By guest contributor, Doug Christy
If you’re a fan of HGTV, you have likely come across the show “Love It or List It,” starring Hilary as the interior designer and David as the real estate agent. Every episode features an individual, couple, or family who have lived in a home for quite some time but grown out of it for a variety of reasons. Hilary’s goal is to redesign the home for them so at the end of the episode they “love it” and decide they want to stay; meanwhile, David tries to find a new home for them so they will choose “list it” and sell the current one.
It usually ends up being a very hard choice, because Hilary and David do a fantastic job of providing options. (And also because like most reality shows, creating drama and tension is basically the entire purpose.)
I’m not on TV, but as a business coach, I face similar situations with many of my clients—I specialize in helping the owners of family businesses make their own “Love It or List It” choice. When I first talk with these clients, typically Baby Boomers, they have been contemplating their options for transitioning out of the business and need help moving forward.
The “love it” crowd wants to keep the business going by passing it down to their children and/or key employees. This is often driven by a desire to see their hard work turn into their legacy. By comparison, “list it” clients couldn’t care less about their legacy—they simply want to sell to the highest bidder.
Like the subjects of the HGTV show, a lot of business owners are torn. They just don’t know what’s right for them.
Getting that ‘house’ fixed up
Whether the business owner wants to love it, list it, or they don’t know yet, one thing is certain: They will want to get that business as healthy as possible before they pass it down or sell to an outside third party. After all, you would want to leave your family or key employees in a good position, or maximize the sale price, wouldn’t you?
I find that this is where the owner’s decision can shift from “listing” to “loving.” Once all the remodeling (so to speak) is done, they see the business in a different way and think about keeping it in the family—especially if the profits can help fund their retirement.
It’s extremely difficult for a business owner to do this on their own; outside perspective and expertise is vital for both enhancing the health of a business and making an informed decision about transitioning. Ultimately, the key service I perform for these clients is providing that knowledge and guidance, so they can confidently make the right choice for their business, their family, and their retirement.
Your brand needs the same attention
I have been Josh’s business coach for over six years and know that most Chalkbox clients come to Josh and his team after they have survived that early start-up stage. Often, the logo is tired or outdated, as are the website, print collateral, and other materials. Although the business has moved past the point where DIY branding is appropriate, and the owners know this, the decision to change is still complicated. It’s their brand, their business, their identity—the “house” they moved into years back, perhaps after building it themselves. There’s a lot of investment there.
Chalkbox provides these business owners with the same kind of outside perspective I give to my clients. They might simply need refinements (the “love it” option), or it could be time to “list it,” getting rid of the old brand and starting with something new. Just like with Hilary and David, the idea is what’s next, not what’s in the past or what worked before. And in the end, Josh and Chalkbox will help you make the right decision for the future of your business.
Are you facing a ‘Love It or List It’ decision of your own?
By all means, bring in Dave and Hilary if you live in Toronto and your decision is about your home. But when it comes to figuring out how your business is going to move forward, call on experts like Josh and Chalkbox Creative. You probably won’t end up on TV, but you will end up with a brand that’s ready for prime time.

Doug Christy is the owner of Pro Vision Coaching, a highly specialized business coaching and counseling firm focused on family-owned and closely-held businesses.
Based in Arizona, he has coached hundreds of clients over the last 13 years. He works with business owners across the country to help evaluate options and uncover opportunities that can transform their companies, their most important relationships, or both.