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In his fantastic book Outlive, Peter Attia (we carry the book at The Painted Porch and did a fantastic 2-hour interview with him on the Daily Stoic podcast) looks at this idea literally and figuratively. Will you want to be able to go skiing with your adult children? Will you want to be able to travel to see your grandkids? Will you want to live long enough to maybe get to see them get married or bring you great-grandkids? Just as important as whether these things are physically possible is will you have the kind of relationship that allows for this? Will your kids want to do those things with you?

These are the questions you have to be thinking about. Not just thinking about, but making decisions and investments about and in. If you eat whatever you want, let your weight balloon, smoke, drink to excess—it doesn’t matter what dreams you have for your twilight years. You are making a powerful statement in reality about the actual value of those things to you. The same goes for how you balance work and life, whether you have put in the work on your issues, whether you’ve improved at repairing with your kids, whether you support and root for them or whether you judge and criticize them. Again, you can fantasize about family trips when you’re retired, but if, while you’re working, you’re a self-absorbed, miserable jerk—that’s never going to happen.

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