Ward & Uptigrove

The Psychology of Selling Your Business

May 26, 2023

Whether you’re an established business proprietor, a generational business owner, or an entrepreneur, you've put your heart and soul into building your company. Still, there comes a time when you need to move on, and that's where selling comes in. However, it's more than finding the right buyer and negotiating the best price or contract terms. Many owners, like you, find themselves struggling with a deep-seated reluctance to sell, which can be hard to understand and even harder to overcome.


You may have invested so much time and energy into your business that it's become a part of you. Or there are family issues that are holding you back. Whatever the reason, it's essential to recognize that this reluctance is not uncommon, and it's perfectly normal to feel this way.



You may find yourself delaying the acceptance of a fair offer, stalling the process, declining, or otherwise sabotaging the deal without really understanding why. You may think it just didn’t “feel right”, the buyer wasn’t the right fit, or you convince yourself you’re not ready. Perhaps it is one of these reasons, but often this is not the case. 

The Psychology of Selling Your Business

Selling a business that has been painstakingly created, nurtured, and struggled with, and one that is ultimately successful, is akin to a child leaving home to take on the world for themselves. For owners like you, a business can be like having a child. Whether you’ve conceived the business from an idea, inherited the family business, or purchased an established enterprise, you’ve put your blood, sweat, and tears into your business to make it successful.


Like new parents, you can often feel nervous, unprepared, and overwhelmed, having never done this before. Regardless, you push through as the reward and satisfaction far outweigh the fear; the effort is fulfilling and long-lasting. Over the years, you’ve spent many hours cultivating and nurturing the business, celebrating its successes, and watching it grow into a successful, independent, self-reliant enterprise that is ultimately valuable to the world. 


You and your business struggled together, overcame obstacles in the face of adversity, stumbled, got back up, and learned and grew through it all. Like a baby, you initially carried the business when it could not carry itself. Over time, your business grew and found its legs and rhythm. As your business matured, it became important to others – clients, staff, suppliers, and, most importantly, you. Like a child, the business gained independence over time and needed you less and less, becoming an entity unto itself. You no longer manage every aspect of the enterprise, coddle it, and protect it. Your business has become a thriving entity that can stand on its own.


Letting go of what you or your family created, nurtured, and grew is often very difficult. Like a child, you are proud of what it has become but still worry about what might happen if you let it go. Will it be okay without you? Will it be damaged if you are not there to protect it? Will it even survive if you are not guiding it in the future? 


With business, as with children, you reach the point where you have done everything you can to prepare it for the world, and you must let go. Let it move on. Let it continue its evolution, whatever that may be. 


Considering a different perspective about the sale of your business and understanding the emotions you may be experiencing often helps you conquer the reluctance of finalizing the sale. Selling is a very difficult time for many business owners, which could result in a lost opportunity to monetize your lifelong achievements if you can’t overcome this obstacle. 

How We Can Help

Work with your trusted accounting and financial advisors under our TriCert™ integrated approach. We specialize in owner-managed businesses to help you overcome many psychological hurdles of selling your business. 



Leveraging the experience of accountants and tax specialists, and integrating these advisory services with your financial planner, can give you the peace of mind and the confidence to work through one of the most significant events in your lifetime with a strong team supporting you every step of the way.


Have Questions?


Contact a Ward & Uptigrove Wealth Management representative at 519-291-3040 or email info@w-u.on.ca

Southwestern Ontario's Top Employers Award
February 5, 2025
We are th rilled to announce Ward & Uptigrove was selected as a recipient of the Southwestern Ontario's Top Employers Award for 2025. The award is based on the following criteria: 1. Workplace, 2. Work Atmosphere and Social, 3. Health, Financial and Family Benefits, 4. Vacation and Time-Off, 5. Employee Communications, 6. Performance Management, 7. Training and Skills Development, 8. and Community Involvement! Here are some of the reasons why Ward & Uptigrove was selected as one of Southwestern Ontario's Top Employers (2025): Ward & Uptigrove increased its full-time workforce in Canada by over 13 per cent in the past year and lets everyone benefit in the company's success with profit-sharing -- the company also offers generous referral bonuses of up to $5,000 per successful candidate as an incentive for employees to recruit friends Ward & Uptigrove hosts three major social events each year, giving employees the opportunity to unwind and connect with food, beverage and entertainment covered by the firm's partners -- events include a post-tax season party (employees plus a guest), a fall golf tournament, and an annual holiday celebration Ward & Uptigrove matches employee donations in kind, and encourages them to lend a helping hand in the community with a paid day off to volunteer Emily MacRobbie, human resources manager at Ward & Uptigrove, says clients appreciate the close connections and sense of care their small-town environment fosters. “We’re big enough to attract and retain some of the best and brightest minds in the industry, while simultaneously being small enough that staff and clients are known on a more personal level,” says MacRobbie. “Employees really appreciate the flexibility the firm offers, such as work location (in office or hybrid) and hours of work arrangements. We keep a pulse on what’s happening and make sure we remain competitive with things like paid time off and flexible health benefits.” To learn more about career opportunities at Ward & Uptigrove visit www.wardanduptigrove.com/careers
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