Selling Your Business Isn’t the Finish Line You Think It Is
Written with assistance from ChatGPT
What owners underestimate about life after exit
For many business owners, selling the business feels like the ultimate goal.
Freedom. Relief. Time.
And yet, a surprising number of people who exit successfully describe the period that follows as disorientating rather than liberating.
The reason isn’t financial.
It’s psychological.
Celia Dodd’s Not Fade Away explores what happens when long-held roles, routines, and identities fall away — a transition that many business owners experience immediately after a sale.
The Business Is More Than an Asset
Owners don’t just sell a company.
They sell:
Structure to their days
Status and relevance
A sense of competence
A reason to be needed
For years — often decades — the business has answered the question:
“What do you do?”
When that disappears, the gap can feel larger than expected.
Why Some Exits Feel Empty
Many owners plan meticulously for the transaction, but not for the transition.
Common assumptions include:
“I’ll finally relax”
“I’ll work out what’s next later”
“I’ll enjoy the freedom”
But freedom without direction can quickly become restlessness.
As Dodd highlights, thriving after a significant life change requires continuity of meaning, not just the absence of obligation.
Identity Doesn’t Retire Just Because You Do
High-performing owners are used to:
Solving problems
Being consulted
Having influence
Removing that overnight can feel like a loss — even when the sale went well.
This is why some exited owners:
Drift back into work, they said they were done with
Struggle with motivation
Feel oddly disconnected from people who are still “in it”
None of this means the sale was a mistake.
It means the human side wasn’t planned for.
The Best Exits Are Gradual, Not Abrupt
The most satisfied sellers tend to:
Reduce involvement before exit
Develop interests and roles outside the business
Separate identity from ownership early
Redefine contribution, not just income
They don’t “stop”.
They shift.
The business sale becomes a transition point — not a cliff edge.
A Better Question Before You Sell
Instead of asking:
“How much do I want for the business?”
A more revealing question is:
“What do I want my days to look like afterwards?”
If the answer is vague, the risk isn’t financial — it’s personal.
Selling Well Means Thinking Beyond the Deal
A good exit strategy considers:
Financial security
Tax efficiency
Timing
A complete exit strategy also considers:
Purpose
Structure
Identity
Ongoing relevance
Ignoring these doesn’t just affect life after the sale — it often affects decisions during the sale as well.
Closing
Selling a business is one of the most significant transitions an owner will ever make.
Handled well, it creates freedom and fulfilment.
Handled narrowly, it can leave an unexpected void.
If you’re starting to think about exit — even if it’s years away — those conversations are often most useful before anything feels urgent.