The weight of unmade decisions
If you’re waiting for certainty, you’re already losing to someone who isn’t.
We often treat the possibility of regret as proof we shouldn’t act. But regret belongs to a future self with different values, different information, and a different vantage point. Perfectionism tries to appease that judge in advance. It keeps us polishing instead of progressing. Better to act honestly now, gather real feedback, and improve your ratio over time. High performers don’t wait for certainty. They move, learn, adjust. Regret is part of being alive, but inaction is the variety that lingers longest.
Stop living for the approval of someone you haven't become yet.
Every meaningful decision carries the possibility of regret. Change careers and you might wish you had stayed. Stay where you are and you might wonder what could have been. Start the business, speak up in the meeting, publish the article, ask the difficult question, or choose to do none of those things. Every path closes off another.
Yet we often treat the possibility of future regret as if it were proof that we shouldn't act. It becomes the final argument against taking the leap. But what if regret is simply part of being alive? And what if the greater danger is allowing an imagined future version of yourself to dictate the choices you make today?
The judge who hasn't formed an opinion yet
Start with who is actually doing the regretting. The philosopher Derek Parfit, in his landmark work Reasons and Persons, argued that we are wrong to treat regret as a rational response to our past decisions, and wrong to warn people off decisions on the grounds that they will regret them later. His reasoning rests on two ideas.
First, every decision is made by a particular person, in a particular situation, with the information available at the time. Your present self is not being careless when it chooses. It is doing the best it can with what it has, which is all any of us can ever do.
Second, and more radically, the future person who might look back with regret is, in a meaningful sense, not the same person who made the decision. Parfit rejected the idea of a single, fixed self-persisting unchanged through a life. What we call the self is a chain of psychological states, each connected to the last but gradually transforming. The person judging the decision in five years will hold different values, occupy a different vantage point, and know things the decision maker could not have known. Their verdict is delivered from a world the original decision maker never inhabited.
What is striking is how well the empirical research has caught up with him. In a study published in Science, Jordi Quoidbach, Daniel Gilbert, and Timothy Wilson surveyed more than 19,000 people and found what they called the end of history illusion: at every age, people acknowledge how much they have changed in the past decade, yet predict they will change very little in the next one. We consistently underestimate how different our future selves will be. So when someone says you will regret this, they are forecasting the emotional reaction of a person who does not exist yet, and whom the evidence says we systematically mis-imagine.
On this view, carrying the weight of regret is a kind of category error. You are holding your present self-accountable to the standards of a person who does not exist yet, or punishing them on behalf of a person who no longer exists. Neither is coherent. Your past self-acted on reasons that were valid at the time. That is the only test they could ever have passed.
Perfectionism is the warning turned inward
Once you see the structure of the warning, you start to recognise it in an unexpected place: perfectionism.
Scratch the surface of perfectionism and you usually find the same fear underneath. Not fear of the mistake itself, but fear of having to live with it. The imagined version of yourself, months or years from now, looking back and thinking, why did I do that?
Perfectionism is, at its core, an attempt to make a decision that your future self cannot fault. It is pre-emptive appeasement of a judge who has not yet formed their opinions.
And it shapes behaviour in exactly the way you would expect. The perfectionist prepares past the point of usefulness. They polish, delay, and hedge, all in the name of certainty. What looks like rigour is often risk avoidance dressed in professional clothing. The clinical literature bears this out. Paul Hewitt and Gordon Flett, whose work has defined the field, distinguish healthy striving from perfectionism proper, and find the latter reliably associated with procrastination, burnout, and avoidance rather than with excellence. Brené Brown puts it more bluntly: perfectionism is not the same thing as striving to be your best. It is a defensive move, a shield carried in the hope of avoiding blame, judgement, and shame. And the cost is real. While the perfectionist refines a plan for the one attempt they are too anxious to make, someone less prepared is already on their fiftieth attempt and learning faster than any amount of preparation could teach.
Parfit dissolves the authority of the judge the perfectionist is trying to appease. The future self who might regret your imperfect attempt will be assessing it with information you do not have, from a position you cannot occupy, according to values you may not share. You cannot satisfy them in advance, and you owe them no such attempt.
What the best performers already know
Consider how the best performers in any field actually operate. An elite basketball player converts roughly half their attempts, and that ratio is considered exceptional. A venture capitalist builds a portfolio knowing most of it will lose money. Celebrated authors accumulate rejection letters before anything reaches a shelf. None of these people succeed by attempting only the sure thing. They succeed by attempting a great deal, absorbing the misses, and improving their ratio over time. The miss is not the failure point. It is the feedback.
This is not a new insight. Voltaire warned centuries ago that the perfect is the enemy of the good, and the economist Herbert Simon, who won a Nobel Prize for the idea, showed that effective decision makers do not optimise endlessly. They satisfice: they choose the option that is good enough given real constraints of time and information, and they move. Carol Dweck's decades of research on mindset points the same way. People who treat ability as something built through effort and error consistently outperform those who treat every attempt as a verdict on their worth. The miss teaches. The verdict paralyses.
The high performers, in other words, have already answered the question in the heading. Yes, some of this will sting later. So what? Volume plus feedback beats a small number of protected attempts, and the sting of a miss fades faster than the drag of never trying.
The regret you should actually worry about
There is one more finding worth sitting with, because it turns the original warning on its head. Thomas Gilovich and Victoria Medvec, in their research on the psychology of regret, found that in the short term people regret their actions, but over the long run they overwhelmingly regret their inactions: the risks not taken, the conversations not had, the shots never attempted. If you insist on managing your future self's regret, the evidence suggests the surest way to create it is to hold still.
So the honest answer to you will regret this is not a denial. It is a shrug, followed by better questions. Regretted by whom, exactly? Judged from what vantage point, with what information, against what values? And if regret is coming either way, why choose the variety that research says cuts deepest, the regret of the thing never attempted?
What you can do is act well now: gather the information that is genuinely available, decide with honesty, and move. If the attempt misses, the miss becomes data for the next attempt. If a future version of you winces at it, that future version is entitled to their view, but their view arrives too late to be a useful instruction and was never a fair one to begin with.
This is not an argument for recklessness. Preparation matters, and some decisions deserve real deliberation. The distinction is between preparing in order to act and preparing in order to avoid acting. The first builds capability. The second builds a very well documented standstill.
Progress was always the standard
Samuel Beckett compressed the whole philosophy into a handful of words: try again, fail again, fail better. Parfit gives the same instinct a philosophical foundation. The regret you are pre-emptively managing belongs to someone else, and the mistake you are so determined to avoid is the raw material of every skill you will ever build.
You are doing your best with what you know now. The person you become will be doing their best with what they know then. Let each of you handle your own end of the arrangement.
Imperfect is better than incomplete. Take the shot. Your future self can decide what to make of it. Your present self has work to do.