Delicious Ambiguity

“Some stories don’t have a clear beginning, middle, and end. Life is about not knowing, having to change, taking the moment and making the best of it, without knowing what’s going to happen next. Delicious ambiguity…” - Gilda Radner

One of the things I like best about traveling is that you just never know. From the moment you leave your house and all the accoutrements of your life and routines, it’s all bets off. You have no idea whether the Uber driver will be in a bad mood, or if the flight will actually take off on time, or who you’ll sit next to on the plane. Then you arrive at your destination and—if you’re like me—you’ve done just enough planning to insure you have a place to stay in a decent neighborhood. The rest is in the outstretched hands of the Universe.

When I travel I am absolutely thrilled by not knowing what’s around the next corner, or what’s at the end of the enchanted alleyway, or who I’ll meet at the next bar. A couple of years ago I was in Vienna (because I am a child of the 80’s and Billy Joel hasn’t lied to me yet) and after arriving late in the evening I dropped my bags and set off into the city to let things happen to me. I doubled back on what looked like a dive bar from the outside, but on the inside was a very cool cocktail bar where one of Europe’s leading mixologists was guest bartending. In a suit, no less. (Hi Marcus!!! Go see him at the Savoy if you’re in London.)

After a couple rounds of next-level martinis, I wound up getting adopted by a gorgeous 24 year-old German girl named Kimberley who invited me to go wine tasting with her the next day in the Austrian countryside. Like, say less Kim. The next morning I met her at the train station and we set off on an hour long journey that dropped us at a nondescript spot in the middle of actual nowhere. She said she believed the winery was just up that hill, so we hiked it. And sure enough, there was the most incredible winery where an incredible artist called Flowsofly was having a show.

We then crossed highways and literal rivers on foot, now carrying framed art, to two more wineries. Just as we finished our tasting at the second one, it started pouring… but we still had one more stop! Kimberly had the in for a bougey party at a cathedral in a village called Krems an der Donau. So we showed up dripping wet and dried our hair with the Dyson hand dryer in the bathroom, drank from the open bar, and ate fried food on the street after.

With more than my fair share of experiences like these, how is it that I spend so much of my day-to-day life clinging to any semblance of certainty? Every path I have chosen that is well-worn and clearly marked has made me deeply unhappy. I need to explore or I will die. And yet I find myself futilely attempting to envisage a future that is perfectly defined. I consult tarot cards and ChatGPT and friends to tell me what’s going to happen next. I over-think and second-guess and pathologize which never actually leads to a certain outcome anyway, all to find out how it ends. And when I said this all out loud to my brilliant friend Candace, she said, “Death. What happens in the end is death.”

For all of my future-tripping and meaning-making, I have chosen a career that is famously uncertain. I chose to leave a life and relationship behind that was as close as it comes to being able to guarantee a certain kind of future, and instead rebuild a life from scratch at 37. I still take big leaps of faith and spend my days writing like every word is an essential contribution to humanity’s endowment, even when it is shamefully, aggressively bad. So I’ve come to realize in this first month of 2026 that what’s actually more important to me than certainty is stability, and that’s something real we can actually create for ourselves.

Stability is the byproduct of living in a way that supports your happiness. For me that looks like showing up as authentically as I possibly can—even (especially) when it feels weird or disorganized, doing my best to be a great friend and family member, trying to mine the value out of every ridiculous situation I may find myself in, and continuing to do the work even though nobody’s watching.

Certainty is a myth anyway. We literally never know what’s going to happen in the next moment, and when I’m not terrified by that, I find it fucking magical.

Gilda was right. Ambiguity is actually delicious.