How do I know if I should sell now or wait a few more years?

There's no fixed formula for this, but the question is usually better answered by looking at trajectory than by picking a number of years in advance. If the business's revenue, margins, and customer base are improving and likely to keep improving, waiting can genuinely increase what you'd eventually get. If they're flat or starting to slip, or if you're the one holding things together and your own energy for that is declining, waiting often costs you more than it gains.

The trap is treating "a few more years" as free time that doesn't need managing. Whatever timeline you choose, the years leading up to a sale are exactly when preparation matters most — cleaning up contracts, reducing owner dependency, and getting comfortable with your financial records. Waiting without using that time deliberately just delays the sale without improving your position.

A useful way to decide is to set a rough target window, then check in with a business lawyer and accountant partway through it to see whether the business is actually tracking toward being more valuable and more sellable, or just older. That turns "wait a few years" into an actual plan instead of a default.