Should I sell my business or keep it? Five honest questions

Should I sell my business? To answer it well, split it into two smaller questions: are you ready to step away, and is the business ready to be sold without you? If both answers are yes, selling may well be right. If only one is, the better answer is usually to prepare first, or to keep it.

Owners often bring me the big question as if it must be settled in one sitting. It rarely needs to be. It gets much easier once you pull it apart.

Should I sell my business or keep it?

The two questions run on different clocks. You can be tired of running the company while the company is at its best. You can also feel ready to go while the business still depends on you for every big decision. Here is how the answers combine.

The yellow box is the hardest one to be in, because it needs time, and time is what many owners are short of. Among Canadian owners planning to sell within two years, only 24.4% say they have enough time and resources for the transition, according to Statistics Canada. Five questions will tell you which box is yours.

1. Do you still want to run it?

Be honest about your energy, not just your age. Some owners are bored. Some are worn down by the same problems every Monday. Others love the work and dread the day it ends. None of these is wrong, but they point to different answers. If you would happily keep going for another five years, there is no reason to sell just because people your age are selling.

2. Does the business run without you?

This is the question that sets the price. A buyer is paying for the next five years, without you. If the key customers, the pricing and the hard calls all run through you, a buyer sees risk and discounts for it. We cover the full list in what buyers look for when buying a business. If the honest answer is no, the business is not ready yet, however ready you are.

3. What do you need from the sale?

Work out what you need to live the life you want afterwards, and work back from there. Start with what you keep, not the headline price. In Canada that depends a great deal on structure. A share sale may let you use the lifetime capital gains exemption, which is $1,275,000 per person for 2026, and only half of a capital gain is taxed. Our guide to share sale vs asset sale in Canada explains why the same price can leave you with very different amounts. Ask your accountant to run your own numbers.

4. Should I sell my business and retire, or step back first?

Selling is not the only way to stop working every day. Some owners hand the day-to-day to a manager and keep the shares, and the income. Some sell to family or to their management team over time. Others sell a majority now and keep a minority stake. Every one of these routes needs the same thing a buyer wants: a business that runs without you. It is why preparing pays even if you never sell.

5. Is now a good time to sell my business?

No one can time the market reliably, so time yourself and your business instead. Still, today’s conditions are worth knowing. BDC reports that for every 10 Canadian businesses looking to buy, only seven are looking to sell. The Bank of Canada’s policy rate is 2.25%, down from 5.00% in 2023 and 2024. More buyers and cheaper money help, but only for businesses a buyer can understand and trust quickly. A good market will not rescue a business that is not ready.

Should I sell my business or close it?

For a profitable business, closing is usually the most expensive answer. Close, and the customer relationships, the team and the name go with it. Sell, and someone pays you for them.

Yet Statistics Canada found that among owners planning to sell within two years, 30% say they are very likely to scale down or close if no suitable buyer appears. Some of those businesses may have had little a buyer wanted. Others will simply have run out of time, with an owner ready to leave before the business was ready to be sold.

What to do if you are still unsure

You do not have to decide today. You can do the work that makes either answer better.

• Get a realistic view of value, with your numbers adjusted the way a buyer would adjust them.
• Find where the business depends on you, and start handing those decisions to others.
• Know your after-tax number and your walk-away price before any buyer calls.
• If an offer has already arrived, do not let it make the decision for you.

Whether you sell is your decision. Whether the business is ready is work you can start now.

That work usually takes 1 to 2 years, and it leaves you with a better company whichever way you decide. Our method shows how we approach it.

If this question has been on your mind for a while, a short, private conversation is a good place to start.