Fuel from Mary Carns and Halftank Studio
The situation
I was halfway through a sales presentation for an international client when I knew it was time to go. The new VP of sales kept cutting in while I walked through the solution architecture. He told the client how much he wanted their business and how he’d work the pricing in their favor. We lost the deal to a boutique firm that talked about its experience and didn’t budge on price.
By then I’d been at that firm for over two years. It had changed owners, and a culture built on mutual support had turned into squeezing every dollar. Every contract I helped pitch got lowballed out of the same desperation.
I saw every red flag, and I stayed anyway.
What I missed
Every December, I tax-loss harvest. I sell my losers. At work, I kept the losers around.
Investors learn the sunk cost fallacy the hard way: you hold a falling stock because selling would make the loss real. I was doing the same thing with my career. I counted the years, the late nights and the reputation I’d built. Every one of those was a cost already paid, and none of them could tell me whether next year would be worth it.
A bad job is worse than a bad stock. A losing stock just sits there. A bad job is like a stock that charges you a monthly fee to keep holding it, paid in sleep, energy and the ideas you stop offering. Over time, it wrecked my confidence. I started to believe that maybe I was one of the losers too.
The part that stings
The company never had a sunk cost problem with me. When I wasn’t billable, they paid me severance to cut their loss and sent me packing. I was holding on out of loyalty. They were trading on the numbers.
I’m not alone. In Monster’s 2026 workplace mental health report, 71% of U.S. workers said they had stayed in a job they knew was toxic (source link: Monster).
The better test
Investors ask: has the reason I bought this changed? When the thesis breaks, you sell, no matter what you paid. And selling doesn’t have to mean dumping everything at once. Investors trim. In a career, trimming might mean freelance or fractional work alongside your job, or a small client base you build before you need it.
This week’s leadership question
Who on your team is holding on out of loyalty while the company trades on the numbers, and would they still choose this job today?
Read the full essay on Medium: friend link​
I’m not a financial advisor, and nothing here is financial advice. It’s what happened to me.
P.S. Bad Fit tells the full story of how I finally got out of my own way. Buy Bad Fit here.
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