Escaping from the Shadows

How A Single Meeting 25 Years Ago Destroyed My Creative Confidence

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Resistance in full force.

Welcome to the inaugural edition of The Creativity Guild! We are kicking this whole shebang off by serving up a personal confession of creative shame.

First, I want to clearly acknowledge that I have had a very lucky career. I know how exceptionally fortunate I am - so this is by no means a pity party and I hope it doesn’t read that way. I’m sharing it as an exploration of how and why we choose our creative paths.

I’m also really nervous about publishing this. But as you will see… getting over the fear of what you might think of me is part of why I’m doing it.

Ready? Here we go…

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Have you ever had a life-changing meeting or moment? A “Sliding Doors” fork in the road where you went down one path and have always wondered about the path not chosen?

This is the story of why I left my job to revisit a single meeting from 25 years ago that changed my life and career path.

Ever since I can remember, I have been drawn to creativity - drawing, writing, performing, music, video, audio… you name it. As a kid, I dreamed of a career in creativity. And at 25 years old, I was on the precipice of making it a reality.

I was about to meet one-on-one with the President of the biggest national TV network in Canada. A broadcasting legend and someone with the power to make an entire career. 

He had a fabulous white mane of flowing hair, was a fan of Nicholas Negroponte’s Being Digital book, and was a prescient thinker about the future of the media. Rumour had it that he had an exotic playback deck in his office that could play any tape format in the world. I was heading into a BIG meeting with a really smart and experienced media guru at a very early stage in my career.

And you’re not going to believe what happened next! (Hat tip, Buzzfeed)

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Before we dive into The Meeting That Changed My Career (TMTCMC), let’s fast forward 25 years to the spring of 2022…

Leaving the company I co-founded

A few months ago, I left my job as the Co-founder of Pacific Content and VP of Podcasting at Rogers Media.

I missed collaborating on creative projects. I missed coming up with show ideas. I missed pitching and signing new clients. I missed telling stories. I missed coming up with marketing strategies for the shows. I missed ALL the best parts of my job that I had relinquished over the years as the company grew and grew.

So I made a fairly momentous career decision to leave and then figure out what I want to do next. 

The Call of Creativity Beckons

It ALWAYS comes back to creativity. I always feel the need to scratch a serious creative itch. I have a continual urge to make something fun, unusual, compelling, or entertaining. 

But here’s the thing… I recently turned 50. FIFTY! I’m supposed to be in the prime of my career! And the more I thought about satisfying my desire to create something new… the more I began to ask worrisome questions of myself.

• “What will everyone think if you leave this great job and you don’t have another big project?”

• “What will everyone think if my next chapter is doing something purely creative?”

• “What happens if everyone hates what I put out? What if it’s not very good?”

• “Aren’t I too old to be creating content for fun? I’m FIFTY! My kids will be mortified! Everyone will make fun of me for being the really lame ‘old dad’ who is trying to have fun.”

• “What if people think I’m trying to copy the Holderness Family or become the world’s oldest TikTok influencer?”

All the chatter in my head is fear-based shaming to try to get me to avoid taking any risks. It is afraid that my creativity will change the way people think about me or embarrass me and my family. Or even more worrisome, it tells me I’m not good enough to make anything purely creative. The voice in my head is, as Steven Pressfield aptly named it, Resistance.

Meet Resistance

I have long been a fan of Pressfield and his seminal book about creativity, “The War of Art.” He has several excellent non-fiction books about the self-imposed challenges and barriers artists must overcome to do their best work and evolve from amateurs to pros. Foremost among those challenges is dealing with Resistance:

“Resistance will tell you anything to keep you from doing your work. It will perjure, fabricate, falsify; seduce, bully, cajole. Resistance is protean. It will assume any form, if that's what it takes to deceive you. It will reason with you like a lawyer or jam a nine-millimeter in your face like a stickup man. Resistance has no conscience. It will pledge anything to get a deal, then double-cross you as soon as your back is turned. If you take Resistance at its word, you deserve everything you get. Resistance is always lying and always full of shit.”

So yes - Resistance has been aggressively shaming me about doing something creative at this age (lack of confidence) and in public (fear of judgment).

Why is Resistance so strong for me?

So how did I get here? Why is this creative urge so strong, and why is the Resistance even stronger? 

When I was a kid, I was obsessed with comedy, cartooning, and writing. I loved SCTV and SNL. I bought all the Far Side and Bloom County anthology books. I bought joke books. I listened to comedy albums, from Rodney Dangerfield to Steven Wright. I discovered authors like Kurt Vonnegut and John Irving, whose imaginations and characters and storytelling chops deeply inspired and daunted me. I even read (and continue to read) ALL THE BOOKS about the behind-the-scenes of comedy, from oral histories of SCTV and SNL, to Steve Martin and Judd Apatow books. 

In high school, I had my first seminal creative moment - a teacher pushed me into doing public speaking and debating, and it changed my life. I was terrified to get up in front of people but also thrilled. I turned it into a form of standup comedy, and I ended up doing a ton of ‘comic essays’ at speaking competitions and school. In university, I took a literature degree with the hopes of learning even more about storytelling and structure. As an extension of my public speaking from high school, I also began doing improv and standup comedy at university, and it became a significant and hugely enjoyable part of my life. After university, I was reluctant to let it go, so some of us started a professional improv troupe that had weekly gigs in a Toronto bar for several years.

Meanwhile, career-wise, I got a summer job at a Toronto TV station and my boss (now a very good friend) somehow agreed to let me do some stories on-camera for a daytime talk show, even though it was weird stuff. I would do things like taking a tour of the Hockey Hall of Fame, but my interviews were constantly disrupted by a hockey player that would bodycheck me out of frame mid-question. I LOVED doing this stuff so much! It was like improv with cameras and editing.

Then I got my first full-time media gig as a producer on a brand new weekly entertainment journalism magazine show called e-Now, which morphed over the years into e-Talk. I was having a blast producing interviews with creatives across the gamut of the entertainment industry - from Oliver Stone to Shania Twain, and from cast members of Beverly Hills 90210 to Oasis! 

But because of my improv background, the programming executives also somehow let me start doing weird stuff on-air on their national Saturday morning block of children’s shows. In between cartoons, there were live-action interstitials, and once a week, I played a half-witted character in an orange jumpsuit that was sent by a computer to random locations. The recurring bit was that I was about the dumbest human alive and would get into trouble wherever I appeared. For example, one week, I went through a car wash on my bicycle.

This led to the pinnacle of my creative life - I was asked to join the production team for a new show for tweens (9-12-year-olds) called RoadCrew. With the other cast members, we would all act, write, produce, and direct. And it would all be improvised in the real world. Think of it as low-budget Spinal Tap or Waiting For Guffman for kids. It was THE BEST. We did 26 half-hour episodes, and we all worked nights, evenings, and weekends because we loved it and wanted to make it great. I remember an Executive Producer telling me, “remember this project because you may never get to do anything like this again. These kinds of projects simply do not happen.”  She was 1000% right.

From there, I was even more inspired. On weekends, a group of us met up at the TV station and made several comedy pilots for a fake documentary series we wanted to pitch to the Comedy Network. Each episode would use the conventions and formats of a particular documentary style, and again, it would be low-budget with a lot of improvisation. Essentially, this show was “Documentary Now” almost 20 years before Documentary Now.

This is when TMTCMC happened.

My boss knew I wanted to do comedy and loved making these mockumentary pilots. However, the network was also opening a brand new TV station in Vancouver, and they needed entertainment journalists on the news team. So to help decide the direction of my career, he set up the big meeting with the President of the entire broadcast network.

Back to the Meeting The Changed My Career (TMTCMC)

So the appointed day and time comes. I am very nervous. I walk into the President’s large, sparse office, note the exotic playback deck that can apparently play any tape format on Earth, and sit across from him at his huge desk. 

Here is a dramatic (but true) recreation of how it went down: 

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FADE IN

INTERIOR - THE OFFICE OF THE NETWORK PRESIDENT

A skinny man (YOUNG STEVE) nervously enters. THE PRESIDENT sits behind his desk and motions for YOUNG STEVE to sit down.

PRESIDENT
So we’re here to decide if you’re going to do comedy or if you’re going to move to Vancouver to be an entertainment reporter. Tell me about your childhood.

YOUNG STEVE
Pardon?

PRESIDENT
Tell me about your childhood.

YOUNG STEVE
It was pretty great. Very ‘Leave It To Beaver’ normal upbringing. I have no complaints.

PRESIDENT
Do you get along with your parents? 

YOUNG STEVE (looking more and more confused and uncomfortable)
Yes, my parents are great, and I have a great relationship with them.

PRESIDENT
No traumatic incidents in your past?

YOUNG STEVE
No - honestly, I’ve been very lucky. I have no complaints about my childhood.

THE PRESIDENT pauses and looks YOUNG STEVE in the eye.

PRESIDENT:
Well, that settles it. You are moving to Vancouver. You will never be funny with a normal childhood and normal parents. Great comedy can only come from a traumatic upbringing. And your mockumentary pilots weren’t that funny. You’re moving to Vancouver to be an entertainment reporter, not a comedian.

FADE OUT.

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And that was it. That was the meeting. That was my fate.

I was not funny.

The Comedy Career Decision Tree (TM)

Do You Have A Shadow Career?

It is here that I want to return to Steven Pressfield. This summer, while exploring the Resistance lurking within me, I also stumbled upon another idea in his writing: Shadow Careers. It DEEPLY resonated with me.

What is a Shadow Career, you might be wondering?

“Sometimes, when we're terrified of embracing our true calling, we'll pursue a shadow calling instead. That shadow career is a metaphor for our real career. Its shape is similar, its contours feel tantalizingly the same. But a shadow career entails no real risk. If we fail at a shadow career, the consequences are meaningless to us. Are you pursuing a shadow career?...

Sometimes we can be professionals in our shadow careers but amateurs in our true calling. How many creative directors at ad agencies have unfinished novels and screenplays sitting in their office drawers?”

So what happened after TMTCMC? 

I moved to Vancouver, became an entertainment reporter, and later had lots of fun doing similar entertainment journalism that focused the spotlight on other creators at places like MuchMusic, AOL, and CBC. I told myself that I was a creative storyteller and would be the person who infused fun and unusual spins on all my work… but almost all my output was focused on showcasing other artists and creative thinkers.

I occasionally dabbled and made the odd video or two of my young kids for a parenting show, or made a comedy video with a friend (we were both obsessed with ‘Tim & Eric Awesome Show, Great Job!’). But that’s it. My dreams of comedy and writing novels and anything else in my own voice kind of died in that room with the President of the network.

To be clear, I don’t blame him in any way - I believe he gave me his best advice and he knows a hell of a lot about broadcasting. However, when you get told you’ll never be funny by someone who’s a BFD, you give it some serious weight. I lost my creative confidence.

And I have had a fantastic career so far. I’ve worked with so many amazing, talented people, been given so many extraordinary opportunities, and had a lot of fun along the way.

It’s just that creative itch that won’t go away, nagging at me in the back of my mind…

Can I Revive The Dream?

I think most people who know me would say that I have a fun sense of humour… but I’m honestly worried that I’m just a bad, cringy dad-joke guy who loves comedy but isn’t actually all that funny. 

And I’m afraid that it’s WAY too late to do anything seriously creative on my own. (Did I mention that I just turned FIFTY???)

And that brings us back to The Creativity Guild. I want to go back in a time machine and stand up for my past self that acquiesced and became a shadow creative / entertainment reporter. I want to fight for the creativity I always wanted to do before the meeting that shook the confidence and belief in myself for a quarter century.

The Creativity Guild is the battle for our creative souls against the powerful forces of Resistance. We are on a public quest to learn how to slay the Resistance, evade shadow careers, and redeem our past. 

The Creativity Guild is not designed for advertisers. 

It’s not filling a time slot for a particular demographic on a television network. 

It’s not a public broadcasting mandate. 

And it’s not solving a brand’s business problem with strategically created content. 

This time, it’s personal. 

This is our journey to explore creativity for its own sake.

So thank you for joining us, whether it is because you see yourself as a fellow self-stifling creative who has pursued shadow careers, or because you simply are curious to see Geoff and I flail around and mortify our friends and families in public. And please... be gentle :-)

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Feedback

Are you in a Shadow Career? Have you had a seminal moment that sent you into a creativity crisis? Geoff and I are curious if you are in the same boat that we are. If you’re up for it, let us know - we’d love to hear from you.