How to Survive a Layoff and Drive Mega-Clicks with Comedy

You may know the feeling of being laid off. I do.

But do you know the feeling of a coworker throwing you a lifeline when you’re nearly drowning?

I know that one too. For me, that lifeline’s name was Tom Wilson.

Tom and I worked together at the now-defunct Chicago ad agency Element79 in the late-2000s. It was a golden, slightly chaotic stretch—the pioneer days of digital and social.

Tom had landed at Arnold in Washington, D.C., under the legendary ECD Woody Kay. Working at Arnold had been a dream since college. Their reel was a murderers’ row of marketing: TRUTH anti-smoking, Volkswagen “Drivers Wanted,” Ocean Spray “Straight from the Bog,” PNC Bank “Brilliantly Boring.”

Tom got me the interview. The interview got me the job. The job eventually got me the chance to write “Discover the Details” for Sleep Inn hotels—one of my highest-viewership campaigns.

But first, I had to earn it the hard way.

I moved from Chicago to D.C. I went long-distance with my girlfriend (now my wife). I found roommates on Craigslist who turned out to be the most aggressively normal people I’d ever lived with—government contractors who kept army barracks’ schedules. 

In my first months, I wrote on smaller assignments for the agency’s client roster. I kept my head down. Then a juicy brief arrived.

Lucky for me, I was fresh out of comedy sketchwriting classes at Second City. I applied the fundamentals like a man with nothing left to lose (because, at that point, I mostly didn’t). The client picked my scripts.

I also had the good fortune of working under Creative Director Don Corrigan, a mentor with a natural feel for comedy timing. It wasn’t his first rodeo. It was very much mine.

During production, working with the improv comedians was the most fun part. As the writer, you don’t always have much to do on set. The scripts are locked in after all. But I got a few moments to punch up jokes—which was exhilarating on the spot!

Our campaign ran during episodes of the TV show Monk. 

The response was amazing. We got a huge click-through rate to our content—and audiences stuck around without skipping. We even brought home a few industry awards to the agency.

In hindsight, I realize how brave our client was. They supported comedy when many brands find it too risky or not appealing to their audience. But comedy can work, even in places you wouldn’t expect, like this TV spot for Intel. 

That’s because it’s tough to do well. Not many places teach it. And few marketers want to take the risk, or even know, that formulas exist to evaluate the work. 

So, to help the people out, here’s what I learned about using comedy to drive serious click-through rates without flying too close to the sun.

1. Follow Tried-and-True Comedy Structures

Comedy feels subjective until you realize it’s often just good math wearing a funny hat.

One core lesson Second City drills into you is simple: focus on character relationships and keep heightening the scene.

For Sleep Inn, we created two characters who constantly one-upped each other in their jobs and their fastidiousness. Their friction became the engine. We didn’t have to invent new jokes every time—we just kept turning the dial on the same relationship and let the comedy find us.

This approach has a useful side effect: it keeps you from the deadly trap of making fun of the product itself. Disparaging the thing you’re selling is the fastest way for a script to end up in the trash (or worse, on air).

2. Go Ahead and Pander to Your Audience (Just Do It Well)

Our strategy team had an unusually tight media plan. We only aired during Monk. That single decision let us build personalities and scenes that felt native to USA Network’s “Characters Welcome” world.

We then used those same original characters as often as possible across digital and social. Banner ads that normally underperform suddenly delivered huge click-through rates because people already understood the joke and wanted another dose while checking out a hotel brand they might never have considered.

Bottom line: nothing beats original assets instead dropping hacked-up stock photos from orbit.

3. Milk Production for All It’s Worth

Production days are stressful for everyone. For me, they meant either staring at monitors or frantically punching up dialogue and last-minute extras between takes.

We packed the schedule: video shoot, photography shoot, and audio recording, all in the same window.

It was extra work. It also made the difference between a campaign that felt intentional and one that felt held together with screenshots and hope. When we went back to build the digital and social pieces, we had purpose-shot photography instead of frame-grabs from the video. The whole thing looked and felt more polished because it actually was.

I’m not saying you shouldn’t enjoy the craft-services table—I’m just saying I was always glad my CD kept pushing us to polish the work and squeeze every usable asset out of the day.

A layoff can feel devastating. Sometimes it’s just the middle chapter that forces you to write something better than you would’ve otherwise.

If you’re lucky, you get a Tom.

If you’re really lucky, you also get a brief, a mentor who understands comedy, and one more chance to prove the work still matters.

You may even get people to click all the way through.