Why Even the Most Successful Leaders Fear Letting Go
We have a natural admiration for entrepreneurs who refuse to give up.
We celebrate the founder who risks everything on an idea nobody believes in, survives the difficult early years and eventually proves the sceptics wrong.
Their stories become part of business folklore, repeated at conferences and in boardrooms as reminders of what determination can achieve.
And rightly so.
Many remarkable businesses would never have existed without that persistence.
But I sometimes wonder whether we have become so accustomed to admiring persistence that we struggle to recognise good judgement when it tells us to stop.
On 6 November, Elon Musk announced that Tesla would wind down Cybertruck production at its Texas factory around mid-2027, making room for increased production of the company’s Cybercab.
Musk has built businesses that have challenged established industries, often pursuing ideas others considered impossible.
Yet even the most ambitious founders must decide which ideas deserve their next investment of money, time and attention.
Whether Tesla’s decision proves successful remains to be seen. Nor can we know Musk’s private reasoning.
What interests me is a question that has very little to do with electric vehicles.
What happens when the idea you have spent years defending is no longer the idea you should be pursuing?
The Cost of Continuing
Imagine a founder who has spent seven years building a business.
It generates revenue, employs good people and has loyal customers.
Nothing is falling apart. From the outside, it may even look like a success.
But the founder knows how much effort is required to keep it that way.
The financial results are never quite where they should be.
Promising opportunities are repeatedly postponed.
Conversations about the future tend to return to the same unresolved problems.
The business may not be failing. It simply no longer offers the future its founder once imagined.
And that is not an easy thing to acknowledge.
We tend to think about these decisions in terms of what has already been invested.
The money, the years, the sacrifices.
But none of those can be recovered by committing another year to something that may no longer deserve it.
Every additional investment of capital or attention is a fresh decision.
Yet we often treat it as an obligation created by decisions made years earlier.
I suspect we are sometimes more willing to lose money than to lose face.
The longer this continues, the harder it becomes to distinguish between protecting the business and protecting our own judgement.
And what makes this uncomfortable is that the original idea may have been a very good one.
IBM helped establish the modern personal computer industry.
Its original PC, introduced in 1981, became one of the defining products of the technology revolution.
Yet in 2005, IBM completed the sale of its personal computer division to Lenovo.
Personal computers had not become irrelevant.
Lenovo would go on to build an enormous business around them.
IBM had reached a different conclusion about where its own future lay, concentrating increasingly on services, software and other enterprise technologies.
What interests me about IBM’s decision is that it did not need to diminish the importance of what it had built to recognise that its future lay elsewhere.
We often feel compelled to defend an idea because we were right about it once.
But yesterday’s good judgement does not oblige us to make the same decision tomorrow.
In an earlier article, How to Lead When You See What Others Don’t, I explored the difficulty of distinguishing conviction from self-deception when the evidence is uncertain.
There is another challenge, though, when the evidence has become harder to ignore.
Knowing what we should do is not necessarily the same as being ready to do it.
The Conversation Nobody Else Hears
I imagine this is where many difficult decisions begin.
Not in the boardroom, or during a strategic planning session, but in the quiet moments when the founder is left alone with their own thoughts.
They know the numbers.
They remember the promises made to investors, employees and perhaps their own family.
They recall the excitement of the early days, when the possibilities seemed endless and the sacrifices felt entirely justified.
They remember telling people, with absolute conviction, that this was going to work.
And then comes a question considerably more difficult to answer than anything in the financial statements.
If I stop now, what does that say about me?
Because the founder is no longer considering only the commercial merits of continuing.
They are confronting what it might mean to be the person who decides that something they believed in should come to an end.
There may be employees to disappoint, investors who deserve an explanation and customers whose expectations must be managed.
There may even be people who warned against the idea in the first place.
And there is no guarantee that the next decision will prove any better.
Continuing offers a peculiar reassurance.
There is always another quarter, another opportunity to improve the numbers, another reason to believe that the breakthrough is just around the corner.
Stopping removes that reassurance.
The decision becomes visible, and the founder must stand behind it.
I think this is why the conversation we have with ourselves can become so unreliable.
We know too much about what we have invested, and we have become rather skilled at explaining why one more attempt is justified.
And the explanations often sound perfectly reasonable, particularly when we are the ones making them.
Sometimes it helps to have someone who is neither invested in defending the original decision nor eager to see it abandoned.
If you were starting again today, knowing everything you now know, would you still choose this?
Or perhaps:
What are you afraid will happen if you stop?
Even very successful people sometimes need a conversation in which they are not required to be the strongest person in the room.
Not because they need someone else to decide for them, but because they need the freedom to examine the decision without defending themselves.
Of course, not every difficult situation should be abandoned.
Some ideas deserve more patience.
Some businesses need a different approach, and some relationships are worth repairing.
But there is an important difference between continuing because we believe in what lies ahead and continuing because we cannot bear to reconsider what lies behind us.
The Confidence to Choose Again
There is another part of this that I think deserves more attention.
When a founder finally decides to stop, the decision may bring enormous personal relief.
But for the people who have spent years helping to build the business, it may feel quite different.
They may have turned down other opportunities, invested their own resources or made sacrifices because they believed in the founder’s vision.
Their disappointment cannot simply be swept aside with an enthusiastic announcement about the next exciting chapter.
I have always thought that how a leader handles these moments tells us a great deal about them.
It is relatively easy to take responsibility when everything has worked out.
It is considerably harder when people are disappointed and there is no obvious success to point towards.
Yet there is a meaningful difference between telling people their efforts have failed and explaining that those efforts were worthwhile, even though the organisation has decided to pursue a different future.
The first risks leaving people questioning the value of their contribution.
The second recognises what was achieved, what was learned and why a different decision now makes sense.
Neither removes the disappointment.
But one treats the people involved with considerably more respect.
And perhaps that is where trust is either strengthened or lost.
A founder who can acknowledge what did not work, without diminishing those who worked hard to make it succeed, may preserve something more important than the original project.
The willingness of those people to believe in the next one.
There is also the question of what becomes possible once the decision has been made.
Think of the attention a struggling project consumes.
The repeated financial reviews, the meetings that return to familiar problems, the conversations postponed until next month.
And the energy that follows the founder home, long after everyone else has left the office.
That cost rarely appears in the financial statements, but anyone who has carried responsibility for a business will recognise it.
Perhaps that attention could instead be directed towards neglected customers, an opportunity that has never received proper consideration or a different version of the original idea that now makes more sense.
There is no guarantee that these alternatives will succeed.
But at least they can be considered on their own merits, rather than continually competing with a decision made years earlier.
I think we sometimes misunderstand confidence in leadership.
We associate it with certainty, with the ability to stand before a room and persuade everyone that we know exactly where we are going.
But there is something equally compelling about a leader who can acknowledge that circumstances have changed, that an earlier assumption no longer holds and that a different decision is now appropriate.
Without treating that admission as a personal humiliation.
What Are We Really Holding On To?
Of course, this is not confined to business.
Most of us have probably remained committed to something long after we first began questioning it.
A partnership that once worked beautifully but has gradually become difficult.
A professional role we spent years pursuing, only to discover that it no longer offers what we hoped it would.
Or an ambition formed at a different stage of life that we continue chasing largely because we have never stopped to ask whether we still want it.
These decisions become particularly difficult when other people have come to associate us with the thing we are considering leaving.
We worry about disappointing them, having to explain ourselves or appearing inconsistent.
And so we continue, sometimes until the situation becomes almost unbearable.
Only afterwards do we wonder why we waited so long.
But hindsight is comfortable.
It does not have to sit across the table from the people affected by the decision.
In The Danger of One More Cycle, I explored what happens when successful founders struggle to step away from the roles that have defined them.
Here, the challenge is different.
The founder may have every intention of continuing to build, lead and create.
They may simply need to release one idea so that another can receive the attention it deserves.
Changing our minds does not necessarily mean abandoning our ambitions.
Sometimes it is how we protect them.
We should not give up simply because something has become difficult.
Equally, we should not require a catastrophe before allowing ourselves to reconsider it.
Perhaps the question is whether we can look at the decision as it stands today, rather than as we hoped it would turn out when we first made it.
Because letting go does not diminish the person who had the courage to begin.
It may simply mean they have found the confidence to choose again.
What are you still holding on to, not because you believe in its future, but because you cannot quite let go of its past?