That boss you can't stand
They aren't a bad person. They're a warning shot. A survival guide for staying good at what you do.
This article is part of The Unseen, our work on decoding the systems and incentives that shape markets and opportunities.
We need to talk about your boss.
You know the one. The guy who was a legend in his last role, a star performer, a brilliant closer, a technical genius.
And now, as a manager? It's painful to watch. His meetings wander. His feedback is useless. His grand strategic decisions make you wonder if he’s reading the right PowerPoint deck. You and your friends complain about him over beers.
But I'm going to let you in on a secret.
Your boss isn't the problem. He's a symptom. A ghost of a future you are actively, and unknowingly, working towards. He is a warning.
He is a victim of a trap that is set for every single high-performer in a traditional company. It's a flaw in the system so perfect, so elegantly cruel, it has a name: the Peter Principle.
The principle is simple: companies reward you for being great at your job by promoting you to a different one. This continues until you land in a role where your brilliance no longer applies.
And there you stay. Stuck.
Slowly transforming from a confident expert into a miserable, ineffective manager. You don't get fired, of course. You just become part of the architecture.
A load-bearing column of mediocrity.
And if you think I'm just dusting off some 1960s management theory, you haven't been paying attention. We just watched this play out on the world stage.
At Apple's 2025 WWDC, the entire tech world expected a revolution in AI. Instead, we got… some very pretty UI updates. (The Liquid Glass does look cool, I'll give them that.) But the question whispered in every group chat was the same: How could Apple be so late?
The insider story points to a tragedy we all should recognize. Apple's head of AI, John Giannandrea, a world-class technologist poached from Google back in 18, was promoted into a political labyrinth. A master of the technology, his new role required a mastery of bureaucracy. Now, there are whispers he might be on his way out.
This is the Peter Principle in Cupertino. A world-class player is made the coach, only to find he’s playing an entirely different sport.
This small, personal failure, when repeated across a company, unleashes a virus. The newly incompetent manager, desperate to feel important, makes a bad call. Then, to protect themselves, they hire people who won't challenge them. People less competent than they are. Not out of malice. Out of fear.
This is how good teams die. A cascade of mediocrity, all because we believe the only way up is the management track.
But you don't have to play that game.
The Escape Route
Smart companies, the ones that are actually building things of value, are realizing they need two different ladders. You need to know what they look like so you can demand one for yourself.
The system requires two parallel, equally prestigious, and equally compensated tracks.
🔳 The Player Track (The Expert): For those who excel at the craft itself. Their success is measured by the quality and impact of their work. They are the master artisans, the genius coders, the visionary strategists.
🔳 The Coach Track (The Manager): For those who excel at leading people. Their success is measured by the growth and output of their team. They are the talent-magnets, the obstacle-removers, the vision-amplifiers.
In this world, a Principal Engineer (a top-tier Player) can and should earn more than a first-line Engineering Manager. It creates a path for your best talent to gain status and compensation, without forcing them to abandon the work they love and are brilliant at.
Happy geniuses, it turns out, build wildly profitable things.
I saw this firsthand at a gaming company I worked with in China. Their lead character artist, a 'Player,' was one of the highest-paid people in the studio, out-earning most directors. They knew her genius was in her hands, not in a conference room approving budgets. They protected her craft like a strategic asset.
Making It Safe to Choose Wrong
Even with two tracks, we can end up on the wrong one. The best systems build in escape hatches.
Ladders Need Nets: At companies like Huawei, a promotion isn't a life sentence. Their famous "up-or-down" culture means you can be moved to a different, sometimes "lower," role to learn new skills. It reframes "demotion" as "redeployment," killing the stigma and building a more resilient organization.
The Test Drive: Other smart companies fund experimental, low-stakes projects. This lets a star engineer "test drive" a management role for a few months. If they hate it, or they're bad at it, they can slide back to their Player track without mess up their career. You wouldn’t buy a car without a test drive. Why do we do it with our careers?
How to Have "The Talk"
The next time you're in a performance review and the vague topic of "your future" comes up, you can stop thinking in terms of "promotion." You can start thinking in terms of your path.
You're armed with a new vocabulary.
You can ask the questions that reveal whether you're in a company building the future, or one stuck in the past.
🔳 Your Script:
"I love my craft. What does the senior 'Player' track look like here? How high can an individual contributor go, in both influence and compensation?"
"Is there a 'test drive' option? A way I can try on a leadership role for a small project before committing to a full track change?"
"What’s the philosophy on moving between the 'Player' and 'Coach' tracks here? How fluid is it if someone finds they’re a better fit for the other path?"
Your boss's answers, or lack thereof, will tell you everything you need to know.
So now, look at your boss again.
See the person, not the title. See the star performer who probably took the only path that was offered to them. The expert who was handed a different job and told it was a reward.
Forgive them.
And then go make damn sure you don't become them.
🔳 About That Other Trap…
My promise is to show up in your inbox once a week, but my real goal is to give you the full picture.
Because spotting the trap of the incompetent boss is a crucial step, but it doesn't solve the next problem: the internal traps set by our own competence and the myth of passion.
So, I’ve written two extra posts this week that I wanted you to have. They're the rest of the toolkit, a practical guide for building your own momentum when the map disappears and the motivation runs dry.
Consider it a bonus for the journey. On the house.
Passion is a terrible co-founder
Your feelings won't save you. Your system will.
A short guide to getting your own momentum when motivation runs out.
Congrats, you know too much to succeed
For the seasoned professional who's tired of planning, let's talk about the art of driving in the dark.
Hi!
I'm Yuehan. After a decade spent building businesses in both the West and China, I'm sharing my most valuable, road-tested lessons right here on Substack.
Since I'm starting from scratch on this side of the world, your support means a great deal. If this piece resonated, a restack or a simple ❤️ is massively appreciated.
