life design

+ matchmaking is open :)

Claude Monet, The Turkeys, 1877

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I keep having this thought of “I don’t feel like I’ve chosen matchmaking, but matchmaking has chosen me,” and I was trying to unpack why. Some thoughts:

1. I’m very into “searching” for things. Like, I spend a surprisingly high amount of time searching for certain Prada S/S 1999 pieces, and I think this also translates to people. I have a pretty granular understanding of what I’m attracted to in partners and I’m good at tracking those qualities down. In some sense, it’s natural to me to do it for other people.

2. I think I’m pretty receptive? Like, we need to be somewhat values aligned (if you’re 55 and looking to date a 22-year-old model, we will not be working together), but beyond that I’m very comfortable hearing about what other people want. People often find me in times of crisis—breakups, big transitions, loss of faith—and I find it easy and natural to witness that in a nonjudgmental way. I like hearing about people’s idiosyncrasies, and I’ve already learned that everyone wants very different things. People have vastly different tastes in face shapes, for instance. I find that kind of thing genuinely interesting and really like exploring it.

3. I’m interested in weird social experiments. I was telling a friend on the phone today that I used to think my strength was communication, and now I understand it’s something more like, my tolerance for weirdness. I think I’m just pretty open, and that openness makes it possible to be creative.

4. I’m comfortable asking. I’ve had a very privileged life where I’ve learned that if I ask for things people will often say yes. And it’s much easier asking on the behalf of other people than for myself.

5. I’m so obsessed with love. It’s really, really motivating for me. I like prestige and money as much as the next person but I don’t think anything else in the world is half as motivating as the idea of ~love~. It’s the thing I’ve spent 10,000 hours thinking about with zero effort.

I’ve been thinking a lot about what Henrik wrote about the design process for a fulfilling life. Like him, I feel like my own process feels more like an unfolding, and less like a top-down design (what he calls a “vision”). I rarely sit down and go, This makes sense. Instead my best discoveries come from a recognition of what’s already going on. I started my Substack not because I wanted to write, but because I was already writing and needed a place to put it. My relationships have historically begun not because we sat down and decided “This makes sense,” but quite literally because we couldn’t stop hanging out.

This design process can often feel unnerving. It’s been hard for me, someone who’s addicted to authority and control, to learn how to let go. I prefer to drive, and I’ve had to learn how to let my own context drive me. But the truth is, my environment has better ideas than I do. When I pay attention to the cues around me, the next step is obvious.

*

I’ve been meditating a lot lately on stuckness. You see it everywhere: someone who says they want to write, and then gives up after a week. Someone who says they’re miserable in their relationship, and then proceeds to stay in it for another five years. Someone who procrastinates on replying to the point where they literally ruin their own life. I have, at many points of my life, felt acutely stuck, realized I was stuck, and absolutely could not get unstuck. And then I would try to rationalize myself out of it to no avail. The thing I’ve understood since then is stuckness is fundamentally an emotional problem, not a mental one. You absolutely cannot think your way out of it.

Whenever I’m experimenting with something new, there’s so much stickiness in my own mind. Is this stupid? Will no one sign up? What do I do if I can’t find any more people? What if I’m sick of it next month? It’s too much work to make a website. If I listen to my own fears, I would never do anything except sit there and circle around.

Last week I was hanging out with my friend M, who is well described by the buzzword of the year, agentic. She goes out and does novel and difficult things and usually does them at a very high level. We were discussing why she’s able to do this, and the difficulties and rewards of helping other people get unstuck.

When M wants to do something, she tells me that she visualizes the end state and then she breaks it down into five steps. For instance, let’s say that she’s just moved to a new city where she doesn’t know anyone and wants to make friends. So she visualizes herself surrounded by a positive, loving friend group. What are the steps?

1. She could first brainstorm a list of places where she could plausibly meet people she could get along with. This could include a yoga studio, a dog park a running club, a bookstore that regularly hosts literary events, a Substack meetup, the Internet, etc.

2. She could then start regularly going to all of these places and notice people she particularly enjoys talking to, who feel resonate.

3. She could ask several of these people to get coffee, lunch, or drinks with her.

4. She could keep hanging out with the ones she really gets along with, and over time become friends with their friend group too.

5. She could repeat, expand, and modify this process as needed, until she has 5-10 people in this new city she could consider good friends.

We were jokingly referring to this as “running a process.” The funny thing is, I remember trying to convince an ex-boyfriend to do exactly this. He was living in a new city at the time and felt isolated, and I wanted him to put himself in situations where he could meet more people. You just don’t get it, he said.

Why is it that he got stuck, and M generally does not? On some level, it’s about desire and drive: M is very motivated to do things. A lot of people might say they want something, but they may not want to actually inconvenience themselves to get it. Getting the thing you want often involves extreme and prolonged discomfort. You can avoid that by, well, never getting started.

On another level, it’s about experience and intuition: M trusts that when she comes up with a plan, it’s roughly accurate. She knows this because she’s made other plans before and followed through with them, and they more or less worked. We talked about how it’s becomes much easier once you’ve run even one process all the way through—you know that you can get something done.

The most competent people I know are pretty good at basically anything they put their minds to, because they just design a process and run it. I think this is largely mental and emotional—the hardest part isn’t figuring out the steps, it’s enduring the psychological discomfort of doing them and then adapting.

*

Last year James Clear gave me really good advice about life design. He told me to pay attention to what I enjoyed most about my lifestyle, and try to preserve it while I experimented. This is one reason why I haven’t really considered becoming a coach—I don’t enjoy being on calls all day. The thing I most like about being a writer is having the space to think and go on long walks. If I became a coach perhaps I would make more money, but I would lose the best thing about my life.

Of course, this applies to so much more than just work. In love, I recently realized that the thing I value most is emotional connection. Connection is of course ineffable, and for a long time my lack of vocabulary prevented me from understanding how much I needed it. It’s that warm, fluid feeling, that sense of boundarylessness between two people, the possibility of total understanding. I care about a lot of other things, but emotional connection is the whole point. That’s what I can’t compromise on.

One of the best and worst features of modernity is unlimited optionality. Anything is out there… if you can find it. Unfortunately, I notice that most people have no idea what they’re searching for. They’re at one of those sushi conveyor belt restaurants just randomly grabbing dishes. At the rate they’re going, they’ll probably be full before they ever find what they want to eat.

In love, work, and life, I keep returning to simplicity. There’s a million ways we can make things very difficult for ourselves. There’s always going to be another justification, another rationalization, another frame. And often all of it is beside the point. Simplicity is brutal, and it scares us. When we know what we really want there’s nowhere to run.