Nobody Warns You About the Second Half of a Sabbatical

The first half is Paris. The second half is a question you can’t buy your way out of.

A sabbatical is supposed to be a reward. That’s a myth. Mine came after fifteen years without a real break, a recently sold company under my belt, and a stretch of time that was finally mine. Four to six months, I figured. It was now fourteen. What began as “rest” had quietly become a job search I could not end. I’d convinced myself the call that afternoon would finally break the limbo.

My phone buzzed. It was the executive recruiter for the CEO role I’d spent weeks interviewing for. I was certain it was good news. I’d nailed the final pitch. A managing partner had reached out afterward to thank me for an excellent presentation. It was my first time experiencing that much enthusiasm after an interview. I was confident this job was mine.

Then she started talking. “You know, Nathalie, they loved you,” she said. So much so that they wanted to bring me on as a consultant. But they didn’t think I was right for the top job. They wanted someone who was “more of a CEO.” I still don’t quite know what that means. Perhaps they were looking for a man named Pierce with an impressive collection of Patagonia vests.

I don’t recall what I said in response. Something gracious. I’m good at gracious.

I had just sold a company. As the CEO, I turned it around in twenty-three months, with a baby, in a pandemic. And a woman I’d never met in person was explaining, kindly, that I wasn’t quite CEO material.

This was supposed to be the part where the sabbatical “recharge” paid off. That’s the story we tell ourselves about a break. You take a gorgeous sabbatical in Bali. You earn it, you step away, you come back restored. I was ready to come back and I was being told that I wasn’t good enough.

I took the break because I couldn’t take another job without taking a beat. I wasn’t just tired. I was spent in a way vacation doesn’t fix.

And, I had no idea what I wanted to do next.

That was the part that scared me. I’d taken over an early-stage company and, in two years, reshaped it into something someone wanted to buy. It taught me a dangerous thing: you can become almost anything you want. It sounds like freedom, but it’s really a blank page. When every option is open, no one hands you the next one. I’d have to write my own damn JD. There was no ladder left to climb, no title to hide behind.

I figured the challenge of taking a break would be slowing down. Sitting still. Not checking the inbox. I got good at all of that. I even did the glamour part too. Three months in Europe. (Side note: no one needs three months of pure vacation. Ever. Vacation works because it ends. By month three, the magic does too.)

(The Instagram version of my sabbatical in Paris)

The unraveling started small. When I got back from the Instagram version of my sabbatical, I had to plot what to do with my life. I treated my job search like a J.Crew catalog. Flip the pages, see what’s in season. This Business Development role. That founder-in-residence thing.

First page of the catalog: the handful of recruiters who had reached out before I left. Let’s talk after Labor Day, I’d told them. Crickets. Now I was chasing them.

So I did what every good MBA is taught to do. I built a spreadsheet. Every executive recruiter I should know. Every headhunter. The private equity contacts. Categorized, prioritized, worked in between the hours of 9:30 and 3, because as a parent you never truly take a full sabbatical, and I was still doing preschool pickup.

I worked it. Every call, every coffee. The advice from these calls was always the same. Keep talking to people. Keep putting yourself out there.

So I kept talking. I took on consulting work while I figured it out. It was the fitting room to my J.Crew catalog. I’d try a role or two on for a few months, check the mirror, hand it back. Twelve months into my career break, I’d tried on plenty and bought nothing.

I was getting closer to what I wanted: one meaty role I could throw my weight behind. The interviews for the big jobs started rolling in. Nine full processes. Some were CEO roles. Some were senior seats at prominent tech companies. Some I was overqualified for. Twenty hours of prep for each final presentation. Sixteen conversations deep before every no.

You already know how one of them ended. The nailed pitch, the thank-you email, the afternoon call. “More of a CEO.”

While I was failing to figure out my career, someone I love got seriously ill. The kind of illness you have to put your life on hold for. Forty doctor’s appointments in eight weeks. My lowest week was right before the holidays. Caretaking all day, preparing final presentations until 3 a.m., and then three no’s in one week. Boom, boom, boom.

Somewhere in those weeks, figuring out my career became a luxury. The career crisis stayed open. There was just a more urgent one I was fighting now.

That was the week the regret showed up. “Showed up” is probably a misnomer, since the regret had been lurking there all along for years, apparently waiting for my defenses to subside before it pounced.

Maybe I should have stayed at Google. Maybe I should have taken one of the FAANG offers and never gotten off the ladder to become an early stage co-founder/CEO. The ladder feeds you; it doesn’t ask you to go catch your own dinner.

On the ladder, this year would have looked different. Platinum insurance. A leave of absence, a job waiting for me at the end of it. But I wasn’t on the ladder. There was no safety net underneath any of it. Just me.

Instead I was doing all three at once: getting someone I love the care they needed, watching the medical bills pile up with no paycheck coming in, and pretending the question could wait.

The question being the one I’d taken this entire break to answer: what did I actually want to do with my life? Somewhere in there I started working with a coach again. I was stuck. Help me find the next job, I told him. That was the assignment. So we worked on the practical. We built a system for the pipeline. And then one day he said: I get the sense that following your spreadsheet of people to talk to isn’t going to get you any more clarity. He was right. It wasn’t like ten or fifteen more conversations would get me closer. The spreadsheet could organize the search. It couldn’t tell me what I was searching for. Even the person I was paying for answers was telling me there wasn’t one for sale.

I later came across research that helped me understand what those months of aimless searching and heavy rejection cost me. In 2016, neuroscientists at UCL had volunteers play a game where turning over the wrong rock earned them an electric shock. A 50 percent chance of a shock stressed people more than a 100 percent certainty of one. They could see it in cortisol, in pupils, in sweat. Not knowing was worse than the bad news. The brain would rather have a bad answer than an open question. I was doing the same math with my career. Nine full processes. Sixteen conversations deep before every no. I wasn’t holding out for the best rock. I was grabbing the nearest one so I could avoid the pain.

If uncertainty itself was the injury, any answer, job or no job, would have felt like relief. I wasn’t only interviewing for jobs. I was trying to buy an ending to the not-knowing. Every rejection handed the question back to me. “What do you really want to do, Nathalie?”

Everyone else had an answer for it. People kept telling me I was being redirected. I told them to cut the psychobabble bullshit. I wasn’t being redirected. I was a woman with all the receipts, standing in my living room, being told she wasn’t quite a CEO. Companies founded by women raise about 2 percent of venture dollars. Most venture-backed startups never reach an exit. I’d done both. I’d already cleared a bar most CEOs never even touch. The term “redirected” was one of my son’s flimsy plastic Spider-Man band-aids, slapped over a wound that was oozing.

I’d been living in waiting rooms for weeks by then. Nobody in a doctor’s office thinks they can rush the results. You sit, you wait, you find out when you find out. I’d do that all day. Then I’d go home and run the same search, asking the same people, expecting a different answer. Then I’d spend my nights refusing to learn the same lesson about my own life and career.

It took me too long to hear what the waiting rooms and the no’s were saying in unison. Nobody was going to hand me the answer on this one. Not a recruiter, not a coach, not a spreadsheet with perfect conditional formatting. The question was mine. The answer had to be too. I just wasn’t ready to sit with it yet.

I was tapped out, done fighting it. A career break long past any luster, overflowing with anxiety and regret. Months later, a shaman said the same four words every kind person had been saying to me. “You are being redirected.”

And that time, they landed.

I never did find a rock with the answer written under it. I just, eventually, stopped needing one. The not-knowing didn’t vanish. I’d just stopped treating it like an emergency. The spreadsheet is still in a folder somewhere. I don’t open it anymore.

How I got there is more than one letter can hold. That part is coming next week.

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The Practice

The certainty audit. For one week, catch yourself every time you try to buy an answer. Mine looked like this: the job board scroll at 11 p.m. One more advice call. One more assessment that would finally tell me who I was. Don’t stop doing any of it. Just write down, each time, the question you were actually trying to answer. Then read the list at the end of the week.

The Shelf

Dark Night of the Soul, John of the Cross, the Mirabai Starr translation. I’ll be straight with you: this book is a hard read. A 16th-century Spanish mystic was not writing to hold your attention, and the prose fought me most of the way. Read it anyway if you’re in the worst stretch of your life. It’s the only accurate description I’ve found of what that period actually is. Not punishment. The part where the old instruments stop working on purpose.

The Invitation

What’s the question you keep trying to buy your way out of answering? The one behind the job boards, the advice calls, the assessments. Name it in the comments or hit reply. I read every one.

Made it this far?
Tap the ❤️ so I know it landed.
And forward this to someone who’s in their dark night of the soul.

Nathalie