Most owners ask the timing question backwards. They look at headlines — interest rates, multiples, the M&A cycle — and try to predict the perfect window. The truth is that the best time to sell is when your business is ready, you are ready, and the market is at least neutral. Two out of three is usually enough.
Business readiness means clean financials going back at least three years, documented processes, a management team that can run day-to-day operations without you, and a customer base that isn't concentrated in one or two relationships. Buyers and lenders price risk, and every one of those items reduces it.
Personal readiness is harder to fake. Owners who sell because they're exhausted tend to leave money on the table; owners who sell because they have a clear next chapter — another venture, retirement, a family priority — negotiate from strength. Spend a year visualizing life after the sale before you list.
Market conditions are the variable you can't control, so stop trying. Instead, track three signals: SBA lending appetite in your industry, recent comparable transaction multiples, and buyer demand at the size band above yours (because that's where your buyers are coming from). When two of the three are healthy, the window is open.
If you're 1–5 years out, the work starts now. The businesses that sell fastest and at the highest multiples are the ones whose owners started preparing before they needed to.