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The Seller’s Playbook

Rule 4 of 34 · Part 1, Before You Go to Market

Sell when business, market, and personal readiness align.

Chapter 4: Why Timing Matters More Than You Think

Should I wait one more year to sell?

What sellers often miss

Many owners assume they should sell when they are ready to retire. Buyers typically prefer businesses that are still growing, evolving, and creating opportunity. In many cases, the optimal time to sell is not when the owner is tired of the business. It is when the business is thriving and the future still looks bright.

The takeaway

You cannot control the economy, interest rates, or the timing of unforeseen events. What you can control is the readiness of your business and your personal preparation for a future transition. The owners who consistently achieve the best outcomes are those who prepare early and remain flexible enough to act when the timing is right.

Figure from the book · Chapter 4
Figure from Why Timing Matters More Than You Think. The figures show the typical shape of the trade-off rather than the outcome of any particular deal.
The figures show the typical shape of the trade-off rather than the outcome of any particular deal.

Illustrative, not your deal. Where the book uses dollar figures, they are there to show how something works, not to describe your business. Your banker, your accountant, and your attorney will put real numbers to your own situation. Full note.

Terms this chapter uses

Read the full chapter in the book