Answer first

When should I sell my business?

Sale timing is rarely about the best market window. It is the intersection of personal preparedness, business preparedness, and a tolerable market. Two of three usually triggers. Waiting for all three is rare; waiting for the perfect window often produces a worse outcome than acting on two of three.

Personal preparedness: post-sale identity, calendar, cash plan. The most underestimated axis. Owners who have not modelled what comes after sale often pull out of deals at the last minute or sign deals that look right on paper and feel wrong inside six months.

Business preparedness: operable without you, clean documents, predictable cash flow, defensible story. Owner dependence and customer concentration are the two largest valuation discounts. Both are reducible with twelve to thirty-six months of structural work.

Market window: industry multiples, capital availability, strategic buyer activity. The hardest axis to control. The right time is rarely the visible best window; it is the time when personal and business preparedness meet a tolerable market.