Once upon a time I had a LinkedIn profile. It wasn’t great. I was ashamed of myself and my story when I had created it. I downplayed all of my accomplishments, in a weak attempt at trying to appear more “corporate”. My imposter syndrome at the time also had its hands around me like a choke hold, and I didn’t even list my webinar company, StealthSeminar, by name. I listed myself as some sort of...
I never know when or how my next story will show up. This past Monday I was driving my sixteen-year-old to school. It was an unusually bright and sunny warm October morning. My son sat quietly, looking out the window. Later that same day I was planning to return to one of my old activities, playing with the Toronto Pinball League. I haven’t played regularly since before COVID and I’ve...
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...
During the peak of my DJ career, back in the year 2000, I was banned from entering the US after being caught entering to work as a DJ without having the required paperwork (Longtime followers of mine are very familiar with this story, and I wrote about it extensively in my memoir). I spent many years regretting my actions that led to that. This ultimately led to my eventual retirement from DJing...
(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...
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...
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...
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...
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’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...
For reasons I cannot explain clearly, my momentum on my book has stalled. I went from being excited and inspired, to days and weeks passing with no progress. Once I hosted my recent Zoom on my creation process (with the actual evidence held in my hands of my past books), something about the whole project evaporated for me. It’s clear to me a large contributing factor is that I’ve already...
Last week inspiration struck: I would create my next book and have it completed and for sale in 90 days. I had a few inspired days of clarity, and I announced my plans to my community. I got some work done, and then… the self-doubt started to creep in. I started to regret that I had announced it. What was I thinking? This is completely self-inflicted. However, that was exactly WHY I did it...
Recently, I watched an HBO documentary series called “The Anarchists” about an anarchist collective in Acapulco, Mexico. They thought they had the answers for all the world’s problems, as they saw them. My biggest take away came later in the series when one of the founders realized they were all a bunch of broken people trying to change the world and that they needed to heal themselves first. It...
You’re feeling frustrated. I can understand. It seems like you’re marching around in the dark trying to figure out which way to go. Every time you think you’ve made some progress you’re back to the same old habit of trying to figure out what’s next. Sometimes it feels like two steps forward, and two steps back. But is that really true? Take a look at where you’ve been, what you’ve done...
“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...
A little over a month ago Covid showed up in my home for the second time. The first time it showed up (from my oldest bringing it home from school), it wasn’t a big deal. This most recent time (my youngest bringing it home from school) was far more difficult. I was testing positive for almost 2 weeks, and dealing with flu symptoms which laid me out. My wife got it worse, with their symptoms...
A guest speaker at a function I was attending this past year reviewed my website and told me frankly, “You’d be an incredibly fascinating dinner guest.” His comment made me feel seen and reminded me of how far I’ve come. As recently as 2019, I was a guest at a friend of my wife’s house who was celebrating receiving tenure as a college professor. The house was filled with academics. I was as quiet...
I used a phrase in my last article, calling myself a “lifestyle entrepreneur”. I intentionally stated it, because I could feel the twinge of not wanting to. The most common definition of lifestyle entrepreneur is someone who creates the life they want first, and then a business to serve that. As opposed to most traditional businesses, where the business consumes everything (often at...
When the concept of an “Impossible Dream” was first introduced to me, it was my understanding that it be literally impossible. There’s no way to create 17 steps from here to there. It then becomes a place to come from, instead of a goal to get to. Who would I need to be, to be a person capable of this thing? And simply come from that place? One of my favorite exercises when talking...
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...
If I’m honest with myself, I can see that much of the fear that holds me back today is not my fear of failing at something, but what would happen if it was successful. These are some of the voices currently in my head: I don’t want to create a formal program or offering because people might sign up for it and I’d be committed to running it.The more attention I bring to myself, the more people...
Robin and I are celebrating 25 years together this year (20 of those married). We often joke that we should write a relationship book, and I do think that will be a future book of mine. The early days of our relationship was documented in my memoir, and it was definitely a trial by fire. As young people with no support around them, we had to wrestle with Robin’s mental health crisis and...
I could tell I’ve been feeling in the doldrums lately and decided to take action. I put out a last-second invitation to my Frolic100 list to witness me using my most powerful tool, what I call my Statement of Being. Things began to change for me the moment I committed myself to this. I now had a date on the calendar (only a few days away). I knew it was more important to me to do it, and be with...
One thing that has become crystal clear to me is from my years of working through my imposter crisis is that I have an incredible understanding of “How” I best do things. I learned this because to overcome my crisis I had to switch from feeling like a fake to owning my successes. I learned how to identify my retroactively provable truths, some of which is documented in what I call my “Statement...