“How long have you been thinking about succession planning?”
“I haven’t, really. We’ve been running this business for 35 years. I never actually thought about leaving it.”
He’s 68 years old. He founded the company in 1990; his wife is 60 and they run the business together. Forty-five employees. Solid customer base. Good reputation. No succession plan. No operations manual. No documented processes. No idea what the business is worth without them in it.
And until our conversation, he’d never seriously considered that one day he wouldn’t want to, or couldn’t, come to work.
The Owners Who Never Planned to Stop
There’s a particular type of business owner caught in the Silver Tsunami who’s in a more precarious position than the procrastinators or the optimists.
They’re the ones who genuinely never thought about leaving.
Not because they were avoiding the question. Because the question never occurred to them.
These are typically:
- Founders who started businesses in their 20s or 30s
- People who found their calling and never looked back
- Owners whose entire adult identity is wrapped up in their company
- Those who love what they do so much that retirement seems like a foreign concept
They’ve been so busy running the business that they never stopped to consider leaving it.
Why This Is More Common Than You Think
It sounds naive, doesn’t it? How could someone run a business for 30-40 years and never think about succession?
But it’s surprisingly common, and there are good reasons why:
The business IS their identity. When you’ve spent 35 years building something, when every social connection comes through work, when your reputation is tied to your company name, the idea of not doing it doesn’t compute. It’s not that you’re avoiding retirement. It’s that retirement doesn’t feel like a real concept that applies to you.
They’re still passionate. Unlike burned-out owners desperately seeking an exit, these people genuinely love what they do. They wake up excited about work. Why would they plan to stop something they enjoy?
It’s always worked. For decades, they’ve been healthy, energetic, and successful. The pattern suggests it will continue indefinitely. Tomorrow will look like today, which looks like last year, which looks like the past decade.
They’ve seen others retire badly. They’ve watched friends and peers retire and struggle with purpose, health, relationships. They’ve seen the spark go out. They’ve told themselves, “That won’t be me. I’ll keep working.”
The business needs them. And they’re right—it does. They’ve built something that genuinely depends on their knowledge, relationships, and decision-making. Walking away feels irresponsible.
The Silver Tsunami effect. With approximately 12 million privately held businesses likely to change hands over the next decade, as Baby Boomer owners reach retirement age
The Wake-Up Call
Then something happens.
For the owner I mentioned, it was a routine health check-up that revealed something concerning. Suddenly, at 68, he was confronting the reality that he might not have the choice to keep working.
His first reaction? Panic.
His second? “I’ll just push through. I’ll be fine.”
His third, after his doctor was blunt with him? “What do I do now?”
Other wake-up calls I’ve seen:
- A key employee resigns with no one capable of replacing them
- A client asks, “What happens to our contract if something happens to you?”
- An insurance review reveals massive gaps in business continuity
- A peer suddenly dies or becomes seriously ill, forcing the question: “Could that be me?”
- An adult child says, “Dad, you need to slow down” and you realise they’re right
Why This Position Is So Dangerous
If you’ve never thought about succession, you’re in a worse position than someone who’s been procrastinating. Here’s why:
Zero groundwork. The procrastinator has at least researched options, spoken to advisers, thought about valuation. You’re starting from scratch, and you probably don’t have much time.
No emotional preparation. You haven’t done the psychological work of separating your identity from your business. The transition will be brutal.
Complete business dependency. Because you never planned to leave, you never built systems that work without you. Your business is entirely dependent on your presence, knowledge, and relationships.
No successor in sight. You haven’t been developing leaders or considering who might take over. Your management team (if you have one) has always deferred to you.
Outdated thinking. Business sale processes, tax structures, and succession options have changed dramatically. You’re working with knowledge from decades ago, if you have any knowledge at all.
Compressed timeline. When reality hits, through health, burnout, or circumstance, you may need to compress 5-7 years of preparation into months. It’s rarely successful. Look on the bright side, the worst might not happen straight away, but now is the time to start planning.
The Uncomfortable Questions You Need to Ask
If you’ve been running your business for 20+ years and haven’t seriously thought about succession, you need to confront some uncomfortable realities:
Can you actually work until you die? Be honest. Your energy at 70 won’t match your energy at 50. Your health might not cooperate. And do you really want to?
What happens if you can’t work tomorrow? Not as a theoretical exercise, as a real scenario. Who makes decisions? Who knows where things are? Who has the client relationships?
Is your retirement plan entirely dependent on selling this business? If so, and the business isn’t saleable without you, you don’t have a retirement plan. You have hope.
Would anyone want to buy what you’ve built? A business that requires your specific expertise, relationships, and daily involvement is worth a fraction of one that runs without you.
What’s your legacy? If you’re forced to shut down because there’s no succession plan, 30 years of work disappears. Employees lose jobs. Clients lose a supplier. Your community loses a business.
What To Do When You’ve Never Thought About This Before
The good news: It’s not too late to start. The bad news: You need to start immediately.
Accept the reality. You will leave this business. The only question is whether it’s on your terms or circumstances’ terms. Accepting this is step one.
Get educated quickly. You’ve got decades of catching up to do on succession planning, business valuation, and transition options. Find advisers who specialise in this. Read. Learn. Fast.
Get a realistic valuation. You need to know what your business is actually worth in its current state. Not what you hope it’s worth, what buyers will actually pay given your current dependency on you.
Start documenting immediately. Everything in your head needs to get onto paper or into systems. Processes, client histories, supplier relationships, institutional knowledge. This is urgent.
Develop leadership. You probably don’t have 5-7 years to slowly build a management team. You need to empower people now. Delegate real decisions. Accept that others will do things differently.
Have the difficult conversations. With family about what they want. With key employees about their futures. With your spouse about financial reality. These conversations are years overdue.
Create a deadline. Even if it’s 3-5 years out, you need a firm date. “I will transition ownership by [specific date].” Work backwards from there.
Consider all options. Selling to competitors, management buyouts, employee ownership trusts, strategic mergers, or even winding down. No option is off the table at this stage.
A Different Mindset
You’ve spent decades building this business. That’s extraordinary. You should be proud.
But building isn’t enough. The mark of a truly successful business owner isn’t just what they create during their tenure, it’s whether what they’ve built survives their departure.
You need to shift from thinking like a founder to thinking like a steward. Your role is to leave this business positioned for its next chapter, whether that’s new ownership, new leadership, or a graceful close that honours what you’ve built.
This doesn’t diminish your legacy. It completes it.
The Question You Can’t Avoid Anymore
You’ve been running this business for decades. You’ve never seriously thought about leaving it.
But at some point, maybe this year, maybe in five years, maybe tomorrow, you won’t have a choice.
The only question is whether you’ll be ready when that moment comes.
So ask yourself today: If you couldn’t come to work tomorrow, what would happen?
If the answer makes you uncomfortable, you know what needs to be done.
The business you’ve spent decades building deserves a proper ending. Your employees deserve security. Your family deserves financial stability. And you deserve to leave on your own terms.
But none of that happens without planning.
Start today.
How Exitologists Can Help
If you’re facing any of these succession challenges, you don’t have to navigate them alone.
At Exitologists, we specialise in helping business owners prepare for and execute successful transitions. Whether you’ve been planning for years or are just starting to think about your exit, we provide:
Strategic planning – Understand your options and develop a roadmap that fits your timeline and goals. We look at your personal exit readiness and help you develop your exit strategy.
Business valuation – Get a realistic assessment of what your business is worth today and what it could be worth with proper preparation.
Preparation support – Document processes, develop leadership, and reduce owner dependency to make your business more valuable and sellable. We want to get you exit ready.
Transaction guidance – Navigate the complex process of negotiation, due diligence, and completion with our exit management services.
The best time to start planning was five years ago. The second best time is now.
Let’s talk about your succession journey. Book a confidential consultation to discuss where you are and what your next steps should be.
