The Dumbest Problem I Ever Solved

Throughout our careers, we will be asked to solve problems that seem stupid.

We might think: Is this really my job?

We might say: Find someone else to do it.

But I’ve learned this: Sometimes, the stupidest problems are actually the greatest opportunities.

Here’s the story of the stupidest professional thing I’ve ever been asked to do… and why I was happy to do it. It involves Barack Obama and phone sex — though it’s not (quite) as scandalous as it sounds!

The New Kid

Let’s rewind to the fall of 2008. I was 28 years old, and I’d just moved to New York City for a big job. I was the new kid at Men’s Health! And of course, I was very eager to please. I mean, just look at me…

The Dumbest Problem I Ever Solved

My main job was to edit a 20-page section in the magazine. It contained a grab bag of subjects like workouts, weight loss tips, cocktail recipes, and of course, dating and sex advice. The sex stuff wasn’t raunchy, but it was blunt and straightforward: Here’s how to please a woman this or that way, or what sexy things to do in the bedroom, or whatever. It wasn’t really my thing, but hey—it was part of the job.

Usually, the magazine staff knew who’d be on each issue’s cover months ahead of time. But as we were planning the November, 2008 issue, the cover was kept a big secret. Then, finally, towards the end of production, we learned the news: Then-candidate Barack Obama would be our cover guy.

That’s when I got the call from my editor. It went something like this:

Editor: “Hey, we need you to tone the sex stories down because of Obama.”

Me: “What do you mean?”

Editor: “Just… change words so it isn’t so explicit. You have the phrase ‘phone sex’ in there, for example. You can’t use that.”

Me: “So wait, should I just kill the sidebar on phone sex?”

Editor: “No, we don’t have time to produce new stories. Just… use different words.”

I had many questions. Like: Did Obama’s team ask for this? Was my editor just skittish? Did anyone consider how hard it is to reword an entire page of sex advice so that it meets some impossible standard of non-sexiness?

Nobody ever explained. So I got to work.

The Dirty Work Begins

This was not an easy job. Every time I came up with a new phrase for “phone sex,” for example, I’d send it to my editor, who’d send it to the editor in chief, who’d nix it, and then I’d have to start all over again. I was in the office until 11 p.m. doing this.

Finally, we got there. In one part of the page, an advice columnist answered a question that originally said: “My girlfriend lives far away. Any tips for great phone sex?” After my edit, it said…

The Dumbest Problem I Ever Solved

“Ahem, e-relations.” A phrase nobody in the world has ever used—and certainly not poor Pete from Toronto, who the question is credited to. But don’t worry. A little magazine secret: Reader questions are often made up. There was no Pete from Toronto.

On and on it went. I remember we also changed the photo—going from a semi-nude woman to a close-up of two people kissing. The pull quote, which once had something more explicit, now advised men to “ask her yes-or-no questions”. Here’s the whole cursed page, for your amusement:

The Dumbest Problem I Ever Solved

The Lesson In All Of This

What did I learn from this ridiculous experiment, aside from that someone on Obama’s press team possibly hates, ahem, e-relations?

It is this: There are many ways to be a hero.

This was a stupid problem, but it was a problem nonetheless. Somebody had to fix it, nobody else wanted to fix it, and yet the most important person at my company was very invested in it being fixed. This meant that, while it may have felt like a waste of time, it was also a great opportunity to be the hero. It helped me earn a reputation as the guy who solves problems. Need something done? Give it to Feifer—he’ll get it done. That kind of reputation will take you a long way, especially when you’re new and proving yourself.

Ever since that time, I’ve gotten excited when something goes wrong—the dumber the better. When it happens, I’m your guy. Problems are just opportunities to provide the solution. And when you’re the person providing solutions, you’re the person that everyone else needs the most.

Here’s that final cover, by the way:

The Dumbest Problem I Ever Solved

LOL, collector’s edition. If readers only knew!


Finally: Is boredom good or bad?

Tech critics today say that we're never bored, and that's unhealthy. But people have spent thousands of years desperately trying to escape boredom, and even considered it a sin or disease. So should we really feel guilty every time we fill a dull moment with a screen?

In the new episode of my podcast, I dig into the surprisingly fascinating history of boredom — which once terrified America’s Founding Fathers and has long been a symbol of class and status — as well as the science of what boredom does to our brains.

The Dumbest Problem I Ever Solved


I would love to know what you think! Drop me a line anytime.

You’re awesome.