Hello Readers, throwaway because some of these people are still in my professional network and I’m not taking chances. I’ve been out of that job for five months now, and the sting has dulled to a constant ache instead of a sharp pain. One “casual joke” during a team offsite in September 2025 revealed that my closest work friend—the person I’d trusted with my career, my insecurities, my dreams—had been quietly betraying me for over a year. It wasn’t theft or sabotage in the obvious sense. It was subtler, more insidious, and it made me question every relationship I’d ever had at work. That joke didn’t just end a friendship. It ended the version of me who believed work could be a second family.
I’m 33F, former director of client strategy at a boutique digital agency in Portland. I’d been there eight years—joined at 25 as a mid-level strategist, poured everything into it. Late nights, weekend revisions, mentoring juniors, taking the fall for team mistakes. By 2025 I was leading our three largest accounts, consistently top performer, the one the partners called when a client was about to churn. Good salary, stock options, the kind of role that felt like a career pinnacle. I was proud. Maybe too proud.
My “friend” was “Claire,” 34F, creative director. We started around the same time, bonded instantly over shared ambition and frustration with the old guard. We became work soulmates: daily coffee runs, happy hours that turned into therapy sessions, group trips where we roomed together, crisis Slacks at midnight. She knew everything: my imposter syndrome, my fertility issues (trying for a baby, two early miscarriages), my fear of burning out. I knew hers: pressure as the only female CD, feeling overlooked for partner track, resentment toward her stay-at-home husband. We covered for each other, hyped each other in meetings, cried in the bathroom together after tough reviews. When I got promoted to director last year, she was the first person I told—she brought champagne to my desk. I thought we were ride-or-die.
The offsite was September 11–13, 2025—a “team reset” at a lodge outside the city. 25 of us, trust falls, strategy sessions, bonfires. Classic agency bonding.
The joke happened on the second night.
We were around the fire pit, drinks flowing, playing that dumb game “two truths and a lie.” Lighthearted, silly.
Claire’s turn.
She grinned, tipsy: “Okay: one, I once backpacked Europe alone for three months. Two, I turned down a job at Nike because the offer was too low. Three, I’ve been secretly pitching our biggest client’s competitor behind Alex’s back.”
Everyone laughed—loud, drunk laughs.
I laughed too, at first. “Good one—the competitor thing is obviously the lie.”
Claire kept smiling, but her eyes flicked to me.
The group moved on.
But I felt cold.
Our biggest client—global outdoor brand—was my baby. I’d landed them three years ago, nurtured the relationship, led every renewal.
Pitching their direct competitor would be a massive conflict.
Later, by the fire dying down, I pulled Claire aside.
“That last one—was it really a lie?”
She laughed, hugged me. “Of course! You know I’d never do that to you.”
I wanted to believe her.
But something in her voice…
Monday back at work, I couldn’t shake it.
I did something I’m not proud of: checked the shared drive access logs (I had admin rights for my accounts).
Claire had downloaded the full client folder—decks, budgets, strategy docs—for the competitor’s category.
Multiple times.
Starting six months ago.
I confronted her in the parking lot after work.
“Claire… the competitor thing. It wasn’t a lie, was it?”
She went pale.
“Alex… I can explain.”
She’d been freelancing on the side for extra money—husband’s job loss, IVF costs. The competitor approached her through a connection. Small projects at first. Then bigger.
She swore she never used our client’s proprietary data—just “inspired by” our approach.
But she’d pitched them our renewal ideas—repackaged.
They’d won a piece of business we’d lost last quarter.
I felt sick.
“Why didn’t you tell me?”
She cried. “I was ashamed. And scared you’d be mad. You’re so… perfect at your job. I felt like I was failing.”
I asked if she’d told anyone else.
She hesitated.
“David knows.” (Our managing partner.)
He’d encouraged it—“moonlighting is fine as long as it doesn’t conflict.”
But it did.
I went to David.
He sighed: “It’s gray area. She didn’t use confidential info directly. We can’t fire her over freelance.”
I asked why he didn’t tell me.
“Conflict of interest for me too—I referred her.”
I felt betrayed by both.
The office turned toxic.
Claire avoided me.
People who’d heard the joke now knew it wasn’t a joke.
Whispers: “Alex is being dramatic.” “It’s just business.”
I stopped happy hours. Kept to my desk.
Client noticed tension—started pulling work.
By October, I was burned out.
Job hunted.
Landed director role at a bigger agency—higher title, better pay.
Gave notice October 31.
Claire cried in the bathroom: “I’m so sorry. I lost my best friend over money.”
I said, “You didn’t lose me over money. You lost me over lies.”
David: “We hate to see you go. You’re irreplaceable.”
I didn’t laugh.
New job is great—ethical, transparent, real mentorship.
Claire texted once: “I quit too. Couldn’t stay after what I did.”
I didn’t reply.
A casual joke at work revealed who was betraying me.
It wasn’t just Claire.
It was the culture that let it happen—and called it “gray area.”
I’m not naive anymore.
Work friends are work friends.
Trust is earned—and guarded.
I miss the friendship I thought we had.
But I don’t miss the person who valued ambition over loyalty.
Thanks for reading.
I needed to tell this somewhere.
