The Entrepreneur & The Small Town Kid

Reflections on how to build a life that doesn't require hitting the escape button

It’s hard to write here when I feel like I have nothing going on. But maybe that’s exactly what I should write about. The nothingness. And honestly, my gratitude for it.

I’m in a small coastal town on the Nicoya Peninsula in Costa Rica, sitting on a little daybed on the veranda at my Airbnb. It’s pouring, and I’m reveling in the sound of the rain. In a week or so, I’ll leave this town to adventure across the country in a tiny 4x4 by myself.

This morning started slow. I woke up without an alarm, straightened up, and went for a 3.5-mile run on the beach. I got my shoes soaked as high tide pinned me against a wall of palm trees. A good reminder to just ditch the shoes and run barefoot. That little running window ended up being the only bit of sun today, so I’m glad I timed it right. Then I showered and walked down a muddy dirt road to the local coffee spot barefoot—my shoes were stolen off the beach yesterday. Just a few sips into the first caffeine I’ve had since getting here two weeks ago, the skies unleashed an old-fashioned downpour. After waiting it out for an hour or so, I braved the walk home in the rain.

Since then, I’ve been sitting here. At this little home. Thinking about life and what I really want in this next chapter.

It’s taken me a while to settle into the day-to-day down here—my digestive tract outright rejected it for the first few days, and there isn’t consistent water or Wi-Fi like I’m used to. I learned I’m mega allergic to bees, and I developed a stye in my right eye. These huge thunderstorms keep rolling in and waking me up at night. And the surf? A bit too choppy and dangerous to learn on. This trip hasn’t lived up to the expectations I had about what it would look or feel like.

And yet, it’s exactly the reset my soul’s been craving.

It’s absolutely beautiful here. The jungle quite literally touches the sea. The sunsets are to die for. I take long walks on the beach without my phone and just listen to the waves as I think about life. It’s something of a movie.

post-sunset on my first night here

Costa Rica’s famous tagline is pura vida. I always thought it translated directly to “pure life,” but it actually means something more like “simple life.” Fitting, maybe even poetic, that this is the place that’s been calling me for the past year.

A year. That’s how long I’ve been imagining this state of “nothingness.” Where Slack and email aren’t blowing up, and I can actually hear the sound of my own thoughts. It’s been a year since I finally admitted I needed to walk away from “everything.” For me, “everything” really just meant building companies and chasing big dreams with my friends. And quite possibly, leaving Los Angeles for good.

I didn’t know who I was or what I wanted.

Well, that’s a lie. I did know. It just didn’t look anything like the path I was on—and I had no idea how to get myself onto an alternate path. One that existed only as a kind of sober fantasy: where I felt calm in my body, more connected to nature, and like everything I was creating was coming from my soul, not my head.

I moved to LA because when I was growing up, I’d say I wanted to live in California, and adults around me would say, “Damn, I always wish I tried that.” I didn’t want to be middle-aged, living with that kind of regret.

Lately, I’ve been talking to a lot of people about their “secret dreams.” You know—the stuff you’re not supposed to bring up at the office.

It seems like most people I know have some version of the same secret dream. They want to live the “simple life.” Really, that often means buying a small plot of land and building a regenerative farm. Or convincing their childhood friends to move into the same neighborhood. Or opening a coffee shop in their hometown.

It’s funny that so many of us fantasize about essentially going back to life before we had infinite options. I see nomads and locals down here surfing in the middle of the day, talking about moving their families here, and I think—Oh, them too. Is this just what your 30s is? Are we all trying to heal the bad parts and amplify the good parts of our childhoods?

We all know: the internet is one of the coolest inventions ever. Phones have made traveling to remote places like this easier than ever. And yet, I find myself nostalgic for the simplicity of my childhood. I miss being bored and having to make up stuff to do. I miss calling my best friend’s landline and asking her mom if she could come over. I miss being unreachable. I miss making mixtapes.

It’s easy to romanticize the past. But when I was living in my small New Hampshire town, I wanted nothing more than to get out. I dreamed of big cities—first NYC, then LA. I imagined boardrooms and always thought I’d learn to surf once I got out West.

I remember hearing as a kid that 70% of people live their lives within 100 miles of where they grew up. I thought, fuck, I do not want to end up here.

So yeah, I’ve spent the last 20 years silently judging anyone who chooses to live in small-town New England. Which means I’ve spent 20 years judging my parents, my extended family, and many of my friends. Shit.

I just never understood why anyone would live in a place that’s gray and cold for half the year. And my mom always seemed happier on vacation—at Sanibel Island or on trips to the city. I was happier, too.

But now I see: it’s not the place, it’s the pace. You can be calmer in NYC than in rural New Hampshire, depending on the length of your to-do list and the level of your anxiety. And the reverse is also true.

So the real question is: how do you build a life you don’t need to escape—to small-town Costa Rica—from?

When I finally moved away from home, I became disenchanted with the whole vibe of where I grew up. I often told people I was from Boston (to avoid “Is that the upside-down Vermont?” or “Have you ever farmed before?”).

It’s not that New Englanders are a monolith, but when everyone’s wearing Polo shirts and Sperrys, it can start to feel that way. (Not gonna lie—I wore the uniform, too.)

When I moved from NYC to LA, my whole intention was basically: Might as well try it. I got a job over Skype (yeah, Skype), and things clicked from there.

Leaving LA this year feels similar. I’m on an open-ended quest. I don’t know what I’m doing or where I’m going. I just turned 33. So it’s different than moving across the country with $1,500, no job, and a pile of student loans. But also… it’s really not that different.

When I left home, I was trying to become someone new. On that road trip west, I decided I wouldn’t drink anymore. I told new friends in LA, “I don’t drink,” and I stuck to it. And on our first night in a shitty AirBnb in Los Feliz, I posted a cringy coming out post on Facebook. I wanted to start fresh—with no secrets.

Looking back, I can see I needed 3,000 miles of space to feel safe enough to do that.

I was running from home just as much as I was running toward something new. I wanted to see a sunset over the Pacific—but also, I didn’t want to wear Sperrys anymore.

I don’t know what I’m trying to leave behind this time. Or what I’m trying to find. Hindsight only knows.

But I can tell the urge is familiar, similiar even. I want to know who I am outside the friendships and identities I accumulated in LA. I want to experience myself in different environments and see what comes up. I still love my Vans. And I don’t feel the need to make big declarations about how I’ve changed (except, ofc, for this entire essay and Substack).

The only truth I can name right now is this: there are two energies in me that have been waging war for a decade. The hard-charging Entrepreneur who wants to change the world—and the barefoot Small Town Kid (STK) who just wants to run around with her friends.

The Entrepreneur has won every decision, every battle. I think I even tried to exterminate the Small Town Kid. But looking back, that left me feeling trapped, burnt out, and unfulfilled.

STK wants to rest. Surf. Write poems. Weep when people die and not be too busy to notice. She wants to prioritize what matters and not obsess over the world’s problems.

It would be naive to think the Entrepreneur will just step aside for the next decade while STK runs the show. That’s the fantasy.

Our path is integration. I want to be a whole person—one who isn’t at war with herself. And for that to happen, STK needs to lead for a while. So that sometime soon, we can all sit around a table in my mind and make some decisions about what comes next… together.

It’s taken me a year to get here. To this moment, alone, writing without checking Slack. The Entrepreneur is quiet enough for me to hear STK beg to jump in the ocean.

My work contract ends in a week and a half. I’m finally unhooking. But I’d be lying if I said I know what comes next.

I don’t know what “becoming whole” means. It might just be a story I’m telling myself.

But I was drawn to this coastal town by a suspicion that some essential parts of me were wildly underdeveloped. And if I ever wanted to feel whole, I’d need to dig deep and grow those parts.

Most days, I just feel a little crazy and a little lost. I’m writing this to make sense of some of it. Especially with everything going on in LA and in the world—it feels trivial to be sitting here writing this to you.

So yes, as romantic as this may seem when I write it down, I still spend too much time watching YouTube, reading the news, and dreaming up a retreat center I may never start.

This work is messy. It’s not clean-cut. There’s no formula. I’m not severing old habits or making big declarations for someday. I’m not trying to exile the Entrepreneur and run to the jungle. I’m trying to carry all of me forward—including that scared twenty-something who left home in the first place.

Slowing down has made more room for the energies of the world in my heart and my spirit. And it’s hard out there right now. I’ve spent a lot of time in weeping and prayer.

I feel selfish. Guilty. And all kinds of things about “dipping out of society” to reset. I’ll get into that another time. But I also know, deep down, I’m right where I’m meant to be. I gotta do this. And I carry with me what a privilege it is to sit here, pause, and reflect like this.

So I’ll leave you with that.

Because no words feel truer right now.

I hope, wherever you’re reading this from, that you’re feeling safe, healthy, and loved. And that you, too, are finding some space to feel whatever is coming up as you scroll through lifetimes of confusing, heartbreaking, and sometimes beautiful information in the span of 30 seconds. All while somehow keeping life moving and loving the people in the small circle right around you.

Love,
Kate