Life After Entrepreneurship

I sat at my computer on that very last day of December, staring blankly at the screen in an empty coffee shop somewhere off I-70. The final document had been signed; the company, sold. I was 30 years old and everything felt, from that moment forward, like Before and After.

You see, we never meant to get where we got. Or perhaps we did but, more likely, we had never fully grasped our own ability to create something that would get noticed in this world. Somehow, I found myself at the intersection of hard work and good timing, building a company with my sister and brother-in-law that would end up making its mark. We were the lucky ones, armed with just enough naïveté to keep going when the going got, well, going. We showed up everyday to build something we believed in. We owned every decision and willingly gave the proverbial man a run for his money as we went. We wore yoga pants when we felt like it and reported only to our own passions. And the crowd went wild for the underdog.

But the era leading up to that sale also looked like neon screens too late into the night, underworked snooze buttons, and always-untimely pings from Slack and Gmail signaling emergencies (and not the kind that save lives). It was ever-scurried morning departures and a black hole of coffee mugs in a desk drawer that never made their way back home. It was forgetting birthdays and the I-can’t-tonights that tried the ones I love most. It was a full-bore, everywhere-scheduled, the world-on-my-shoulders kind of grit. For a moment, I felt I understood all of those new moms in the world — the ones who had found their lives expanded with unimaginable gratitude yet still couldn’t find a fix for the worries that stole the night or make room for self-care.

I would, between meetings and conference calls, imagine a future day when I’d go into a yoga class without worrying about the texts waiting on the other end of that hour, when no one would need me. I began to miss the parts of myself that I once knew — the girl who once entertained the idea of being a park ranger or of living in the mountains or on a farm or alongside a river, the girl who sought simplicity in the stars and longed to feel small against the sky. On the trying days, I’d question why the writer in me traded in the quiet of the pen for an executive’s role with projects to plan, calendars to mind, and not a second to spare. And I’d miss, for her, the wild-and-free backpacking trips of one’s twenties that so many others had known. Truth is, when I looked in the mirror I saw a woman who had become more than she ever imagined she could, but still less than she dreamt she might. I pictured setting her free, like the fireflies we’d catch in jars as kids and let go, their wings shining deep into the summer’s night.

So when I decided to leave, 20 months after the sale, I wore my choice with more bravery and intention than most decisions that had come before. Up to now, I had carefully leapt from opportunity to opportunity — always putting a generous Type-A bridge ahead of my next move. You know how it goes: the playing it safe, marching in sync with the lockstep, the internship in college that would lead to the job following graduation that would lead to a career that would become your life — only to wake up one day and realize you’re 65 and have never looked up. At every turn, I’ve had an insurance plan set and a ladder in place, ready for the reaching.

But this decision was different, a voluntary departure from safe bets and that ever-so-American sense of obligation. I could stay put, and watch my 32-year-old self turn 33 and then 34 and then — all behind the same computer at the same desk. I could deny myself what felt like a singular shot at cashing life’s check to see the world as newlyweds and drink coffee slowly from front porches.

Or I could go.

And so, with bags packed and hearts full, my husband and I left our respectable careers and the financial certainty that went with those jobs and took on the world. We ripped off the rearview mirror of regret to reclaim part of what was lost in our twenties, knowing full well we would return to new careers and someday soon start a family — all of which would create a new kind of Before and After. This was our moment to set the firefly free.

It was an era far different from the rest — a homecoming to ourselves, to myself. We wandered through the days in foreign lands, not so preoccupied by phones and clocks and lists and futures. We were more human being, less human doing. We read books and savored breakfasts and watched the sun fall below far-off horizons — each a panacea for my entrepreneurial hangover. We restored that sacred commitment to our health, both in body and in spirit. I made room for people — connecting with family and friends in conversations that turned minutes into hours. I listened more and talked less. And somehow, slowly and then all at once, I realized it was never about getting somewhere. It wasn’t about chasing daylight or making good on an itinerary or a resume or LinkedIn profile. It was much simpler than that — yet somehow impossibly more difficult to learn. That chapter was an invitation to pay attention. To find more in less and understanding in the untamed.

It does not pass me by to recognize just how lucky I was and am to have been handed a ticket that afforded choice — the choice to get on that plane and leave behind my best out-of-office reply yet. Still, I cannot let it escape me that these choices — the ones that hold the lives we’ll never lead — are everywhere…and they dress in disguise. They are the Before and Afters tangled up in the minutiae of our everyday. They obscure themselves as busyness and promotions, as guilt and obligation, as material and dinner-table success.

We can choose the buried but not forgotten path. Or we can let ourselves be taken by the current.