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Scott Neal

Scott Neal, CPA, CFP, is the president of D. Scott Neal, Inc., a fee-only financial planning and investment advisory firm with offices in Lexington and Louisville. Reach him at or by calling 1.800.344.9098.

Turning a Deaf Ear to “Shoulda, Coulda, Woulda”

If you’re like me, you’ve likely experienced a sense of regret or disappointment at some time in your life. All too often shame, guilt, and fear over money arise because of the message of “shoulda, coulda, woulda.” One of my good friends, an accountant, is fond of saying, “If ‘shoulda, coulda, woulda’ were nickels, we would all be rich.”

The idea that we should have done something implies that we feel a certain sense of obligation towards acting a certain way. That we could have implies missed opportunity. And, would have implies a certainty of action which was prevented by an intervening event. The phrase denotes a sense of dismissiveness over something in the past. Both the fear born of past regret and the fear of future regret can lead to both action and inaction in our lives.

It’s important to realize that action, inaction, and reaction are caused by a feeling. Fear may spur us on to take necessary action, like running away from a serious threat. It can also cause us to take harmful action or to react in a way that does not produce a beneficial result. In fear, we may, at times, resist taking any action whatsoever. The paradoxical thing about living in such a way—so as to avoid regret—is that such efforts often lead to regretfulness all the same. “What if I had done this or that? Would it have made any difference?” We see this so often as people approach retirement, enter elderhood, or approach life’s end.

The nagging sense of what we could have, should have, and would have done, but didn’t, is a source of complex motivations driving decisions about what to do with our time, effort, and money. Perhaps it is what we should have, could have, or would have done with our money, but didn’t, that reinforces a sense of fear and regret.

Getting Off the Hamster Wheel

As a hospital chaplain, I would find myself in the room with people facing imminent death, with many fighting for more time. You’ve been there, I am sure. If we simply had more time, then perhaps we could get some things right, couldn’t we? If we had more time, then we could somehow combat the feelings of guilt and shame and fear buoyed by the regret we feel at not having done enough, said the right things, or made better decisions. Regret at any point in our lives can leave us fighting for more time, trying to make up for the lost opportunities of the past, and attempting to apply the wisdom we felt we should have exercised so much earlier. But, is more time really the key to overcoming the message of the “shoulda, coulda, woulda?”

I saw this happen with my own mother on the day before her death. She looked at me and asked with no small amount of surprise, “Am I dying?” I reassured her that, at least not in that moment, was she dying, and I asked her what difference knowing that would make. She replied that she had so much to do.

I wonder what would happen if we focused less on trying to gain time and more on knowing what matters to us and why. What if we took the time to express what is most important to us? And, to express it in time for our loved ones to be able to do something about it? Then, we would have the time to pursue more of what is meaningful and focus less on regret.

Knowing what matters, and why, can also help focus a financial plan to be more effective at accomplishing future goals. What could you accomplish if you didn’t have all the time in the world? If you could get rid of “shoulda, woulda, coulda?”

Scott Neal is President of D. Scott Neal, Inc., a fee-only financial planning and investment advisory firm with offices in Lexington and Louisville. Find his blog at or call the firm at 1-800-344-9098.