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  • Writer's pictureJeff Eaker

Winning Worst.

Updated: Aug 1, 2021

I was a real bratty little shit when I started in this business. I totally thought I was hot stuff and I wish I could go back in time and punch myself in the throat.

I started my first job as a junior copywriter at Leo Burnett in Chicago about six days after graduation. I went to the University of Texas and did the Texas Creative Program which was absolutely phenomenal. At the time, it was maybe the hottest creative program in the country. I got my whole book put together as an undergraduate and at our final review there were agency people with jobs to hand out. I was lucky. I got one.

But as is the case for many, my path to the glamorous world of advertising was a circuitous one.

When I went off to college I had absolutely no clue what I wanted to do. Totally zero idea. And as more and more of my friends declared their majors and set out on their paths to glory, the more freaked out I got about having absolutely no inkling of what I wanted to do with my life. So in the absence of any particular ambition, I decided pre-med was the way to go. Seemed easy enough. Take the classes. Go to medical school. Do a residency. Buy a Mercedes.

Cool. I’m glad I finally got that figured out. Let’s party.

So off I went to pursue my journey of becoming a doctor and Mercedes Benz driver. What I quickly discovered, was that shit is hard. The successful pre-med students just got it. They worked hard but it came fairly naturally to them. This was not the case for me. I studied twice as much and did half as well. So as I puttered along and my GPA got lower and lower I started to go through the mental bargaining process of being a lower tier pre-med student.

You start off with Harvard Med as your school of destiny. As time goes by and the GPA descends you begin to consider other non-Harvard institutions. As it plummets you begin to get creative.

There was a school in Grenada that you could get into with the GPA trajectory I was on. But after Organic Chemistry I would need to continue my search. I started looking at Mexico. There were some fine institutions there that I could still probably sneak my way into if I nailed the MCAT.

Biochemistry dashed those hopes.

That’s when you start to consider dental school. Which was fine with me. My dentist was a good guy. He seemed pretty happy. He didn’t have a Mercedes but I bet he could get his hands on prodigious quantities of nitrous oxide.

But the bargaining continued even on the dental path. Zoology 220 is seriously crazy hard. I didn’t know what the fuck that guy was talking about. Even the syllabus was tricky for me.

Which left me with my last option.

The US Navy.

I’d enlist. I’d go through the Navy’s dental school. I’d owe them seven years after that. And then I’d be set. I’d be a dentist. And I wouldn’t have to worry anymore about making all of these major life decisions which were really bumming me out and getting in the way of my college experience. Dentistry would be fine. I’d just learn the stuff. And do the job. Easy peasy. Done and done. Whip-it anyone?

But then came Organic Chemistry 2. The sequel. Fuck. That. Shit.


One of my best friends was in the advertising program. This asshole would go on to do some amazingly famous work at some amazingly famous agencies and now owns his own shop. Such a talented guy. Such a great person. Yes, I’m jealous. But I am so proud of him and what he’s accomplished. If you’re reading this, I love you brother.


He told me to go talk to Deborah Morrison. And if you don’t know who Deborah Morrison is, just Google her. Type in most amazing woman to ever walk the planet. She’ll come up. Oprah comes up first. But if you scroll down just a little bit you’ll get to Deborah Morrison. She was the person who not only gave me my passion for advertising but also said the most magical phrase anyone had ever uttered to me in my entire life.

“No one in advertising will ever give a shit about your GPA.”

That did it. I’m in. Sign me up.

Three semesters later and I’m in the lobby of Leo Burnett Chicago. I don’t care what you say about Leo. I know things change. I know all the hottest stuff about all the hottest places and all that jazz. Don’t need to hear it. Going to Leo Burnett Chicago as a junior is like going to graduate school at Harvard and getting paid for it.

I don’t know if they still do it this way, but when I was there you begin in what’s called the Associate Program. It’s cool because they usually hire all the associates at once. So you’re all kind of in the same boat. It’s like being in a pledge class. There were like 20 of us. All kids. We hung out together. We partied together. And we leaned on each other. I’d end up working for a few people in that pledge class later on in life. Which is humbling but also great because they sort of feel sorry for you and cut you a little more slack than other people.

The first thing they do is team you up with your partner. Then they stick you into various groups around the agency that have different accounts. There was Kellogg’s, Nintendo, Reebok, Dewar’s. United Airlines. McDonalds. Altoids! Hallmark. Miller Lite. Jesus, they had everything. So you got put into one of these groups. And then every 4 months they would rotate you to a new group. Once you found your home, you stayed.

You got amazing training. Great mentoring. And so many opportunities to learn from watching other people. The big presentations were called CRC’s. Creative Review Committees. You could go around and sit in on big CRC’s and watch. There’d be a line out the door of creative directors holding boards under their arms full of Miller Lite ideas. You’d sit crisscross applesauce on the floor in the back and watch. You learned so much just by watching other people present their work. I went to every CRC that I could.

I was really lucky that I got at least a few years in the business before the holding companies took over. Advertising agencies used to warehouse their talent. It’s not like today where every salary needs to be covered by a client scope. In those days, agencies wanted their benches to be as deep as possible. They had so many great creative directors. I ended up working for one of the best in the entire place.

He’s the most amazing presenter I’ve ever seen in my entire life and trust me when I say I’ve seen a lot of amazing presenters. Holy. Shit. Could this guy sell.

He was so funny. I mean genuinely hysterical funny. It was like being around Dave Chappelle. And so likeable. He was good looking. Charming. Brilliant. And everyone loved him and still does. I got so lucky to work for this guy and he took me under his wing and I just idolized him. Every day I couldn’t wait to see him and present something to him or watch him present something to someone else. This guy was so fucking good. And to this day I’m still inspired by him.

So that’s how I started my career. And after a few years and a few tiny awards I really believed I was going to be the next great advertising superstar. When I swung, I swung for the fences every single time. To continue with the baseball analogies, which advertising is full of, I did not throw fast balls down the middle. I was there to throw the curve balls. We were the kids in the room. The MTV generation. They wanted us as out there as possible. The weirder the better. Which was so much fun. And we all had a great time being in these enormous meetings with these enormous clients and all they wanted was for us to be goofballs and bring in the MTV stuff. Which sounds horribly dated. But fuck you. I’m Gen X. And Gen X is cool ‘til death.


But then you go other places. Places that aren’t like that. Places that want you to be young and weird but still bring in the shitty stuff that they could actually sell.

Well I didn’t do that. I was too good for that. I didn’t do shitty. If I didn’t altogether just turn down the assignment, I’d go completely off strategy and do something weird that they couldn’t use. Fuck it. There was always another team on the assignment. Let them do the shitty work. Fine with me man. Whatever.

This is a horrible way to act.

Do not do this.

It will get you nowhere. Trust me. I know where nowhere is.

I was not a misunderstood genius. I was an asshole and I needed to grow up. Yes, you should shoot for the moon. But for God sakes, man. Be a professional and bring usable, sellable stuff that answers the brief and will please the client too.

And pro tip. Always show the usable, sellable stuff first. It calms the client. They know they have what they need and it won’t get them fired. That relaxes them. You can actually see them lean back in their chairs a little. That’s when you show them the fun stuff. Twist their arm a little and you can get it into testing along with the meatballs. Then it has a chance.

That’s how you should operate. Like a fucking professional.

So I decided to grow up. It was time to stop being a bratty little shit. And it's actually made me a much better creative, so I'm glad I did.

Even though this happened.

I was working on a giant car account. A bunch of people were out on production. And a bunch of other people were out on vacation. I was pretty much the only writer in the building that day. And that’s the day the assignment from the butthole of shit came in. I remember it like it was yesterday.

Account people have a certain look on their face when they walk into a creative’s office with an incredibly crappy assignment that has to get done quickly. It’s a look of intense meekness. Usually they send the most junior account person possible to deliver these types of assignments. But when the SVP walks into your office with one of these stinkers, you know you’re in for it.

Everything about the assignment was completely prescribed by the client. It had to be this certain type of commercial. And it needed to have this very certain type of person in it. And that person needed to say some very specific stuff. None of which was in the least bit funny or weird or in the slightest way interesting at all.

But it came from the client. Not the little client. And not the little client’s boss. But the big client. The head honcho. The guy with the wallet.

That’s when I learned another great phrase. Not as great as the one Deborah Morrison said to me back at the University of Texas so many years ago. But a pretty great one none the less.

"When you are handed a shit sandwich, it’s best not to nibble."

In other words. Don’t fight it. Do what the fucking client says on this one. Don’t be so God damned precious. This is a business and people’s jobs are depending on you doing yours.

So I ask every ounce of talent and taste I have to temporarily leave my body and I write the script exactly like I’m supposed to. We show it to the big client and he loves it and everyone’s happy. Two days later I’m in a very nice hotel room in Los Angeles getting ready for the pre-pro the next morning.

Phone rings.

It’s my boss.

"Hi, boss."

“Hey Jeff. We’re all down at the bar. Come hang.”

"Cool, boss. I'll be right there."

So I go down to the bar. And it’s kind of like a scene in Goodfellas. The whole crew was down there. My ECD. My CCO. The head of production. And of course the SVP. When I walk in, they greet me like I’m Henry Hill after getting popped for selling cigarettes with Joe Pesci.

“The guest of honor!” My CCO says.

“The man of the hour!” Shouts the head of production.

I realize they’ve probably been in this bar for quite a while now.

“We’re glad you’re here, Jeff. We ordered you a drink.”

"Cool. Thanks, boss."

They all turn to me and raise their glasses.

I’m weirded out. I don’t know what’s going on or what to do. I’m still fairly young and these guys are older and really cool and have been around the block a bunch of times. And now they’re fucking with me.

"What’s up guys?"

“Well, Jeff. We wanted to congratulate you. You’re the winner.”

"Awesome. The winner of what, Boss?"

“Jeff. We make a lot of commercials during the year. And some are great. Some are good. And some suck donkey dicks. But every year, one sucks the most. And this year, it’s yours.”

My heart, soul and major parts of my nervous system begin to shut down.

“Congratulations, Jeff. For being the big winner and making by far the worst commercial we'll do all year, this tab will remain open to you for the rest of the time you’re in LA. It’s all taken care of. Enjoy yourself”

And with that, they all slam their drinks. And one by one, they pat me on the back and walk out of the bar.

I’m left just standing there holding my drink.

Now, if there’s any question. I want to be clear. These people were some of the best people I ever got to work with in my life. They were so cool. They’re all still my friends and have continued to help and support me for years. They weren’t being dicks. They were just having some fun.

It’s a weird business. And I’m glad that I’m still in it and trying to do cool stuff. But I’m really glad that I grew up and I now know how to do my job as good as anyone in this business.

Leo Burnett gave me my first job as a real writer. But these kind and wonderful people turned me into a pro. I still swing for the fences. But now I know how to do it and also be on strategy. And when there’s work that needs to be done that is far from sexy, I don’t leave people hanging like some bratty little shit.

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