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Harness the stunning power of financial regret

Here are 5 ideas to consider.

By Karen Datko Oct 6, 2009 2:43AM

This post comes from partner blog The Dough Roller.


Regret over past financial decisions can have a powerful hold on you.


At 23, you may regret running up $20,000 in credit card debt during college. At 35, you may regret never having gone to college. At 45, you may regret having never started that consulting business you always dreamed of pursing. And at 65, you may regret not having saved more for retirement. In recent days, many financial chickens have come home to roost.

Regret, financial or otherwise, can have a powerful grip on your life. For most, the question is not whether you have financial regret. The question is how you harness the power of that regret to make sound financial decisions today that you will not regret tomorrow.


Here are some ideas to help you do just that:


Stop beating yourself up over past financial mistakes. We all have made stupid financial decisions. Even Warren Buffett has made dumb investments, which he readily admits. We can spend a lot of time and energy lamenting those past decisions, but it will not help us make better decisions today. We need to stop obsessing about the past and, instead, use the lessons it can teach us to make better decisions today.

It is better to look ahead and prepare than to look back and regret. -- Jackie Joyner-Kersee

Regret for wasted time is more wasted time. -- Mason Cooley

Learn from that which you regret. If regret has any positive value, it comes from evaluating the decisions you made that caused the regret. Take out a piece of paper and write down your financial regrets in as much detail as possible. Think about not only regrets from things you did, but also regrets from things you chose not to do. It is the things we did not do that often cause the most pain. We will use this list of regrets to make new and fresh decisions today that can at least keep the regretful decisions from continuing.

Never regret. If it's good, it's wonderful. If it's bad, it's experience. -- Victoria Holt

Regret for the things we did can be tempered by time; it is regret for the things we did not do that is inconsolable. -- Sidney J. Harris

To regret deeply is to live afresh. -- Henry David Thoreau

It is never too late. Reread the quote from Sidney Harris above. Does it describe any of the financial regrets you wrote down on the piece of paper? In most cases, our most profound regrets come from things we were too scared or busy or distracted to do. Whether it was going into business, going to college, or investing in the stock market, what we chose not to do can be a major source of regret.


If you are reading this article, it is not too late. Many go to college during retirement, or start investing in their 50s (or later), or start a business only after retiring from a career. Sometimes we convince ourselves that it is too late to accomplish this or that because it eases the pain of regret. But it is a lie. Believing that it is too late to change may make us feel better, but it also causes us to repeat the same inaction that caused the regret in the first place. Look at it this way. If you are 45 and considering getting a college degree, you have two choices: turn 50 with a college degree, or turn 50 without one.

There is no old age. There is, as there always was, just you. -- Carol Matthau

Do not go gentle into that good night,

Old age should burn and rave at close of day;

Rage, rage against the dying of the light. -- Dylan Thomas

Change the bad habits. Many regrets are born out of a lifetime of small, insignificant bad money-management decisions. You may have lived for years spending just a little more than you make. But after a lifetime of such living, you find yourself in unimaginable debt, with little or no savings. It wasn't one big mistake, it was thousands of small financial missteps. If that describes some of the regrets you have written down, changing those bad habits will be much like breaking free from addiction.


People are addicted to eating out. They are addicting to shopping. They are addicted to their gadgets. Of course, nothing is wrong with any of these things if you are properly managing your money. But if you are not, these are some of the daily, weekly and monthly decisions you make that have added up over a lifetime to create the financial regret you now experience.


As a starting point, wipe your financial slate clean. Put your past financial decisions where they belong, in the past. The question now is what financial decisions are you going to make today. If regret is born out of uncontrollable shopping, put something else in your life to take the place of the shopping. Ask a friend to hold you accountable. Give your spouse your cash and credit cards to hold for you. Do whatever it takes so that tomorrow you will not regret the decisions you make today.

My one regret in life is that I am not someone else. -- Woody Allen

Focus on today and tomorrow, not yesterday. Take another look at that piece of paper that lists all of your financial regrets. That paper represents the past. Take stock of the regrets, and make decisions today so that those regrets do not repeat themselves. And once you have done that, throw the paper away. Make decisions today so that tomorrow you will look back without regret.

When one door closes, another door opens; but we often look so long and so regretfully upon the closed door that we do not see the ones which open for us. -- Alexander Graham Bell

All saints have a past; all sinners have a future. -- Warren Buffett

Regret is a stunningly powerful emotion. Allowed to run amok, regret can ruin a life and even a family. With some honest introspection, however, you can turn that powerful emotion into a motivator that helps you make better choices today. Whatever your past, make today great, so tomorrow can be even better.

One success can wipe out 10,000 failures. -- The Dough Roller

Other articles of interest at The Dough Roller:

Published Oct. 8, 2008
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