The Best Reason to Prepare your Business for Sale Is That you Might Not Sell It

Jennifer Stewart built a communications firm for 17 years, prepared it for sale, went all the way to seven days before closing—and walked away. What she discovered was that the entire process of preparing to sell had transformed how she ran her company. She now understands adjusted EBITDA, enterprise value multiples, and what actually drives her numbers. She removed herself from every decision. She set boundaries she never thought possible. And the business became more valuable, more resilient, and infinitely more enjoyable to own. Exit preparation and business improvement are the same work. If you sell, you sell well. If you do not, you own a better business. Either way, nothing is wasted.

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Colleen O'Connell-Campbell

Wealth Advisor

August 25, 2026

From time to time, I encounter resistance when I raise exit planning with business owners who are not thinking about selling. Their reaction is polite but unmistakable. They are busy building. They have no intention of stepping away. And the whole conversation feels premature at best, and a little morbid at worst - like being asked to plan your funeral while you are still training for a marathon.

I understand it. But I think the framing is backwards, and I want to offer a different one.

The work you do to prepare your business for sale is not really preparation for a sale. It is preparation for a better business. And the proof of that is what happens to the owners who go through the process and then decide not to sell at all.

Jennifer Stewart is exactly that case, and her story is riveting. Jennifer spent 17 years building a strategic communications and public affairs firm in Ottawa, starting at 25 with her own name and not much else. Then, an email arrived from a New York brokerage that had scanned the Canadian market looking for small to medium firms with strong retainers and government contracts. Her company was on the shortlist. She was, by her own admission, naive at the time - she had not even realized a service-based business could be sold.

She agreed to a valuation. The number came back higher than she expected. And then things moved very quickly. Within two weeks of going to market she was in discussions with a buyer, had an NDA signed, and was into due diligence. Other interested parties surfaced within a week. She went all the way to seven days before closing.

And then she walked away.

Jennifer describes the entire experience as something she is deeply grateful for - not despite walking away, but because of what the process taught her. It fundamentally changed how she runs her company. And every one of those changes has made the business more valuable, more resilient, and more enjoyable to own.

Start with the numbers. Before the process, she looked at her business the way most owners do - margin, profit and loss, cash in the bank. After going through a valuation and due diligence, she looks at those same numbers through an entirely different lens. She monitors adjusted EBITDA. She understands what multiple a firm like hers commands, and how that multiple is shifting as service-based businesses become more attractive to investors. She can now answer the question most owners cannot: what is this asset actually worth, and what moves that number?

That knowledge is useful at a transaction table and it is also useful every single day. When you understand what drives enterprise value, you make different decisions about which clients to pursue, which contracts to structure differently, where to invest, and what to stop doing. Jennifer now assesses whether she is chasing the types of clients she wants to chase, and whether she is building something of real wealth while treating her team well. That is a strategic filter she did not have before, and it came directly from preparing to sell.

Then there is what happened operationally. Saying no to the deal, in Jennifer's words, meant saying yes to a great deal more. She made adjustments to her team. She said yes to expansion, including a new office in Vancouver. She thought bigger about retainers and government work. And critically, she put real boundaries around her own time, protecting her mornings until roughly ten o'clock and building in a workout - something she had never done through the years of raising two young kids while working from the couch at 4:30 in the morning.

Jennifer describes herself as a recovered micromanager. She used to review everything, because the business was small and her name was on it. Now she is deliberate about not stepping in. She has shifted her team's mentality so that decisions do not funnel upward to her. She says: "You are failing as a business owner if you are in every decision point". She built the team, she trusts them, and she has removed herself as the bottleneck.

That single change - reducing founder dependency - is the most reliable value driver in any small or mid-sized business. It is what buyers look for. It is what makes a company sellable. And it is also, not coincidentally, what makes a company scalable, what makes it survive a founder's illness or absence, and what makes ownership sustainable rather than exhausting. Jennifer did not do that work in order to sell. She did it because going through a sale process showed her what was missing. And now the business is better whether she ever sells it or not.

Exit preparation and business improvement are the same work. Clean financials help you make better decisions and satisfy a buyer. Documented systems reduce your daily load and reduce buyer risk. A capable leadership team gives you freedom now and transferability later. Understanding your value clarifies your strategy today and protects your leverage at the table tomorrow. Tax and corporate structure done early saves you money regardless of what happens next.

There is no version of this work that is wasted. If you sell, you sell well. If you do not sell, you own a better business - one that runs without you, generates more profit, and gives you actual options. That is the whole point. The founder who has built a sellable business has a choice. The founder who has not is stuck, whether they wanted to sell or not.

And there is one more benefit that Jennifer talked about, which is harder to quantify but I suspect matters most. The process made her a more confident business owner. She went into it thinking, in her words, "oh gosh, someone wants to buy me, this is great". She came out of it thinking she is worth it, probably worth more, and wants to see how far she can take it. That shift - from being flattered by an offer to knowing your own value - changes how you negotiate, how you lead, and what you are willing to accept. It is worth the exercise on its own.

So, if you are a business owner who has no intention of selling, I would encourage you to prepare anyway. Not because you should sell, but because the preparation is the work. Get your financials to a standard that would withstand scrutiny. Understand what your business is worth and what drives that number. Reduce the number of decisions that require you. Build the bench. Formalize what lives in your head. Then, if a New York brokerage ever emails you out of the blue, you will be in a position to make a real choice - rather than being swept into a process you did not plan and do not control.

If you want to understand where your business stands today and what the gap looks like between what you have built and what you would need to fund the life you want, that is exactly what a Wealth Gap Analysis is for. Book a one-on-one with me Colleen O’Connell-Campbell. Reach out on LinkedIn or email me.

TTFN (ta ta for now)

- Colleen O'Connell-Campbell

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