One Question to Fuel One Great Year After Another, One Day at a Time

Roadmapping your year, an 18-month reflection, and stepping into the unknown.

In January 2022, I sat down with a legal-sized sheet of paper, positioned it in a horizontal landscape, and started to map out my year.

In one-to-three-month blocks, I decided what I wanted each period of my life to look like. Some months were filled with work, learning, and courses, and others with travel, adventure, and play.

I didn’t have a plan for the logistics—turning my lofty plans turn to reality—but I was determined to make it happen.

Looking back at 2022 during my annual year in review, I couldn’t help but smile. My roadmap turned into reality and it was a hell of a year.

I explored Provence and Riviera in Southern France with my Dad and partied in Prague with buddies. I hiked to mountain peaks in British Columbia with my best friend and his girlfriend. I enjoyed cottage weekends at the lake in my native land of Ontario. I scuba dived in Colombia and swam under waterfalls and hot springs in Costa Rica. I took my Mom and Stepdad on a trip of a lifetime, snorkeling with sea turtles and sharks in the chilly volcanic waters of the Galápagos and hiking to Machu Picchu.

I continued growing my newsletter, became a better writer, and even landed a side gig as a Freelance Writer. If you told my parents back in my high school days that I would get paid to write at age 23, they would have laughed you out the door!

I kept fit, improved my endurance, trained Krav Maga for 3 months, and even got a little bit stronger and more flexible.

Despite its fair share of road bumps, stress, and anxiety, I can’t complain. As my Dad would say, I planned the work and worked the plan. I had a vision for a period of my life and willed it into reality.

Happy with how 2022 went, I set out with the same practice for 2023.

Pen in hand one crisp January evening, I split my year into chunks, finding space for all of the things that are important to me.

Inspired by Bill Perkins’ conversation with Peter Attia, I initiated a trip to Egypt with my Dad with the goal of creating an experience we would never forget. I will smile and laugh with joy at memories from that trip until my final day. And our bond will be forever strengthened as we recall stories and crack jokes from those three weeks together.

Goal achieved.

I explored the Grand Bazaar in Istanbul, cruised down the Bosphorus, and bathed in the beauty of the Blue Mosque.

I traveled through Italy with my girlfriend, trying just about every pizza, pasta, pastry, and gelato you can dream up, hiking through the picturesque Cinque Terre, studying ancient Roman architecture, admiring Michelangelo’s David and Sistine Chapel, and getting lost in the canals of Venice.

My Longevity Minded newsletter hit 500+ subscribers, I feel great about my fitness, and I have some exciting plans with friends and family on the horizon.

So far, so good.

Now the year is just about halfway up and I find myself needing to revisit my roadmap to replan the last 6 months of 2023.

But the future feels uncertain and I’m not sure where to go next.

Maybe I need to allow myself to engage in a process of discovery, one step at a time.

To walk a path of unknowns that has equal chance of ending in triumph or disaster.

To listen to the wild part of myself that knows, deep down, what I need and how to get it.

To seek discomfort and uncertainty rather than complacently accepting stability and unhappiness.

To trust that doing enough of what needs to be done today can, with time, create an outcome that could be great.

“As you start to walk on the way, the way appears.” ― Rumi, 13th-century poet and scholar

The quality of your questions is said to determine the quality of your results.

And although I don’t know where I’m headed, based on how the last 18 months turned out, I’m pretty sure I’m asking the right questions:

What experiences must I have in the 24th [insert age] year of my life, or risk never having at all?

Can I live without experiencing/doing X? Or will I regret it on my deathbed?

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