The In-Between"-- Lessons from My 1.5-Year Sabbatical After Google
What I learned about career pauses, self-worth, shrimp breeding, and landing the next big role in a tough tech market
After leaving Google at the end of 2023—with over a decade at the company and as part of the broader restructuring of our Google Health moonshot—I wasn’t planning on taking a year and a half off between executive roles. But here we are.
If you’re in between roles, considering a break, or just wondering how senior tech folks navigate uncertain chapters—this one’s for you.
1. Don’t treat the job search like a full-time job
Unless you enjoy feeling miserable and unproductive, don’t make finding your next gig your whole identity. Especially if you’re targeting senior roles, the timeline is going to be longer than you want—and you can’t force it.
The market is slower, more cautious, and flooded with talent. Sending out résumés every day like it’s a numbers game will wear you down.
This is counterintuitive for many of us. We’re used to always being employed, always in motion, sometimes getting poached before we even realize we’re looking. Being out in the wilderness—with no micro-kitchens, no recruiter pings, and a lot of loops that go deep but end up being the #2 choice —is a new experience for many of us.
The truth is, even candidates with rock-star résumés are taking 6–12 months to land the right role. I’ve seen this firsthand and in my executive coaching practice. There’s a lot of top 1% talent available, but not a lot of available roles. It’s a bit like the Bay Area housing market—tight inventory and long timelines. Trust me, my wife is a realtor.
2. Make the most of your free time
Once I accepted my new role, I found myself scrambling to squeeze in all the bucket list items I’d put off. Luckily, I didn’t wait to start living.
During my sabbatical, I:
Made 30+ angel and public equity investments (including into OpenAI, Anthropic, Perplexity, Anduril, Nuscale, and a bunch of early stage gambles)
Took five classes (psychology, interpersonal dynamics, Python, AI RAG systems, and stand-up comedy)
Wrote a short biography about my mom’s life during WWII in China
Worked on two presidential campaigns—including the only elected Democrat to challenge Biden in 2024 and on Harris’ data team in Pennsylvania
Designed a board game (currently in pre-production playtesting)
Advocated for Ranked Choice Voting at public meetings in Santa Clara County
Ran two 5Ks (my first since the 1980s) and am now training for the SF Marathon 5K
Dropped my triglycerides from 425 to 85
Started breeding neocaridina shrimp (yes, really)
Did consulting work for a Series A startup, a Fortune 500 pharma company, and a private equity firm
Coached over a dozen executive and career coaching clients
Taught courses on Maven and guest lectured at Stanford, Berkeley, and Babson
Wrote over 50 Fireside PM Substack posts (usually video guest interviews)
Took four solo backcountry backpacking trips—two in Yosemite
Learned high-heat Cantonese cooking with a carbon steel wok and an outdoor high-output burner
Rode an ebike 50 miles through the Grand Tetons
Did whitewater rafting for the first time
There’s no blueprint for this kind of time off. But I tried to lean into curiosity, service, and health. You don’t get this kind of freedom very often—use it! Think of it as another opportunity to be in college :-)
3. Avoid the front door
I didn’t land my next role by applying to a job posting. I reached out to companies I genuinely admired—some of which didn’t even have a VP-level or CPO role open. Cold emails, warm intros, and candid conversations got the ball rolling.
Weirdly, once one opportunity starts to get traction, others tend to appear too. Like dating, there’s an energy shift.
That said, I’m not against applying through the front door. One of my best friends landed a VP role at Amazon because his wife submitted an application on his behalf via the careers page 15 years ago. But with so many resumes flooding in—thanks to layoffs and AI-assisted job applications—the process has become more of a crapshoot than a meritocracy.
I had two instances where I applied via a careers site, heard nothing or got an instant email rejection, only to be contacted weeks later by a recruiter who thought I’d be “perfect” for the same role and were wondering if I’d consider their company. When I mentioned I had already applied, they just waved it off and said “let’s schedule you for a loop.” The signal gets lost in the noise.
4. Prepare, but don’t turn into a robot
When you’re interviewing for senior roles, execs aren’t looking for someone who can regurgitate a five-point framework or deliver a perfect STAR story. They want to know: Can I trust this person to solve hard problems with good judgment?
Earlier this year, I had a third conversation with a hiring manager and decided to go full framework mode—framing the problem, validating assumptions, methodically checking boxes. It was like I was taking a driving test at the DMV. He clearly just wanted to riff and explore ideas conversationally. It didn’t land well.
Later interviews where I took a more relaxed, collaborative approach—treating them like jam sessions instead of case studies—were far more enjoyable. And those convos led to offers.
Still, preparation matters. Research the company, the product, and the market. Be insightful. Say at least one thing the interviewer hasn’t heard before. And have great stories that showcase your range, your impact, and your values.
5. Know your worth
Yes, it’s an employer’s market—but that doesn’t mean you can’t negotiate. I researched comp trends, talked to friends, modeled out equity scenarios, and when the time came, I countered thoughtfully.
Having a credible Plan B helped me negotiate from a position of strength. It made a difference.
You want to feel good about your comp after the adrenaline wears off and you’re three weeks into your onboarding sprint.
That said, you also need to strike the right tone. Be fair, be informed, and recognize that while you may be their top choice, they likely have strong backups. At some point, the team needs to get back to work—and they want someone who’s ready to partner, not someone dragging things out over a few more bucks.
This sabbatical wasn’t always comfortable. But I wouldn’t trade it.
It helped me reset, grow, and show up stronger for what’s next.
If you’re going through your own in-between chapter, don’t waste it. Design it.
OK. Enough pontificating. Let’s get back to work.
Wow - that's a long list of fun and inspiring sabbatical accomplishments! One of your early posts helped me flip the script and I've been striving to thrive regardless of employment status. I too have been leaning into curiosity, service, health, and getting together with people. It has been good for the soul. Thanks for sharing Tom!
Thanks for sharing! Particularly loved the “avoid the front door” point