Should I sell now, or hold for another five years?

Owners tend to frame the sell-or-hold decision around valuation multiples and market timing. Those matter, but they're the easier half of the question. The harder half is personal: what does five more years actually cost you, in time, in energy, in the parts of your life the business has been standing in for.

Businesses rarely stay flat. Five more years usually means either meaningful growth, which can significantly change the eventual sale price, or a plateau that starts eroding value as competitors catch up or the owner's energy for the work fades.

There's no universally right answer here, but there is a wrong way to decide: waiting passively until the decision gets made for you, by burnout, by a health scare, or by a market downturn you didn't see coming.