There’s a specific kind of regret I’ve watched business owners carry, and it doesn’t come from making bad decisions. It comes from not making the right decision early enough.
They got to the point where they were ready to exit and realized the business wasn’t ready for them to exit. The financials weren’t clean. The team wasn’t developed. The systems lived in their head. And now they were trying to build all of that while managing a deal process under pressure.
They weren’t careless. They were busy. Exit planning got pushed to later, and later kept moving.
Here’s how widespread this problem actually is. According to the Exit Planning Institute’s 2025 Generational State of Owner Readiness Report, only 13% of business owners have a formal exit plan. Not 13% of Baby Boomers specifically. Thirteen percent across all owners surveyed. And among Baby Boomers; the generation closest to exit; the picture is even more striking: 58% plan to exit within the next five years, but only 5% have a formal exit planning team assembled. That gap between intention and preparation is where most of the pain in small business exits comes from.
Here’s the practical reality of what preparation time actually buys you. Three years of clean financial records is the minimum a sophisticated buyer wants to see. You can’t manufacture that retroactively. Building a leadership team that a buyer trusts requires time for hiring, for development, for the team to earn their credibility. Documenting your systems so the business has transferable value; so a buyer can look at how things work and feel confident they can run it without you; that’s months of deliberate work.
Every one of these activities requires runway. And the only way to have runway is to start before you think you need to.
The family therapy practice that worked with Exit Factor had 12 months. That was enough time; because they started with that window and used every bit of it. Valuation increased 64% in that period, adding $390,000 in value. It required focused, disciplined work across operations, team development, and financial clarity.
Twelve months is a real window. But it required starting immediately and using every week intentionally. The owners who wait until they’re six months from wanting to close a deal rarely have enough runway to move the needle meaningfully.
With $9 trillion of privately held business wealth expected to transfer in the next five years alone, according to the Exit Planning Institute’s 2026 State of the Institute, the window for preparation is narrowing faster than most owners realize. The second-best time to start was a year ago. The best time is right now.
Rodrigo Passalacqua is Managing Partner at Exit Factor of Raleigh-Durham. If you’ve been putting this off, reach out directly or visit https://exitfactor.com/raleigh-durham.
Let’s figure out what window you’re actually working with and what we can do with it.
