It’s easy to look back at past decisions and think, I should have done it differently. I sometimes think I should have spent less and saved more in my 20s and 30s. When we lived in London, maybe we should have kept that Swampscott house for rental property instead of selling it. The challenge is never knowing if things would have turned out better, worse or just different.

What would you be willing to risk losing if you could go back and do things differently?