Woulda Shoulda Coulda – How to Deal with Regret About Past Lifestyle Choices

Do you ever look back on your life and regret past choices you’ve made which have kept you from achieving some of your dreams today?  I know I do.

I believe I have a healthy perspective on the situation, though.  I don’t send myself on guilt trips or get depressed about it.  However, I do have a sense of regret about money, time, and opportunities wasted.

I think my biggest regret revolves around my relationship with money.  Despite the many people in my life who encouraged me to systematically save money (starting with my parents, teachers, employers, and friends), I saved virtually nothing through my teenage, young adult, and early marriage years.

I know money isn’t everything.  But when it comes to living the lifestyle of your dreams, it sure does help. Because money buys you both time and opportunity.

I graduated from high school 21 years ago.  When I add up all the money that has passed through my hands since then, I’m flabbergasted.  And when I calculate how much money I’d have if would have saved just 10% of my income each year for 21 years (aside from what I’ve saved for retirement), I’m amazed.

That money could have fulfilled a lot of my dreams.  It could have made some decisions easier.  It could have opened up new doors of opportunity.  But it didn’t, because I didn’t let it.

What should you do when you feel regret for past lifestyle choices?  I say let it be your guide, your motivation, to make things different from this point forward.

I think you’ll find that bold action is the best medicine for regret.  Whatever it is that you know you need to start (or stop) doing, resolve to do it today!

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