“Best Advice” is a recurring column on The Message, in which industry veterans Jack Neary and Kevin Spreekmeester—and some of their colleagues—dispense practical advice for people who are just entering the industry.

This week Best Advice talks with Jae Goodman, CEO of Observatory. Jointly backed by Stagwell Media and Creative Artists Agency (CAA), Observatory has won best-in-show at every major creative award show globally, including four Cannes Lions Grand Prix, four Emmys and the 2018 YouTube Ad of the Year ‘That Rewrites the Rules’.

Observatory’s Effie record includes three gold Effie’s and five Top-Twenty rankings in the Effie North American Effectiveness Index. Los Angeles-based Goodman, meanwhile, has been named to Fast Company’s Most Creative People in Business 1000, Adweek’s Creative 100, Ad Age’s Creativity 50, and PRWeek’s Hot List.

What were some of your early career challenges you wish someone had warned you about?

To be honest, my biggest early challenges were totally self-inflicted. I wish someone had warned me about my own blind spots. There were several that were correlated.

Homework! I didn’t always do my research, and this made me feel both unprepared and insecure. In meetings with colleagues, clients and collaborators, my inside voice would be screaming, “Jae, you really should know more about the situation you’re stepping into here. Why didn’t you go to their restaurant and taste their food? Why didn’t you go to a dealership and test-drive the car? Why didn’t you call someone who works in their industry and get their point-of-view? Why didn’t you watch this director’s movies and ads so you could reference their work?”

Feeling unprepared and insecure would lead me to the next problem: Not asking simple questions. As the most junior person in the room, I felt like I should be the one who had researched the most. Because I hadn’t done my homework, I was afraid to embarrass myself by asking simple questions.

Which leads me to my next challenge: Feeling like I had to prove I was the smartest person in the room, often in the face of it being very clear I was not. So there I am, feeling like I had something to prove. This is a recipe for panic, bravado, attempted conversational sleight-of-hand—“…Here’s something semi-correlated that I happen to know a lot about, so I’ll blurt it out and hope for the best!”—and worse.

So, basically, my early challenges can be summed up as me being a train wreck in important meetings.

If I had to do my first hundred professional interactions over again, I would do my homework, ask the questions that come to mind, and generally get over myself as far as attempting to impress anyone.

What was the most valuable lesson you learned early on?

Oooh, there are lots of early, valuable lessons. But this one sticks out: I had just joined Wieden+Kennedy. My boss Andy Berndt and I were walking out of a meeting in Redmond, Washington, world headquarters of Microsoft. I was feeling quite good about myself, having convinced a room full of mid-level executives to see things our way.

“We won!” I exclaimed.

Andy put his arm around me, and I thought “Here it comes… the congratulatory moment…” and Andy says, “Well, I guess we got what we came for, but if right now you’re feeling like we won and our clients lost, then how do you imagine they’re feeling? You know they pay us, right?”

While it was, and still is, my job to offer advice and counsel, to sell ideas and business solutions, it’s definitely not my job to leave people feeling like they’ve been “beaten” in a debate. A valuable lesson, indeed.

Who did you lean on most in your early days? How did that dynamic work?

I leaned on some legends who had no idea I was leaning on them. Early in my career, I worked for a legendary music promoter and then a legendary ski filmmaker. While it wasn’t necessarily my job to work directly with them, I studied their every move. These were mavericks, real pioneers in their industries, creative souls who built massive businesses by following their instincts and dreams. I watched when they listened and when they spoke, when they commanded a room or let the conversation flow around them, who they surrounded themselves with, how they sold ideas… I learned a lot.

Did you ever make any missteps that really mattered, and how did you recover?

More than once in my early career I sold an idea without having any sense of whether it was actually possible to produce it. Recovering from this misstep involves these wonderful humans called producers. The best ones can make anything happen, given enough time and money. I owe more than a few producers a lifelong debt of gratitude, and I probably owe some of them actual cash. I’ve also had enough uncomfortable client conversations about time and money that today I would never think of presenting an idea without knowing it’s possible—even if it’s never been done before—and can be delivered on time and on budget.

I also talked too much. I still do. The advice I give myself all the time is “Listen.” On this one, I need to listen to my own advice.

What should young people be most aware of when starting in the industry today?

There are no rules. I know that sounds like bullshit, but seriously, all bets are off. Interruptive ads are not the answer. We all fast-forward commercials on our TVs, or we look away from the TV to the device in our hand, which has mobile ad-blockers, or on YouTube we look at another window while counting down six seconds before clicking the “skip” button. If no one is watching ads—meaning no one is playing by the old rules—then what are the new rules?

Make a Broadway play—Skittles did. Make a statue—Fearless Girl seemed to get her point across. Make a hit song—Willie Nelson’s cover of Coldplay’s “The Scientist” was created for Chipotle and it became the number one song in iTunes Country. You can make content and experiences that attract and engage audiences while simultaneously driving brand and business results. But, in order to do it, you’re going to have to break some rules.

If you had to boil down your best advice, what’s the one Golden Rule for someone planning a career in marketing today?

Read Tibor Kalman’s manifesto, Verlyn Klinkenborg’s Several Short Sentences on Writing, Michael Lewis’ Coach and Ed Catmull’s Creativity, Inc. I give each of these to at least a dozen people a year.

Oh, you said be succinct? The Golden rule? How about the Golden Triangle? Be bold, be nice, and listen.