What if winning itself creates regret?
There is an uncomfortable idea in auction theory known as the winner's curse.
When several people compete for an uncertain asset, the winner is often the person with the most optimistic valuation.
Which means the person celebrating victory may also be the person most likely to have overpaid.
There is a broader human version of this.
To win something competitive, you usually have to be willing to pay more than the people who lost were prepared to pay.
More money. More time. More sacrifice. More obsession. More travel. More missed dinners. More stress. More political capital. More of yourself.
This complicates ambition because there may be no perfect victory.
You Cannot Always Avoid Regret
Suppose two people want the same business.
One is willing to pay ₦900 million.
You are willing to pay ₦1 billion.
You win at ₦950 million.
Immediately two thoughts become possible:
"Excellent. I got it."
and:
"Why was nobody else willing to pay this much?"
Ambition can operate similarly.
You become CEO.
But another candidate decided he was unwilling to sacrifice his family life for the role.
You become governor.
Someone else decided he was unwilling to tolerate what politics demanded.
You build the largest firm.
Another founder built a smaller one and sees his children every evening.
Who won?
That question cannot be answered by title alone.
Sometimes the cost of winning is invisible until after the trophy arrives.
The Power Chaser Has a Mental Health Problem Too
We spend time discussing the psychological weight on powerful people.
But the person chasing power can suffer long before he acquires it.
Comparison. Restlessness. Chronic dissatisfaction. The inability to enjoy present achievement because the next level has already become psychologically necessary.
Hypervigilance around rivals. Constant networking. The sense that every room must produce something. The fear of being forgotten. Failure to rest because somebody else is working.
The ambition that originally gave life direction can eventually make life feel like one long audition.
This is one reason I have found M.I. Abaga's A Study on Self Worth: Yxng Dxnzl so interesting.
Even the structure of a track such as The Self Evaluation of Yxng Dxnzl points toward something achievement culture rarely encourages:
stop and examine yourself.
Not the brand.
Not the career.
Not the ranking.
The self.
His Last Night I Had a Dream About a Hummingbird closes with an unsettling meditation on elevation: once someone becomes a hero, the pedestal itself creates the conditions for people to want to bring the hero down, raising the question of whether to relinquish that position voluntarily or wait to be removed.
That is not merely a musician's problem.
It is a chairman's problem. A president's problem. A founder's problem. A senior partner's problem. A patriarch's problem.
Every Pedestal Produces a Successor
Power creates an inevitability we rarely discuss while climbing.
Someone else is coming.
The brilliant young manager. The younger politician. The new artist. The ambitious deputy. The son. The daughter. The protégé.
At first you celebrate their potential.
Then one day people begin mentioning their name in sentences where yours used to appear alone.
This is a difficult moment for the ego.
You can become the sponsor of the next generation.
Or its principal obstacle.
Many great leaders make the second choice without admitting it.
Every talented junior becomes "not ready."
Every successor has "character issues."
Every new idea is immature.
Every discussion of succession is premature.
Until eventually the transition is no longer theirs to manage.
There Is a Time to Become Less Important
This may be one of the highest disciplines of leadership.
At first, you are the protagonist.
Then you must become an institution-builder.
Then a sponsor.
Then perhaps an elder.
People who cannot make those transitions frequently destroy what they built.
Because the institution exists increasingly to maintain the founder's psychological importance.
This is where stepping down becomes profound.
Leaving while you still possess enough authority to bless the next order is different from being removed after everyone has concluded you stayed too long.
The first can enlarge a legacy.
The second can consume it.
But Why Is Leaving So Hard?
Because power is rarely only power.
It becomes identity. Attention. Community. Deference. Invitations. Entourage. Relevance. Phone calls. Meaning.
If you spent thirty years answering the question Who am I? with:
I am Chairman,
then retirement sounds less like a change in job description and more like a form of death.
That is why preparation for leaving cannot begin in the final year.
A powerful person needs an identity that survives power.
Friendship. Family. Faith. Intellectual life. Mentorship. Service. Interests unrelated to command.
Places where nobody needs permission from you.
Otherwise you will cling to the throne because the throne has become the only place where you know who you are.
What Was All the Ambition For?
Years ago, I wrote about happiness after realizing that degrees, owning a business and material achievement had not automatically produced the internal happiness I assumed should accompany them.
I wrote:
Don't let ambition snuff out your joy.
That thought becomes more important, not less, as ambition succeeds.
There is always another level.
₦100 million becomes ₦1 billion.
Partner becomes managing partner.
Vice chairman becomes chairman.
Chairman wants another term.
Governor wants the Senate.
The finish line moves because perhaps the finish line was never external.
At some point, the ambitious person has to ask a question that cannot be delegated:
What is enough?
Not because achievement is wrong.
Not because power is inherently corrupt.
Not because ambition should be extinguished.
But because a person can spend his entire life accumulating instruments for living and eventually discover he forgot to live.
The Final Discipline of Power
This series began with the need to recognize power accurately.
Do not assume the person above you must be more competent.
Do not become contemptuous because you have seen his humanity.
Preserve access.
Preserve yourself.
Understand what proximity is worth.
Choose confrontation intelligently.
Build power of your own.
But every philosophy of power that ends with acquisition is incomplete.
Because all earthly authority eventually changes hands.
Every CEO leaves.
Every governor becomes former governor.
Every chairman eventually stops chairing.
Every celebrity discovers a younger audience.
Every king eventually leaves the throne.
The final question is therefore not merely:
Can I obtain power?
It is:
Can I possess it without being possessed by it?
And eventually:
Can I recognize the moment when holding on costs more than letting go?
The truly powerful person may be the one capable of stepping off the pedestal while people are still asking him to stay.
End of the Managing Power series