We’ve all had spine-tingling, stomach-roiling episodes of  embarrassment. Whether we slip up ourselves or miss a thousand and one warning signs, we’ve all had OMG moments. However, with time and distance, we can often look back and smile rather than cry. In the spirit of having a collective laugh, we asked a few of our favorite designers to relive a time that made their faces burn.

To get us started, Arianna Orland recalls taking a project shortcut and drawing blood, illustrator Ping Zhu remembers botching her first big break with a major publishing house, and Zak Kyes recounts how he flew all the way to Asia just to be mistaken for someone else. Here are their stories.

Don’t cut corners when no one is watching.
Arianna Orland, Creative director, and founder of Paper Jam Press

I was freelancing in the 2000s, and I had to design these cardboard shipping boxes for one of my clients. It was also my responsibility to ‘comp the box’ – make a facsimile of the final packaging. I had ‘comped’ quite a few boxes in my career, so I thought this was going to be just another job.

Because I was freelance, I didn’t have a studio. I decided to use a service bureau to get the large-scale printouts I needed. And I asked them if I could use their production table. ‘Sure,’ they said. ‘But this is a favor. We can’t have nonemployees using the facility. Whatever you do, don’t cut yourself.’

“The boxes I had done in the past were all on standard card stock. But these were a heavy gauge cardboard: a much thicker challenge for my X-Acto skills. When it was time to cut the cardboard around the curved edge, my hand slipped, and yup, I cut my finger.

X-Acto cuts bleed fast. I was bleeding all over the comp, all over the table, all over the floor. So there I was, a potential liability in someone else’s workspace, and still on a deadline to complete the job.

In a perfect world, I would have mustered the courage to ask for a Band-Aid right then and there. But instead, I told myself, ‘You can’t ask; they’ll kick you out!’ Then I remembered there’s an REI a block away! They’ll have first-aid kits. 

I stuck my finger in my mouth and ran down the street to REI. Thirty minutes later, I was back on the job. I tried to hide my Band-Aided finger for the rest of the day. 

The lesson? Obviously, I can’t resist: Don’t cut corners.

The real lesson? Never attempt to cut a curve on heavy-gauge cardboard with a dull blade.

Take your presentation cues from Madonna.
Sean Adams, Acting chair, Undergraduate and Graduate Graphic Design, Art Center College of Design

In 1996 I was invited to speak at the first AIGA National Business Conference. It was my first major speaking engagement. Most of my friends and design heroes made up the audience.

I was standing backstage, ready to go on, and the organizer told me, ‘I’m sorry, we’re running behind. You need to cut your presentation from thirty minutes to fifteen.’ I stepped up to the podium and began.

Rather than focusing on what I was actually saying, I watched the clock and cut sections of the presentation on the fly. The end result was a schizophrenic mash-up of words that made no sense together. I don’t think I was finishing sentences. Then, the time was up and I received a very, very lukewarm, mostly silent, sad applause.

I was sure I’d ended my career right then and there. I walked Central Park for hours, replaying the train wreck over and over. Soon after, a magazine article singled the presentation out as the ‘worst low point ever’ and suggested, ‘Children should be seen and not heard.’

As awful as this was, it was a blessing. It knocked me down to earth and reminded me that I was not ‘all that.’ It taught me to be prepared down to even seemingly spontaneous comments. I learned that I should have said, ‘No. I prepared for 30 minutes. That’s what I need.’ From that point forward, at each speaking engagement, I took a cue from Madonna demanding that the AV be tested, the lighting fixed, and the timing confirmed. That doesn’t mean becoming a total jerk, just holding my own. Over the thirty years since, I messed up many other times. But mostly because I said something really stupid, not because of something that I didn’t get to say.

Treat every job prospect as an opportunity to break through to the next level.
Ping Zhu, Illustrator

I was still in school, and I went out to New York, where my professors had given me contacts of people to show my portfolio to. One of those people was Rodrigo Corral, an amazing designer who does book covers. 

I met with Rodrigo, showed him my work, and he was very kind. A few weeks after I got back from New York, he wrote to me and said, ‘We’re doing a book cover. Would you be interested in doing the illustration?’

That’s a huge opportunity. Normally when people get a job offer, they stay up all night doing the best they can. But I had no understanding of what it takes to be an illustrator. I didn’t sense the gravity of the situation. So I took it as a school assignment: Come up with some ideas, do some rough sketching, then paint something. I did my sketches on graph paper. I thought, I’ll just use a felt-tip pen, draw something really loose, and put it on paper that’s not even plain.

I sent back some really crummy drawings. But I thought it wasn’t terrible. Rodrigo would understand what I was going for. His email back ‘This isn’t really what I had in mind. Maybe we should just stop here without wasting anyone else’s time.’

I didn’t know what to say. I was so ashamed that he thought, ‘These are so bad, I don’t even want to engage.’ I’ve never cried that hard again for any reason regarding work. I was like, ‘I’m never going to make it. I’m a failure.’ I was desperate. But I was also determined to make things right. As horrifying as that experience was, it shook me into place mentally.

I wrote him an email to say, ‘I’m so sorry. Please take me back. I can do better than this.’ And Rodrigo let me try again. I painted three finals: super refined; everything as polished as possible.

He wrote back, ‘Oh yes, this looks much better.’ Unfortunately, it dropped off the map at that point. He never got back to me on whether they used any of them. At that point, I was too afraid to ask him anything else. In my professional career, I’ve never worked with Rodrigo. Maybe I’ve been blacklisted.

If you ever get an opportunity, just don’t screw it up. Give it everything you’ve got. Do your best. Underperforming won’t get you anything. As horrifying as that experience was, it shook me into place mentally. I said, ‘No more phoning it in. Even if you think it’s okay, you have to do better.’

If Rodrigo ever sees this: I’m very, very, very sorry. But I really hope he doesn’t remember.

A red flag means “stop” not “charge!”
Mac Premo, Stuff Maker, Mac Premo, Inc.

When my wife and I met, we were both broke artists. As we built a life together, she realized that she needed a sense of security. So she got a corporate job as a product manager. I continued making art and was like, ‘This is going to work.’ Then the recession hit and everything took a dive. Nobody was looking for talent. Then this interesting opportunity to work on a print publication came up. I was going to be the everything for it: creative director, making videos, designing the website.

To hear the guy putting it together talk about the project – ‘It should be a print magazine. It should be online. It should be both!’– you could see this history of him not being decisive. One perfect example was when he’d plan how to get from one place to another, his time estimate was always about how long it would take if it was 2 a.m., when there was no traffic on the road. He was constantly running late. That’s indicative of an overpromiser-underdeliverer. That behavior meant we were always late, always stressed out, and I’d have to say to him, ‘No, we can’t possibly have that by the time you promised.’

I’ve gone into situations ignorant to red flags, but more often than not, honestly, I plough through the red flags. Plus, this was the middle of the recession and I had just had a second child, so for a few months, there was economic stability. As things started going bad at the publication, I continued to ignore them with the hope that the stability would continue. He ended up not paying me for a few months of work. It put us in a bad financial situation, and I should have seen it coming.

It was tumultuous. I had to downsize my studio. During that time, my wife was carrying the weight of the whole family. And the whole time, I was thinking, ‘But this is a good idea. It has to work. But he said he was going to pay me. He can’t not.’

About five years ago, my wife quit the corporate world. Now I’m technically the full-time breadwinner. I still get some prospective client calls and hear the dodgy, sketchy, vague talk that I used to hear. But that experience honed my instinctive decision-making skill set. I came out of it learning to trust myself more. Yes, there are times when you kick yourself, but that’s the hard part of freelancing; it’s a leap of faith every time.

Let your work, not your title, define you.
Zak Kyes, Creative director, Zak Group

Confusion is common in projects that have large teams from different cultures. But rarely does it lead to a case of mistaken identity.

Several years ago, a well-known museum in Asia invited me for a site visit to discuss a new project. At the time, I was the director of Zak Group, the graphic design studio I established in 2005. I was also art director of the Architectural Association School of Architecture. 

I landed late at night and was brought directly to a dinner. When I arrived, the museum director hushed the room to introduce me to his team as ‘the great architect from London.’ A polite moment of reverence ensued. This would have been very flattering. But only if I actually was an architect.

While my work as the art director of the Architectural Association had become well known, that certainly didn’t make me an architect. I felt like Brian in Monty Python’s Life of Brian, who is born in a stable right next to Jesus and is mistaken for the Messiah. That story doesn’t end well for Brian. I blurted out, ‘Graphic designer!’ I’m sure this sounded strange as a greeting. The director was puzzled. ‘Architect,’ he corrected me. This went on for some time. I was concerned, even panicked. I thought about going back to the airport. I’ve always fought for more porous boundaries between disciplines, so it felt surreal to be reasserting them.

The result of the confusion was that Zak Group received its first commission to design both the architecture and the graphics for a large-scale, citywide exhibition. It ended up influencing curatorial decisions in ways that would never have been possible if we were ‘just’ a graphic design studio.

Last year, for the first time, an architect joined Zak Group’s team of art directors, graphic designers, developers, and a project manager. She has since been mistaken for a graphic designer.