Not to live.
To leave.
Let’s just imagine for a moment that you were visited in a dream and found out that you had six months before you would step away from your business. Six months before you exit. Six months before the company you built must operate without your daily involvement.
Not for bad reasons though. In fact, for good reasons. No dire message from the doctor, no family emergency or anything of the sort. Instead, the next chapter beyond the business would be even better in new and exciting ways.
What would happen next?
If you’re like many business owners, that question creates a knot in your stomach almost immediately and probably not because you want to keep grinding forever. But because deep down you know something uncomfortable:
The business may not actually work without you.
That honest realization has very little to do with retirement age. I’ve sat across the table from successful owners worth millions of dollars who still approve most meaningful decisions, solve every major problem, carry every key relationship, and hold the company together largely through force of personality, reputation and sheer experience. The business looks successful from the outside because revenue is strong, employees are busy and customers are loyal. But underneath it all, there is a hidden dependency.
You.
Dan Sullivan, founder of Strategic Coach®, once posed a thought experiment he referred to as The Retirement Trick™. Imagine you had to retire in six months and not this open ended “someday” that you might talk about. Not “after a few more good years” or what I often hear in our industry – “sometime in the next 3 to 5 years.” Six months.
What would immediately have to change? Which responsibilities would need to be delegated? Which decisions would need to move down the org chart? Which clients or relationships are too dependent on you personally? What systems are missing? What fires only you know how to put out? What would break first if you disappeared for 90 days?
What would you immediately stop doing and what would you immediately do more of? Those are uncomfortable questions. But they are also incredibly clarifying, because exit planning, at its core, is not really about leaving. It is about building something transferable.
A business that depends entirely on the owner is often just a great job… disguised as a company. A business that can function, grow, and create value beyond the founder becomes an asset. That distinction matters more than you might realize.
The highest-value companies are rarely the ones with the most charismatic founder. They are the ones where the value survives the founder and that’s why this six-month exercise is so powerful. A buyer is only partly interested in what the business was, but they are keenly interested in what it will be going forward.
It forces owners to stop asking: “How long can I keep doing this?” And start asking: “How do I build this so it thrives without me?”
Ironically, owners who do this well often discover something unexpected. They become even more valuable, not less important. Once they stop being trapped inside the machine, they can finally work on the business instead of being consumed by it. It’s not a loss of purpose, it’s a more focused purpose.
They have more time to think strategically, more energy for key relationships, more margin for creativity, more ability to mentor future leaders, and more freedom to enjoy the life their success was supposed to create in the first place.
The twist here is that the goal isn’t to leave in six months – it’s to build a business that could.
That mindset changes everything – valuation, leadership, succession planning, culture and even your personal stress level. And ultimately, it changes the odds that the business and the people who depend on it will continue to thrive long after your eventual exit.
So here’s a worthwhile exercise for every owner reading this:
If you had six months before stepping away, what would you stop doing tomorrow? What should you have handed off a year ago that you can do right now?
Don’t wait for the bad version of this – for a doctor to tell you that “You’ve only got six months”. Because the best exit planning is not about preparing to die. It’s about finally building a business fully capable of living without you.