
Jennifer Dziura writes life coaching advice weekly here on TheGloss, and career coaching advice Fridays on TheGrindstone.
The above is a still from the end of the 1988 classic Heathers, from right around the part when Winona Ryder blows up her boyfriend and declares herself the “new sheriff in town.”
Let’s see a letter from a reader who’s friend is stuck in a shrubbery-filled rut.
My good friend “Gloria” has been in a long-time terrible relationship. She wants to get out and move far away from her on-and-off ex “Jesse” (yes, I have sent Gloria Bullish Life: Breaking Free from Terrible Situations).
Gloria’s major stumbling block: she started a landscaping business with Jesse in Atlanta several years ago. Jesse’s parents bought the (very expensive) van, and Gloria invested her small savings into getting the business off the ground. Early on, Jesse dropped out of the business and was content to let Gloria do all the work. Jesse has not had a job in years — he alternates between living with Gloria and her parents, and “borrows” money from all of them.
The business is doing reasonably well, but Gloria is not a bookkeeper (she hasn’t kept invoices of her appointments), and is about 3 years behind on her taxes. Atlanta is threatening to garnish her wages for unpaid taxes. (Not to mention Jesse regularly has some “emergency” that requires thousands out of Gloria’s pocket.)
Gloria wants to sell the business and give Jesse’s parents a potion of the profit, then move away — she feels like she owes them a chunk of money because 1) they bought the van and 2) she lived with them rent-free for a time before she got her own apartment. Recently the parents lost their home to foreclosure because of the father’s drug addiction (Jesse’s own drug problems and drunk driving accidents also took a toll on the family purse) — Gloria feels sorry for them.
My opinion: while it is admirable that Gloria wants to honor her debts, Jesse’s parents bought the van for Jesse, not Gloria — Jesse abandoned the van and the business. From the beginning, Gloria has paid for all maintenance on the van. Gloria actually tried to give back the van once or twice to the parents, and they just seemed bewildered on why she thought they’d want it.
I’ve advised her to go to a free local tax preparer and get her taxes in order, then hunt for a certified business broker to see how much she could sell her business for (BTW, she definitely does not want to continue landscaping in a new location after she’s done with the business—she only got into it in the first place because Jesse was a professional landscaper). I’ve also told her there is no shame in selling the van, giving a token of the money to the parents, and then moving away, but she finds this idea unacceptable because she has worked so hard and invested so much (literal) blood, sweat, and tears into her business.
Maintaining a business is challenging, selling a business is challenging, and trying to do both when you are being treated like a scullery maid/sex doll with a built-in ATM by an intimate partner is infinitely more challenging.
Should she push on to sell the business, or cut her losses now?
So many things going on here! Here we go.
On selling a business
Gloria is quite reasonable in wanting to sell her business.
When my company was in the process of slowly failing (see Bullish: To Give Up or Not to Give Up?), I was surprised that a lawyer I knew felt I could sell the business. Sell what? My business was basically three computers, some cheap office furniture, and me working my ass off. Sure, we had a name and website and a nice logo, but it’s not like customers worldwide recognized and trusted the brand. Without my continued participation, the assets of this company could conceivably been worth $5K or so to someone wanting to start an extremely similar business in a nearby location. It wasn’t really worth it for me to try to find that mythical beast of a creature.
Gloria, though, has a van, some landscaping equipment, happy customers, and presumably some means of getting the business’s name out there. Yep, you can totally sell that, although sometimes it takes a couple of years. Business brokers often counsel owners wanting to retire to start looking for a buyer years ahead of time; such a buyer may want your continued participation while he or she gets up to speed.
There’s no right move here. Sell the van and leave right away. Sell the whole business and leave … later.
As an alternative, there are many other van-based businesses one could pursue, only some of them creepy!













