1. Are You Really Ready to Sell?
A journey into the emotional, practical, and psychological pivot point of letting go.
James stood alone in his factory office, the hum of the fluorescent lights above competing with the low whir of the machines down below. From his window, he watched Ravi unload pallets from the truck, something James used to do himself when the business was still just him, a van, and a rented unit with a leaking roof.
Nineteen years. That’s how long he’d poured himself into this place. Late nights and early starts. Missed birthdays. A heart scare at 52. He’d weathered recessions, supply chain collapses, and a pandemic. And now, with a buyer potentially in the wings and his broker Sarah talking next steps, James feel adrift.
They’d just finished a meeting. It was cordial, even positive. But as Sarah packed her notes, she looked up and asked gently, “James, are you actually ready to sell?”
It caught him off guard.
He had his reasons - the long hours, his wife's recent talk of “slow mornings,” and that tugging feeling that maybe, just maybe, there was something else he wanted to do with whatever time was left. But under all of that, something deeper stirred. Fear, maybe. Or uncertainty.
What if he walked away and realised he missed it? The staff. The rhythm. The Monday-morning truck. What if this business was more than just a business, what if it was him?
Sarah had said one more thing before leaving - “The best deals fall apart when the owner isn’t ready and no multiple will fix that.”
James sat down at his desk. Everything looked the same, but everything had changed.
The Psychological Perspective
Exiting a business is often misunderstood as a purely commercial transaction. But for SME owners, it's a rite of passage, like a retirement, a divorce, and a graduation all at once. Psychologically, it can stir up complex responses: grief, liberation, anxiety, excitement.
This internal storm isn’t random. It’s rooted in identity. A business owner isn’t just someone running a business - they are the business, in the eyes of staff, clients, suppliers and often, themselves. Letting go can feel like erasing oneself from the story.
The healthiest exits are made by owners who’ve wrestled with that sense of self and started crafting a new one, before the handover. This might mean journaling, seeing a therapist, or mapping out a post-exit life that’s compelling enough to move toward. Because unless you’re running toward something, the pull of what you’re leaving can keep you stuck.
HR Best Practice
Leadership casts a long shadow. If you're torn, your team will feel it.
That’s why best practice from an HR perspective starts early, long before “For Sale” signs go up. Planning leadership transitions, succession scenarios, and team communication strategies should happen before exit conversations leak out.
A trusted HR adviser can help you identify internal talent for key roles, create retention frameworks (such as bonuses or phased promotions), and prepare a culture of trust during the uncertainty. It’s not about revealing everything too soon, it’s about preparing the ground so when the time comes, the roots don’t pull up too.
If James wanted a clean exit that wouldn’t leave a mess behind, he’d need to empower his operations team months before any buyer shook his hand.
Red Flags To Be Mitigated Against
Emotionally unprepared sellers often unconsciously throw roadblocks into the process. These red flags include -
Pushing back on reasonable due diligence steps
Insisting on inflated valuations based on effort, not earnings
Withholding information from the broker
Backtracking on timelines or conditions
Buyers can spot these signals instantly. They sense hesitation. And that uncertainty erodes confidence, not just in the deal, but in the business itself.
A good broker can navigate these moments, but even the best can't override a seller who isn’t truly in.
Ideal Owner Mindset
Readiness isn’t about indifference, it’s about integration. It’s about the owner who:
Can acknowledge the role the business has played in their life
Is willing to trust others (team, advisers, buyer) with what they’ve built
Has spent time defining what a fulfilling post-exit life could look like
Knows the sale is a transition, not a defeat
James didn’t need to be fearless. He just needed to be honest. And then brave enough to move forward anyway.
Key Takeaway - Exiting your business starts inside, long before due diligence or deal terms. Real readiness means reconciling who you’ve been with who you’re becoming.