The webinar business I co-founded over 14 years ago just completed due diligence and closed its sale to a $100 million private equity fund that specializes in SaaS (Software as a Service), and now that particular part of my life is done. Even though I exited an active role with the company several years ago, I still retained 50% ownership and monthly dividends from that. It feels good to have...
Success Guilt vs Imposter Syndrome
As someone who suffered from crippling imposter syndrome for many years (and eventually overcame it and even wrote a book about it), I am very familiar with the feelings of being a fake, of thinking someone is going to find out the truth, and everything I have is at risk. There can be no expansion without contraction, and those years of contraction, no matter how painful, were an essential part...
This is what happens when you get selfish
It was literally only a month ago when I was invited to attend the COP28 climate conference in Dubai. I was a powerful yes. As soon as I decided to go, I knew I wanted to get on a stage while there. That was my selfish desire. I didn’t give into the story in my head that it was too late. Within days, I made it onto the standby list for the Canada Pavilion, which even though I didn’t...
The Paradox of Too Much Freedom
“Freedom” is a huge value of mine. For my entire life I’ve lived a life of freedom and possibility. I haven’t had a “job” since I was 20 years old. Since then, I’ve worked for myself, doing what I wanted to do when I wanted to do it. Part of what motivated me was that I needed to make a living. I just happened to choose things that I was extremely passionate about. I lived on the edge and forced...
Elon Musk needs to go to therapy and talk about his dad
A truth I’ve been discovering about the super-rich and powerful is that they are no smarter than any of us. When Elizabeth Holmes, the convicted fraudster of Theranos, was able to get hundreds of millions of dollars from super-powerful people, I realized she only accomplished this simply because she got into the same room as them. They were blinded by a fraudster like what can happen to anyone...
Where are you hiding?
This past week I received this private message from someone new to me. Upon receiving it, I realized this was the first time ever I had received a compliment directly for my work on the company I co-founded over 12 years ago, that has been used by tens of millions of people. I had made it impossible before that. This made me profoundly sad for the person I was for an entire decade. Initially, I...
What is “Deep Work”?
On my recent “Ask Me Anything” someone inquired about what I refer to as “deep work”. This is an abstract thought and term, and this morning I was inspired to write this article about it. I would describe it as a culmination of everything I’ve been doing these last 4 years. Of a journey looking inward. Of understanding myself. Of healing. Of learning what drives me, and why I do things. Of...
My Ask Me Anything recording
Here is a capture of the Ask Me Anything I hosted on January 3, 2022. It was an experiment of me testing myself, showing up in a different way, sharing my wisdom in whatever way it was called upon, and kicking my year off in a strong way. Topics included Blue Ocean Strategy and using “pain” in your marketing, amongst anything and everything else that came up. I was very...
There’s only 1 person I need to like me
A colleague once offered some constructive feedback, they said “You sure want me to like you” in response to one of my posts. I can see why they thought it, I write a lot about myself, my experiences, the things I’ve learned. The thing is, they had it wrong. It wasn’t that I wanted them to like me, it’s that I wanted to like myself. Almost everything I write about for the Frolic...
Want to see my new book cover?
Release Date: August 10, 2021. Available through Amazon. Also, I’ll be hosting an INVITATION ONLY book release Zoom on August 9, 2021 at 1pm Eastern / 10am Pacific. I don’t host Zooms very often and they’re always memorable. Hear me tell the powerful story of how this book came to be.Hear about my own debilitating imposter syndrome, something we all suffer forms of.I’ll share my...
My self-doubt still creeps in
A couple of weeks ago I handed over the first draft of next book (Unorthodox Success, Secret Shame) to my wife, Robin, to edit and review. When she was done, she had sent me the file back with notes. The next morning as I reviewed the notes, I immediately began to start doubting myself. What were Robin’s constructive and instructive feedback, I saw as evidence that I had bitten off more than I...
How to Write a Book in 60 Days
We’re surrounded by overwhelming marketing messages online from gurus all promising to teach you their easy paths to success. Now, here I am undertaking a very real challenge of creating and releasing a book in 60 days. I have no doubts I will be successful. The thing is, yes this is a very real challenge, and yes it is going from idea to publishing within 60 days, AND there’s no way I’d ever...
You have a front row seat watching me complete my next book
This past week I was inspired to complete my next book. There’s a feeling I get sometimes, of “Fait Accompli”, and knowing that something will happen with complete confidence. I sensed it, and decided to take it on fully. I’ve had some clarity recently on who it is I want to help. In the end, it’s always a version of me. I’m the greatest expert on myself. I...
I caught myself feeling like a fake again
Despite my best efforts, I still fall into comparing myself with others and then feeling less than. It happened this past week. I was doing a bit of research on podcasts I might want to guest on. I did some searches around the idea of life after you leave your business. I found some, and then I started seeing the little bios of the successful “exits” of the guests. Here’s the thing – I’ve...
I abdicated instead of delegated and learned to forgive myself
At the depths of my crisis, my acute imposter syndrome, my overwhelming anxiety, it got to the point where I felt you could hold a gun to my head and order me to do the work I needed to do, and it still wouldn’t get done. You would have to kill me and I would accept my death. The fact that I was making millions of dollars during this same time period compounded everything to me. I couldn’t...
Failing My Way to My Dream Life
I used to carry so much shame about my failures. I never spoke them. I hid them from the world. I projected my strengths and hid my weaknesses. I only spoke about my victories. Yes, that sort of works, and it will impress some types of people, but at some point it just wasn’t working for me anymore. It fed my imposter syndrome. My list of failures I carried like the chains the character Marley...
I still get scared I can’t do it again
At the worst of the depths of my imposter syndrome I felt like Bernie Madoff. I had fooled the world, or at least that is what I thought. It was only a few years ago, as I looked for things to do with myself, I didn’t even feel qualified to judge a high school business competition. Seeing those teenagers in their suits and ties, future MBA students, and here I was, the high school drop out...
My secret identity is revealed
I recently was watching the movie Kill Bill on Netflix. I saw it when it was new and was enjoying revisiting it. There was a scene that jumped out at me with new gravitas. It was a scene between “Bill” (played by David Carradine) and “The Bride” (played by Uma Thurman). This is a transcript of the monologue from that scene. Bill As you know, l’m quite keen on comic books...
The difficulty in claiming your value
“I’ll work for free” was how I got my first job. At age 12 I walked into a newly opened computer and video game store and somehow had the courage to ask for a job. When I was turned down, working for free was my solution. They accepted. I worked for free for the next several months, then below minimum wage (because I wasn’t even at legal working age). I was paid $3.00 an hour, when minimum wage...
One thing you can’t copy from me
During the years I felt like an imposter, I was under tremendous fear of my ideas being ripped off. I would go through such lengths to hide and obfuscate my innovations. At the time I believed it was the only thing I had. That if someone copied it, I was useless/worthless/replaceable. Recently I watched someone share in public their business building strategy. I know this person, have spoken to...
What is real work?
I was recently watching The Chef Show on Netflix. It’s hosted by Jon Favreau (Movie director of Iron Man, Lion King, The Jungle Book, actor). He was visiting Wolfgang Puck’s steakhouse in Las Vegas, and was grilling steaks in front of Wolfgang. He then handed one of them off to Wolfgang to inspect. Wolfgang cut it open, saw the perfect medium rare, and then they had this exchange: Wolfgang: Jon...
You can’t feel like a fake unless you’ve done something
“Woah… I stopped hearing anything you said after that first sentence”, said my friend on Zoom. I was sharing the outline of what might be my next book, about my crippling Imposter Syndrome and how I learned to get over it and love myself. “Which one? That you can’t feel like a fake unless you’ve done something?” “Yes. Holy crap, my life just shifted. You know those moments of insight when they...