The Grief of a Thousand Lives

the curse of the full-time traveler

I’m living in my own version of The Midnight Library, and it makes me sad. I’m grieving.

Have you read it? Matt Haig’s novel follows Nora, a woman who finds herself in a magical library where she gets to try on the lives she could have lived. In one, she’s running a British pub with her ex-fiancé. In another, she’s a rockstar playing to crowds in São Paulo. Next, she’s an Olympic swimmer, traveling the world, powered by her athleticism.

But every “could’ve been” is laced with its own griefs: infidelity, addiction, death. The point is clear: no life is free from pain. Each version carries both roses and thorns.

Right now, I’m writing this from a church/coffee-shop in Cape Town, South Africa. And as I sip my iced matcha and eat a sugar-bomb of a cookie, staring at the ornate, stained glass windows, I feel the weight of that truth. What chapter comes next in my Midnight Library?

Five years ago, I walked away from corporate America. I booked a one-way ticket to Sydney and started my own version of Eat, Pray, Love. I partied with Australians. Did key bumps in beach bar bathrooms. Headed to Bali for yoga teacher training, where I realized how tense and rigid I’d become after six years in sales. From there, I bounced all over Europe: Germany, Spain, Portugal, Croatia. London became a regular stop in the rotation. I was living my dream of being a full-time traveler.

I did stints in Argentina, Colombia, Peru, and Mexico. I spent weeks in a coastal Albanian town to decompress, isolated in an attempt to recalibrate. Bucharest was supposed to be a two-week trip. I stayed two months. I fell in love with Copenhagen at Christmas and dreamed of a life there; fireplaces, soft lighting, a Danish husband named Lars, and lots of hygge.

I fantasized about a minimalist, Greek island home near rocky beaches. Waking up to saltwater swims. Starting slow. Moving through days with intention and reverence.

Other times, the dream took the shape of a New York life. I’d be buzzing around in Ubers, fielding calls with clients, giving interviews on top podcasts, ordering a black coffee with a slicked-back, high ponytail that said: don’t fuck with me. I imagined building an empire… maybe even creating the next Call Her Daddy or Diary of a CEO.

But then I remember the pressure. The grind. The debilitating hustle. Constantly needing to outperform yourself, to keep brands, networks, and algorithms happy. I’d tasted that cycle of hustle, win, repeat. Classic capitalism: produce more, scale into outerspace, stay relevant or disappear, bitch. There’s no space for mystery, no patience for slowness. I don’t want it.

Or maybe I do. I’m not sure.

When I picture my ideal life, it involves sun, saltwater, and stillness… somewhere far from the rat race and the hedonic treadmill. But I always crave that lil’ zap of electric city energy.

The twist? I’ve already lived so many versions of these lives. I spent six years in Chicago in high-pressure sales, flying to NYC for client meetings with Fortune 100 brands, schmoozing agency execs at rooftop happy hours. That’s also where I started my podcast. I’ve done the grind. Six figure salary. High rise apartment downtown. Designer bags, overpriced cocktails, constantly inflating my lifestyle.

And I’ve done the complete opposite. I lived on a rocky hill in Sarandë, Albania, for almost 2 months. I paid less than $800 in rent for the entire stay. It was a quiet beach town where walking to the local grocery store was a hike. I read for an hour every morning. Wrote for an hour right after. I watched the sun set over the sea, alone, asking big questions about purpose, identity, and meaning. It was the “writer era” we’ve all dreamed of. No back to back meetings, no massive commitments; nothing but space to let your mind crack open and let the words spill onto a page. It’s where this Substack was born.

But with all that movement came a slow-building grief. I could have rooted myself in any of those places. Bought a home. Built a life. Started a family. The American Dream, just on new soil.

Because I didn’t just fall in love with places. I fell in love with people.

Mexico welcomed me with warmth I’d never experienced as a foreigner. In Mexico City, I felt held, safe, seen. It was supposed to be a month-long stop; I stayed all summer.

Cape Town has a similar effect. The people are effortlessly cool. The nature captivates you, like a spell. It doesn’t let you go. It’s why I keep coming back.

I fell in love with a German boy in Australia. We met at a hostel BBQ, and one month later, during the pandemic, I took a leap of faith and moved to Germany with him. We lived with five roommates and, eventually, a pitbull named Gloria. I loved her. I loved him.

And I’ve fallen in love with people I barely knew. The curly-haired, skinny French guy in Medellín with piercing blue eyes who reminded me of a dreamy, fictional love interest. He was kinda eccentric and it magnetized me. We spent three days together, partying around the city as friends. Nothing happened. I don’t know how he felt about me. I still think about him.

Or the guy in NYC in casual sweatpants, reading a fantasy novel on a park bench. We made eye contact. My heart fluttered. I chickened out and said nothing. I still wonder…what if I had just said hello?

There were of course, the intense flings and situationships that felt like the start of love stories. Whirlwind romances. Passion. Intensity. Some were chaotic. All were illuminating. We were often on different pages, but I invested in emotionally and physically anyway — for the glimmers of reciprocation, the electricity of a wild night of kinky sex, or the high of maybe this time.

Any of those lives could have lasted longer. Or ended sooner.

What if I’d married the German guy? What if I bought a house in Mexico City and filled it with books, plants, and beautiful light? What if I’d gotten pregnant in Cape Town and moved back to Florida, raising a baby with the help of my family?

Or what if I’d gotten hurt… drugged, assaulted, disappeared?

None of those things happened. But I got close enough to taste them. And now, I’m stuck between the ache for more — the Part 2 of the movies I’ll never get — and the pull to keep moving forward. I’ve seen maybe 10% of the world. There’s still so much left to explore.

That’s where I sit now: in the aching tension between planting roots and chasing wonder. Between building a big, beautiful life with someone and continuing to be on the run like a vagabond, into the vast unknown. Oscillating between settling and searching.

I want to know everything. Or become a philosopher of one thing. Goddammit, choose one, Chelsea, I often think to myself.

I want to be respected in places like New York. To prove I have the grit and tenacity to survive a city that chews people up and spits them out. Yet I want to disappear somewhere on the Mediterranean coast, saying little more than ciao and buongiorno to baristas and fishermen.

Maybe this feeling never goes away. Once you know how big the world is, you can’t unknow it. Once the shell cracks open and you see the pearl, you don’t want to close it.

Like Nora, I’ve lived a thousand lives. The difference? I don’t know if I want a thousand more… or just five really rich ones I can sink into.

This is the grief of the full-time traveler.

You exist in multiple dimensions, various identities, overlapping timelines. You never know which one is the one.

Some might be portals. Others could be galaxies.

Maybe that’s why life is a mystery. Nothing is certain. Nothing is guaranteed. If it was, curiosity wouldn’t exist. Pings of electricity down your spine would be useless. Wonder would be obsolete.

So here I am, letting the mystery reveal itself, through the glimmers. Catching the cracks of light in the darkness. Feeling the pull in my chest. Accepting the not-knowing.

Grief is a strange, sometimes unwanted, companion. But it’s a wise one.

So grief, I’m giving you the green light to lead me. Let’s go.