On being … well intentioned, but
By Ingrid Sapona
At a recent Friday night BBQ at my sail club, Paul, a former member of the Club, turned up. I didn’t know him too well, but I knew that sometime before Covid he took his boat and headed south. Every now and then, over the years, his name or photo would pop up on a Club Facebook group, so I knew he was still living aboard a boat somewhere.
From the small crowd gathered around him that night, it was clear I wasn’t the only one surprised to see him. It was quite sweet watching as various people noticed him and then made their way to him for a big hug. Listening in, it was clear some in the crowd had kept pretty close tabs on his whereabouts. One Club member, for example, surprised me when he even knew the name of the (unknown to most of us) woman standing next to Paul. (It was Paul’s wife, a kindred sailing spirit from the UK who has been sailing around the world for 10 years versus Paul’s “mere” nine years. Apparently, they married in the Caribbean a few years back.)
It was interesting to watch my fellow sailors’ reaction to Paul’s visit. Many in the group have sailed far and wide – some for months at a time. But none, to my knowledge, have left their life on terra firma with no plans of returning. While I admire the adventurous spirit of Paul and his wife, the thought of living on a boat full-time does nothing for me. So, I was surprised when more than a few seemed a bit jealous, as they commented that Paul was “living the dream”.
I left the Club that night thinking about “living the dream”. It seems to me there are two distinct ways it’s used. Sometimes it’s said to poke fun or to mock someone who may be surprised at some unpleasant activity that may go along with an otherwise favourable activity. For example, though you may love having a dog, as you’re bending over to pick up its warm, smelly poop, a small part of you might think that activity isn’t what you dreamt of when you thought of the joys of owning a dog.
But sometimes “living the dream” is said in wistful admiration. That’s certainly how I heard it when people said it to Paul that evening. And, I got the sense that for more than a few of them, they said it with a twinge of jealousy. As though, that by comparison to Paul, somehow their own sailing experiences – and lives – hadn’t lived up to their own dreams. Maybe, I’m reading too much into it, but…
That whole “living the dream” notion reminded me of “Freedom 55”, a phrase that was popular 20+ years ago here in Canada. I didn’t remember what company came up with it, but I know it was part of a marketing campaign. The idea was that we should all strive to achieve financial freedom by the age of 55. A Google search of that expression indicates it was coined by a life insurance company and their goal was to help people focus on how much they need to save/earn to retire.
While that company may have had a laudable intention, for many, the idea of having the financial freedom to retire at 55 was more undermining than aspirational. For most people, the goal of retiring at 65 is ambitious enough. So, like the grimacing realization that at any given moment you may not be “living the dream”, the reality that Freedom 55 is out of reach just makes you feel bad about what you’ve accomplished financially.
I talked to a few friends about the way I see expressions like “living the dream” and “Freedom 55”. One friend mentioned the expression “having it all” and how trying to live up to that is daunting, especially for women. This friend, a professional woman, has concluded that it’s possible to “have it all”, but that what most people don’t tell you is that you can’t necessarily have it all at the same time. She had a fulfilling medical career, then she was in a financial position to quit work after having a child late in life, and now she’s enjoying being an empty nester and pursuing other interests. So, as she sees it, she’s had it all, just one thing at a time. I found that a healthy, refreshing perspective.
Concepts like “living the dream”, “Freedom 55”, and “having it all” can certainly be motivational and inspirational. But maybe they should come with a warning that they can also undermine one’s sense of achievement.
©
2025 Ingrid Sapona
