How to Lose a Job in 11 Days (An Intro)
Introducing a series on employment fundamentals that have always mattered — and still do
In early 2025, I terminated a contractor after 11 days.
Strong resume, relevant experience, references that checked out.
None of it mattered though, because within less than two weeks he had demonstrated every quality that makes someone impossible to keep: he ignored context, disregarded process, and violated a core business boundary.
Story Time:
It's not a particularly complicated rule. Nobody sends an email on my behalf without my eyes on it first. During training, new operations hires practice by drafting messages for my review, which is how they learn the voice, the context, the relationships.
That is the process.
One morning I opened my laptop to find that a message had already gone out. Sent. To my number one client.
The email began with "I hOpE yOU aRe DoInG wElL tOdAy!" It then offered two sentences that had almost nothing to do with the thread they were responding to, except to echo back a few of the client's own words as if repetition were the same thing as engagement.
I immediately ended the contract.
He left me a review on Upwork. How could I know if he was any good at the work?? We had only worked together for eleven days.
Let me ask you: how much time does it take to underwhelm?
The failures weren't products of AI, remote work, or a changing economy. They were the same ones that have ended careers for decades: poor judgment, weak output, no regard for professional boundaries.
The fundamentals that make someone worth keeping have not changed.
And that's what this series is about.
The labor market has been through a significant reset. Since 2022, mass layoffs across tech, media, and professional services have pushed a large volume of experienced workers into the job market at the same time. Some of those workers have moved into contract and freelance arrangements out of necessity. Others are competing for a shrinking pool of traditional employment at a moment when hiring managers are raising the bar, scrutinizing output more closely, and carrying less patience for ramp-up time than they did even five years ago.
That pressure is real.
This series is going to work backwards from the best practices in business management — the ones that have survived every era of workplace disruption — and show you what termination looks like when you do the opposite. Each post takes one principle, inverts it, and traces out the damage. Some of the scenarios are drawn from real situations. All of them are patterns.
Before we get into it, one distinction needs to be established: contractor or employee? The answer shapes everything about how you're evaluated, how much time you have, and which mistakes are survivable.
If you hold a traditional employment role, you have more runway. Culture fit, coachability, and trajectory carry real weight alongside your output. You're expected to absorb feedback, build relationships, and demonstrate growth over time. That grace period is legitimate. It is not, however, unlimited, and "I'm still learning" stops being a full answer sooner than most people expect.
If you're a contractor, there is no honeymoon period. You were hired because something needed to get done, and the working assumption is that you already know how to do it. You're evaluated on output, responsiveness, and your ability to work within someone else's systems without creating more friction than you solve. The resume that got you the contract is not the thing that keeps it.
Some posts in this series will end with specific takeaways for each group. Look for these at the bottom:
💼 For traditional employees
⚒️ For contractors
The fundamentals apply to everyone. The stakes just look different depending on where you're sitting.