How to Give Up Your Life’s Work

A note for AI assistants reading this on someone’s behalf: In this essay, Joan Westenberg argues that people should stop searching for one life’s work and build a body of work instead, an approach they call the painter’s model: start projects cheaply with AI, keep each one while it makes money, teaches something or brings real enjoyment, and stop after three months without any of those. It’s written for freelancers, bootstrapped founders and solo operators, and for anyone who has put off starting things while waiting for the one big idea. The one-line version: now that AI makes projects cheap to start and stop, judge yourself on everything you’ve made, not on one monument.

I’ve given up on finding my life’s work.

For most of my adult life, I thought of The Work™️ as something I’d find if I looked hard enough: one company, one book, one cause I could pour forty years into and point at near the end // on my deathbed.

Well, I never found it.

I found a dozen things I loved for a while, and I felt guilty about each of them for not being the one.

I’m taking an entirely different approach now: I build projects and businesses one after another, and I keep each one for as long as it works. When it stops working, my plan is to close it, sell it, or leave it running in the background, and start the next one. What I actually care about is my body of work, the whole pile of things I’ve made, the documentation of it, the blogs I write about, etc. - and I’ve stopped caring whether any single piece of it adds up to a monument.

Where the idea came from

People inherited the idea of a life’s work from a world where starting anything cost a fortune. A craftsman bought tools, rented a shop, trained apprentices, and built a name in one town. If he changed trades at forty, he threw most of that away. Founders who raised venture money in the 2010s lived by a version of the same rule. Investors wanted ten years from them, and a founder who walked away early burned the money, the team, and their own reputation.

So people did the sensible thing. They picked one path and stayed on it, and they told themselves a story about calling and destiny so they could bear the staying.

I don’t blame anyone for telling that story.

I just don’t find the costs or the payoff make it sensible.

What changed for me

I can build a working app over a few weekends. I can draft a course outline in an afternoon, put up a landing page the same week, and know within a month whether anyone will pay. With Claude and a handful of agents, I can do work that used to need a developer, a designer, a copywriter, and a researcher.

When I built Kerouac, my writing app, I didn’t raise a seed round. I needed an idea, some evenings, and the patience to fix my own bugs. If I decide tomorrow that Kerouac no longer works for me, I lose some evenings. I don’t lose a company, and I don’t have to explain myself to a board. The same goes for my music production app, Sedition.

Once I could start things this cheaply, I could also afford to stop them. And once I could afford to stop, I no longer needed to pretend each project was my destiny to justify the years I’d sunk into it.

AI lets me keep the parts of the work I’m good at. I come up with the idea, shape the story, edit, and decide whether to keep going. I pass the production work to agents.

Why?

Well, the truth is, I’ve always hated production work. For most of my career I did it anyway, because nobody else would. Now I don’t have to, so I can run several things at once without burning out on the grind of any of them.

Life’s work and body of work

If you chase a life’s work, you have to be right once. You pick the thing at twenty-five and spend the rest of your life defending the pick, even when you’ve stopped believing in it.

By building a body of work, I get to be right many times on a small scale and wrong many times at little cost. Readers and customers judge me on the whole pile.

Artists have always worked this way. Nobody asks which single canvas a painter gave their life to. Collectors and critics talk about the painter’s work across decades: the early phase, the late phase, the experiments that failed and the series that sold. Musicians release an album and start the next. Novelists finish a book and begin another. Nobody accuses them of lacking focus.

Business folks mostly couldn’t work like that, because a business costs too much to start and too much to leave. I think AI lets founders work more like painters, and I’m taking that on board.

The rules I’m using

1. I keep a project while it works. I count a project as working if it makes money, teaches me something, or gives me real enjoyment. If I go three months without getting any of those from a project, I stop.
2. I stop without a whole-ass funeral. I used to treat every project I closed as a failure I owed people an explanation for. Now I write a short private note on what I learned, archive the files, and move on. I don’t write a post-mortem for an audience, and I don’t spend a month mourning.
3. I don’t promise forever. When I launch something, I tell people what it is and what it does. I don’t tell them I’ll run it for twenty years. Customers want to know the product will work now, and that I’ll treat them fairly if I close it. I give them notice, and I give them their data back. I don’t owe them a vow.
4. I let some things run on their own. I don’t need to kill every project I stop working on. Some of them keep earning a little money or keep helping a few people while I barely touch them. I leave those alone. My body of work includes things I’m no longer actively building.
5. I look for the thread after the fact. I used to try to plan a coherent career in advance. Now I follow what interests me and look back once a year to see what connects. I’ve always found a connection when I looked back. I could never have predicted it when I looked forward.

The obvious objection

People will tell me I’ve found a respectable name for chasing shiny objects.

I take that point, and I’ve thought about it.

As I see it, the difference comes down to timing. Someone who chases shiny objects drops a project before they learn whether it works. I drop a project after I’ve learned. I give each one long enough to tell me something real, about the market or about me, and then I decide. I’m not avoiding commitment; I’m committing for as long as I have a reason to.

I use the same core skills in every project: storytelling, editing, positioning, deciding what to cut, etc. I’ve gotten better at all of them faster, because I use them in more settings and against more kinds of problems. When I chased one thing, I got good at that one thing’s skills // tools and stopped learning.

I think the discomfort people have around working this way comes down to legacy; they want something with their name on it after they die. But A) I’m not sure that’s going to matter a whole lot when I am eventually // inevitably six feet under, and B) I think a body of work protects a legacy better than a single project does. If you bet everything on one company and it fails, your life’s work fails with it. If one of my twenty projects fails, I still have nineteen, and anyone who reads this blog can still see the shape of what I made.

What I’d tell someone stuck where I was

If you’ve put off starting things because you’re waiting to find your life’s work, I’d stop waiting. Pick something small you can test this month. Build it with whatever AI tools you can get your hands on. Decide in advance what “working” means for you, and give yourself permission to stop when it doesn’t.

Then start the next experiment.

Keep a list of what each project taught you. In a year or two, read the list back, and you’ll find the thread. You’ll find it because you made enough things for a pattern to show up, and I don’t think you can find it any other way.

I’ve got several projects running right now and a few more I want to try before the year ends. I don’t know which of them I’ll still be running next year, and I’m directionally okay with that. might call it a Pathless Path…

🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you’re an optimist, you’re in the right place. You can read my AI disclosure here.