More than a decade ago, I worked at IDEO as a design intern. I was in graphic design grad school at the time and I was accepted into the agency’s summer placement program. IDEO, even as an intern, was a prestigious gig to land.

Little did I know it would lead to the most embarrassing moment of my career.

Like any design agency, IDEO’s projects were highly variable depending on the client. My first project was a poster for an extension brush that the elderly could use in the shower. My next, and biggest project, was production graphics for the Korean megabrand Beanpole. And my last project was to innovate on pants for Levi’s.

Based on the title of this post, maybe you can guess what happened next.

Pre-smartphones, so I only have this one blurry photo from this fateful day.

Levi’s had signed up for a creative workshop (“salon series”) with our design team. The plan was for us to spend a few days brainstorming amongst ourselves, followed by a few afternoons of collaboration with their leadership. Essentially we were trying to improve pants. How might we demystify the purchase process? How might we make zippers obsolete? How might we bring back bell-bottoms?

You get the idea. We put lots of sticky notes on walls.

During one of our early brainstorms – “Project Toolbelt” – we wrote up a massive list of every possible idea we could think of to make pants better. I was the amanuensis. I diligently wrote down every idea the team came up with. We were printing our output onto lifesize posterboards, eventually to be dispersed around the office for Levi’s leadership to peruse.

No-pinch zipper
Built-in belt
Laser-guided fitting room

I typed and typed. As we filled up each posterboard, I’d send it to the massive printers in the back office, where another intern would supervise the print and paste process. We churned out poster after poster.

Magnetic buttons
Convertible shorts
Tear-proof fabric
Masturbation pocket
…

The leader of our team shouted the last one with glee. He had drawn an elaborate concept for a concealed pocket, where you could slip your hand and you know...do your thing...without anyone noticing. I was the intern so I wrote it down – who was I to deviate from my instructions? We had a brief laugh and the ideas kept flowing.

When it came time to print the last poster, I sheepishly asked our leader if I should keep his idea on the list. “Do you want me to um, delete the master..the uh...the pocket one?” Of course, he said, that was just a joke. Obviously I should delete it. So I did. Masturbation pocket expunged. Rubbed out. Deleted.

Print.

The next day, the Levi’s leadership team arrived at the office to perform a “Gallery Walk”. They were going to browse our idea boards and paste little red dots on anything that appealed to them. Whichever ideas got the most red dots would make it to the next round to be “synthesized”.

Right before they arrived, our production manager rushed over to me and asked if I could resend the files from the day before. Something had gone wrong with the printing. I hurriedly reopened the files and sent them over. As the posters were printed – this time successfully – they were arranged like a fort. 8’-high posterboards towering over the catered lunch that awaited our clients.

The Levi’s team sauntered in and began surveying our work. Red dots started peppering the pages. Our creative team stood off to the side, nervously watching our ideas get critiqued by the Important Men. We had prepared to discuss each idea in detail. We had illustrations, models, and ev…

“Masturbation POCKET?! MASTURBATION! POCKET?”

One of the bosses chortled these words loudly to the room. Everyone froze.

My eyes rapidly darted between the posterboard – where “masturbation pocket” was printed in bold letters right there on the 8’ tall page – and my team leader, who was staring at me the way you might stare at a soccer ball after scoring an own-goal. Betrayed by an inert object.

Our team was motionless. Meanwhile the rest of Levi’s leadership huddled giddily around the not-deleted-after-all bullet point for how to make pants better. How might we let our customers masturba...you get the idea.

In that brief moment, I imagined myself getting fired 100 different ways. Surely it would happen soon. As a crowd grew around my mistake, I wondered if the Levi’s team would storm out before or after I got fired. Maybe we’d leave together – me, the disgraced intern who ruined the project, and them, the enraged client who had wasted money on immature creatives.

In those deathly 10 seconds of silence I realized what had happened. When I was asked to reprint the files, I had opened the saved version of the project. The version I had tried to print the day before – the one where I had deleted the pleasure pocket – was correct when I printed it that afternoon, but I hadn’t saved my changes. When I reprinted it in the morning I just assumed the file was good to go. It wasn’t.

“Ha that’s hilarious.”

The bossman who spotted my mistake chuckled as he gave it a red sticker of approval. His teammates followed suit. Each of them inspected it up close, muttered a snicker of endorsement, and left behind one of their red stickers.

Masturbation pocket was the most popular idea of the day.

Our team breathed a sign of relief.

I didn’t get fired.

Very Long Press

The Masturbation Pocket