Bill Connolly’s insights on work, marketing and comedy

By @SimonCocking. Great interview with Bill Connolly Storyteller, Speaker, Leader . Contributor to . &. Author 2 books, & .

Your background briefly?

I’ve long been interested in the connection between marketing and psychology. My entire career has been spent working in marketing and content strategy, as well as developing personal branding blueprints for entrepreneurs and executives. Early on, as a hobby I started performing comedy. Soon after, I recognized that the skills required to get on stage were the same as the skills required to succeed in the workplace. This realization sparked a passion for helping people develop their “softer” skills, like public speaking, creativity, and leadership. In a world driven by technology, people still are motivated by a human connection. I’ve tried to marry my marketing, psychology, and comedy passion into something of a career.

Does it feel like a logical progression to where you are now?

I’m not sure that it’s a logical progression, but the more I study success, the more I learn that most success stories are “illogical.” I try and think of my career (and my life) through a lens: Helping people gain better self-understanding, and develop personal paths to success. When I think about the jobs, projects, and relationships I’ve taken on throughout my career, none of them may seem logical, but if they fit into that broader lens, I see them as a positive use of my time. I’d be lying if I said that I had a master plan, or even a distinct roadmap for where it will end up, but I’m confident that if I remain focused on the vision, interesting opportunities will continue to find me.


We love the subtitle to Success Disconnect. Tell our readers why this might be?

If you look up the definition of “success” in the dictionary, it is something to the effect of, “the acquisition of wealth, power, and honor.” Isn’t that such a broken model for defining how individuals feel success, especially today? The subtitle, “Why the Smartest People Choose Meaning Over Money,” is a bit misleading in the sense that not everyone will make that choice, rather, it is meant to illustrate that success can be defined in many varying ways, and the most fulfilled people tend to prioritize a deeper meaning in their work over personal wealth. One primary reason is that we are creatures of habit. In other words, human beings get used to our circumstances, and there are diminishing returns as a result. If you are wealthy, making more money won’t provide as much fulfillment as it once did. But there are other ideals that we don’t habituate to, such as meaning, seeking challenging work, building relationships.

And how did you research / explore this theory to show the importance of it?

Success is wildly complex, and certainly, I knew that it would take more than a book to fully understand it. For my purposes, I took a qualitatively-led approach, and used quantitative third-party research to help support the arguments. Because success is such a highly personal ideal, I aimed to feature case studies with unique perspectives and pathways to success: A professional basketball player who was forced by injury to shift and became an administrator at a New York City high school. Someone who battled hard drug use and recovered to create a multi-million dollar business. I believe that everyone has specific experiences that define what they value in their lives. Additionally, I worked with a clinical psychiatrist at Columbia University to help identify the trends and characteristics required to overcome trauma, build resilience, and ultimately succeed.

Are we seeing a rise in the people, who, after a certain level of income, would ‘rather learn than earn’?

The short answer is, yes. In the book I feature research from a company called Imperative that has defined, among others, “purpose-driven employees.” Without placing a value judgment, it used to be that people found meaning in their jobs by making a living wage to provide for their families. They followed the belief that you work, build a career, and then give back. Today, more and more people, particularly millennials, are wanting to do all of those things at once. It’s not better or worse, it is just different. Companies need to structure their employee programs to recognize those interests, and society needs to catch up as well.

What tips would you give to others looking to find the right work role for them?

First, I tell people that it’s alright to make mistakes. In our hyperconnected world, where everyone shares every micro-success they have on social channels, there is so much pressure to always be performing. And the reality is that we all fall flat on our faces sometimes. That’s not a problem, it’s part of being human. So that’s the first thing, be willing to make mistakes. Secondly, I would say to stop looking for a specific role, and look for an opportunity that allows you to use the skills you value most, and affords you a good mixture of relationship-building, growth, and work/life integration. Also, build relationships well before you need them. I take meetings with people all of the time, just to learn about their interests and perspectives. Most of the time, that cross-section of information is the most that comes from the interaction. But once in a while, a great opportunity to work together also results, sometimes further down the line. So be open to where your career can take you.

Are we reaching the point where ‘work’ becomes a series of different paying gigs with multiple clients?

For many people, yes. The idea of work is more fluid than ever before. And people, like myself, have multiple side interests and hobbies that bleed into their careers. Certainly, this can cause stress and disorganization if not managed properly. But when done successfully, it can result in a far more impactful skillset, and a more fulfilling career. In a world where we are all ultra-connected and working at all times, we need to have passion and interests that can give us new perspectives. In comedy, there is a quote I love, “The job of the improviser is to lead an interesting life and share it with others on stage.” The same is true in our careers.

How do you blend all your different interests?

As I said, I try and connect them where appropriate, and I’m fortunate that the skills required to do well in comedy are the same required to do well in business. People still run the world, we still buy from people, we still are motivated by people. What I’ve done isn’t unique, everyone can find a way to integrate their passion, hobby, and career. In my experience, it will make you more effective in each focus area.

I’ve always enjoyed those comedians that tell stories first and make me laugh second, Eddie Izzard, Stuart Lee. What’s your style of comedy? 

I typically perform improvisational comedy, so I make up each set on the spot, along with a cast of other performers. Each show is the only one of its kind. In improv, your question is particularly relevant. Trying to be funny might be the way to a quick laugh, but it won’t result in the deeper engagement you’re referencing with really talented comedians. We’re taught to replicate real life situations on stage, and they will become funny. Because life is funny enough, sad enough, frustrating enough. In comedy as in business, focusing on the relationship is the most effective way to make an impact on an audience.

Anything else we should have asked / you’d like to add?

I tell everyone to try and not take life too seriously. Take chances, live without regrets, of course these are wonderful principles. But we get stuck in our routines and it can be easy to get caught up in our day-to-day challenges and stressors. Let yourself find contentment in what you have done, in who you are, in what you have to offer. Because it is more than enough. Be specific about what you want, and then take decisive action to get there. Wishing all of your readers personal success!

If you would like to have your company featured in the Irish Tech News Business Showcase, get in contact with us at [email protected] or on Twitter: @SimonCocking

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