Be Romantic

Over dinner this weekend, a friend told me about a hotel she'd stayed at where the room key came in a biodegradable envelope with wildflower seeds inside. When you got home, you could plant them (in your garden?). We both laughed at how ridiculous it was. A room key is a room key. But then we sat with it for a second, because someone had looked at that room key and asked: what could this become? What if a trip didn't have to end at checkout?

That's an example of what I mean by "romantic." Not sentimental or optimistic, but romantic in the sense of seeing something for exactly what it is and then asking what's possible. The seeds come with the key because someone felt what it was like to leave a place you loved, and they cared enough to ask whether it had to be that way. Nobody told them to. It wasn't on a roadmap. They just couldn't leave it alone.

That's what feeling deeply does. It's what makes you notice the difference between a conversation where someone is truly listening and one where they're waiting to talk. Between a meal someone made for you and a meal someone just made.

I've started to think of feeling deeply not as a liability but as an instrument. It's how you calibrate what matters, and it's what compels you to do something about it.

Legible care vs. responsive care

A Marriott or a Hilton performs care in a way that is consistent and recognizable. The bed will be made a certain way. The check-in process will follow a script. This is care as a system, and it's genuinely valuable. It scales, it sets expectations, and it delivers. But it can't surprise you, because it wasn't designed to see you.

When you walk into a Four Seasons, or an Aman hotel, or the hotel with the seeds, you know they're going to care about you, but what you can't predict is how. That's because their care is a response to you, not a playbook they're applying.

The most interesting work I've seen, the work that actually moves people, comes from care and romance. From someone who looked at a problem and didn't just ask what it needed, but what it could become.

Early in my career, I helped rebuild Design Camp at Facebook, the two-week onboarding program for the design org. What I kept noticing was the curiosity in the room, but the entire program was structured around talking at people.

Nobody asked me to fix this. But I felt it. I suggested we create an AMA session at the end of the second week, and I ended up hosting it for the next year, enlisting designers and researchers from around the company because they too cared about welcoming and setting up our new colleagues for success.

The feeling isn't separate from the work. It's the primary instrument of the work.

Romance is rarely asked for. It can only be rewarded. Most of the time, you're noticing something that doesn't seem to bother anyone else, and you have to decide whether to act on it knowing that if it works, it'll seem obvious in retrospect. If it doesn't, it was never your job in the first place. It's a lonely way to work. You're caring on spec, driven by something internal that you can't always explain and that nobody requested. The people I know who work this way wouldn't trade it, but they'd also tell you it's not easy to keep choosing it.

The infinite romance

Here's the thing about being romantic about your work: it turns the work into play.

Not play as in frivolous. Play in the sense James Carse meant when he distinguished between finite and infinite games. A finite game has external boundaries. Defined winners, clear endpoints, and rewards that someone else controls. An infinite game is internally defined and internally rewarded. You don't play to win. You play to keep playing.

When you're romantic about your work, you are implicitly an infinite player. There is no external reward that's going to sustain you. Not the title, not the promotion, and not the recognition. What sustains you is the deep interrogation that the work demands: Am I bringing all that I can to this? Am I seeing clearly? Am I caring responsively, or have I started performing care legibly because it's easier?

The reward for playing is that you get to keep playing. The economic outcomes are real, and they matter (they're what let you stay in the game), but they're adjacent.

I think most professional environments talk about work in the opposite direction. We talk about impact, about outcomes, and about measurable results. And those things are important. But the people who produce the most remarkable work, the seed key people, the Four Seasons people, the people who build software that makes you feel something – they are almost always infinite players. They're romantic about the work itself, not the rewards that follow from it.

Being romantic is a choice about how closely you pay attention and how seriously you take what you feel. I find myself coming back to this idea more and more lately, and I think it's because the alternative is becoming clearer.

For the ice

It feels like AI is eating everything right now. The tools are getting faster, the outputs are getting cheaper, and the question of what humans are actually for in the work is getting harder to avoid. I don't think the answer is to out-produce the machines. I think the answer is to be more romantic than they can be.

At the Olympics this year, Alysa Liu won the women's figure skating gold. She was the first American woman to do so in twenty-four years, but what made it extraordinary wasn't the medal — it was the way she skated. Liu had retired from the sport in 2022, come back two years later on her own terms, and described herself as an artist first and a competitor second. She said she doesn't feel pressure. She doesn't feel nervous. She said she was at "peak happiness" out on the ice and you could see it. While her routine was difficult and took years of training, in the moment, the thing that came through was joy. It was so beautiful precisely because you could feel that the performance wasn't for the judges. It was for the ice.

As the world changes around us, I believe the thing that will sustain us is pursuing the work that feels like play. When I look at the people I admire most, in any field, they are invariably romantic about the thing I know them for. They see it clearly, they feel it deeply, and they keep asking what it could become. Not for any audience, but for the work itself.