The Three Legs of the Stool: How to Build a Business Exit That Won’t Collapse Beneath You

Most entrepreneurs don’t start a business thinking about how they’ll leave it.

Yet, at some point, every business owner faces the reality that they will exit—by choice or by force. Whether it’s through selling, passing it on, or shutting it down, the transition is inevitable. The real question is: will your exit be a triumphant leap into the next chapter of your life or a chaotic, last-minute scramble?

The answer depends on the strength of your Three Legs of the Stool™—Business Readiness, Personal Readiness, and Financial Readiness. If one is weak or missing, the whole thing collapses, often leaving the owner with regrets, financial instability, or a business they can’t sell.

Let’s break this down.

1. Business Readiness: Is Your Business Strong Enough to Stand Without You?

Let’s get brutally honest—can your business run without you?

If the entire operation depends on you showing up every day, then congratulations—you’ve built a job, not a business. And that’s a problem. Buyers don’t want to purchase a job; they want a scalable, independent asset.

What Buyers Look For:

• A management team that can run the business smoothly without you.

• Strong financials with clean, transparent books.

• A repeatable, scalable revenue model that isn’t overly reliant on a few customers.

• Clearly documented processes and systems that ensure continuity post-sale.

  
  

Buyers aren’t just looking at the profitability of your business; they’re assessing the sustainability of that profit without you at the helm.

Takeaway: If your business can’t thrive without you, it isn’t sellable—at least not for the price you want.

2. Personal Readiness: What Happens When You’re No Longer ‘The Boss’?

Here’s a little-known but brutal truth: 75% of business owners regret selling their company within a year.

Why? Because they spent decades building their business, but zero time planning for what comes next.

Many business owners underestimate how much of their identity is tied to their company. You’ve been “the boss” for years—your phone rings constantly, your inbox is flooded, your decisions matter.

Then, one day, it all stops.

Ask Yourself:

• What will you do after you sell?

• Will you feel a loss of purpose when you’re no longer running the show?

• Have you talked to your family about how life will change post-exit?

• Do you need to stay involved for a while, or do you want a clean break?

  
  

The more emotionally anchored you are in your business, the harder the transition. And if you don’t have a clear vision for life after the exit, regret is almost guaranteed.

Takeaway: Selling your business isn’t just a transaction—it’s a transformation. Make sure you’re ready for the life that comes next.

3. Financial Readiness: Can You Afford to Exit?

Your business exit is supposed to be a launchpad, not a financial trap. But here’s the problem—most entrepreneurs have 80-90% of their net worth tied up in their business. That’s like putting all your chips on one bet and hoping the casino never closes.

The moment you sell, everything changes. Your financial structure moves from active income (running a business) to passive wealth management (living off investments, savings, or other ventures). If you don’t plan ahead, you could be rich on paper but cash-poor in reality.

Key Considerations:

• Do you know your number—the amount you need to live comfortably for the rest of your life?

• Have you worked with a financial planner to diversify your investments post-sale?

• Have you stress-tested different scenarios (market downturns, tax implications, lifestyle changes)?

• Have you optimised your sale structure to minimise taxes and maximise long-term wealth?

  
  

Many entrepreneurs think a high sale price means instant financial security, but if you don’t manage your wealth properly, you could run out of money faster than expected.

Takeaway: A big payday doesn’t mean financial freedom—it’s what you do with that money after the sale that truly matters.

How It All Comes Together

A business exit isn’t just about the deal—it’s about your future.

• If your business isn’t ready, you’ll struggle to find a buyer or be forced to sell at a discount.

• If you’re not emotionally ready, you’ll hesitate, second-guess yourself, and risk seller’s remorse.

• If you’re not financially ready, you may end up with a great sale but a precarious future.

  
  

The best exits are strategic, not reactive. They happen because the owner has planned ahead, ensuring that all three legs of the stool are strong.

So, Are You Ready?

Most business owners think about selling when they have to. The best ones plan their exit years in advance.

If you’re serious about getting the best outcome from your business sale, ask yourself:

• Is your business structured for a high-value sale?

• Are you mentally prepared for life after exit?

• Do you have a financial game plan that secures your long-term future?

  
  

If you’re unsure, now is the time to start strengthening those legs.

Final Thought: Don’t Let Your Exit Be a Crisis

Most entrepreneurs wait too long to prepare—until burnout, market shifts, or personal circumstances force their hand. By then, options are limited and value is often lost.

A strong, stable Three-Legged Stool isn’t just a metaphor—it’s your insurance policy for a successful and regret-free exit.

Your Next Step:

If you’re thinking about selling your business in the next few years, let’s have a conversation. The best exits aren’t rushed—they’re engineered. Let’s make sure yours is built to last.

Key Takeaways:

• Your business must be able to run without you to command maximum value.

• If you don’t plan for life after the exit, regret is likely.

• A big sale price doesn’t guarantee financial security—proper planning does.

• The best exits are strategic, not reactive—start preparing now.

  
  

Would love to hear your thoughts—what’s your biggest concern about exiting your business? Let’s talk.