Embracing the Do-Over—A Journey in Wealth, Wellness, and Second Chances

There’s a phrase I’ve come to love: “the great redo”. It’s the idea that life, much like financial planning, sometimes gives us a second chance to get things right—or at least to do them better. I recently lived this lesson firsthand, and I want to share how it shaped my approach to both personal growth and wealth management.

Last year, my wife and I embarked on what was supposed to be the trip of a lifetime: ten days sailing between the islands of the Azores. The anticipation was high, but so was my anxiety. I had to have a wisdom tooth removed days before departure and, as fate would have it, I suffered an allergic reaction to prawns on the second night. That set off a chain of events—illness, a broken tooth, a cold that swept through our group, and relentless heat. Despite it all, we made memories, but I couldn’t shake the feeling that we’d still somehow missed out on the true magic of the experience.

This year, when the opportunity arose to take the same trip again, I hesitated. Was it indulgent to try for a do-over? But then I realized: giving ourselves permission to try again isn’t just okay; it’s essential. In wealth management, as in life, we’re often told to get it right the first time. But the truth is, growth comes from reflection, adaptation, and the courage to revisit our goals with new wisdom.

Preparation was key this time. Kitty and I worked on our physical fitness, so we could better handle the demands of life on a 50-foot sailboat. I paid close attention to my allergies, steering clear of prawns and being mindful of what I ate. I even took an art lesson on a rainy day, stretching my creative muscles in new ways. The result? A trip that was not only smoother but richer in every sense.

This experience reminded me of the importance of self-awareness and adaptation in financial planning. Sometimes, our first attempt at investing or saving doesn’t go as planned. Maybe we encounter unexpected expenses, or the market throws us a curveball. The instinct might be to shrink away, to avoid risk or change. But real progress comes when we give ourselves permission to try again—armed with better information, stronger preparation, and a willingness to ask for help when needed.