Answering 'How Long Have You Been Doing This?'

Two seconds of silence after that question does more damage than any answer you could give. The buyer is not waiting on a number. They are watching what you do with being asked.

The standard advice is to be vague, change the subject, or quietly round up. All three read the same way from the other side of the table — as someone with something to hide — and a buyer who suspects you are hiding one thing stops believing the rest.

Why the question is about risk, not years

Years are a proxy. Nobody wants a tour of your calendar. They want to know that the last person who paid for this got what they paid for.

Underneath the question sit three others: will this actually get done, will it get done right, and what happens to me if it does not. A long history answers all three at once without anyone having to say them out loud, which is exactly why people reach for it.

Seen that way, a short history stops being an automatic loss. You answer the three directly instead of borrowing the shortcut.

Answering the question underneath the question

Give the literal answer, then answer what they meant, in the same breath.

"I started this year. I have done four of these, all for people on this street, and I will show you the last one before you decide anything."

That is the shape. A true fact about time, a true fact about the work, then something they can look at. Never the time fact on its own. Left alone in the air, it invites the buyer to fill the silence with whatever they already feared.

If the worry underneath is what happens when something goes wrong, answer that instead of the years. "If it is not right, I come back and fix it, and you do not pay for the second visit." A specific remedy lands harder than a specific date.

The honest short answer and the sentence after it

"Not long" is a complete and acceptable answer, provided it is not the last thing out of your mouth.

The sentence after it carries the weight. It has one of three jobs: point at evidence, point at a related history, or shrink what the buyer is risking.

• Evidence: "Not long. Here is the last one I finished."
• Related history: "New to doing it for money. I did it for my own family for years before that."
• Shrunken risk: "Six weeks. Which is why I would rather start with the small job and let you decide after that one."

Do not apologize. Do not explain your circumstances. Do not pad the follow-up sentence with adjectives about how dedicated you are, because adjectives are the one thing a nervous buyer discounts entirely. One clause, one concrete thing.

If the reason your history is short is that you had nothing to start with, there is a way to say that without handing the buyer your situation to manage — how to talk about starting with no money works through the wording.

Redirect to what you can show

The redirect only works if something is waiting at the other end of it. "Let me show you," followed by thirty seconds of scrolling a phone gallery, is worse than having said nothing.

Set it up before the conversation. One item, openable in a second, that resembles the thing this buyer wants. A photo of finished work. A short clip. A one-page document. The name and number of someone who will pick up if called.

Then say the line that makes it land: what it was, who it was for, and which part of it you did yourself. A small precise claim outperforms a large vague one every time, because the buyer can test a small precise claim and cannot test the other.

If you have nothing to point at yet, that is a problem to solve before the next conversation rather than a reason to dread this question — building a portfolio when nobody has hired you is the mechanism for it.

And when the strongest thing available is somebody else's name rather than your own work, standing on borrowed credibility has honest versions and dishonest ones, and the line between them is worth knowing before you lean on it.

When the honest answer really does disqualify you

Sometimes the true answer is: not long enough for this particular job. Electrical work behind a wall. A load-bearing beam. A tax filing. A medication schedule for someone who cannot check it themselves. Get those wrong and a do-over does not undo the damage.

Say so immediately, and say what you can do instead. "I would not take the panel. I can do everything else in the room and you get a licensed person for that part." You lose one job and keep the relationship, and the relationship outlasts the job you would have botched.

There is a quieter version. The buyer needs someone who has already met the failure modes, and you have not met any yet because nothing has gone wrong for you so far. If you are one step ahead of the customer rather than genuinely ahead of the work, be explicit — working or teaching one step ahead of where you are is defensible when it is stated out loud and indefensible when it is hidden.

Buyers no answer will satisfy

Some people were never choosing between you and inexperience. They were choosing between you and a company with an office, and the office was always going to win. The question was a formality on the way to a no.

You can spot it inside a couple of exchanges. They ask about years, then insurance, then references, then a written scope, and nothing you say moves them a single step. That is what it looks like when the stated objection is not the real one.

Let them go. Quickly, politely, and without cutting your price to chase them, because a buyer who does not trust you at your number will not trust you at a smaller one and will be the hardest work you take all month.

Spend the hour you just saved on somebody who has already shown interest. Go back to the last person who said "maybe later" and ask whether later is now.