My First Big Screw-Up: Lessons From 8 Top Designers

It happens to the best of us—even the likes of Susan Kare, Sagi Haviv, and Tobias Frere-Jones.

My First Big Screw-Up: Lessons From 8 Top Designers
[Photo: WestLight/iStock]

Every successful career has its fair share of failures. The most memorable ones often happen early on—when you’re trying so hard to prove yourself, and haven’t yet realized that screwing up is an inevitable part of getting better. You will make a mess of things many more times throughout your career, but the sting of that first big one never quite goes away.


Fortunately for us, our favorite designers have also made their fair share of mistakes, and it didn’t keep them from getting where they are now. Type designers sometimes screw up a font’s weight. Identity designers are haunted by the failed logos of projects passed. Susan Kare, for her part, designed an icon for systems failure—that turned out to be a failure itself. (Why? It scared people.)

We asked eight designers to divulge: what was your first big work screw-up? Check out their answers below (and when you’re done, read about their other career firsts here, here, and here).

Sagi Haviv, Partner And Designer At Chermayeff & Geismar & Haviv

My partner Ivan Chermayeff has always said: Never present something to a client that you cannot live with, because they will pick that one, and you’ll be blamed for it. Despite hearing this over and over, I had to go through the experience to learn it for myself.

A few years ago, we were retained by a major financial company to revise their identity. We thought there was an opportunity there to create a good modern mark—but we were very wrong. They asked that we present a revised version of an old-fashioned mark from their history as one of the design options.

We thought we could argue them away from it, so we presented it, alongside other, better options. They immediately picked the worst option—they are delighted with it!


I see this logo almost every day in every media—a painful and constant reminder that Ivan was right.

[Image: courtesy Susan Kare]

Susan Kare, Product Design Lead At Pinterest

Not a screw-up, but a fail! : n )

Because user interface graphic design isn’t an exact science, images can be perceived differently by different people. I was asked to design an icon for the Macintosh to symbolize system failure, and was assured that it would rarely be seen, if ever, because a severe error like that would almost never happen. The icon we chose resembled a cartoon bomb, based on my fond childhood memories of Looney Tunes. I’m sorry to report that shortly after the Mac shipped, a call from a frantic user was forwarded to the software group; someone had seen an error message with the bomb and was worried that their computer might blow up!

Erik Carter, Graphic Designer & Art Director

I screw up all the time, in work and in life, but here’s a select list of frequent follies:

-Saying “Yes” to a job when I clearly don’t have the time to do it


-Sending files to the wrong “Dan”

-Inconsistent CMYK levels

-Forgetting to send invoices

-Forgetting to follow up on invoices

-Bad kerning


-Lazy typography

-Getting “inspired” by a design I found on Tumblr

-Intentionally insulting certain sects of graphic design on Twitter in order to distance yourself from a perceived set of ethos but really just hurting your reputation and losing jobs

-Way undercharging on practically everything

-Starting every email with “Hey guys”


-“Forgetting” to reply to emails

-Burning bridges with an intern who of course later becomes an art director

-Going out to lunch instead of meeting a deadline

-Missing the revised deadline

-Missing the final, final deadline


-Putting my career first, everything else second, leading to the inevitable collapse of nearly every meaningful relationship I’ve tried to maintain

Tracy Ma, Graphic Designer

Working for a married couple.

Tobias Frere-Jones, Founder And Design Director Of Frere-Jones Type

While my boss was out of town (and unable to see what I was doing) I spent a week digitizing the wrong weight of a family for a client. It ended with him yelling over a scratchy overseas phone call: NO NO DON’T DO THE MEDIUM. STOP. WHAT? YES, STOP. THEY NEED THE BOLD. GOT IT? YES? THE GATE IS CLOSING. BOLD NOT MEDIUM. BOLD.

Alexander Tochilovsky, Curator Of The Cooper Union’s Herb Lubalin Study Center Of Design And Typography

My first big screw-up happened a year or so into my first design job. I designed a collateral system for an event, which included an invitation card, envelopes, reply cards, etc. It was also the first job I got to go on a press check for, and was responsible for signing off on. I was nervous but excited that I was trusted to do this on my own. During the press check, I had to proof everything one last time—mostly checking for color and alignment. I also reviewed the text one more time. Something didn’t seem right with one of the phone numbers listed on one of the cards, but I didn’t listen to my gut and signed off on it anyways. Sure enough, the phone number turned out to be incorrect, and the job had to be reprinted, costing a decent amount of money. I learned to listen to my gut more often from then on.

Luke Woods, Head Of Product Design At Facebook

I’ve made plenty of screw-ups, but the mistake I consider my biggest is not telling people how much I appreciate them often enough. So many people took risks on me, helped me get access to opportunities and taught me invaluable lessons about design. Without them I wouldn’t be where I am today and I hope they know how much I appreciate them. I wish I had shared my gratitude more often and try to pay this forward by helping others as much as I can.


Marisa Gallagher, Head Of Design At Amazon Music

I got lost in the desert. It was one of my first big “lead” roles on a project and I was so excited to get to a big vision that I came up with a super-complicated approach that I was having a hard time even explaining to my boss—the day before our big stakeholder review. He did the most compassionate thing and totally called me on it: he stopped me cold with a “Well, what is the goal you’re trying to hit?” D’oh. Right. Had totally lost the thread, missed the point. Mortifying. The question instantly cleared my thinking, though, enabled me to get to a good review (and rest of the project), and has kept me out of countless deserts since.

About the author

Meg Miller is an associate editor at Co.Design covering art, technology, and design.