Disappointed Optimists

I don’t care if it’s a book cover or a poster, an advertisement or a social media site. Everybody’s trying to change something. A huge percentage of the time, the thing they want to change is your wallet. If you are a designer, this is your fate. I know we talk all the time about beauty and balance, gestalt principles and saving the world.

But most of us are just trying to get people to buy stuff.

Taking a design job is committing to getting people to do what the company wants. And if the company is a public one, what it wants is shareholder value.

You can tell yourself you’re making users’ lives easier. On good days that’s even true. But do you know why you are making users’ lives easier? To prevent them leaving.

B corps are better… as long as they stay B corps. (Look at Etsy.) Nonprofits are also better… as long as they stay that way (Look at OpenAI.)

At a nonprofit, you are definitely committed to behavior change. It’s just that the behavior might be a social good, or it could be in service to fundraising.

If you think money is icky, don’t be a designer. Money is oxygen for organizations.

Disappointed optimists

Lenny Rachitsky and Noam Segal ran their second annual tech worker survey this month, and UX designers and researchers were the least willing of anyone to tell a newcomer to go into design.

Segal put it as a ladder: the tools (looking at you, GenAI) keep climbing the rungs, and they pull each rung up behind them as they go. If you’re a senior practitioner you’re high up enough to feel safe. You’ve been in the business long enough to have developed that mythical human quality “taste.”

If you’re near the bottom, the rung you were about to step on is gone.

So a designer can be okay and still look at the kid behind them and say, “The water’s fine. Don’t get in.”

One line from the survey sticks with me. AI lowered the floor of what anyone can produce, but it didn’t raise the ceiling of what’s good. So your team ships more stuff but none of it is better. If you’re the kind of person who got into this to make good things, that’s depressing.

I’ve been watching designers be unhappy since well before anyone had to argue with a chatbot about a design system, so let me offer the older theory.

I’d argue they’re disappointed optimists, and that the disappointment is part of the job and part of why they’re any good at it. Designers always see the world as it could be. How could they be anything except disappointed that the world is the messy, sometimes corrupt, often moneygrubbing place that it is?

It is a Sisyphean struggle to constantly try to make good things happen in bad places.

It’s a cursed problem

There’s a great GDC talk by Alex Jaffe called Cursed Problems in Game Design. A cursed problem, in his definition, is an unsolvable design problem rooted in a conflict between two promises that can’t coexist. You made both promises, on purpose, and they contradict each other, and no amount of clever tuning gets you out. You just have to give something up.

Design-as-a-career is a cursed problem.

You want to make the world as good as you imagine it could be.

You want a paycheck from an organization whose actual job is to produce shareholder value.

Those rarely coexist. There is no magic phrase, no framework, no seat at the table that dissolves the conflict, because the conflict is the premise. And the corporate version is darker than Jaffe’s. In his talk the designer holds the knife and chooses what to cut. At your company the choice was already made, and the thing that got cut was the user. You’re the promise it kept just well enough to keep you from quitting. You are the marshmallow in the fire.

So stop looking for the solution. There isn’t one. What’s left is the only useful question, which is what you’re actually willing to give up.

Think of the company as a bad boyfriend. You can stay and try to change him, which mostly ends the way you’d expect. You can leave him. You can go find a better one. Or you can build a better one from scratch, which is its own kind of gamble. Those are the four options. They’re all sacrifices, and none of them makes the problem stop being a problem.

Option one: stay and change him

The option that isn’t leaving but isn’t giving up either is to be a dissenter on the inside. Nudge the bad company toward less bad. This is real work, it sometimes moves things, and I want to be honest about both halves of that sentence.

Richmond Wong at Berkeley interviewed twelve UX people at large tech companies about exactly this and wrote up what they actually do, in a paper called Tactics of Soft Resistance. It is the closest thing I’ve found to melatonin for guilt-related insomnia. Three of the tactics are worth stealing.

The first is translation. One researcher in the study found that arguing something was good for the user had a short shelf life, but the moment she could show it was costing revenue, the product team was suddenly willing to have the meeting. Another took her worry about the warehouse workers stuck using her company’s software and reframed it as reputational risk to the company, borrowing her employer’s own stated corporate value of trust to do it. That isn’t selling out. It’s learning the only language in which your concern is audible. If you want to get good at it, read Rich Mironov’s Money Stories, which is about teaching makers to talk about their work in the terms executives actually use. It’s under ninety pages, which matters when you’re the most tired role in tech. OK, Rich is a friend and I blurbed the book. He’s still right.

The second is the ethical debt log. A senior researcher at an edtech company started keeping a backlog in Jira of the social issues her team had surfaced and then quietly not acted on, and brought them up again and again. Her manager loved it. Ethical debt, filed next to technical debt, in a system the executives already read.

The third one I get to be smug about. A senior designer pushed to write cultural outcomes into her product org’s OKRs as an explicit objective with key results underneath, and the org went for it. Someone at a research meetup put it more bluntly: you have to be in the room when the OKRs get defined. I have spent years arguing that OKRs are how a company decides what it actually cares about. Apparently they also work as a crowbar.

Wong is careful about what these tactics are not. They work by borrowing the company’s own logic, which means they never lay a finger on the logic itself. The people doing this described it as exhausting and repetitive, one of them calling it futile and necessary in the same breath. And nine of the twelve people interviewed were women or non-binary, which tells you something about who ends up doing the emotional labor of caring out loud.

So learn the business model, well enough to know which lever your work is attached to and which number your VP gets judged on. Then spend the five or ten years. Patient persuasion and proof, social capital, trust from execs and peers, nudging things along.

Honestly, I don’t have data that any of this works and neither does Wong. What I believe, after a couple of decades of watching, is that if you’re patient and stubborn and you have the right allies, you can improve your local environment. Your team. Your product. That is not nothing. But the rot at the top is untouchable unless you are the top, and even then culture eats strategy for breakfast. I have a friend who joined Uber to change Uber. Six months later he was job hunting.

You can make him a better boyfriend. Don’t ever bet on him becoming the husband you wished for.

Or: leave, find a better one, or build one

If staying and nudging isn’t enough, you can try one of the other three.

You can leave. Straightforward, except you give up the paycheck, and in this economy that’s not a small thing to hand-wave past. I’m not going to tell a stranger with rent to walk. But the survey I mentioned is blunt about where the happy people are, and it isn’t the big logos.

You can go find a better one. Somewhere less actively harmful. There’s no shame in a company that isn’t changing the world as long as it isn’t wrecking it either, where you can do work you’re proud of and go home at a reasonable hour. Sometimes what really matters is the paycheck and the craft and getting to close the laptop, and that is a completely honest answer to the cursed problem. You gave up the fantasy that the job would also be your mission. Plenty of people are happier the day they accept that sometimes a job is just a job.

The reverse of this is accepting a worse paycheck for a better job. I made that choice. While I’m jealous of the newly minted millionaires who are my neighbors, I am happy. I know the work I do is helping.

Or you can build one. Start your own thing, which is easier than it has ever been. The founders in that survey are the happiest people in tech. (Read that carefully, though: Lenny only surveyed people who are founders right now, so everyone whose startup died is not in the room to comment.)

You trade the bad boyfriend for the risk of becoming one yourself. If you get popular enough that the vibe-coded stuff starts breaking, hopefully you’re popular enough to hire a real engineer.

If you do build one, build it so it can’t rot. This is the whole argument of Eric Ries’s new book, Incorruptible. His point is that companies don’t go bad because bad people take over. They go bad because the structure rewards extraction, and eventually someone “rational” shows up and does the extracting.

When you start a company, someone hands you a stack of boilerplate incorporation documents, and you sign them, because you have a product to build and no reason to think the default is an important choice. But it is. The boilerplate is the extraction structure. You wired your company to rot on day one and didn’t even notice, and by the time you’re big enough for it to matter, it’s too late to change. So if you’re going to build, treat the legal structure as a design decision, not paperwork. This is also why the designer stuck inside a bad company can’t fix it from her desk. The wiring was set before she was hired.

None of these is a fix. There is no fix. It’s a cursed problem, and the only move is to decide, on purpose and with clear eyes, what you can live without.  Do you really need the free food and foosball table? Do you really need the great health insurance? Are you young and able to take on risk? Is it time to start planning for retirement (it’s always time to start planning for retirement, fyi)?

Figure out what really matters to you. Then pick your compromise. It’s ok. You don’t have to be perfect to be fabulous.

Do you like posters? I like posters. Here are some famous ones.