“Everyone Has a Cool Story:” Advice from Marketer and Comedian Bill Connolly

bill connnolly director of content monotype

By Susan Johnston Taylor, Freelance Writer

No Doubt About It

By day, Bill Connolly leads global content strategy at visual marketing company Monotype. By night, he performs improv and sketch comedy. Connolly combines his marketing and comedy skills in his work as an author, branding consultant, and public speaker.

He’s authored two books, The Success Disconnect: Why the Smartest People Choose Meaning Over Money and Funny Business: Build Your Soft Skills Through Comedy, and is a frequent speaker on personal branding, marketing strategy, and more.

We turned to Connolly to find out how he handles self-doubt, what he learned from writing his first book, and where he sees content marketing headed in the future. The following conversation has been edited for clarity and brevity.


The Beat: What challenges have you overcome to get where you are now professionally?


Bill Connolly: Pretty much everybody has to overcome their own personal challenges to succeed. I really think that our biggest roadblocks are in our own minds, and that has been certainly true for me. I've had to overcome a lot of second-guessing of myself, and a lot of failure, because I think if you want to succeed you have to put yourself out there. And putting yourself out there, you become vulnerable, and a lot of times it doesn't work out. You have to learn to be okay with that and live in that.

How did you learn to be okay with that and overcome the second-guessing?

I don't think it gets easier. I had a professional failure just recently, and it still sucked, but you have to tell yourself that it's all part of the game. Honestly, most people just play everything safe. When I wrote my first book, people told me I wasn't qualified to write a book, and I didn't have anything to say, and I shouldn't have written a book. They may have been right, but I was still like, "I don't care, I'm going to do it anyway." And honestly, I don't know if my first book was any good, but I certainly learned a hell of a lot from doing it, and I don't regret working on something that I care about.

I think you have to just keep reminding yourself that, and I think you have to also align yourself with people who are going to be realistic with you but are also going to build you up and not tear you down. You need people that are there to support you and your dreams, but aren't just going to blow smoke. They’re going to help you get where you want to go.

What were some of those lessons from your first book?

Well, I think one of the lessons was how valuable and meaningful it can be to pour yourself into a big project like that. We're so focused today in society on short-term creativity and being tethered and constantly producing just to stay relevant that it's easy to forget that some of the most compelling projects are ones that you have to work on really hard and for a really long time. So that was a big lesson.

I also just think I learned a lot about people. I talked to hundreds of people during that process and they all had just wildly interesting and different stories. And that very much ignited me as both a content producer as well as comedian and a performer. And that I wanted to explore humanity in that way.

What do you think makes for good content marketing?

It’s got to be human. I think that good content marketing tells a compelling story that provides value to the end user. What a lot of companies get wrong about it is they focus too heavily on their own products and on their own sales strategy.

Certainly, no company is doing content marketing without wanting it to lead to sales, unless you're a journalistic organization or something. I think that a lot of companies shoehorn their product and they don't take into account what their reader will find valuable.

I want to approach content marketing from a strategic value standpoint. Is what I'm creating adding value to the consumers’ lives even if they don't end up purchasing anything from us?

Where do you see content marketing heading in the future?

I think content marketing is pervasive across every medium. There was a big boom in content and companies needing an inbound marketing strategy and needing to create content more effectively. It's going to become continually more pervasive. And I think you'll start to see other departments and other parts of the organization use content in a more natural way.

How do you define good writing?

The Supreme Court defines pornography by saying "you'll know it when you see it,” and I think that's that same with how you know good writing. You'll know it when you see it. I think good writing is anything that moves you. And that doesn't necessarily mean that it has to emotionally move you. Anything that makes you think or moves you to take some sort of action. Or makes you question what you thought to be true previously. I think that's good writing and it takes form in a million different varieties which is why it's hard to put tactical constraints on what makes good writing.


Anything else you want to add before we sign off?

I think everyone has a cool story to tell and I want to emphasize that point. People instinctively undervalue their intelligence. One of the biggest things I hear when I talk to people or try to generate content is, “I have nothing good to say.” The reality is, most of the time, the things that you consider to be simple day-to-day tactics or strategies or thought processes, many people might find value in because it might not be how they think or behave. Never downplay the value you have in your own unique experience.


Amen to that. Check out Bill’s latest book: