You'll never know, but you'll get a hint...

Photo: You'll never know, but you'll get a hint...

In December, I wrote an article about trial and error being the necessary course for human improvement:

“It’s the entrepreneur in all of us - the innovator. The reason we have prospered as a species is our appetite for problem solving. Trial and error, generation after generation.”

Humans are a grand experiment, none of us know which path forward is best. In reality, there is no “best”, there are varying degrees of consequences. Ideally we learn from our mistakes and grow to be better, chasing the pleasure and absorbing the pain. This is ‘The Human Experiment’.

Our personal lives are no different. Success is unevenly distributed to those who achieve the most trial and error throughout their lives. This requires a durability and resilience that is not slowed down by failure, but instead motivated by it, so that we move quickly to the next experiment.

The goal is to create a ledger of wins and losses to pull lessons from.

Some failures serve us more than others. I used to go to the bar every weekend. In the morning, I would remember that I didn’t like being hungover, and would stay sober for the remainder of the week. By Friday, however, I would be inclined to see if this time it might be different. It never was.

I completed this trial every Friday night for years. Every Saturday, the results came in.

I was very persistent with my attempts.

Eventually, I thought I would try a new experiment. I tried a full year without alcohol. It was a more committed trial and error process - a years-long commitment. I was worried about the risk - what if after committing a full year, my life was worse?

I weighed the pros and cons and determined that after one year, in all likelihood, the parties would still be there.

Understanding the risks, I took the plunge.

This time I woke up a year later, and it was different. The trial was not an error.

Why did I repeat my weekly experiment for so long before trying a yearly commitment?

I lacked a North Star - The higher purpose that hints at which direction we should be headed.

The change was that my first son was born. He was six months old when I decided to try things differently.

This is really important - every day we will engage in trial and error. But without a higher purpose, the trials are random, and the errors may not provide the lessons that we need.

If we can focus the direction of our trial and error through the lens of our purpose, it won’t tell us what to do, but it will leave hints.

I wrote an article recently on the importance of core values - “When you are clear on your core values, big decisions become easy.”

The article was about an exercise I completed five years ago, where my coach and I uncovered the elements of life that I will value most on my final day. I landed on My People, and Adventure.

When I did this exercise, I was a new dad, living in a condo downtown. Today I am a father of three and I have moved my family away from the city to a gorgeous little mountain town. The business I was running blew up during COVID, and I rebuilt a media company with a new focus, new products and a new team.

My life has changed dramatically. Have my core values changed? Or have they stood the test of time?

If anything they have solidified. I find I am organizing my entire life around achieving more Adventures with My People.

Here is a superficial example.

Last year I totalled my Range Rover, so I have been on the market for a new car. 2021 was not a good year to buy a car - prices had escalated for used vehicles and wait times for anything new was over six months.

To delay pulling the trigger on an overpriced vehicle, I signed up for a subscription based program, which gave me access to a diverse portfolio of cars, of which I could switch as often and I wanted. I am not a “car guy”. I did not have a vehicle in mind that I wanted - so this seemed like a great way to demo several vehicles before purchasing something.

There were a couple fun sports cars in the portfolio, and I ended up driving a little two-door M series BMW for most of the year. Turns out, I am a sports car guy - I loved it. It was fast, agile, and looked great. I got a speeding ticket in the first 45 minutes. Despite the complete lack of practicality for me (3 young kids) it was a seductive vehicle. I decided I needed to buy something similar - I decided on a Porsche.

But I didn’t buy one.

In December my older boys started ski school. I started thinking about the spring and the activities I wanted to get them into next. My five year old can already shred on a bike, my three year old is right behind him. Bear, my infant, will be there before I know it.

So despite “thinking” I wanted a Porsche, I ordered a Toyota Tacoma with a three inch lift and an off road package.


Either car would have been fun, but one moved me closer to my North Star: Adventures with my People - Accessing rivers, mountains, camping trips, biking, skiing, fishing and hunting with my boys.

My core values were my North Star.

The North Star concept was serving me even before I fully understood it. I often do visualization exercises where I will spend a week journaling on one idea, attacking it fresh each morning. A couple of years back, the topic was “visualize five years into your future, and journal about the first two hours of the day.”

Every morning I revisited that topic - “Today I woke up, and I…”

There were subtle nuances in each day's creation - the location, presence of other people, variations in activities etc, but there were very distinct repetitions. In each version, my mornings were slow - I would get up, medidate, make some coffee, hang out with my boys and then retreat to my office to read and write.

This doesn’t seem like a very audacious goal - but at the time, I was running nine large scale conferences per year, managing an incredibly high maintenance staff, and there was no peace to my mornings. I would be rushed the moment I opened my eyes. Mornings were a perpetual race to get to my desk and get as far ahead as I could before the rest of the world woke up and demanded my schedule.

That was two year ago. This morning, I woke up, stretched, I did a light meditation, and turned on the kettle while my kids came downstairs. I had my first cup of coffee chatting with my wife while my kids ate breakfast. I kissed each of them on the forehead, refilled my coffee and retreated to my office to write.

It is not random. I had my North Star, and it materialized.

The Porsche would have been cool, sure, but I have a vision of taking my son hunting in a few years. I followed my North Star.

It's a simple thing - but we are so good at staying “busy”. Every day we trade our time in exchange for a result - are we getting the result that we truly want?

It’s the time of year that so many of us set new goals or revisit old ones. I do my best to set mine through the lens of my North Star.