My granny in her 80s.

The summer I turned 14 a neighbour gave me my first job. She started up a day camp for seniors—gathering up folk from retirement residences in a school bus and bringing them to a park for the day.

My job was to set up a miniature golf course every morning, assist players, and then pack the course away before lunch. I’d learned to putt in Scotland with my granny, so I was somewhat qualified.

It was a good first job. Simple, outdoors, nearby. I was made responsible and left to figure it out. I got paid. Felt like a sweet deal to me.

I didn’t know it would be life changing.

One of my regulars was an 80-something man. I wish I could remember his name. He appreciated that I changed the golf course up every day. And we enjoyed each other’s company. He spoke to me with respect, as if we were equals.

We’d play a round and sit at a picnic bench and chat. He told me a bit about Australia and coming to Canada. I don’t remember the details, except that he came from Perth. I probably told him about school stuff, but I don’t remember my end of the conversations either.

What I do remember is that one day he told me to be bold. “When you’re old you don’t regret the things you did, you regret the things you didn’t do.”

Hit me hard at the time. I’m not sure why. At 14 I hadn’t racked up many (any?) big decisions or regrets. Maybe it was the truth of it that hit me. Sometimes words have a ring of truth and you can feel it.

You may have come across the book Top Five Regrets of the Dying. It seems to have been everywhere for a while—online, podcasts, etc. It was put together by someone who worked in palliative care and she asked the dying what their regrets were. My friend from Perth’s idea was spot on.

What would 80 year-old Lindsay do?

For me his words became a touchstone, a way of evaluating an important choice. I’d ask myself, “What would 80 year old Lindsay think? What would she want me to do?”

Predictably, this led to some excesses in my 20s. I don’t think my friend from Perth had in mind some of the choices I made. My understanding of his directive was pretty unsophisticated back then, but it did lead to adventure and experience.  

Later on, it led to more meaningful choices. To try new things. From the small, like paddleboarding at Ashbridges Bay in Toronto (now a mainstay of my summer mornings). To big decisions like quitting a job and starting my own graphic design business. To leave the city I called home for decades. And to embrace making art.

You have to be afraid to be brave

I don’t think I’m particularly brave. I’m just more afraid of regret, of sleepwalking through my life, of not doing something important because of discomfort, inertia, or fear.

I still return to his words and think of my 80 year-old self. At this point in my life I appreciate the perspective it gives me and the reminder that my time is finite. I find myself saying “If not now, when?” a lot.

68 x 68″ canvas dominating the studio

In the studio

And it comes up in the studio too. Recently I realized I wanted to try bigger canvases, but felt conflicted because I have an important show coming up (The Artist Project). I wondered if I should stick to sizes I know I can handle—and that fit in my car. But 80 year-old Lindsay piped up and soon I had enormous stretchers looming over my studio.

She helps keep failure in perspective too. Better to try and fail than wait and wonder. I think of failures as experiments, the first iteration, experience.

Lately, my older self tells me I should do more resistance training and mobility work, which is excellent advice. I must admit I prefer her wilder ideas.