We often wish we could change our past, forgetting that our past is what shaped the way we think today
Why the decisions we question today might be the very experiences that changed how we think.
I’ve attended quite a few business events, conferences, and networking sessions over the years. There are often guest speakers sharing their experiences, talking about their careers, businesses, and the challenges they’ve faced.
And I’ve noticed something.
During the Q&A, people often ask the same questions.
“Is there something you wish you had done sooner?”
“Is there anything you regret doing?”
“What would you do differently if you could start all over again?”
Different events, different speakers, but almost the same questions.
I understand why people ask them. They’re probably hoping to learn something from someone else’s experience.
But whenever I hear these questions, I find myself questioning the questions themselves.
Why are we so interested in what we could have done differently? And why do we assume doing something earlier would have produced a better outcome?
Maybe I think too much about ordinary things. But to me, there’s something interesting about the assumptions behind these questions.
We seem to believe that if we could go back and change certain decisions, our lives would somehow be better.
But would they?
You Didn’t Know Then What You Know Today
Let’s say someone started a successful business at 40.
Looking back, they might say, “I wish I had started my business when I was 25.”
But would they have had the same knowledge, experience, relationships, and judgment at 25?
Probably not.
Maybe those fifteen years working for other people, making mistakes, dealing with difficult situations, and learning how businesses actually operate were what prepared them to succeed.
Maybe they needed those experiences to understand what they wanted, what they were capable of, and what they weren’t particularly good at.
We often look backward using everything we know today and assume we could have applied that knowledge to our younger selves.
But that’s not how life works.
The person we were ten or twenty years ago didn’t have the same understanding we have today.
And even if we’d made a different decision, there’s no guarantee the outcome would have been better.
Maybe we would have succeeded.
Maybe we would have failed.
Or maybe we would have ended up somewhere completely different.
Starting earlier doesn’t necessarily mean succeeding earlier.
And more importantly, starting earlier doesn’t necessarily mean learning earlier.
Experience Isn’t Measured in Years
I think people often confuse time with experience.
I’ve met people who have worked in the same industry for decades but still approach problems the same way they did years ago.
I’ve also met people with far less experience who constantly question things, observe, learn, and develop a much deeper understanding of what they’re doing.
To me, experience isn’t simply about how many years you’ve spent doing something.
It’s about what you’ve actually learned during those years.
Two people can go through exactly the same situation and walk away with completely different lessons.
One might blame the circumstances or the people around them.
The other might ask what happened, why it happened, and what they could have done differently.
The experience was the same. What they learned was different.
That’s why I don’t automatically believe someone would have been more successful just because they started earlier.
They might have had more time, but that doesn’t mean they would have developed the same understanding.
Time gives us opportunities to learn. It doesn’t guarantee that we will.
And sometimes, what we learn isn’t something entirely new.
Sometimes, it’s realizing that something we believed for years was never quite right in the first place.
What Made Sense Then Might Not Make Sense Today
There’s another part of this that I find interesting.
Something you strongly believed ten or twenty years ago might make absolutely no sense to you today.
Maybe you once believed that working harder automatically meant becoming more successful.
Maybe you thought having a certain job title, earning more money, or reaching a particular position would make you happy.
Maybe you trusted certain people, followed certain advice, or believed there was only one correct way to do something.
At the time, those beliefs made sense to you.
But then life happened.
You worked with different people. You experienced different situations. You made mistakes. You observed things that challenged what you thought you knew.
And gradually, your perspective changed.
What you once considered important might no longer matter.
What you once thought was a good decision might now seem completely unreasonable.
But does that mean your younger self was foolish?
Not necessarily.
You were making decisions based on the understanding you had at that time.
Of course, sometimes we were simply wrong. Maybe we ignored good advice, overlooked something obvious, or refused to consider another perspective.
That’s part of being human too.
But sometimes, the only reason we recognize something as a mistake today is because we experienced the consequences of believing it in the first place.
We don’t just learn new things as we get older. Sometimes we have to unlearn what we once believed was true.
And I think that’s an important part of developing judgment.
It’s easy to say, “I would never make that decision today.”
But the more interesting question is why.
What changed?
Was it something you experienced? Someone you met? A mistake you made? Or perhaps something you witnessed that completely changed how you understood the world?
If those experiences hadn’t happened, would you still believe what you believe today?
That’s something worth thinking about.
The Life We Imagine Never Actually Existed
There’s something fascinating about how we look back at our lives.
What if I’d started my business ten years earlier?
What if I’d taken that job?
What if I’d invested in that company?
What if I’d moved somewhere else?
We ask ourselves these questions and imagine how different our lives could have been.
And somehow, we often assume things would have turned out better.
But there’s a problem with that thinking.
We’re imagining ourselves making those decisions with the knowledge, experience, values, and judgment we have today.
That’s not the person we were back then.
The person I was twenty years ago didn’t think the way I think today. I didn’t have the same understanding of people, business, relationships, or the world around me.
And much of what I know today came from the decisions I made along the way, including the mistakes.
So here’s something I’ve always wondered.
If you removed the experiences that shaped who you are today, would you still be the same person making that decision?
Think about that for a moment.
We wish we had made different decisions in the past, but we want to make those decisions with the wisdom we have today.
Yet that wisdom came from living through the very experiences we now wish we could change.
We want the wisdom without the experiences that created it.
And that’s the contradiction I find so interesting.
If I could go back and change a major decision twenty years ago, I might have followed a completely different career, met different people, or experienced different challenges.
Would I still think the same way?
Would I have developed the same judgment?
Would I still value the same things?
Would I even be asking the same questions today?
Maybe. Maybe not.
There’s no way to know.
Yet we spend so much time imagining that alternative life as though we already know it would have been better.
We want to change the journey without changing the person who came out of it.
But those two things aren’t independent of each other.
Why We Romanticize the Past
There’s actually a psychological aspect to this.
Our minds are capable of imagining alternative versions of events that have already happened. Psychologists call this counterfactual thinking.
We think about what might have happened if we’d made a different choice.
Sometimes this is useful. It helps us recognize mistakes, understand consequences, and make better decisions in the future.
But it can also become a trap.
We start comparing our actual lives with imaginary alternatives.
And because those alternatives never happened, we can make them as perfect as we want.
We imagine the successful business we could have built, the money we could have made, or the opportunities we might have enjoyed.
But we rarely imagine the additional problems, failures, or sacrifices that might have come with those decisions.
What if starting that business earlier meant failing because we didn’t understand how to manage money?
What if taking that job meant missing an opportunity to meet someone who later changed our career?
What if buying that property ten years ago had created financial pressure we weren’t prepared to handle?
We don’t know.
There’s another psychological tendency called hindsight bias.
Once we know how something turned out, we tend to believe the outcome was more predictable than it actually was.
It’s easy to say, “I should have invested in that company ten years ago,” when we already know how successful it became.
But ten years ago, we didn’t know.
There were risks, uncertainties, and countless other possibilities.
We judge our past decisions using information that wasn’t available when those decisions were made.
And then we regret not knowing what we couldn’t possibly have known.
I find that rather strange.
Of course, not every regret comes from hindsight bias. Sometimes we genuinely knew better and made a poor decision anyway.
But there’s a difference between recognizing a mistake and spending years imagining a better life that may never have existed.
Just because we can imagine a better outcome doesn’t mean that outcome was ever guaranteed.
Everything Happens for a Reason
I’ve always believed, in my own way, that things happen for a reason.
Maybe not because everything is predetermined or because there’s some grand plan controlling our lives.
But because our experiences are connected.
A decision we make today can influence an opportunity tomorrow.
A mistake might change how we approach a problem years later.
A conversation with someone might lead us in a direction we never expected.
And sometimes we don’t understand the significance of an experience until much later.
I think about how differently I see certain things today compared with ten or twenty years ago.
Some things I once considered important no longer seem particularly important.
Some things I used to believe were true turned out to be much more complicated.
And some experiences that seemed frustrating or meaningless at the time eventually changed how I approached other situations.
That doesn’t mean every difficult experience was necessary.
It doesn’t mean every bad decision was secretly a good decision.
Sometimes things simply go wrong.
But what happens afterward matters.
Do we learn something? Do we change our thinking? Do we recognize something we previously overlooked?
Or do we keep repeating the same mistakes?
I don’t think life is simply about reaching certain milestones as early as possible.
It’s also about developing the understanding to recognize what those milestones actually mean to us.
And sometimes, what we wanted ten years ago isn’t even what we want today.
So why do we keep judging our past based on what we value now?
Perhaps the person we were back then was pursuing something that made sense to them.
And perhaps the experiences that followed are exactly why we see things differently today.
Learning From the Past Is Different From Living in It
I’m not saying people shouldn’t look back.
Reflection is important.
We should question our decisions, understand our mistakes, and recognize what we could have done differently.
But there’s a difference between learning from the past and living in it.
Learning from the past helps us make better decisions today.
Living in the past keeps us attached to decisions we can no longer change.
And I think people sometimes spend so much time wondering what they should have done that they overlook what they can actually do now.
The past is the past.
We can’t go back and change it.
We can’t undo every mistake, recover every missed opportunity, or rewrite every decision.
And even if we could, we wouldn’t know what the consequences would be.
Accepting the past doesn’t mean believing every decision was correct.
It doesn’t mean avoiding responsibility or pretending we have no regrets.
It simply means recognizing that what happened has already happened.
We can learn from it without spending the rest of our lives wishing it had been different.
There’s also something else I think people overlook.
If our beliefs and values are constantly changing as we gain experience, then the person we are today isn’t necessarily the final version of ourselves either.
Ten years from now, we might look back at what we believe today and wonder why we ever thought that way.
And that’s perfectly fine.
It means we’re still learning.
Maybe We’re Asking the Wrong Question
Going back to those events, I understand why people ask guest speakers what they regret or wish they’d done sooner.
It’s an easy question, and sometimes the answers make interesting stories.
But personally, I’d rather ask something different.
“What did you believe ten years ago that you no longer believe today, and what experience changed your mind?”
To me, that’s a much more interesting question.
It tells me how someone thinks.
It shows whether they’re willing to challenge their own assumptions, recognize mistakes, and change their perspective when they learn something new.
I’m not particularly interested in hearing that someone wishes they’d started their business earlier.
I’m more interested in understanding what made them capable of building that business in the first place.
What did they learn about people?
What assumptions turned out to be wrong?
What did they once believe was important but no longer consider important today?
And what experiences changed their understanding?
Those are the things I find valuable.
Because the interesting part of someone’s journey isn’t necessarily when they started.
It’s how they became the person they are today.
And perhaps more importantly, how their understanding continues to change.
The Past Is the Past
Of course, there are decisions I would make differently today.
But that’s because I’m not the same person I was ten or twenty years ago.
I’ve learned things. I’ve made mistakes. I’ve experienced successes and failures. My understanding of people, business, technology, and life has changed.
Some beliefs I held years ago no longer make sense to me.
And I’m sure some of the things I believe today will change as well.
That’s part of life.
I don’t think we should expect ourselves to have everything figured out at a certain age.
Nor should we assume that someone who achieved something earlier necessarily understood more or made better decisions.
We all experience different things, under different circumstances, at different times.
And we don’t always learn the same lessons from those experiences.
Maybe I could have started something earlier.
Maybe I could have avoided certain mistakes.
Maybe I could have made more money, taken a different career path, or reached certain goals sooner.
Or maybe doing those things would have changed everything that followed.
There’s no way to know.
And perhaps that’s something we need to accept.
We don’t get to live every possible version of our lives and compare the results.
We only get to live the one unfolding in front of us.
The person I am today exists because of the life I’ve actually lived, not the life I sometimes imagine I could have lived.
And the person I’ll become ten years from now will be shaped by the decisions, experiences, and lessons that haven’t happened yet.
The past is something to learn from, not somewhere to live.
Rather than spending so much time wondering what could have been, I’d rather understand why I think the way I do today, what has changed my mind along the way, and what I might still have wrong.
Because the past is the past.
What matters is whether we’re still learning from it.
