Success by doing everything the wrong way, 20 years of freelancing

If you had watched my freelance career over the past twenty years, there were times you would have been appalled by the decisions I’ve made. I’ve done everything wrong. And yet, here I am: I’m middle aged. I have a great career, and a good many of the ugly bumps in my personal life have been worked through. I’m pretty content. And I got here by doing everything wrong. Today’s post is the first of a multi-part series where I outline how every terrible career-related mistake I’ve made has actually been a huge blessing for me. I’ve been a constant screw up. And I wouldn’t have it any other way.

I’ll start by doing it wrong here and pick up my story somewhere in the middle

Well, the latter part of the first third really… Shortly after my first child was born, I was at a hotel in Sarnia, Ontario. I was attending Ontario Contact – a trade show for touring performing artists in Ontario. I was there to do a showcase performance of a solo children’s touring show that was one of my gigs at the time. I was under intense pressure to do a good showcase to sell the show. At the same time I was feeling intense pressure to provide for my family. Intense pressure to increase my income. My boss and my wife were both pretty happy with me and how I was in the world. The pressure I was experiencing was completely internal.

What’s the right thing to do as an underemployed freelancer with a new baby?

Get a trade? Get a job? Am I right? That would have seemed logical. I liked working with wires and electricity. I knew a thing or two about that. There were jobs for electricians. I was a smart guy. I could probably learn, then prove myself pretty quickly and move up in that world. That seemed a reasonable idea, and I did toy with it. Then I saw what my employer was charging for the show I did for him versus what I was being paid. The difference was staggering. I wanted to earn that kind of money. I wanted to earn it doing something I loved. And I had a story to share. It was (and still is) a story that I loved. I noticed that others loved my story too.

I made a decision

In that little hotel room in Sarnia Ontario, I decided to do what was at the time the most reasonable thing I could think of: I would create, sell, and perform my own clown show. I would tell my own story. Then and there, I started writing. There was a bit of a problem however.

My show is a clown show for children and their families about death

Right? Faced with feeding my family, what did I do? The skilled trade idea? Naw. Teach myself to code? Nope. Did I go corporate and get a job at a bank with chances for advancement? No siree. I could have even decided to do something obvious and easy to sell like a really didactic show about bullying. Schools loved ‘message performances’. I chose instead to create a clown show for children about death.

It gets worse

I test high on all psychological meters I have taken for long term thinking. So, as one would expect, my career advancement strategy was designed for the long-term.

I created a show with three characters in it: a narrator, a young boy, and a grandfather. I knew as I was creating it that the performance would be at its most poetic, most beautiful, most meaningful if I could play it in my 60’s and 70’s. I was thirty-three years old at the time.

I felt compelled to increase my income so my newborn daughter would have a better life. To do this? I created a performance that would take at least thirty years to be the best it could. She could likely have children long before the show was at its best.

It would be difficult to make a more absurd choice

And ultimately I was successful in many ways. I performed for thousands of people over an eight-year span. I learned a lot about myself. I told my story of love and loss. And I earned an income. Perhaps not the income I would have liked, but that’s where my other gigs came in. In fact, I learned so much from the process of creating and performing this show, in retrospect it was like a paid masters degree.

Over the next post or two I will go into my inefficient, convoluted, and unconventional creative process and how what it taught me about this funny business of being alive. You’ll get a bit of a syllabus of what I learned.

One final note:

It seems I’m going in circles – introducing ideas in a post with a promise of follow ups. The follow ups are coming. Eventually. It’s the curse of lateral thinking.

This post made two promises:  I would relate my personal history of screwing up and that I would share the creative process involved in the screw ups and the wisdom gained from them. I have shared here a big career screw up – the clown show about death for kids. Next post in this category will expose my big learning takeaways from engaging in that process.

I also stated that I would publish a new blog post every day. This was an ambitious goal that I have yet to live up to. And, fueled by this ambition, I’m writing every day. Four to five posts end up being published each week. My ambition? It’s not an end destination, just a direction.

Thanks for reading!

#freelance #career #leadership #failure

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