Sunset on the seawall of Stanley Park
I was having a client session the other day and the conversation went to a place I know well. Everything in his life was working; his professional success, his family, his marriage… everything he had accomplished in the world was falling into place. I felt the familiar stirrings of having had a life that looked like his. When you hit a place where everything has worked out, you don’t always know what’s next. It might be because you have too much to lose. Or you don’t want to fail. Or you don’t want to fall back into the trap of working as hard as you did before.
We were building his new life. Melding his career capital and life capital into something created, chosen, and not taken for granted.
I told him what I told myself at 40.
I can’t turn 60 and regret the life I had chosen.
Up until that point, I had been existing in life. I was numb, stressed out, and had zero idea what I was doing it all for. I was growing the business, making money, paying off a mortgage. All I did was worry about work, trying to create the perfect plan, the perfect scenario, so that everything we manufactured would go out on time, and would meet 100% quality standards we were famous for. All to have it continue, grow and expand. And for what?
I couldn’t ask myself that question because I couldn’t answer it honestly.
I was very unhappy. I was barely existing in my marriage. I didn’t have much to look forward to except every Wednesday, when I left work a little early and went downtown to Stanley Park. I went to the beach, walked the seawall and sat by the ocean trying to forget it all.
My shift didn’t happen all at once and I didn’t have an aha moment of great awareness. Within the slowly dying embers of my life, that I knew something had to change drastically.
The first thing that shifted was that future I imagined based on my present circumstances. I imagined what twenty more years of this life would do to me. The stress. The unhappiness. Doing what I knew I didn’t want to be doing but didn’t know what else I could do.
By that time I had already been to Japan twice, visiting the factories where our manufacturing equipment was made. I had been to Europe several times, visiting my old home in Paris. I remembered the days when I was happy. I remembered the days when I was excited about life and was alive. It was on one of those Wednesdays alone that I began to reflect on what life I would really want.
It wasn’t a straight decision. It started with knowing what I didn’t want. Up until that time I had been a very good yes man to everything. Agreeing to things in my marriage and my social life that I really didn’t want to agree to. When I started to speak up, a new layer of friction occurred. A new layer of disagreement. I didn’t know how to handle disagreement. Instead of having a conversation, I withdrew. The more I withdrew, the more my starter wife withdrew. The arguments became fierce, followed by weeks of silence.
Our relationship was so strained and painful to exist that we found a therapist. We went once and she never went back. I continued, and slowly opened up to all the sadness I had been holding inside. Having someone to talk to helped. I began doing things for myself. I studied Japanese. I taught English. I went out with friends, something I hadn’t done for years. The more time I spent outside the house, the more I felt my old self coming back alive.
It was at that point I had to make the hardest decision of my life. Should I stay or should I go? Should I continue this lie of a life or leave it all behind?
I told myself: I can’t turn 60 and regret the life I had chosen at 40.
Rationally, it made sense to stay. We were almost at the point where I could hire competent people to relieve the weight of the stress I was under. I could travel where and when I wanted. I could finally oversee the company without miring myself in the day to day logistics. And… I just didn’t want to live that life any longer than I had to. I didn’t want the marriage anymore. I didn’t want the business anymore. No matter how much money I was guaranteed to make, it was not worth the debt of mortgaging my soul.
Leaving it all was an impossible decision because of everyone who relied on me: my starter wife, my parents, my business partner who was primed and ready to take over the business with me. I had to cash out on the life I had built and go all in on a new life that was far from certain. The odds were so stacked against me that no sane man would have chosen that bet.
Lucky for me, I was living in a moment beyond the realm and scope of sanity or insanity. My options were life or death.
My previous life was very successful. I didn’t have to do much except stay on that path and everything would not only turn out all right, it already had turned out perfectly. But it had turned out perfect for the young man who was afraid of life and chose an easy path, a nice path, a logical path. It was not an easy path, but it was straight forward and carried little risk.
The new path had no directions, no map. No guardrails for my financial well-being. No safety that would ease my fear of being alone.
Saying no had me take one small step after another through the gilded cage door that was always open. It had me follow my heart in the smallest of ways. It had me live a life of adventure. For the first time in my life, save for two years in Paris, I didn’t have a plan. I did what I wanted to do. Moment by moment, the path unfolded. The plan materialized.
The moment I shared this with my client, our work shifted. Oftentimes when you are building something, you get mired in the day to day and you lose track of the small things. Date nights with your wife. A walk with your children to school. Time spent with them doing nothing in particular other than being with them. Those are the moments we miss.
Those are the moments I did not miss in the last 21 years of my life.
I’m sitting here in the September sun at 5:18pm. There’s a gentle breeze, the sky is blue, the grass is swaying.
This moment is exactly how the moment was 21 years ago, when I said: I will not be 60 and regret my life.
I’m 61. I don’t regret a single day of it.



Thank you for sharing the amazing path that you have taken. I feel exactly the same. No regrets. Especially no regrets about meeting you in Paris and getting to know the wonderful soul that you are.