Michael, 60
Creative, curious, passionate
“When I look back on almost four decades of work, I realize that every experience taught me something. Even in jobs where I was absolutely not the right person, I learned something. “
✨ Twinsight: Michael’s career shows us that life doesn’t have to follow a straight line to be successful. His journey, filled with diverse experiences and lessons, proves that it's possible to grow and reinvent yourself continuously. This zigzag path gave him unique insights and skills, reinforcing that every stage of life offers opportunities for personal development and growth.
For anyone thinking they're too old to change, Michael’s story has a clear message: it's never too late to alter your course. His journey is a reminder that every experience is a chance to grow. We think his story can motivate you to take bold steps and see every new challenge as an opportunity.
How old are you and how are you feeling about that?
A: I turn 60 this year. I feel like I am in my mid-thirties - mentally, spiritually and most of the time, physically. But like most people dealing with a diamond anniversary (aka 60th), there are times when my body, in a not-so-subtle way, reminds me who the boss is. I am comfortable with who I am and happy to roll into the next chapter.
Three words that describe you.
A: Creative, curious, passionate.
What’s the one life lesson that you would tell your younger self?
A: KNOW YOURSELF FIRST. Take a values test to truly understand your why. Take a Kolbe test to figure your how. Take the Clifton Strengths test to figure out your what.
What is your proudest accomplishment so far?
A: Personally: having an incredible family. Professionally: being an architect of change/disruptor within the world of skateboarding
Who are you?
A: Family is a massive pillar in my life. Music and skateboarding are the other two. I spend a lot of time thinking about the future and helping improve it. I have a deep passion for being in "flow state." I keep curious about the world.
Michael places importance on giving back
What is your message to the world?
“If you can, donate blood or blood plasma. You will help save at least three people's lives each time.”
Talk about your transition from career to next stage of life.
A: The first 38 years of my work/career were a ramp-up for what I will do next. I started in the music business in the beginning (summer of 1986). I thought this would be my career, but things didn't turn out as I'd hoped.
I thought I would transition to another job in media, but I wound up in sales. I decided to stay with sales until, thanks to a chance meeting, I wound up in book and magazine publishing. I chose to remain in publishing until I worked in the deathcare field. I thought I'd stay there until I returned to the creative field.
When I look back on almost four decades of work, I realize that every experience taught me something. Even in jobs where I was absolutely not the right person, I learned something. Sometimes I feel I am channeling Colonel Sanders—it took him until he was 65 (and dozens of jobs) before he found the secret ingredients to make his career work.
So, my next career move has me thinking about what it was like at 39 to quit my day job and start running my magazine full-time. It's both terrifying and exhilarating. I am incredibly excited to unleash my ideas on the world.
Have you experienced ageism?
A: Yes—but it was quite subtle. It was after I sold my business in 2018 and started to apply for jobs. I got the sense that if you graduated high school (or university) in the 1980s, your resume was flagged and discarded. I also went online to look at the kind of jobs "older" people were supposed to be doing, and I didn't find they met my expectations.
I don't want to diminish these jobs—they are important. But they didn't mesh with my skill set or creative spark, which is still firing constantly in my brain. It would appear that ageism contributes to pigeon holding people. I intend to work around this problem.
What sparks your joy these days?
A: Three key things
Connecting people to ideas and ideas to people. I have created something brand new called The Wise Hive. It is all about connection, conversation and collaboration - not necessarily in that order. It aims to help small businesses, nonprofits and those who work in independent media/marketing. So far, the reaction has been positive.
Mentoring others - I genuinely enjoy helping support younger people in their journey.
I help people capture and preserve memories. I believe there is no time like the present to capture the past. I am involved with a new app that is about to be unleashed to the world. It's called Storied Life, and it captures memories effortlessly. Anyone who owns a smartphone can be guided to tell their story. The app will write for you!
What does your future-self look like?
A: The future will be filled with building The Wise Hive, being an evangelist for capturing memories and enjoying the unique combination of having time, money, and health to do the things I want to do. For me, it's not about objects (hello, Lamborghini!); it's mostly about spending money on experiences with my wife and family. I will continue to write and publish. I will never stop skateboarding. My future self is happy, passionate and still full of energy.
What were your greatest hurdles, challenges or regrets along the way? Any advice on how to overcome these?
A: In truth, I’ve had a very mixed career. As I keep repeating, your career/life starts with knowing yourself. Many people (and I am one of these people!) say, "Wow if I'd only known then what I know now." The truth is that some people know what they were meant to do in life. They pursue this goal, and their life is a straight line. For example, my wife, from age 5, knew she would be a teacher, and she did this for over 30 years remarkably well.
My life is anything but a straight line. I've zig-zagged through multiple jobs where I thought I had found the right place. Then, after just a brief amount of time, I was miserable. I did this more times than I care to admit.
Your path becomes much easier once you triangulate your values, strengths, and operating style. I found this out at the age of 59. Some people NEVER truly discover this. Like me, they repeat the same mistakes because they never truly quantify things.
I am a big fan of the butterfly effect - serendipity and coincidences are truly magical moments that can change your life. I also love the story about the red paper clip and how, after several trades, the owner wound up with a house. When you combine these two ideas, you get something I call "The Butterclip Effect." I intend to create as many of these as possible.
Should you retire? Is retirement dead, as many say they will never retire. What's your view on retirement?
A: It really depends on the person and where they are financially, physically, and mentally. Everyone has the same 24 hours in the day, but not everyone spent their working years the way I did. I am still driven by a relentless curiosity about life.
Ironically, there are many antonyms for the word retire (engage, advance, remain, thrive), but we don't seem to utilize them much. So, for this interview, I'll say that I am heading into thrivement, not retirement.
If you are in the Toronto area, come meet Michael on May 4, 2024.
Friends House, 60 Lowther Ave, Toronto, ON