Most owners think they have more time than they do.
Not because they’re careless — but because the business still feels “fine” right up until the moment it doesn’t.
And that delay, even just a few years, can cost more than people realize.
I’ve watched this play out with seasoned Mississippi owners who built strong companies and assumed the market would always reward that strength. Then something shifts — not dramatically, but subtly. A key employee leaves. A competitor upgrades equipment. A loyal customer base ages. The owner loses a little passion. None of it feels urgent in the moment, but the valuation starts to soften.
Here’s what surprises people: buyers don’t pay for what the business used to be. They pay for the trajectory they see today. When revenue levels off, even slightly, buyers read it as a warning sign. When the owner looks tired, buyers assume the business might be tired too. And when the financials stop moving upward, so does the offer.
I remember sitting with a business owner outside Tupelo who kept telling me, “Next year will be better — I just need one more push.” He meant it. He was sincere. But each year, the business slipped one step at a time. Not enough to panic, just enough to matter. By the time he finally listed, the value was down nearly 30% from where it could’ve been five years earlier.
Waiting didn’t cost him time. It cost him leverage.
There’s another cost people overlook: energy. The longer you wait — especially when you’re already feeling ready to be done — the harder it becomes to keep the business sharp. Buyers notice when the owner is worn down. They see it in maintenance records, employee turnover, marketing that hasn’t been updated in years. Small things, but small things add up to big valuation drops.
And then there’s the emotional toll. I’ve had owners confess they felt stuck — not ready to run the business at full speed anymore, but not ready to sell either. That in-between space drains momentum. It makes the exit feel heavier than it needs to be.
When owners sell at the right time, the process feels clean. When they wait too long, the process feels complicated.
Here’s the part I always share, even if it’s uncomfortable:
Your business will never be more valuable than when it’s healthy, growing, and well-led — even if you’re tired of leading it.
The best time to sell is almost always the moment right before you feel ready.
If anything in you is wondering whether you’ve already waited too long, don’t ignore that feeling. It’s usually the first sign that it’s time to get a valuation, tighten your operations, and map a clear exit plan. You don’t have to move fast — you just need to move intentionally.
Selling shouldn’t be a reaction. It should be a strategy.
If you’re weighing the timing of your exit, Vision Fox can help you understand the numbers and protect the value you’ve built. Reach out and let’s talk through your best window to sell.
And if this would help another Mississippi owner who’s been wrestling with timing, pass it along.
