The Safe Job Was the Dangerous One

I had four FAANG offers. I took the one with four months of runway.

In 2020, I was working at Airbnb. The world was falling apart. I had just had a baby. And the thing I couldn’t admit out loud, even to myself at 2AM with a newborn in my arms, was that changing companies had not saved me.

I had joined Airbnb because I love to travel. I thought working at a travel company would give me more of it, that the job itself would fill the part of me that came alive on a plane, in a new city, ordering something I couldn’t pronounce. The logic felt airtight. Go where the energy is. Work where your curiosity already lives.

I took one business trip the entire year I was there.

Here’s what I’d like to tell the 34-year-old woman who leaves a corporate job because she loves the idea of travel and thinks working at a travel company will give her more of it: just make more money and go on your own vacation. Working at Airbnb does not mean you get to travel. It means you get to sit in Zoom meetings about travel, from your kitchen table, in a city where your gym is closed.

Three months before I joined Airbnb, a voice in the desert had told me I’d be the CEO of a wellness company by the time I was 40. I thought leaving Google for Airbnb was the leap. It wasn’t. It was trading one cage for a slightly different-shaped cage.

Here’s what the voice kept saying, even when I tried not to listen:

There has to be more.

I started doing the thing the restless woman always does before she actually leaps. I looked sideways. I followed early-stage wellness companies on LinkedIn. I read founder interviews. I told myself I was “getting inspired.” I was actually auditioning for a different life.

One of the companies I found was called Expectful. A small wellness brand in the maternal space. They had an opening for a Head of Business Development. There was zero chance I was going to leave my Airbnb salary and RSUs for a pre-seed role. I live in San Francisco. I had a nanny. A baby. The math didn’t math.

But I reached out anyway, because the voice was loud, and I pitched myself to the founder sideways: I can’t take the full-time role. But let me be a BD advisor. A few hours a week. I’m good at what I do. I’ll deliver what you need.

He said yes.

In my first few weeks, I helped him close a major deal. And then the founder called me and said something I was not prepared for:

I think you’d be a great CEO of this company. Would you come on as a CEO?

Reader, I was holding an infant when he said this.

Here’s the part that makes the story complicated and honest.

At the same time I was moonlighting at Expectful, I was also interviewing at every FAANG company you can name. My cage-brain was hedging. If the voice was wrong about entrepreneurship, I wanted an escape hatch. I ended up with four very senior offers in Product Management, a leap from where I currently stood. Each one promising slightly more scope, slightly more comp, slightly more autonomy. Each one was the next rung on a ladder I was no longer sure I wanted to keep climbing.

And then there was Expectful. Pre-seed. Months of runway. A title that sounded impressive and a bank account that did not.

This was the hardest decision of my life.

I could not sleep. Yes, I had an infant, and people kept assuming that was why. It wasn’t. I was awake because the voice was getting louder, and the voice was excited about Expectful in a way I could not rationally explain, and turning it down was starting to feel sinister - like a betrayal of something I couldn’t yet name.

So I did what I always do. I went to my mentors.

I want to tell you something about mentors, because I think it’s the most important thing I’ve learned about making big decisions, and almost nobody says it out loud:

Mentors can tell you how they’d make your decision. They cannot tell you how to make yours.

Some of mine said stay. Some said leap. The split was roughly fifty-fifty, which is exactly what happens when a decision is actually yours. If the answer were obvious, the smart people around you would converge. They didn’t. Because the answer wasn’t in them. It was in me.

Do not outsource your inner compass. You lose your power every time you do.

The thing that finally broke the tie was a podcast.

I was listening to Guy Raz on How I Built This, and he was telling the story of Jim Koch, the founder of Sam Adams. Koch had been at Boston Consulting Group, making a fortune, on the exact trajectory smart people tell you to stay on. And when he finally left, he said something that rewired me on the spot:

Staying at BCG was dangerous, but not scary. The danger was continuing to do something that didn’t make me happy, and getting to sixty-five and looking back and going, “Oh my God, I wasted my life.”

Guy Raz’s distillation of it: Failing is scary. Wasting your life is dangerous.

I pulled over to write it down.

I had been conflating “risky” and “dangerous” my entire career. The four FAANG offers were safe. They were also, for me specifically, dangerous. Because I knew, with the kind of knowing you cannot un-know, that taking one of them would cost me something I couldn’t get back.

The pre-seed role was scary. It was not dangerous.

Once I could tell the difference, the decision made itself.

I joined Expectful.

I raised $4.2 million in my first 90 days. I came in, grew the business. We sold the company 23 months later.

I’m not telling you that to brag. I’m telling you because the receipts matter. Somewhere in this newsletter’s audience is a woman who is about to turn down the “safe” role, and she needs to know that the woman on the other end of her decision is still here. Still doing the work. Still packed a kindergartner’s lunch this morning.

The voice was right. The voice is almost always right.

The work is learning to hear the difference between the voice and the cage-brain that mimics it. The cage-brain says: stay, this is practical, what about the RSUs. The voice says: this is dangerous, and you know it, and you’ve known it for months.

Listen to the voice. She’s not asking you to be reckless. She’s asking you to stop being quietly dangerous to yourself.

The Practice

Try this week: The Risky vs. Dangerous Inventory

Take out a piece of paper. Make two columns.

Column A: What would be scary to change about my life right now? (Leaving the job. Ending the relationship. Starting the thing. Saying the true thing out loud.)

Column B: What is dangerous about my life right now if nothing changes? (The version of me at 65 who stayed. What did she become? What did she lose?)

Most of us have never actually written down Column B. We let it live as a vague dread. Put it on paper. Read both columns side by side.

The scary things are almost always smaller than the dangerous things. They just feel bigger because they’re closer.

The Shelf

Things I’m sitting with this week:

Listen: How I Built This with Guy Raz. Any episode, but the back catalog on founders who left “good jobs” is where the risky-vs-dangerous frame lives.

Read: The Artist’s Way by Julia Cameron. I know. Every spiritually-inclined woman has read it. Read it again. The Morning Pages practice is where the voice gets louder.

Use: A mentor audit. Write down the five people you ask for advice. For each one, ask: Is this person giving me their truth, or telling me what they would do? The difference is everything.

The Invitation

What’s the scary thing you’re avoiding because it feels risky?

And what’s the dangerous thing you’re choosing, every day, because it feels safe?

Hit reply and tell me. I read every one.

Onwards.

With warmth,

Nathalie