Above you can see my great-grandmother (Beatrice). Bea was born in the late-1800s. In knowing five-generations of my family, I am the link from the 1800s through to the 2100s.

My family was involved in the early days of the province of British Columbia (forestry and shipping). Shipping sounds glamorous but the reality was barges, booms and tugs. I love being near water and trees.

I never worked in the resource-focused businesses but I did work on the water at YMCA Camp Elphinstone – the photo is plaque that’s still in the Longhouse. I loved my time working in Howe Sound and summer camp. Below is where I spent many happy summers.

There were successful businesses up both sides of the family tree and some very, very good business people. None of the financial capital from my elder’s success will make it through to my kids generation but the human capital of the family has remained strong.

If my great-grandparents could survey the scene today, they would likely observe that, once sold, a family business is very difficult to replace. I think they would also realize that their financial success had many unintended consequences.

Over the years we’ve been caught out by bank guaranties and leverage. It’s important to remember that one mistake, particularly when combined with bank borrowings, can blow a generation’s worth of hard work.

Indeed, in my own case, I was saved from personal bankruptcy by getting spooked by the boom of 2003-2005. I spook easily (!) but it served me well as I got through the Great Recession of 2008/2009 intact.

Always consider a bank guaranty to be the equivalent of an immediate equity investment, without operational control. Also, remember to ask, “Can I hold this investment, for up to ten years, assuming I lose my job?” Every generation has been hit by unexpected unemployment.

My elders would tell you that appearances matter, especially when you’re the little guy (in business or stature). The picture above is my great-grandfather, lone survivor of a mid-air plane collision. His son, my grandfather, made a habit of being kind and fair to everyone around him. This habit stuck with him, even as his mind unwound. Lacking kindness was my greatest weakness as a young man.

One of my earliest financial memories was being taught to never have more than 10% of my net worth in something I don’t directly control. Ignoring this advice proved costly, financially, but didn’t damage my quality of life. So pay attention to that tip, it saved the hard work of my generation of the family and you hear it repeated over-and-over by elders that have lived through severe recessions.

I’ve been an outlier with how I’ve chosen to live my life and can waste a lot of energy trying to make the world more like me. The best advice that I’ve received about living with other people is to optimize your life for the way things are, not the way you wish them to be.

There’s plenty of compulsive people in the family tree and we have a bias towards action. This trait helps you get things done. However, remember that if it won’t make a difference then you’re best to wait.

Daily, I remind myself that kindness makes a difference.

Seeing choices flow through 80 years, I hope my children develop a sense of personal success, then shift their emphasis towards loving their families, connecting with friends and improving their communities.