Selling a business is one of the most difficult—and emotional—decisions any entrepreneur can make. For many, the “should I or shouldn’t I?” debate can become agonizing. We asked five business owners who’ve sold their companies to share the exact moment they knew it was time to pack it in.

“We were growing so fast we were having a hard time managing it; we were up 90% year-over-year in January. We’re not a huge company, and we knew our main demographic was growing. If we really wanted to capitalize on the growth in our business and our market, it was a good time to sell.”
—Lorna Vanderhaeghe, who sold her Vancouver-based wellness firm, Lorna Vanderhaeghe Health Solutions, to Jamieson Laboratories in June 2014.

“I joined the family business in 2004. At one point, a management consultant we’d hired said to me, ‘The business is not a gift that’s been given to you; it’s an asset and has to be treated as such. If your parents gave you money, would you reinvest it in the business?’ I realized the answer was no. That was the trigger event.”
—Jeremy Miller, who sold Toronto-based LeapJob to another family business in 2013

“I started VRX Studios 15 years ago; a few years back, I added an arm called MediaValet. When it became the fastest-growing and highest-margin part of my business, I had a choice to make: bring in outside money or sell some assets. The sale of VRX allowed me to fully fund the MediaValet business without experiencing any dilution. The decision was emotional, because I love both businesses, but it was easy because one has bigger market potential.”
—David MacLaren, who sold Vancouver-based VRX Studios Inc. to an affiliate of Local Hospitality Inc. in August 2014

Read: The Secret Reason Most Entrepreneurs Don’t Plan Their Exit

“In my early 60s, I started talking to a younger guy who wanted to take over the practice and buy the building—and who was prepared to put the money up to do it. We arrived at a price three years before I sold. Then his practice started to grow, and I started to run out of steam; the administrative bullshit was taking up more and more of my time. The timing ended up being perfect.”
—Don Maybin, who sold his Trenton, Ont., chiropractic centre to a fellow practitioner in 2009

When it is time to sell, it is time. I have watched many entrepreneurs hang in way too long and run their businesses into the ground.”
—Brent McLean, who sold a controlling interest in Calgary’s McLean & Partners Wealth Management Ltd. to Canadian Western Bank in 2013

Read: An Entrepreneur’s Guide to Selling Your Baby

This story is part of the package in the October 2014 issue of Canadian Business. Click here for more useful, business-building tips, or here to subscribe to the magazine!

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