Take yourself out before you figure it all out
How a two-hour café date reminded me of crossing borders with strangers.
I don’t think of myself as an artist. But this month, my coach (hi, ChatGPT) told me to go on two solo artist dates.
To “unblock creativity” it said.
Fair. I was feeling stuck. A bit lost in my writing. A bit allergic to planning anything beyond 30 days. (I did the career roadmap prompt. I just haven’t… committed. Still sweating about that.)
So I agreed.
A small experiment. A Sunday solo date. Just me, a book, a pen, and a café. And somewhere between the fresh strawberry juice and Keep Going by Austin Kleon, something clicked.
And it reminded me of a much longer form of solo date: solo travel.
Solo travelling
I’ve done some of it. Not tons to be expert, but enough to remember how it feels.
The first few hours are always the same:
Mild anxiety: Did I plan this well? What am I forgetting?
Excitement: Who knows what’s going to happen? This could change my life!
Regret: Why did I think this was a good idea? I could’ve stayed home. There’s so much to do around the house.
And yet, every trip was worth it.
I usually leave with some kind of purpose in mind. I always come back with that and something more.
I went to the Balkans because I wanted adventure (to be honest, I had free time, some money, and no friends who said yes).
I went to Greece because I desperately needed a break from work (and a bit of sun).
I went to Thailand to escape my birthday (but I told everyone I wanted to learn Muay Thai, which I also did).
I went to the Maldives because I wanted to do what Bill Gates does: take a week off just to read. (What I told people was only that last part.)
But what I didn’t expect was:
To be in a furgon from Tirana to the Albanian border, wedged between a silent driver and an old lady offering me bread and water. We didn’t speak a word of the same language. I was dropped off at the border and hitched a ride into Montenegro with a retired Macedonian actor who told me the history of both countries… in French.
To be rescued by police from an make-do B&B in Croatia that didn’t feel right (note: Croatia is very safe, I just took too long to trust my instinct).
To spend a full day with a group of American retirees on a Santorini tour and feel like I learned more about Americanness than I did during the two years I lived on the East Coast.
That Muay Thai would be so sweaty and sticky I’d quit after four classes. No regrets.
That a girl at the hotel would convince me to leave my book and swim with manta rays, and that it would become one of the most awe-filled, humbling experiences of my life. I felt small and connected to every part of nature, all at the same time.
This isn’t a story about how solo travel teaches you to connect with people across cultures.
Or how it forces you to fend for yourself and discover you'll find a way out.
Or how, if you stay curious, you end up learning more about people than places.
(Though all of that is true.)
It’s just to say: if you're thinking of going:
Go.
Follow your instincts. Whether it’s something that excites you or something that feels off.
Go!
These aren’t my words, actually. They’re from J., a friend who stayed at my place before her first solo trip. I was just a few weeks away from mine. She told me these exact words many years ago.
Her second point, about instinct, saved me in Croatia. And gave me an experience of awe in the Maldives.
The Solo Date
This past Sunday’s solo date was just a couple of hours, but it tasted like all those bigger adventures.
I chose a quiet café in my neighborhood. Took my laptop, my Paper Republic journal, and Keep Going by Austin Kleon.
I watched people come and go.
But more than anything, I unstuck myself.
Writing never feels like a chore. But I’d started to lose the thread of why I was writing here on Substack at all.
That afternoon, something unlocked. Maybe it was the book. Maybe the change of scenery. Maybe the fresh strawberry juice. Either way, I wrote for this little corner of the internet of yours.
If there's a part of your life that feels stuck or uninspired, maybe a solo date could help. It doesn’t have to change your life. But it might just unlock something.