Dear Designer

Dear Designer: How You Can Tell You’re Getting Better

Being a better designer is about being a better person

Mike Monteiro
Aug 8, 2019 · 8 min read
Illustration: Jinhwa Jang

his week’s question comes from Twitter, instead of a reader email. I began to reply and then quickly realized it was better answered here, where we have the room for a little more thought and nuance. And this question needs thought and nuance, because it’s not as cut and dried as you’d think.

bviously, you can tell you’re getting better as a designer when your craft is a little more polished, when you start thinking more about systems rather one-offs, when you start caring about how someone will move through a page more than how the page looks, when it takes you an hour to do what used to take you all day. These are some of the obvious signs you’re getting better as a designer. You can tell the work of a first-year designer from the work of a ten-year veteran. That’s the obvious stuff — the maturing-of-talent that comes with getting more experience doing the thing you do. That shouldn’t be discounted.

But to really get better as a designer, you have to get better as a person. Because there’s a point at which the craft skills hit a wall that can only be climbed by growing as a human being.

Let’s start with an admission: When I was in my twenties I thought I was a fucking great designer. I thought I had the answers to everything. I thought I could solve everything by myself; I thought I was a genius. The journey to getting better as a designer was a journey toward understanding how much of an idiot I actually am. Now that I’m in my fifties I understand how little I actually know, how much better the people around me are at a lot of things, and how much help I need from those around me. The journey toward getting better as a designer means being okay with all of those things.

Getting better as a designer means valuing curiosity more than mastery and embracing what you don’t know more than fearing it.

I used to have panic attacks thinking about a boss or a client possibly asking me a question I didn’t have an answer for, or asking me to use a skillset I didn’t have yet. Now, I get excited about the opportunity to either learn a new skill or work with a colleague who already has it. Getting better as a designer means valuing curiosity more than mastery and embracing what you don’t know more than fearing it. Especially in an industry where things change every few years.

Fall in love with what you don’t know. Because getting better as a designer starts with understanding that you really don’t know much at all, and getting really, really good at it means that the percentage of stuff you think you know gets lower and lower as you grow.

I look forward to all of you realizing you’re as ignorant as I know I am. Or as my boy Socrates once said, “All I know is that I know nothing.” This is also known as the Socratic Paradox. (Ironically, we used to be sure that Socrates said this, but we’re not so sure anymore, since Socrates never wrote anything down and all we have are Plato’s meeting notes.)

So without further ado, let’s go into some of the lessons you’ll need to learn to get better as a designer. And let me just say, I’ve had to learn all of these the hard way. Some stuck more than others. Some I still struggle with. Some I have to relearn every single time.

Most of what you make is trash

Strap in — I’m about to use a sports metaphor. In 1941, Ted Williams of the Boston Red Sox finished the season with a .406 batting average. He was the first player in MLB to finish the season with a batting average over .400 since 1930, and no one has done it since. (In the interest of justice, let me just say that every baseball statistic before racial integration deserves an asterisk, but that’s another article — one someone else is better qualified to write.) In short, in 1941, Ted Williams had the most successful offensive season of the modern era. He hit .406. That means he succeeded in getting on base 40% of the time. It also means he failed 60% of the time. For comparisons’ sake, a good batting average these days is considered to be .280, more or less. That means that a professional baseball player can fail 72% of the time and still be considered good.

Designers fail way more than that.

Most of what we do is trash. In over 20 years in this business, I don’t think I’ve gotten better at making things; I’ve just gotten faster at realizing when I was making trash. I can still recall entire days of laboring over one idea trying to figure out how to make it work, or trying to “save” it, all in the name of preserving my ego. I was terrified that I was making trash. But these days, I just assume I’m making trash. And into the trash can it goes. Trash work for the trash god! Every once in a while, I catch myself making something that’s not trash, and I’m pleasantly surprised.

Just accept it: Most of what you make is trash.

Listen more than you talk

The odds that you have the answer to everything are zero. The odds that you have better answers than the people around you when you all put your heads together are also zero. So listen to the people around you. And surround yourself with people who are different from you; otherwise you’re just listening to yourself, and that’s just another version of you talking. Listen to the people you disagree with more than the ones you agree with; listen to the ones who make you uncomfortable.

People have great stories, and if your mouth is moving you’ll never get to hear them. “Tell me more about that” is the gateway to learning something you didn’t know, and to gaining the respect of the people around you.

“Oh, but Mike! I know what they’re going to say next. I’ll get major points if I say it before they do!” No, you won’t. You’ll look like an ass. And what if you’re wrong? Never take away someone’s opportunity to surprise you.

Get comfortable admitting you don’t know something

No matter how much you prepare, no matter how much you’ve researched, no matter how smart you actually are, someone, at some point, is going to throw you a question that you have no answer for. The most confident phrase that can come out of your mouth at that point is “I don’t know.” Let’s look at the options: You could lie, but that’s a jerk move. You could try to change the subject, but c’mon, they’ll see through that. You could hem and haw and hope an answer falls out of the sky, but deus ex machina isn’t an odds-friendly strategy.

Telling someone you don’t know something tells them you’re not willing to lie to them, because if you’re going to lie to someone, that’s a prime place to do it. And instead, you did the hard thing. You admitted you didn’t know. That takes confidence! Also, it opened up an opportunity for learning. Because they’re either going to tell you about what you don’t know, or tell you to go find out.

I’ve worked with a bunch of designers over the years, managed more than a few of them. I’ve explained things to them, I’ve gone over project briefs, I’ve given them all feedback. Afterwards I’ve asked them if they had any questions. If someone asks me to reexplain something I know they’re paying attention; if they tell me it all made sense, I start worrying. Because for one thing, I’m just not that thorough at explaining things — there’s no way I got everything on the first pass. For another, most people aren’t good enough at understanding things to get it all the first time around. Get comfortable asking for clarification.

Stop being afraid of getting fired

I’ve been fired more than once — fewer times than the number of digits I’m typing with, but not by much. At the time, all of those firings seemed totally unfair. In hindsight, I can’t believe I didn’t get fired sooner from a lot of those jobs. I got fired for various reasons. Some of them because I was being a jerk, some of them because I wasn’t doing good work, some of them because I refused to do something that didn’t feel right, and some of them because I should have never been working there to begin with.

Every time I got fired it felt bad. Every time I got fired I learned something.

Now, I don’t feel good about the places where I was being a jerk; in fact, I’ve since apologized to those bosses. (Running your own company, and hiring your own jerks, is a great way to develop empathy for your past bosses.) But I’ve never regretted getting fired for standing my ground and refusing to do something that felt sketchy. Jobs come and go, but trading a paycheck for building something that tricks people, or lies to people, or takes advantage of people is something that never goes away. Which brings us to our last point…

Start caring more about people than pixels

When I was a baby designer I was really good at pushing pixels around. Getting them into the right place. Making them all perfectly aligned. Making sure they were all having a nice little elegant conversation on the screen. Making sure they got along. I still enjoy doing it. It’s why I became a designer!

But to be a better designer, a good designer, you need to graduate from the pixel. The pixel is the absolute smallest unit of measurement you can design. Get bigger. To be a good designer you need to care about more than the cleverness of your ideas: You need to care about how those ideas affect people. You need to care about the people on the other side of the screen more than you care about what you’re putting on the screen.

You need to care how your work affects their world. You have chosen a profession that touches people’s lives. And that’s an amazing responsibility. And ultimately, the way you can tell you’re getting better as a designer is when you stop caring about the stuff you do, and start caring about the stuff they do.

When someone gets to spend an extra hour with their kid or with their dog or with their family, or sitting alone with a book, or at a show, or whatever, because of something you did? That’s when you’re getting better as a designer.

If you have a question, email me and I’ll be happy to answer it. Maybe. If it’s a good question, and answering it could help a lot of people, I’ll be more likely to answer it. “Should I quit my job because my boss is a dick?” is not a good question (and you already know what the answer is anyway).


Helping designers thrive.

Mike Monteiro

Written by

English is my second language. You were my first.



Helping designers thrive. A Medium publication about UX/UI design.

Mike Monteiro

Written by

English is my second language. You were my first.



Helping designers thrive. A Medium publication about UX/UI design.

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