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Please Allow Me to Introduce Myself

The first thing you should know about me is that I've had a squiggly career.

And that's a good thing.

In his book, Control, Alt, Delete, Mitch Joel says that a squiggly career is the new normal. It used to be you'd start a job at a big company and then work your way up, and then eventually out into a blissful retirement.

It looked something like this.

For a lot of people, that's not the way it works anymore. And I for one, am glad. You see, I get bored easily. Hence all the squiggles.

I think my boredom problem stems from growing up in a large family. I'm the seventh of eight kids and I think growing up with so many other people affects you in a few ways.

One, you get so used to constant action and chaos, you get bored easily. And I think too, it made me kind of pushy. You don't think I can do that job? Oh, I can do that job. You think I can't launch that product? Oh, I can launch it, on time, and under budget.

The problem is, I didn't always stop and think about what I was pushing myself into. Would I like it? Was it for me? I had no idea.

So, straight out of university, in the middle of a deep recession, I pushed my way into a newspaper job. I started out in the marketing department and quickly pushed myself into a director position. It was fun at first, at least for me, because I got to analyze vast amounts of data all day. I had an awesome team and we did great work.

And to the outside observer, my story was looking pretty good.

Only to me, it wasn't. Over time, I'd grown restless.

I felt stuck.

Then one day, while in a magazine store, back when people still read print magazines, I noticed that all of the American celebrity magazines had pictures of celebrities taken in Canada because back then, it seemed as if every movie and TV show was shot in Toronto or Vancouver. And I thought, why are we letting Americans cover this for us? Why don't I just launch a Canadian celebrity magazine? So I ran some numbers and convinced the newspaper's board of directors to let me do just that.

And it was pretty cool.

So there I was, thirty-four, and having just launched a national magazine. It was pretty exciting.

For instance, this happened.

Yup, that's George Clooney reading my magazine.

And to the outside observer, my story was looking pretty good.

But I felt stuck.

We had a wonderful group of very talented people putting out a high quality magazine every week, but the truth is, getting newsstand attention was a hard scrabble. Not enough Canadians bought it. We shut it down after eight months. It was a pretty crushing blow for a pusher like me.

But, I didn't let that stop me. Soon, I pushed myself onto the digital side of the newspaper. And it was awesome. I launched four websites and found myself promoted to Vice President. I loved the digital world so much, I started a blog and wrote long posts about the new economics of media.

And Craig Newmark, as in Craig's List found one of them and tweeted it to the world. My blog grew from 25 page views to more than fifty thousand.

And to the outside observer, my story was looking pretty good.

But I felt stuck.

The newspaper industry couldn't move as quickly as I wanted to. No matter, I was laid off a month later. Because that's the way it goes in the newspaper world.

Oh well, I'd always wanted to work in the start-up world anyway. So I pushed my way into a start-up called CanSport LIVE. We worked with amateur sports organizations. Honestly, you don't need to know much more about it.

And to the outside world, my story was looking pretty good.

But I felt stuck.

I had zero passion for the sports world. Zero.

So I went in search of a start-up that really mattered to me. And that's when I met Aron Jones and Matt O'Leary, my co-founders at Shopcaster.

We were aggregating small independent retailers onto an e-commerce platform. Together, we raised a million dollars in VC funding. Soon, I was promoted to CEO. And over the next year and a half, we launched in 20 cities across North America.

This was our launch ad in New York.

F* the Mall was the brilliant idea of Jodee, our head of sales and merchandising. I loved that ad.

And here's an email from Adrian Grenier telling me how much he loved that ad too. No, I don't know why he called himself "Ducontra", but if you look closer, you'll see that it's signed "Adrian." That was a good day.

Shopcaster was named one of Deloitte's Companies to Watch and as one of the Canadian Innovation Exchange's Top 20 Most Innovative Companies. So obviously, to the outside observer, my story was looking pretty good.

But I felt stuck.

This time, I wasn't really sure what was wrong. Despite our success, rather than energized, I was stressed and tired and when I was honest with myself, I knew that I didn't have the same fire in me that I'd seen in other start-up CEOs.

The very best outcome for Shopcaster would be to become a billion dollar, publicly traded company. A unicorn.

But the thought of being the CEO of such a company filled me with dread. It wasn't me. I was exhausted, joyless and had a constant string of sinus infections. It felt as if a gnarly tree branch had lodged itself in my chest and wrapped itself around my heart and lungs. I couldn't breathe.

I kept going. I had investors, employees and customers to worry about. I was last on the list.

And then one spring day, I was on a flight to Chicago where I would pitch yet another VC. As I stared out the window, watching the clouds, I contemplated my existence.

I knew I wasn't a magazine publisher. Or a corporate VP. Or a sports person. Or a start-up CEO. But what was I? The answer came, and it was simple. I'm a creative person seeking to live a creative life. And for some reason, upon that realization, tears began to flow. Where that gnarly branch had lodged itself, there was now a window. An opening. And through it, I had my first, all be it fuzzy, glimpse of what a new life for me could look like.


But how? I'm analytical. I'm a business woman. Creative people are flakey! I don't want to be flakey! And you can't be both analytical and creative. Right?

Well of course you can be both.

Turns out, I didn't have to worry about being the CEO of a unicorn (ha!). The true unicorn in the e-commerce space, Shopify, was already well on its way. We ended up selling Shopcaster. And it wasn't the kind of deal where everyone makes a lot of money.

But, now I was free to pursue my creative life.

The first thing I did was get on a plane for Cambodia.


Because a career has an agenda. A creative life has a verandah.

Isn't that beautiful? I didn't come up with that. A 69 year-old guitarist, songwriter, poet, author, TV comedy writer and visual artist named Mason Williams did. He's most famous for the 1967 hit song Classical Gas. The name might not be familiar, but you've heard it. Trust me.

Mason Williams is my spirit animal.

He taught me to follow my curiosity.

So I wrote a novel. And then another. Neither of them have been published, but I don't care. Richard Linklater, my favourite film maker, once said, "It's a long way before your skills and technical abilities catch up to your ideas". So I'll keep trying. The third one is already whispering in my ear.

Next, my curiosity led me to freelance strategy consulting. I love solving problems, especially when they're someone else's. Over time, I realized that I spent as much time helping my clients with their personal stuckness as I did helping them with their strategic stuckness.

I turns out, a squiggly career is the perfect preparation for helping people get unstuck. I've seen it all. And what's more, I love helping people.

So, I became a coach. And to my surprise, coaching is an extremely creative occupation. Not only am I constantly searching for new ways to inspire my clients, I'm helping to nurture and deliver their creativity to the world.

And here I am. A newspaper person who launched a magazine, a print person who launched a slew of websites, a media person who launched an e-commerce site, a business grad who wrote two novels and a squiggly career person who's become a coach.

Ain't life grand?

The Unstuck Leader book is now available.
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