One of the reasons planning for your future can be such a challenge is that many, if not all of us, fall under the spell of the End of History illusion.

Which is really just a fancy way of saying that when we look back on our life, we can easily see that we’ve changed a great deal, but when we look forward, we find it hard to imagine that we’ll really change all that much.

We tend to think that who we are now is basically who we’re going to be in the future, even though it’s not who we were in the past.

In other words, we tend to underestimate how much we’ll change.

I see this all the time when I first start discussing retirement with people. Instead of imagining their future self, they tend to imagine themselves in the future, with all the same worries and priorities that they have today.

But difficult as it might be to imagine, we know that’s not going to be the case.

That’s why I try to make the conversation more concrete and bring in more details. How old will you be? How old were your parents when they retired? What was that like? How do they spend their time? How old will your husband or wife be? Will they still be working? What about your kids? Where will they be in life?

I try to get them to stop projecting their current self into the future and to start imagining what that future will really look like. How different their priorities might be. What things might matter more to them then than they do now.

I try to get them to paint a picture and try to really see it.

In the end, life will never turn out just like the picture we imagine. But going through the exercise is helpful because it forces us to consider all the different possibilities and figure out steps you need to take now to get prepared.

If nothing else, it’s helpful to pull back the curtain and realize that we’re fooling ourselves if we think who we are now is who we’re going to be for the next thirty or forty years.

History hasn’t ended. Change is inevitable.

Even if it’s hard to imagine, we must plan for it to happen to us.

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