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I was watching the Sylvester Stallone documentary the other night on Netflix, and there was a moment in the film where he recognized life was getting predictable and stagnant. From past experience he knew that it was time to shake things up, so he decided to pack up his longtime home in Hollywood and move across the country to Florida.

This scene in the documentary really stuck with me because I have found myself in that exact same situation so many times in my own life. And no, I’ve never sold a house for 58 million dollars to the pop star Adele, and then moved to Florida, but I have had many moments in my life where things became predictable and stagnant, and I knew it was time for change.

  • It happened when I moved to Korea to teach English after spending four years at university. Those four years at school were some of the best in my life, but I knew it was time to move onto something new.

  • It happened upon my return home to Canada when I turned my back on lucrative corporate job offerings, and instead followed my heart by going all in on producing a motivational show for high school students.

  • It happened years later when I pivoted from high school shows into writing motivational musicals for adults. I knew it was time for a change after I caught myself thinking about what I wanted for lunch, while performing to an audience of 1000 teenagers.

  • After four years of producing those musicals, it happened again when I shut it all down to try my luck at becoming a corporate keynote speaker. I quickly found out that I’d need to own more than one suit!

  • And yet again, it happened when I created the Top Ten Event, when I realized I needed to expand my offerings into some form of philanthropy. That charity event went on to celebrate its ten year anniversary at the height of the pandemic.

In between these leaps in life I also took a stab at things like writing two books, launching the Wonder Women Festival of the Arts, starting The Human Detour Initiative, building a self development app, and creating an online human connection series called The More More. Some survived, while others became springboards to new adventures. And with each new change came the usual fear, anxiety and uncertainty.

During the pandemic my pattern of leapfrogging every few years came to a complete halt. I was quickly faced with the harsh reality that worldwide viruses and a business that relies on audiences gathering in one room don’t mix! As you know, the world creeped its way out of that little blip in human history, and by the end of it I began noticing that familiar feeling of it being time to shake things up. So, without much of a plan, on October 8th, 2022, I moved my family from Toronto to Manhattan. While driving across the border, with our entire lives packed into a Uhaul, I said those words I've said to myself so many times before.....“what the hell am I doing?!”

To offer a little context as to how this decision came to be, let’s backtrack to July, 2022. My family was coming to the end of a three week road trip where we had been hitting quaint little towns along the East coast of the United States. Being so close to NYC, we decided to pop in for a few days to see some friends. As fate would have it, while leaving to come home to Toronto, we hit rush hour traffic that was so bad, we decided to pull over and book a hotel room for an extra night. Well, one night turned into two and the party continued. Finally, it was time to go home, and while driving, I turned to my partner Marina and said, “Could you picture all of us living in New York?”

She said she liked the idea, but that she didn’t welcome the possibility of us living in a “shoebox”. At this point in our lives we were living in a three bedroom house, with a two car parking pad, in one of the most progressive and fun neighbourhoods in Toronto. Moving to New York would mean downsizing from a 1500 square foot house to a 900 square foot apartment, losing our private parking and home office spaces, having 95% less friends to connect with regularly, paying between 10-15k USD for healthcare, while no longer living close to family members who happily gave us much needed breaks from the kids. All for twice the amount of money than what we were paying to live in Toronto.

Well, about two months after that conversation, we received a text message from an apartment complex, where we had put our name on a list saying they had a two bedroom unit just come available. They couldn't show us pictures, and only offered a floor plan and the address. We were in the midst of driving to a cottage where we would be spending the weekend with extended family, and we had about thirty minutes to make a decision. We looked at each other and started laughing, while saying "screw it, let's do it!" Five weeks later we found ourselves walking down a street in the East Village to the local school to see if they would “pretty please” take our kids. Personally, I think my begging won them over. Not to mention the tears!

And now as I write these words, I can look back on that decision and say that it propelled me into the hardest year of my life. Don’t get me wrong, throwing my business degree away for a life in theatre was difficult. Going 250k in debt by the age of 28 to build my first company was almost an insurmountable challenge. Having to live in a 300 square foot basement apartment during a botched renovation on our new home with a six month old, while speaking around the world wasn’t what I would call “good times”. And over the years, placing deposits on event spaces I didn’t know I could fill certainly caused many bouts of night sweats and nausea. But those experiences, and many more just like them, paled in comparison to the shit storm I’ve gone through over the past year. Had I known it was going to be this hard, it’s likely that I wouldn’t have done it. Or more accurately, it’s likely that I would have doubted whether I had what it takes to do it.

And isn’t that just it? We don’t know that we have what it takes until we have to overcome the unexpected. If I could use one word to describe the last year, I would say "unexpected". I didn’t know Canadian credit doesn’t easily transfer to American credit. I didn’t know all of the afterschool programs in NYC fill up immediately in September, and if you arrive in October you could expect to be taking care of your kids starting at 2:50 pm every day. I didn’t know that we were moving into an apartment next door to a woman with mental health challenges that caused her to scream from the top of her lungs multiple times throughout the day. I didn’t know that everything my children needed such as camps, swimming lessons, baby sitters, ice skating and more all cost exactly twice as much here as they did back home. And I didn’t know that New York doesn’t give a shit about what it can give you, but rather only cares about what you have to offer. And let’s just say a pint of blood isn’t enough.

As a result, I was left with sleepless nights, unexplained health issues, high levels of anxiety and bouts of depression. And you want to know what? A part of me kind of liked it, because I knew it was ripping me into a new version of myself. Sure, if I could snap my fingers and take it away most days I would, but as I’ve gone through it, I’ve had an eerie knowing it was exactly what I needed. It’s like the depths of despair we feel after a break up with a lover, or the dread that comes days after losing a job or the moment we watch a parent pass away. Your heart feels like it’s just been soaked in a heavy molasses, and yet it still manages to taste the sweetness of the situation. It’s a knowing that part of you just rooted yourself into soil that you blindly trust is fertile, and will one day push you toward a sun you get to see through new eyes.

Now, I’d love this to be the part of the story where I tell you that I’m now through it and find myself collaborating with Jimmy Fallon, performing once a week at Madison Square Garden and writing for SNL. Instead, it’s where I tell you that it’s taken me a year to get to a point where I’m no longer living life pinned under a pounding waterfall. After about 365 days, I’ve managed to wriggle free just enough to catch my breath and look up more often instead of down most of the time. And while I’m still wet and a little cold, I am finally beginning to see the beauty of my surroundings. The sun is showing its face a little more often, and when it does I notice it trickling across the leaves of the tree outside my window in a way that mutes the sounds of sirens. The mean looking faces of strangers on the street are now presenting as an appearance of determination and focus I hadn’t seen before. And the guy at my local pub seems genuinely happy to see me as he says, “Hey Stuart!”, as opposed to “What’s up man?”

It’s funny, because it doesn’t matter how many times I’ve been here before, it’s still so easy to believe this latest life transition will be different than the others. This is where your brain tries to persuade you that past success was just luck, and now that luck has run out. But then you remember that you’ve fought those thoughts before, and managed to usher them out the door with the other imposters. And before you know it, you move past the blank pages, and toward the realization that this chapter might just top the rest.

This cycle has rinsed and repeated more times than I can count, and through each one I’ve learned that the biggest growth comes to those willing to act without guarantees. It happens when you are prepared to bet everything you have gained thus far on the potential of achieving something even more ludicrous than before. While writing these words, I find myself yet again in that dizzy space I speak of as I am in the midst of launching my latest hair brain scheme to the world not knowing the outcome. It’s something I’ve poured my heart and soul into over the past year, while watching my savings pour out of my bank account. Ha! To a practical person, risking so much at the age of fifty with a family to feed is asinine. However, to those same people I would ask if there is anything more intriguing than watching to see if someone can light a match in a hurricane? And with the short amount of time we are given on planet earth, do we not owe it to ourselves to at least try?

Alas, it is there where I’ll leave this off by posing one last question. If you were to take a leap of faith that could potentially stretch you in fantastic ways, what would it be? You don’t have to commit to it, just say it out loud, which by itself is a powerful thing. Now, I don’t know what that thing is for you, but I do know this. If you don’t take that leap of faith, an opportunity will be missed. And missing it won’t diminish your golf swing, or sever the love you get from others. It won’t make you a bad person, or change the fact that lasagna is your favourite food. However, not taking that leap will make it very difficult to ever meet a version of yourself you might like better. To me, that’s something worth thinking about. People often find themselves wondering what the meaning of life is, and I think I’m getting closer to what it might be. I don’t think it’s about finding the meaning of life, but instead bringing meaning to the life you were given. And with every leap of faith we are willing to take, the more meaningful life becomes.

Much love,


P.S. If you want to take a glimpse at my latest “no guarantee” offering to the world, check out

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3 commentaires

29 nov. 2023

What comes to mind is "maybe"


29 nov. 2023

What comes to mind for me when I read this is…. Hey it is good to hear from you. Wondered where you’d gone. ( I knew you were in NY, I just didn't know where you'd disappeared to) You are inspiring, insightful and brave. Thanks for being so open and vulnerable. Thanks for sharing. You’ve got this.

29 nov. 2023
En réponse à

Thanks so much for posting this comment! It feels good to know others are thinking of you and are picking up what I’m putting down! ;) Stuart

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