What Business Owners Are Saying About Their Futures

The Quiet Countdown

By Alyssa Mandeville

Ask most business owners when they plan to step back from the company they built, and the honest answer is usually “not yet.” But new national research suggests that day is closer than many of them let on — and that the years immediately surrounding it deserve far more planning than they typically get.

Raymond James recently released its 2025 Business Owner Report, a survey of 540 privately held business owners conducted in April 2025. The headline finding is striking: 88% of owners plan to financially exit their business, in part or in full, within the next decade. More than half — 56% — expect to transition their financial stake within just five years. Whether they realize it or not, a large share of the business community is already inside the runway to a major transition.

The encouraging news is that most owners are not flying blind. Eighty-five percent reported having a transition plan in place. That is a meaningful figure, and it reflects a generation of owners who take the responsibility of a smooth handoff seriously — to employees, to customers, and to the families who depend on the business. The harder question is whether those plans extend beyond the operational handoff to the personal financial picture that surrounds it.

That picture is more concentrated than many owners appreciate. The survey found that 44% of owners say their business represents more than half of their total wealth, and nine in 10 say it accounts for at least one-quarter. Among Baby Boomers, the concentration is more pronounced still: 31% reported that more than three-quarters of their personal wealth is tied up in the business — a rate nearly three times higher than among their Gen X and Millennial counterparts.

Concentration like that is the natural result of decades of reinvesting in something you believe in. But it also means that a single event — a sale, a partial recapitalization, or a transfer to the next generation — can reshape an owner’s entire financial life in a matter of months. When most of your net worth is illiquid and bound to one enterprise, the transition is not just a business decision. It is the single largest personal wealth event most owners will ever experience.

What strikes me most about the data is what owners intend to do next. Nearly two-thirds (63%) say they plan to keep working in their business or start or invest in a new venture after they exit their current financial stake. This is not a generation looking to disappear; they are looking to redeploy. And 85% expect they will need a capital infusion to fund their next stage of growth, though there is little consensus on whether that capital should come from private equity, lending, or personal resources. The appetite to build again is alive and well — but it requires liquidity, and liquidity requires planning.

That is where the window matters. In our experience, the 18 to 24 months before and after a transition are the most consequential — and the most overlooked. It is the period when succession structure, income and estate tax mitigation, estate planning, risk management, investment objectives, and short-term personal cash flow all collide at once. Decisions made hastily in that window, or deferred until after a deal closes, are difficult and sometimes impossible to undo. Decisions made deliberately, well in advance, are where real value is preserved.

The practical takeaway for owners is not to rush toward the exit; it is to start the conversation earlier than feels necessary. If you are among the 56% who anticipate a transition within five years, the planning work ideally begins now, not when a buyer appears or a family member raises a hand. And if you are among the 44% whose wealth is heavily concentrated in the business, diversification and liquidity planning deserve a seat at the table long before any transaction is on the horizon.

Business owners are some of the most capable planners I know — it is how they built what they have. The opportunity this research highlights is to bring that same discipline to their personal financial lives, and to treat the transition not as an endpoint, but as the next phase of a long and deliberate plan. The countdown may be quieter than it sounds. The owners who thrive will be the ones who start preparing while there is still plenty of time on the clock.

Alyssa Mandeville is senior vice president, head of Wealth Management at PeoplesBank.