The Owner’s Dilemma: Running the Business vs. Preparing to Sell It

Every business owner will eventually leave their company, whether through sale, succession, or circumstance. Yet research from the Exit Planning Institute reveals a sobering statistic: only 20 to 30 percent of businesses that go to market actually sell. The primary reason is not lack of buyer interest or unfavorable market conditions. It is lack of planning. According to a 2023 Exit Planning Institute study, nearly half of business owners plan to exit within five years, yet 48 percent of those who want to sell have no formal exit strategy. This gap between intention and preparation creates real financial consequences: studies indicate that business owners who don’t plan properly can lose 20 to 50 percent of their potential value due to rushed sales.

The challenge for most owners is fundamental: the skills and focus required to run a successful business differ significantly from those required to prepare one for sale. Building customer relationships, managing operations, developing products, and leading teams demand daily attention. Exit preparation requires a different kind of sustained effort that can feel removed from urgent demands. In surveys conducted by ideas42, 63 percent of business owners say it’s “too early” to begin succession planning, while 45 percent report being “too busy” to start. The problem is that windows for maximum value close while owners focus elsewhere.

Research from the University of Chicago’s Booth School of Business suggests that company valuations often peak when founders reach the seven to eight year mark of ownership, after which growth may plateau. Waiting until burnout, health issues, or market shifts force a decision typically yields suboptimal outcomes. A phased approach to exit readiness addresses both the psychological and practical dimensions of the owner’s dilemma: honest assessment of operational maturity, building transferability through documented systems and deeper leadership, and financial positioning through clean books and consistent margins.

Importantly, the work of exit preparation produces immediate benefits regardless of whether an owner ultimately sells. Stronger processes, deeper management teams, and cleaner financials all contribute to better business performance today. The owner who invests in exit readiness is simultaneously building a more valuable and more manageable company.

For founders wrestling with the competing demands of daily operations and future planning, that dual benefit offers a practical path forward. The best time to begin exit planning is years before you intend to exit. The second-best time is now.