Why We Find It So Difficult to Let Go
Some Chapters Stay With Us Longer Than Others
Another conversation I want to share that has been the topic of many high performers I have worked with.
I started to work with someone who, from the outside, appeared to be in a really good place. They had built a successful business, they had a supportive family around them and life had gradually begun moving forwards after what had been a difficult couple of years.
As we talked, the conversation naturally moved away from work and onto life. They became quieter, paused for a moment and then said something that I think many people can relate to.
"I don't understand why I still think about it."
They weren't talking about something that had happened last week... It wasn't even last year.
It had been several years, yet one moment still found its way into their thoughts more often than they felt it should.
I've heard versions of that sentence many times over the years.
Sometimes it's about the end of a relationship.
Sometimes it's a business that never became what they hoped it would.
Sometimes it's a sporting moment that still replays in their mind, or a decision at the poker table they wish they could take back.
The circumstances are always different... But the feeling rarely is.
We Think We're Holding On to the Past
One of the biggest misconceptions about letting go is that we believe we're holding on to an event.
I'm not convinced that's what we're really holding on to.
Take the end of a relationship.
At first, it feels as though you're grieving another person. With time, however, many people realise they're grieving something much bigger than that. They're grieving the future they had quietly started building in their mind. The plans they never got to live, the conversations they imagined having and the version of themselves they thought they were becoming.
The same pattern appears far beyond relationships.
I've seen entrepreneurs struggle to let go of a business that failed, not simply because they lost the business, but because it challenged the identity they had built around becoming successful.
I've seen athletes carry one performance with them for years, not because of the result itself, but because it changed the story they believed their career was going to tell.
I've seen poker players replay one hand long after thousands of others have been forgotten, because that hand became attached to a narrative far bigger than the cards themselves.
The event isn't always what stays with us.
It's the meaning we gave it.
"Sometimes we don't struggle to let go of the past. We struggle to let go of the future we believed the past was leading us towards."
Why High Performers Often Find It Harder
One thing I've come to recognise through working with high performers is that they don't simply experience life... they invest themselves in it.
Whether it's building a company, preparing for competition, leading a team or pursuing mastery in their craft, they care deeply about what they do. That level of commitment is often what allows them to achieve remarkable things.
The challenge is that the same quality can make disappointment feel heavier.
When you care deeply, experiences naturally carry more emotional weight.
That's not weakness.
It's evidence that what you were building genuinely mattered to you.
The difficulty comes when that emotional investment quietly becomes part of your identity.
Instead of saying, "That business didn't work," the mind slowly shifts towards, "Maybe I'm not who I thought I was."
Instead of, "I lost that competition," it becomes, "Maybe I wasn't good enough."
The event finishes... But the story continues.
Research Insight
Interestingly, psychologists have begun looking at letting go as something more specific than simply overthinking. A 2022 study from researchers at the Georgia Institute of Technology found that the inability to let go predicted anxiety, low mood and reduced wellbeing independently of other forms of rumination. In other words, struggling to let go isn't simply "thinking too much"... it appears to be a distinct psychological process that influences how we experience emotional recovery.
I find that reassuring...
Not because it makes letting go easier, but because it reminds us that this isn't a personal flaw. It's part of being human.
Letting Go Doesn't Mean Forgetting
I think one of the reasons so many people become frustrated with themselves is because they confuse letting go with forgetting.
They're not the same thing.
There are experiences in my own life that I'll probably remember forever.
Not because they still control me, but because they helped shape the person I became.
The goal isn't to erase meaningful experiences from our memory.
The goal is to stop allowing them to define our future.
That shift is subtle, but it's powerful.
When we stop asking, "How do I stop thinking about this?" and begin asking, "What have I been making this mean about me?" something starts to change.
The memory doesn't necessarily disappear.
Its grip begins to.
A Moment to Reflect
Before reading any further, take a moment to ask yourself:
- What experience came into your mind while reading this?
- What story have you attached to that experience?
- If that story wasn't true, how differently might you see your future?
Sometimes the answers we're searching for don't appear when we think harder.
They appear when we become curious enough to question the story we've been believing.
Final Thoughts
If there's one thing I've learned through working with people over the years, it's that healing rarely arrives because someone finally forced themselves to move on.
More often, it begins when they stop fighting the fact that something mattered.
The relationships that changed us.
The businesses that tested us.
The competitions that humbled us.
The conversations we'll never forget.
They're all chapters of the same story...
We don't honour our past by living in it forever, but neither do we honour it by pretending it didn't shape us.
Perhaps letting go isn't about closing a chapter as quickly as possible. Perhaps it's about understanding why that chapter deserved to be written in the first place.
Once we understand that, we often discover something unexpected.
The chapter hasn't disappeared... It simply no longer needs to be read every day.
One last thing...
If this resonated with you, perhaps there's a reason for that. Sometimes the greatest shifts begin with a single conversation. If you'd like to explore what we've discussed here in more depth, you can {Request Mentorship}. I'd be honoured to support you on your journey and I look forward to connecting with you.
Speak soon,
Basim
