That’s been the reaction to most of my life.
High school dropout. World-famous DJ. Got banned from the US. Went bankrupt. Built a multi-million dollar tech company. Hypnotized 5000+ people on stage. Wrote 4 books. Took on climate change because why the hell not.
Now? I’m chasing serendipity instead of goals. Waiting to be in the room when something impossible becomes inevitable.
350+ articles and 7 years of figuring this out in public are here if you want them. So is my story.
I love “boredom”. I love playing with what are seen as negative words, and twisting them on their ear. Boredom to me is creating space for inspiration and creativity. If I fill my days with busywork, I remove the possibility of those “eureka” moments. Some of my most profitable and successful innovations were made walking to the store in my neighbourhood and simply walking without distracting...
I’ve had multiple distinct professional chapters in my life (the “what do you do?” question). Less spoken about, but very significant and formative to me was the eight year span I worked for a franchising video game retail chain. I started working for this company when I was only 12 years old, and spent 8 years there. For as much as I talk about my lack of paper education, this was an...
For the last 6 years I’ve committed myself to writing one article a week, which has generated 323 articles so far. That makes me an expert. When creating blog content, it’s important to get clear on 3 elements. Here are my own answers to these: What do I want? Clarifying my own thoughts into digestible form Creating a legacy of content and articles Create a story of how I’ve been spending my time...
A good friend of mine, Shermain Melton, asked me a simple question last week: What do you stand for? What comes up for you when you think it? To take a stand means to believe in something. To defend something. To fight for something. Taking a stand means it’s worthy of you getting up in the morning and working towards it. It means you care enough about it that you want others to have...
(The following is an excerpt from my memoir, Requiem for My Rave. I’ve been asking myself lately what lessons I can share from this time in my life with audiences today.) It was March 2000. Robin, my girlfriend at the time and I were in the middle of making dinner. It was a night no different than any other. Robin was cutting some tomatoes, and I was working the stove with tilapia. It sizzled in...
It’s the end of summer, and both my kids are home from school wrapping up their summer vacation. My oldest is now in college, and this could be the last “lazy” summer I ever have with her in hanging out in the house. I’ve been kicking around ideas for new articles, and had some things I was excited to share, but then I realized “It’ll wait”. I’m...
Over 2 years ago my mother suffered a brain aneurysm. She was found confused on the street, brought to the hospital, had emergency surgery, and then was in a coma for over a year. At her advanced age brain elasticity isn’t the same as for a young person and her prognosis wasn’t good. She didn’t recover, was moved out of the neurology ward, and 6 months later was moved to a long...
There are 2 words/phrases that almost always show up when I’m feeling bad about myself: Should and Supposed to “I should be working harder on my book” Or “I’m supposed to be making the world a better place.” Here are some more of the ones I live with: I should lose weight. I’m supposed to be doing more with my life. I should make some more money. I’m supposed to be a good son to my parents. I...
Can a single day at an amusement park redefine years of anxiety and personal growth? Let me tell you how it did for me. After a lifetime of precarious financial living, personal bankruptcy, homelessness, living on the edge, dealing with eviction notices for late rent while juggling my young family, booming and busting multiple times, my financial situation permanently changed in 2012. I had...
Earlier this year I announced my 2024 book project, I made some progress, and then… something wasn’t right and I decided to listen to myself and put it aside instead of push myself through it. Four months later I was inspired again, and I realized that’s a big part of it… inspiration. It’s important for my process. It’s also the most common word used when people describe what they receive from me...
Last week I shared about a trip I was about to embark on with my sixteen-year-old son. The idea came from a conversation we had a few months ago, about a desire to do something one-on-one with each other, and he suggesting we do something we’ve never done before. I suggested that we take a trip and let serendipity guide us. We’ll make no plans, and see where we end up and what we do...
As you read this I’ve gone on an serendipitous adventure with my youngest. The plan is that there is NO plan. The only thing known is that we’ll be gone for 2 nights. Fully lead by serendipity. We will leave our house, and randomly choose a direction. We’ll follow instinct. After that, who knows what will happen or where we’ll end up. I’ve chosen to go with only one...
My Uncle Ugor just passed away. I’m actually attending his funeral as I write this. He spent a week in palliative care before he passed, and during that time my cousin’s asked for anyone that had stories to share to share them now while he could still hear them. I sent this. I was told he he got to hear it and was deeply moved. For that I am grateful. To Uncle Ugor from Christopher...
A paradox is generally defined as something (person, situation, action) having seemingly contradictory qualities or phases. I’ve come to the conclusion lately that my life is full of paradoxes, and they leave me in a state of feeling like I’m supposed to be doing something about them. However, what if by their nature of being a paradox, there wasn’t actually anything to fix or change? Because...
If I had to name a single thing that I am always in pursuit of, and that feels most missing from my life, it’s ‘Passion’. It seems like I once was filled with passion, and now I experience it much more fleetingly. Or, it at least feels that way. I’ve started to question my own memories as unreliable. Did I really feel in this passionate state all of the time when I was younger...
“But what if we’re caught? It will be humiliating”, was the fear in my head. Thirty minutes before this moment, my wife and I went out for a spontaneous walk in our neighborhood. Where I live, in Toronto, is near the factory for Bombardier Aerospace. They make passenger jets. On this particular Saturday afternoon we could tell there was something happening, with lots of people...
I’m not sure where I picked up the phrase “quality problem”, but I’ve been using it recently to describe the doldrums I have found myself in. I’ve written previously about the not-so-helpful habit of comparing my “quality” problems to other people’s “real” problems. Like some prior advice to myself, I’m going to “stop...
Here’s a powerful tool that I’ve created to help myself deal with some of my feelings lately around success and guilt. The point of it is to bring clarity in, and get out of the amorphous haze of letting the emotions run roughshod over you when they’re simply not even true and certainly not deserved. This has been modeled on previous tools I’ve created, except this time focused on the particular...
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...
The best word I can describe my state of mind lately is “confusion”. It’s something I’ve felt before, and makes answering questions like “What’s next?” or even “What do you want?” very difficult. Nothing comes up. I’ve decided to be kinder to myself and stop asking, at least for a while. Confusion is different from “I don’t know”. “I don’t know” can be played with, and creatively explored. “I...
I recently wrote about banning myself from asking “What’s Next?” for 6 months. Since then, I’ve shifted my focus to understanding the implications of the word “next”. Whether it’s a “what’s next?” or a “next chapter” or even “who’s next?” made me realize something: Always looking towards the “next” thing left me unsatisfied with what I currently have. The base premise of looking towards “next”...
So you’ve been going through some old note books looking for inspiration from yourself. You’re seeing a lot of recurring and ruminating thoughts around “What’s Next?” going back for years and years. Stop it! Just stop it. Stop asking yourself that. If it worked, you wouldn’t keep asking. It doesn’t work – so stop it! You are forbidden from asking that again. It doesn’t work. It’s never...
I’m a big fan of The Sopranos TV series. I’ve watched it more times than I can remember. It’s such a superbly crafted and written show that every viewing gives me new insights into myself. I’m a different person, so how I experience it changes, every time. A quote from that show has been with me the last week or so: “You’re only as good as your last envelope.” The direct meaning of that is...
“There’s no way my doldrums compare to your grief”, I said matter-of-factly to my wife, while in front of our couple’s therapist. The whole session was a departure for me, to even allow the session’s focus on me at all. Almost always I pivot to how Robin is doing, and we start there, and often stay there. Because as far as I’m concerned my problems don’t compare. Robin is dealing with elderly and...
We’re living in a time of peak nostalgia. It seems everything was better back in the day. The thing is, we’re comparing the VERY BEST of the past with now. We forget all the crap. For every hit song, there are countless forgettable ones. For every iconic movie, there are dozens of others we can’t be bothered to watch again. I’ve been wondering if I’m suffering from nostalgia for my old life. One...