Retirement often involves making important decisions with incomplete information when the stakes are high. You won’t have everything figured out on Day 1. More likely, you’ll arrive at your ideal retirement through a process of trial and error. You’ll make mistakes. That’s unavoidable. The important thing is that you learn from them. How best to do that?
Ray Dalio is an investment legend on par with people like Warren Buffett. He owns Bridgewater, the largest hedge fund in the world. Ray has a saying:
Pain + Reflection = Progress
In other words, pain is a good instructor and a strong signal. According to Dalio, success is nice, but it just causes you to do more of the same. You don’t learn much from it. Pain, on the other hand, has a lot to teach you. Whenever you make a mistake about anything, you feel some sort of pain. There’s a message in that pain somewhere. It’s hard to see while you’re going through it, but if you reflect on it once it’s over, you’ll probably be able to see what that message is.
As you experiment with retirement, write down these pain points and think about them. What caused the pain? What should I learn from it? What would I do differently in the future? If you do that, you’ll come out with a principle that relates to the people, places, activities or philosophy of your retirement. That principle is the progress in the equation above. It’s the newfound wisdom that gets you a bit closer to your ideal life and retirement. The more you experiment, learn and iterate, the better your odds of having a happy, meaningful retirement. In some ways, you might even learn to enjoy the pain as an indication of progress. Again, Ray Dalio:
“Encountering pains and figuring out the lessons they were trying to give me became sort of a game to me. The more I played it, the better I got at it, the less painful those situations became, and the more rewarding the process of reflecting, developing principles, and then getting rewards for using those principles became. I learned to love my struggles, which I suppose is a healthy perspective to have…”