Bullish Life: When To Cut Your Losses And Walk Away

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?

Gifts from Brooklyn, Not Billionaires


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!

On walking away from money

Recently, I wrote Bullish: A Metaphor About Shoe Shopping That Is 100% Relevant To Hard-Nosed Business Thinking, which contained an itemized list of times I’ve walked away from a financial loss. For instance, a landlord never returned my deposit. My car was stolen in 2003 and I had to make payments on the $9,000 loan for three years.

In Bullish: How One Best Responds to Massive F*cking Disrespect, I answered a question from a woman who had taken relocation funds to relocate for a terrible job; if she quit, she had to pay it back. I suggested (among other options), doing exactly that. There’s nothing wrong with a moving loan. Sometimes it’s worth almost anything to buy back the rest of your twenties.

People are remarkably irrational about financial loss. People will chase pointlessly after a lost $500 when they could be pursuing a brand-new, unrelated $5,000.

You can combat this with self-knowledge! If I lose $500, I’m going to ask myself: Do I need to pursue this for the sake of justice, to keep other people from getting hurt? If not, I ask, “Would I rather spend $500 worth of my time doings things I’m good at (writing education books! starting little businesses!) and making up for the loss elsewhere, or endlessly calling people on the phone and arguing with them (“My stolen car was once parked here!”), or trying to think of a magical way to erase all my past mistakes?” I pick option A.

Also, everyone should pay their taxes, but you’d be amazed how many seemingly normal people you know are also behind on their taxes. Falling behind is different from being a multimillionaire who hides his money in an underground bunker and tells the government to fuck schools and roads and clean water.

When you’re in the throes of failure and crisis and stress, it’s hard to see that most of the really bad shit you’re afraid of doesn’t really kill you or put you in jail, and also mostly happens really slowly.


Older people who help you have their own reasons

It’s possible that the parents — who’ve spent half their lives helping their n’er-do-well son and who bought a van in the attempt — would be embarrassed to take money from their son’s girlfriend. Kind of like when you open the door for an old man who’s kind of struggling, and you hope he thinks, “Kids these days have such good manners!” and not, “This is really emasculating.”

Also, when you give someone an awesome gift and then they try to “pay you back” in a way that’s sort of uncomfortable (as in, not a bottle of wine or something, but actually putting a dollar figure on your gift), it kind of lessens the good feeling you got from giving the gift in the first place. So, don’t force van-money on people who don’t want it. Maybe Gloria could take the parents out for a nice dinner on her last night in town.

You will not convince others to be ballsier.

But let’s stop talking about Gloria, because she didn’t actually write in for advice; you did. Eeeenteresting.

I am super, super aware that I only give advice for certain kinds of people. The kind of people who click on links for articles entitled Bullish Life: What To Do When You’re Surrounded By Lazy Idiots (and Sweet, Fragile Simpletons). Once, in elementary school, I sat behind this kid who wore the same t-shirt at least twice a week. It was surfing-themed, and said, “The unaimed arrow never misses.” Yeah, I don’t write for that guy. (It’s possible his mom bought the shirt, not him, and he grew up to be Ryan Gosling or something, in which case that’s cool.) You really can’t push people towards more bullishness.

Your friend already knows she wants out. You don’t need to stage an intervention.

I know some really unbullish people. You cannot change these people. One such person — let’s call her “Mary” — once sent me an email that began, “I’m sick and tired of living like this. Do you know how I can make $50,000 per year…” At this point, I became excited! I thought, “Probably!” I AM SO FULL OF IDEAS. The email continued, “…without working too hard or learning any new skills?” Oh. Well, no. No, I do not. So I interpreted the email as a joke, and sent a friendly response, something like, “Haha! If only. Sorry you’re having a hard time.”

You can still take those people out to lunch and listen to them.

While that describes the large mass of humanity, there are also some people who don’t want your or my or anyone’s advice because these people are too ballsy. They already know what they’re going to do, and they just need to summon the inner resources; outside ideas just throw them off their focus.


What makes people take drastic action?

As I wrote in Bullish Life: Breaking Free from Terrible Situations, people who are mired in painfully stagnant and mediocre situations are less likely to break free than people for whom the suffering has become acute and unbearable. If Jesse were really sweet and well-meaning but just hapless, it would be much harder to break free. (“I don’t know why I keep getting fired, but I will happily give you my last crust of bread!” ARGH.) But he sounds like an asshole (at least the way you tell it).

So, if this guy’s really as bad as you make him out to be, well … great. That’s good motivation.

BUT SERIOUSLY: Another reason people take drastic action is so they can surprise everyone, turn their lives around, take credit, and go from being deep in a hole to being REALLY IMPRESSIVE ALL OF THE SUDDEN.

So, if you push too hard, you kind of take that away from Gloria.

When my company failed, I sold off my few possessions and fled to NYC, alone, with $400 and a beat-up car, which was then stolen. It took longer than I thought it would to get back to what I consider successful. However, back then, I also thought 30 would be way too late to consider myself successful. It isn’t. You’re going to get older no matter what — and when you’re older, you’ll still feel like you, not some other, mysterious future-person — so you might as well start setting up your future self for success ASAP, even if you feel like you’re getting started (or starting over) a bit late.

In any case, my first years in New York were very difficult. I didn’t have an impressive career, or even any career, exactly. But people were certainly impressed that I had failed, and then moved to the city with no friends or contacts, and virtually no money. No one could take that from me. The move itself was a sort of character calling card.

I wish Gloria well! If I were her, I’d probably be full of all kinds of ideas I wouldn’t share with anyone, because big, crazy, scary, ambitious ideas are fragile — at one moment, they seem glorious, and at another, they deflate and seem foolish. So, the right move is probably to stand back and watch for a bit.

As for everyone else wondering whether to walk away from something terrible — plot out where you want to be in 5 or 10 years. If there’s no logical path from where you are now to where you want to be, you have no business staying. If you leave behind everyone you’ve ever known to go do something better, trust me: when you get where you’re going, you’ll meet more people just like you.

How do you know when it’s time to (figuratively) blow up your problems and walk away? Find out onThe Gloss!
As first published by Alloy Digital, LLC (www.thegloss.com)


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