Published on: Tuesday August 4th 2026
People often cringe when they look at old photos of themselves, mostly because of clothing and hairstyles that don’t seem as appealing as they once did. But as I get older, I don’t mind looking at a younger me. I never thought back then that I would look like this today. I mean, I knew I would age, but I didn’t have a vision of how I would look in the future. I think all you can picture is the way you look at that moment.
Of course it’s not just how we look. Think about it. How much do you think you’ll change as a person over the next fifteen years? If you’re like most people, the honest answer is “not much.” We look backward and see a completely different person. We look forward and picture roughly the same person we are today, just older.
Psychologist Daniel Gilbert and his colleagues at Harvard ran a study on exactly this, surveying people from age 18 to 68 about how much their personality, values, and preferences had changed over the past decade, and how much they expected them to change over the next one. Across every age group, people consistently underestimated how much they were about to change, even though they readily admitted how much they already had. Gilbert gave it a name: The End of History Illusion. We seem to believe that history, at least the personal kind, has just finished happening to us, and that we’ve arrived at the finished version.
I think about this a lot in my line of work, because I see it show up in places that matter a great deal in clients’ financial lives.
When I sit down with people in their 50s to build a retirement plan, we’re making a set of assumptions. Retirement at 65. This spending level. This return expectation. A view of what “the good life” looks like in 15 years. And it’s a perfectly reasonable exercise. But I’d gently suggest that the version of you sitting across from me today is not the final one. Kids grow up and either need less help than expected or a lot more. Businesses get sold or don’t. Health changes. Priorities that felt fixed in your 50s can look completely different in your 60s. I’ve had clients tell me with total conviction that they’ll never sell the cottage and then sell the cottage. I’ve had clients swear they’ll work forever, and then not want to or not be able to.
None of that means the plan was wrong. It means the plan is a living document, not a headstone. That’s exactly why I don’t build a plan once and file it away. We revisit it for a couple of reasons. The financial assumptions were just that and we need to account for what actually happened. We expected a certain return, but what did we actually earn? But we also revisit it
because the person it was built for keeps quietly becoming someone slightly different, whether they notice it happening or not.
But that’s ok. There’s a solution. Build things that don’t depend on you correctly predicting who you’ll be 15 years from now. The same thing goes with your investments. A portfolio should be diversified enough across asset classes and sectors that it doesn’t require this decade’s winners to keep winning forever. A financial plan should have enough flexibility built into it that it can absorb challenging markets and the version of you that shows up in 2041, whoever that turns out to be.
Somewhere out there is a future version of you looking back at a photo from today, thinking “I can’t believe I thought that was the finished version.” My job is to make sure that whoever that person turns out to be, they’re in good shape when they get there.
I was in the car listening to the CBC when I heard the news that Gord Downie had died. And then they played Wheat Kings. I think of that and of him every time I hear the song and it moves me.