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Financial PlanningTop Mistakes to Avoid When Exiting a Business


This article was reviewed by Chris Singer, CFP®.

Whether it’s due to retirement or a life change, exiting a business is a complicated process. From transitioning your clients, to determining your market, there are a significant number of considerations to make before you move on.

In our time working with business owners, we’ve seen people make a number of mistakes when wrapping up their businesses. Many of these are avoidable with thorough planning and simply knowing what to expect during this change. 

We reached out to Mr. John Bowling CGA, CPA to provide his advice and experience for clients who are looking to exit their business. 

What is the first thing for owners to consider when planning to sell their business?

For John, there are three main points to consider: 

  • Whether or not there is a market for your business
  • What assets you want to keep (company vehicles, furniture, etc)
  • Making sure you don’t fixate on the sale price too soon

“I’ve seen many businesses have to just close the doors as there may not be a buyer for what they are selling.” Sometimes the buyout price is so high that the purchaser cannot make the business work.

John has seen this mistake many times during his years in business. “One client just recently had an offer to buy their business. The initial offer was very high and piqued their interest. After eight months of due diligence and exploration, the final offer was lower, with payout on future growth and a two-year commitment to manage the business. They said NO in about five minutes. If they kept running the business the way they are currently, and sold their client list at ten cents on the dollar in two years, they would be putting more money in their pocket than accepting the offer to sell and working for two years.”

What advice would you give an owner today if they told you they were planning to retire in five years?

“Start planning today for succession and also a wind down scenario,” John urges. 

The best thing to do if you anticipate leaving your business is to begin planning immediately. Too many people wait until the last minute and find themselves scrambling to find a successor or a buyer, and have no idea what they’re going to do afterwards. 

Five years out from retirement, you should consider:

  • Potentially cleaning up your financial statements. You want to have 3-5 years of your business looking its best.
  • Making sure your share structure is looked at so that you can benefit from any tax planning.
  • Establishing the right leadership and getting them settled in place to manage the potential transition.

For owners looking to retire in the next few years, John also emphasizes the crucial importance of having a plan for after retirement. “The biggest question I ask is, ‘what will your purpose in life be once you retire?’” John says. “Having no purpose often leads to an early death.”

Make sure you have a plan in place so that you aren’t left purposeless and can enjoy these wonderful golden years! We have an entire blog on planning for retirement if you’re in this situation. Travel is an exciting and popular activity in retirement, so consider some travel destinations you may want to explore once you’ve wrapped up your business. 

How can owners better understand the value of their business when looking for a buyer? What are the top factors contributing to a business’ value?

John has a few questions for business owners to consider:

  • Is there value in the business itself or are “you” the value of your business?
  • Are your customers willing to transition to a new owner?
  • Will you have to continue working after the sale to ensure you will get the most value—and are you willing to continue?
  • Are you selling the assets or the goodwill?

He cautions that “many owners think their businesses are more valuable than they actually are.” Make sure you’re being realistic and doing your research before fixating on your ideal sale price. 

What tax implications need to be considered when selling a business to retire?

“I tell my clients to worry about the actual sale first,” John says. “There are too many variables to try to quantify in dollars too soon.” 

Only once you’ve established your sale should you worry about tax implications. At that point, you “need to know if your shares qualify for the Capital Gains Exemption. Are there deferred tax costs hidden in your assets if you have to sell them (such as low tax cost, whether amortized or actual) with a higher sales price?”

“Remember, whatever is good for the seller is generally not good for the buyer—like selling shares vs assets. If you sell assets, we can defer the personal taxes as you take the funds out over the years. Treat your company like you would an RRSP—you don’t need to cash out right away.”

What is the #1 issue that business owners run into when they are selling their business to retire?

“Time. It creeps up on you.”

John has seen too many people believe they have much more time than they do, or expect to do more with their time and find themselves limited by unexpected health issues. “Have a contingency plan for an illness, have your retirement plan mapped out in general terms,” John urges. “Don’t decide to retire then try and sell. You need time to find the right buyer, and the paperwork alone will take more time than you think.”

Ready to start the planning process of leaving your business? We’re happy to schedule a meeting to discuss your financial needs and answer any questions you have about this process. While you’re mapping out your business plan, take a look at our eBook to find some helpful tips on creating a stress-free retirement!