

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:


Should you prepare for a deeper downturn?
Memento Mori