Most of what gets written about selling a business focuses on numbers. Multiples, addbacks, due diligence checklists, the mechanics of a sale and purchase agreement. All of it matters. None of it prepares you for how it actually feels to sell something you built.
I know this because I have done it twice. The first time I sold a small business in the automotive sector. The second time was a much larger sale, an NDIS business with a far bigger team, a far bigger price tag, and a far bigger emotional weight attached to it. Different scale, same feeling underneath. That is the part I want to talk about, because it is the part almost nobody prepares you for.
The stress is different to any other stress
Running a business is stressful. Selling one is a different kind of stress entirely, because the outcome is largely out of your hands. You can prepare your financials perfectly and still have a buyer walk away for a reason that has nothing to do with you. You can be doing everything right and still spend weeks waiting on a decision someone else is making. That waiting is its own particular form of pressure, and it does not switch off when you leave the office.
Due diligence can feel like being judged
Due diligence is a technical process on paper. In practice, it can feel deeply personal. Every decision you made over years in the business gets pulled apart by someone who has never run it and never will. A staffing choice that made sense at the time gets questioned. A slow year gets scrutinised. It is easy to take this personally, because the business you are being asked to defend is not just an asset, it is years of your own judgement and effort.
I remember this clearly from both of my own sales. With the automotive business, the questions were smaller in scale but still felt sharp, because it was the first time anyone outside the business had looked that closely at how I ran things. With the NDIS business, the scrutiny was far more intense, simply because there was more at stake and more people relying on the outcome, including staff and participants who had no idea a sale was even underway. Carrying that quietly, while still running the business day to day, is one of the hardest parts of the entire process.
Negotiation is personal, even when it should not be
Negotiation is meant to be a business exercise. In reality, when the business is yours, every figure discussed feels like a comment on your years of work rather than a line item. A buyer pushing back on price can feel like they are questioning the value of everything you built, even when they are simply doing their own due diligence on the numbers. Separating the business from yourself during that conversation is far harder than it sounds, and I do not think it gets easier the second time around, it just becomes more familiar.
Why this matters to me as a broker
I do not say any of this to discourage anyone from selling. I say it because having sold two businesses of very different size myself, I understand the version of this process that never shows up in a spreadsheet. The nervousness before a buyer meeting. The second guessing during due diligence. The strange quiet after settlement, when something you built no longer belongs to you.
If you are thinking about selling, know that the stress and the second guessing are normal, not a sign you are doing anything wrong. Having someone alongside you who has genuinely been through it, on both a small scale and a large one, makes a real difference. That is exactly the role I try to play for the vendors I work with.