The decisions I struggled with were the ones carrying the biggest risks.
That seemed logical.
The more important the decision, the more careful I should be.
The more potential consequences, the more time I should spend thinking.
I’m not sure that was entirely true.
Some of the decisions that occupied the most space in my mind weren’t the ones most likely to fail.
They were the ones most likely to leave me wondering whether I’d made the wrong choice.
At the time, I wouldn’t have described it that way.
I would have said I was being sensible. Cautious. Thoughtful.
It took me much longer to realise that failure wasn’t always the thing I was trying to avoid.
Sometimes it was regret.
Why Regret Feels Different
Failure and regret often get bundled together as though they’re the same experience.
But they are not.
Failure can happen for all sorts of reasons:
- Circumstances change.
- Things don’t work out.
- Life takes an unexpected turn.
Regret feels more personal:
- It carries the suggestion that we should have known better.
- That the signs were there.
- That somebody else might have made a better choice.
That’s what makes it so uncomfortable.
The outcome may be disappointing.
But regret turns the spotlight back on the person who made the decision.
The Future Version Of Ourselves
Many difficult decisions seem to involve somebody who doesn’t exist yet.
The future version of us who has already lived with the consequences.
The one who knows how things turned out.
The one who can see connections, warning signs and opportunities that were impossible to see at the time.
Without realising it, many of us give that future version far more authority than the person making the decision today.
After all, they have information we don’t: They know what happened next. They know whether the relationship lasted. Whether the opportunity worked out. Whether the change delivered what we hoped it might.
The difficulty is that we’re asking present-day us to satisfy a standard that can only be applied afterwards.
It’s a strange situation when you stop and look at it.
We’re trying to make a decision using today’s information while imagining how it will be judged by someone who already knows the ending.
The Standard We Quietly Create
This is where many decisions become heavier than they need to be.
The goal stops being to make a thoughtful choice.
Instead, the goal becomes avoiding any future version of the story that might leave us questioning ourselves.
It’s an understandable instinct: Nobody enjoys disappointment. Nobody enjoys discovering that something didn’t unfold as they’d hoped.
The trouble is that once regret becomes the thing we’re trying to avoid, the standard quietly changes.
A good decision is no longer enough.
The decision has to survive every future doubt.
Every difficult period.
Every moment where another path appears more attractive.
Every occasion when life fails to unfold exactly as we’d imagined.
That’s a demanding role for any decision to perform.
Particularly when most important decisions are only the beginning of a story rather than the end of one.
The Conversation We Rarely Have
Many of us behave as though regret is something a good decision should prevent.
As though enough thinking, enough caution or enough preparation ought to protect us from ever looking back and wishing things had unfolded differently.
The difficulty is that regret doesn’t only belong to poor decisions.
Sometimes it appears because life offers us information we didn’t have at the time, or because another path also contained something valuable, or simply because every decision leaves something behind.
That’s the part we rarely talk about.
Not all regret is evidence that we chose badly.
Sometimes it’s simply evidence that the alternatives disappeared the moment we chose.
Which means the goal cannot really be to eliminate regret completely.
The goal is to make the most thoughtful decision we can with the information available today.
It Makes Me Curious…
… about the standards we apply to our past decisions.
Particularly the ones that didn’t lead exactly where we hoped.
Very few of us look back and ask: “Given what I knew at the time, was that a reasonable choice?“
Instead, we often ask: “Knowing what happened afterwards, should I have chosen differently?“
Those sound similar. They aren’t.
One judges the decision.
The other judges the outcome.
And it’s easy to blur the two together.
Perhaps that’s why regret can feel so persuasive.
It encourages us to believe we should have acted on information that only became available later.
To expect a version of ourselves from the past to see things that only became visible with time.
That’s a difficult standard for anyone to meet.
Including us.
Your Next Step
The bigger risk may not be choosing wrong.
It may be asking yourself to satisfy a future version of you who already knows how the story ends.
If there’s a decision you’ve been carrying for a while, try asking yourself:
Am I trying to make a thoughtful decision?
Or a regret-proof one?
The answer may explain more than you think.
From Thinking to Doing helps you move forward without waiting for guarantees that no future version of you could ever question.
What’s Coming Next?
Later this week we’ll explore a different assumption.
The belief that choosing wrong is permanent.
And what happens when we forget how adaptable human beings can be.
If You Take One Thing From This
You don’t need to make a decision that future-you could never question.
You only need to make one that present-you can justify honestly.
People Also Ask
Why am I so afraid of making the wrong decision?
Often because the fear isn’t failure itself. It’s the possibility of regretting the decision later and blaming yourself for the outcome.
Is regret a sign I made the wrong choice?
Not necessarily. Regret often appears because we can see information in hindsight that wasn’t available when the decision was made.
How do I stop overthinking important decisions?
Try focusing on whether the decision makes sense with the information available today rather than whether it guarantees a future outcome.
Can you ever make a regret-proof decision?
Probably not. Future versions of ourselves will always have access to information and experiences that weren’t available at the time of the decision.
References
Han, Q, Quadflieg, S and Ludwig, C (2023) Decision Avoidance and Post-Decision Regret: A Systematic Review and Meta-Analysis. PLOS ONE.
Kumano, S, Hamilton, A and Bahrami, B (2021) The Role of Anticipated Regret in Choosing for Others. Scientific Reports.
Kahneman, D and Tversky, A (1979) Prospect Theory: An Analysis of Decision Under Risk. Econometrica.
