My client Tom looked exhausted when he said it: “My daughter asked me when I’m going to retire. Honestly, Greg, I have no idea how to answer that question.”
Tom’s been running his retail business for 30 years. He’s got two kids working in the company, a team of 15 employees, and a customer base that’s been with him for decades.
But he’s also 68 years old, working 60-hour weeks, and starting to wonder what happens to everyone who depends on him if something happens to him.
Sound familiar?
The Retirement Question Nobody Talks About
Most business owners I work with face the same dilemma:
- They’ve built something valuable but don’t know how to extract that value
- Their identity is tied to the business (what would they DO all day?)
- They’re afraid their “baby” will fall apart without them
- They want to take care of their team but also need financial security
The real question isn’t “When should I retire?” It’s “How do I transition from indispensable to invaluable?”
What I Learned from My Own Exit
When I decided to transition out of my mortgage business, I faced the same fears. What if my clients left? What if my team couldn’t handle the complex deals? What if I was walking away from my biggest asset?
Here’s what I discovered: The businesses that survive transitions aren’t the ones with irreplaceable owners – they’re the ones with systematized knowledge.
The Three Types of Business Knowledge
- Technical Knowledge – How to do the work
This is usually easy to transfer through training and documentation. - Relationship Knowledge – Who to call, who to trust, how things really get done
This takes time to transfer but can be done systematically. - Wisdom Knowledge – When to break the rules, how to read situations, what matters most
This is the hardest to transfer and requires intentional mentoring.
Most owners focus on #1 and ignore #2 and #3. That’s why transitions fail.
The Legacy Question
Tom and I spent our next session talking about legacy instead of retirement.
“What do you want this business to look like in 10 years?” I asked.
“I want my kids to be proud of what they’re running,” he said. “I want my employees to feel secure. And I want our customers to get the same level of service they’ve always gotten.”
That’s not a retirement conversation – that’s a succession conversation.
Making the Shift
The shift from “When can I leave?” to “How do I prepare them to succeed?” changes everything.
Instead of trying to make yourself unnecessary, you start making yourself invaluable in a different way:
- As the keeper of company values and culture
- As the mentor who develops the next generation
- As the strategic advisor who helps navigate big decisions
- As the face of the company’s legacy and reputation
The Question to Ask Yourself
If you could design the perfect transition – one that takes care of your family, your team, and your customers while giving you the freedom you want – what would it look like?
Start there. Then let’s figure out how to make it happen.
Thinking about your own transition? You don’t have to figure it out alone. Sometimes the biggest breakthrough comes from talking through your options with someone who’s been there.