15: Compression socks ($18)

I was so swollen. So, so swollen. Like a jumbo pufferfish. Compression socks were a lifesaver for my poor, swollen feet and legs. And this brand is great (and they come in cool patterns). Don’t be boring like me and go with white.

Item #16: (if breastfeeding) Correctly sized flanges for pumps ($15 each)

This was a tip from a friend who had a difficult breastfeeding journey when she used the standard flanges that come with the pump. They are not one-size, and it makes a massive difference to get the correctly sized flanges.

How to buy the right size flange:

• Buy a circle ruler

• Find the hole where your nipple slips in just right: not tight, not loose.

• Add 2mm.

• Buy the flange that matches that measurement.

• Donate the other ones so you never accidentally use them (!)

*PLUS* 2 things I didn’t find very useful during Pre-partum and Delivery:

1. acupuncture. I love alternative and Eastern medicine, but acupuncture doesn’t seem to work for me. I tried to use it for de-puffing and turning the breech baby, to no avail.

2. cute laboring gowns. I bought three really cute hospital gowns (the picture in my head of birthing was vastly different from reality). Within 15 minutes of arriving at the hospital in active labor, I had projectile vomited all over everything, multiple times. Just trust me and stick with the hospital ones. Birthing involves a lot of liquids that you don’t want to have to take home and launder 🧼

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Postpartum

Item #17: Disposable Adult Underwear ($13-$30)

Can’t tell you how amazing and comfortable these are. So wonderful. Just do it. Haters gonna hate, but you’ll have the last laugh (hopefully, without peeing yourself). I went with the classic older adult brands, but you can get these boy short versions from Frida mom if you want to be more stylish. They look like cute volleyball shorts.

Item #18: BabyGo birthing ball ($30)

I bought this ball for laboring, but it was equally useful postpartum to help soothe my colic baby to sleep. Between hubby and me, we’ve put tens of thousands of bounces on this thing with no signs of wear or distress. This particular exercise ball is from the UK and comes with a super nice book of prepartum and postpartum exercises that I also found helpful.

Item #19: Stroller Fan ($17)

Bought it for the baby, kept it for mama. Post-partum night sweats are real! We room-in (this is parent code for “he sleeps right next to me in the room”), so we keep the bedroom much warmer than I would prefer, even before you add in the postpartum hormone cliff. This stroller fan with adjustable legs and convenient USB charging is a staple on my nightstand: I point it at myself to keep cool all night while my baby is warm and cozy in the bassinet beside me.

Item #20: USB Nightstand Plug Station ($16)

Nightlight. White noise machine. Breast pump. Cell phone. Stroller fan. Baby monitor camera. Snoo bassinet. Turns out, there’s a lot that needs to be plugged in. This USB hub is simple, hearty, and non-offensive (design-wise). I think it’s the best one on the market.

Item #21: Ameda ComfortGel HydroGel Soothing Nursing Pads ($30 for 4)

If nipples went to heaven, this is what it would feel like. I tried everything else. Nipple butter, nipple cream, lanolin oil, lanolin stick, lanolin cream, silverettes. This was the only thing that soothed.

Item #22: Bamboobies Washable and Reusable Absorbent Breastfeeding Pads ($7)

A lifesaver on the one night my colic baby slept more than 4 hours and my breasts were exploding, then leaking while I was TKO. I woke up 100% dry, no mess in the bed, with fully saturated pads. What more can you ask for?

Item #23: Therapy (~$150/session) and Fair Play by Eve Rodsky (book $18, deck $18)

I had a therapist before delivery that I was working with on some non-motherhood work. Then the baby came, and so did a whole lot of new challenges, resurfaced issues, and things I didn’t even know were lurking in my subconscious. Therapy was instrumental to survival, and I never even had PPD.

Some advice if you don’t already have a therapist beforehand (because finding one is tough):

(1) check if your company offers Lyra or another mental health provider for free or discounted or even just to get a provider quickly at full cost and

(2) ask other parents you know for references to their therapists. Also, I just need to say that I have struggled with the cost of therapy for a long time, and if you can’t afford $125-$150/hr, I urge you to ask your OB/GYN or pediatrician (since they will be testing you for PPD every time you come in) if they know of any community resources. Social workers are more affordable (generally) and may be available to you from community programs.

Also: consider couple’s therapy. I haven’t done it yet, so I won’t opine on how great it is because that would be hypocritical. But I will say that there is no way to create any semblance of spousal equality in childbirth. The work will always be more on the birthing parent, end of subject.

Any non-birthing spouse who can look at a sleep-deprived mom who hasn’t eaten in 15 hours sitting in the back of a compact SUV breastfeeding a bright red, screaming 3 month old on one boob while juggling a flange and detangling baby’s arms from the tubes while pumping on the other boob and say, “I’m sure I’m doing an equal amount of work” is DELUSIONAL.

People will emotionally handle the unfairness better or worse than others. Therapy can help. So can this book: Fair Play by Eve Rodsky (book $18, deck $18). Fair Play changed our lives and finally helped me and my husband share all the old and new work in our household more evenly. Props to for bringing that book into my life 🙏

👆 Even writing that all out felt therapeutic. Amazing.

*PLUS* 6 things I did not find useful in the Postpartum phase:

1. Breastfeeding clothing. It just made me feel more frumpy than I already felt. I preferred to wear my normal clothes (the oversized stuff).

2. Silverette nipple covers. The edges pinched my breasts. I have a strong preference for hydrogels (see above Ameda product, they are fabulous).

3. Frida Mom acute postpartum care items: ice pads, peri bottle, sitz bath, sitz salts, perineal products, witch hazel foam. I fear-purchased all of these before birth, but the hospital gave me everything I needed.

4. Frida breast care items. I went overboard buying lots of stuff, fearing mastitis issues. I used none of it.

5. Postpartum shapewear / girdle. I read that many women feel their organs are floating around immediately post-partum and feel more comfortable with a girdle, but wearing a girdle exacerbated my acid reflux and made sleepless nights even more sleepless. Skip it if you have acid reflux.

6. My Brest Friend Super Deluxe Nursing Pillow. It was giving too much “I got stuck in a pool floatie” vibes. I kept getting stuck in doorways, and it didn’t markedly improve my breastfeeding skills. Once I figured out how to do reclined nursing (Day 6 postpartum), I never used this pillow again. I think it may be more helpful with twins or preemies.

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Newborn

Item #24: Changing room caddy ($13)

I have one of these felt caddies in every room of my house. I stuff it with the following:

• Diapers (I’ve used Kirkland brand and Kudos and love them both)

• Wipes (Kirkland brand or Water Wipes)

• Aquaphor Baby or Vaseline BlueSeal Baby (apply to bum crack and crevices every change, never had diaper rash again. Don’t forget the underside of the pee-pee).

• Dove hand sanitizer. Poo gets everywhere. Pumping a squirt of hand sanitizer without leaving the room gives me peace of mind that I’m not giving my baby ebola. This particular one by Dove smells divine.

Item #25: Frida Windi Gas and Colic Reliever ($12)

Our baby had issues passing gas and stool, and he would scream in pain. The Windi saved the day (and night!) on at least 20 occasions. Net promoter score through the roof on this one. Buy them in advance so you have them if you need them.

Item #26: OXO bottle brush ($9)

The Cadillac of bottle brushes. So soft, so flexible, so vertical. Easy to use, easy to clean. It’s even more magic than the standard magic we’ve all come to expect from OXO. We also adore our OXO drying rack (we bought them together here).

Item #27: Munchkin sterilizer bags ($9)

3oz water, 2 minutes in the microwave, 20 reuses, and peace of mind. No need to buy an expensive freestanding sterilizer appliance to take up more counter space. Just get the bags. You can use each one 30 times.

Item #28: Hatch sound machine + light ($60)

We bought two $20 Dreameggs, and both died within 5 months. We have a Hatch, and it works like a charm. Worth the spend, and it’s nice to have one device to do light and white noise.

Item #29: Doona stroller + car seat combo ($550)

This is the spendiest thing I’ll put on the list, but it’s been a game-changer for us. Having a stroller that turns into a car seat is magic. It makes it a breeze to go to all the doctor appointments and to lug your baby with you everywhere (since we all do, unless you hire an infant babysitter which will cost you half of a Doona real quick). It comes with all the bits and bobs you need for the baby from 4lb to 35lb, which is a nice long utilization period (longer than pretty much everything else for newborns).

Item #30: Frida baby water pourer for the bath ($10)

I looooove this water pourer for bathtime. It seems weird to be obsessed with a glorified cup, but it beats the heck out of the one that came with our baby tub. Bonus: we used it while I was in labor in the bathtub at home.

Item #31: Baby Bjorn Bouncer and Play Bar ($210 and $60)

Our kid hated it at first, but he loves it now. He’s even figured out how to self-propel the bouncer using this clever kicking mechanism that melts my heart. And it's a safe place to stash baby while you run to the bathroom or get a bite to eat. We also bought this backup play bar ($23) to keep things interesting for him.

Item #32: Lovevery play gym ($140)

We live in 950 square feet with a baby and two pets, so space is at a premium, and our baby only has a few curated toys. The Lovevery play gym has far exceeded our expectations. Baby plays in it for at least an hour daily, and he loves all the little stations. I think it’s a bit of highway robbery that they don’t include the play strands with the play gym, but if you’re into high-quality basic toys that aren’t made of plastic, this is the set for you.

+ lovevery sensory strands ($25). He uses them every day. The lovevery play gym is basically his only toy, so we decked it out.

+ A lovevery play kit subscription ($80 every 2 months). The toys are wonderfully curated and arrive just when the kid needs them for each milestone. We didn't get it, but we regret it. It’s also something that people will be so happy to buy on your registry because it’s beautiful and who doesn’t love wooden baby toys?

Item #33: Full sleeve barber-style wipe-down bib shirt ($16 each for patterned, cheaper for solid colors)

Solids are messy. Like, seriously messy. Many a onesie has been sacrificed to orange stains from carrots and winter squash. The silicone bibs with the pocket do a great job of catching the stuff that goes straight down, but the only thing that could keep our baby’s arms and neck free of runny or caked-in sweet potato mush was this bib shirt. It’s super easy to clean (wipe it down). As a bonus, they have a bunch of new patterns that are even cuter than before. I can attest that the shark one is cute. That pink leopard print is calling out to me.

Item #34: Babylist Boxes (price varies by box, but always cheaper than buying the items on your own)

Babylist makes fabulous sampler boxes (Bottles, Diapers, Pacifiers, Swaddles, Teethers, Sippy Cups, and hopefully more in the future). They are a way to try 3-5 alternatives and determine which one your baby likes before buying more. We found the box for pacifiers especially useful. I didn’t get the swaddle box or teether box because we used a Snoo bassinet which comes with its own swaddles, and we got a dozen teethers as gifts (baby loves them all). We recently got the sippy cup box, testing is in progress 😁

*PLUS* 4 things I did not find very useful in the Newborn phase:

1. Baby clothes. I have a mother and MIL who are shopaholics, so I regret purchasing any of my own baby clothes. Plus, my child was a giant, born in the 99th percentile for height and weight, so he never wore any of the cute newborn clothing I got for him.

2. All the different diaper rash creams. We tried them all. Aquaphor is the best. Don’t bother with anything else unless it gets really bad and you need a more potent active ingredient.

3. Pee-Pee Teepees (for boys). These are way too small and just don’t work at all unless your kid has a tiny weewee that outputs < 5mL of urine at a time. I’m baffled at how often this product was recommended, given that it literally never worked for us, not once.

4. Butt spatulas. Other people swore by this, but I'm not squeamish about poop or touching creams with my hands, so the spatula ended up just being one more thing to wash.

Closing thoughts

Becoming a parent has been a mix of highs and lows, with my baby’s goofy, gummy smile being the highest of highs. The items in this post helped the highs stay high and made the lows less low. I hope they will do the same for you.

Feel free to share this post with someone you know who is just starting their parenting journey, trying to conceive (TTC), or pregnant and wondering, “ok, what do I need?”

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🎉 That’s a wrap!

Note: I may earn a small commission if you purchase using the links in this post. I personally purchased and used all the products here, and no brand hired me to rep for them. My opinions are not for sale.

Fellow new moms and dads: What did I miss? Share your must-have pre-conception, conception, pregnancy, and postpartum items in the comments.

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