When I was growing up in Canada there were a series of commercials by London Life called Freedom 55.  The tag line being “The freedom to choose, the power to get there.”  The notion being, that if you started saving now you can retire at the age of 55.  This was a radical idea at the time.  Now I often meet people that think 55 is the latest that they want to work.

For the first time in a long time, I addressed the topic of work in my last blog.  To recap, it was about asking yourself what you love to do, how much is enough to live a good life, and whether working the way you do still serves you.  The conversations that it sparked were about retirement.  My post was about questioning whether you are living a good life NOW.

Canadians are obsessed with financial planning and retirement.  I find this ironic in a country that takes care of its vulnerable, including its seniors, probably better than most of the world.  But we are a prudent, conservative nation and we want to make good decisions now.  We are also a frightened nation when it comes to fretting about the future and whether there will be enough left for us.  We are afraid of dying, want to live forever, and to the lifestyle in which we are accustomed.

I want to make it clear that I believe in retirement planning.  I have an investment advisor that I trust with my hard-earned funds.  My question is not whether we should invest in our futures, rather how much are we willing to give up now for that to happen?

Gathering at Maycocks for a bit of a surf but mostly to hang with some of my favorite people.

I grew up with an all-or-nothing view of retirement based upon the community of adults around me. They were willing to work to the bone for many years so that at some set point in time they would be taken care of and could “retire.”

What is the balance between living in the now and planning for the future?  A friend here in Barbados just lost a childhood friend to a heart attack in his forties.  His friend group is devastated by the loss of this person and shocked by the youth that was taken away. My father also died of a heart attack when he was 41.  He had genetic health issues and knew that his life would not be a long one but had no idea it would be so short.  My family benefited from his financial planning and for that I am grateful.  My mother told me that he had postponed an EKG test because he was busy at work.  The juxtaposition of that information took a while to settle in.

For these reasons, I have always believed in “retirement in installments.”  When I was 27, I took six months off to travel the world between living in England and returning to Canada.  When I was 34, I took two months off to travel, followed by a six-month period to relocate to Ireland.  When I returned to Canada, I took another 8 months off to get settled in Ottawa and vision my self-employment.  It is true that in between these periods I worked my ass off.  But the breaks may have saved my physical and mental well-being.  The result: I am no further behind my peers, and I have not lost the race.

The race to accumulate wealth that will last us to the day that we die – we have made it up.  Along the way we buy expensive homes and do elaborate renovations. We spend what we make on expensive cars and hobbies that drain our funds.  Many have been through a costly divorce or separation.   This causes us to push off that day when we can retire.

Lorena and I thought we were doing pretty well to accomplish a handstand on a stand-up paddleboard...and then Tristan did one on a surfboard!

Several years ago, I decided that I would always work in one fashion or another.  I am trying to figure out what that looks like for the next few years.  But my vision is to work until the day I die at something creative.  Not full-time, I am already working at a “retirement pace.”  There is no end date here, no finish line.  This Caribbean Island is teaching me to live in the now.

What is your balance between planning for that future retirement and living in the now?

Passing a Rasta house as we hike through St. Thomas.