Section 1
The five questions
1. Could the firm run for a full quarter with you unreachable, and keep its customers, its margins, and its license? This is the master question. A buyer does not inspect your business at its best. They inspect it as it will be the day after you leave. If the answer is no, most of what you think you are selling walks out the door with you. 2. Is there a legally qualified buyer who could own and operate it? In a licensed trade, the buyer must be a Meister, employ one full-time as technical director, or qualify through years of leading experience. If the only qualified person in the building is you, the buyer pool is close to empty regardless of how good the numbers look. If your trade is unregulated, this one is a free yes. 3. Does meaningful value sit in things that are not you: recurring contracts, a brand customers trust, trained staff, systems? Transferable assets are what a buyer pays for. If the value is your relationships, your pricing instinct, and your name over the door, there is little to transfer. 4. Are the books clean enough that a buyer's advisor could verify earnings in a week? Mixed personal and business expenses, cash-basis chaos, and undocumented add-backs do not just lower the price. Past a point they end the conversation, because a buyer cannot underwrite what they cannot verify. 5. Do you have runway: at least two to three years before your hard exit date to fix whatever the first four questions exposed? De-risking a firm takes time. Documentation, delegation, and moving relationships off your name is roughly a two-year project. Started at 65, it usually does not finish.
Section 2
Reading your score
The score is a snapshot, not a sentence. A firm that scores 1 with five years of runway can become a firm that scores 4. A firm that scores 3 with six months of runway probably cannot. Time is the variable that turns a low score into either a project or a verdict.
Section 3
Why the honest read matters
The reason to run this test now, rather than at 64, is that the two exits require opposite preparation. A sale rewards years of quiet de-risking: writing down what is in your head, handing off what only you do, moving customers off your name and onto the firm's. A wind-down rewards the opposite: keeping things lean, avoiding new commitments, timing the close to minimize loose ends. Owners who assume "sale" and prepare for nothing tend to back into a wind-down at the worst moment, tired and out of runway, and take scrap value for a firm that was worth far more two years earlier. The most expensive mistake in this whole subject is not choosing the wrong exit. It is refusing to choose, calling it a demographic problem, and letting the calendar choose for you.
Section 4
The fitness test
Run the five questions again in six months. If your score is rising, your de-risking is working and a sale is getting more real. If it is flat and your runway is shrinking, stop planning for a sale you are not building toward, and start planning the exit your answers actually describe. The dignity is in choosing with open eyes. There is none in discovering the choice was made for you.