All Career Advice Is Bad Advice

Introduction

You don’t want to take advice from 99.9% of people on careers, because you should do everything you can to be the exception.

Fight for it with your life.

If you’re reading this, you’re at least ambitious enough to care, and so, this might sound familiar to you.

Three years into the job and you’ve hit your targets. You’ve done the work, and yet, when you look around, you realize you’re more or less where you were. Perhaps the title changed slightly. But you’re not a superstar.

No, it’s worst, you’re not even noticed.

You’re not alone, most people spend their careers feeling vaguely stuck while following advice from people who took two decades to reach positions they could have reached in five.

Those advice always sound reasonable. Be patient. Build relationships. Do great work and you’ll be recognized.

It’s almost entirely useless.

I’ve crawled and I’ve flew and I can now definitely say that as a consistent winner, there is a simply play to guarantee flight.

The Two Levers You Control

Your career comes down to two things you can actually influence: your environment and your output.

Your environment is the the organization you’re in, the people around you, and the work you have exposure to. Your output is the work you produce and the words you say.

Everything else is outside your control.

Most career advice focuses obsessively on output. Work harder. Communicate better. Develop expertise.

Here’s the problem: exceptional output in the wrong environment is like being the hottest woman in a room full of gay men. They can admire it but they ain’t gonna do anything about it.

I’ve watched brilliant people grind away for years in organizations that simply could not reward them but because the structure (and people) made meaningful progression impossible.

Environment is the multiplier. Output is the thing being multiplied. If you get the environment wrong, nothing else matters enough!

Finding the Hypergrowth Environment

Every “wunderkind” I’ve ever talked to, every person who’ve ran a division or hit the C-Suite (in a large company) by 35, including myself, was in a specific type of environment that made climbing possible. And I’ve distilled that environment into recognizable characteristics you can screen for.

You need to look for two things to be true simultaneously.

First, there must be someone at the top who is genuinely ambitious and is looking for someone to bring about large change to the organization. Someone who actually wants to transform something, build something, disrupt something. Someone who wakes up thinking about how to make a real dent in the status quo.

This can be the CEO who is in “crisis mode” or is looking to “pivot” their primary businesses or build something “cutting edge” in a large company; or even the myriad of entrepreneurs who are looking to build out their businesses.

Second, there must be chaos. Actual change happening or about to happen. A new market being entered. A competitor being fought. A business being restructured. A product being reinvented. A platform being built.

If either element is missing, you’re stuck. A calm, stable organization with an ambitious leader will frustrate you both. An ambitious leader without chaos has nothing to promote you into. And a chaotic organization with an unambitious leader is just hell in disguise.

Why an ambitious leader is important: Non-ambitious people cannot understand, and therefore, cannot reward ambitious people. Try telling someone who took 20 years to become a director that you want to get his job in 3 years.

They literally don’t understand what they’re looking at. They see your drive and it makes them uncomfortable. They see your desire to move fast and they interpret it as impatience or entitlement. They have no mental model for what you’re trying to do because they’ve never wanted it themselves.

What you want instead is to tell the CEO that started the company when he was 30 that you want to run your own show at 30. He will get it, and because he will get it, the only thing left is to evaluate if you’ve got the chops. You cannot convince an unambitious leader to reward ambition. You can only find a leader who already values it.

Why you need an environment full of change: Chaos, messy as it is, creates the openings. When everything is stable, every role is filled, every territory is claimed, every process is locked down. Nobody needs someone to come in and figure things out.

However, when the ground is shifting, when the old approaches are failing, when the organization desperately needs someone to grab an ambiguous problem and just solve it, suddenly there’s room. Chaos is the father of progress. There’s no white space for you to assert your will and ability in a stable hierarchy.

Making Yourself Known

Once you’ve found the right environment, you need to get noticed by the right person.

Most people are terrible at this. They assume their work will speak for itself. It won’t. There is no such thing as an invisible top performer.

Or they network broadly, trying to be liked by everyone. This is a waste of time. You’re not here to be the life of the party.

You only need to be liked by one person - YOUR SPONSOR.

THE KING MAKER.

You need to go to whoever is running things and make it unmistakably clear that you are ambitious, that you are capable, and that you are ready to make change happen.

I know this sounds uncomfortable. It is uncomfortable. Most people can’t do it because they’re terrified of seeming presumptuous or arrogant. But ambitious leaders want to know who are the ambitious people WHEN THEY NEED TO HERALD CHANGE. The reason is simple: they understand as exceptionalists themselves that the average, normal person will not have the iron in him to bring about change of epic proportions. To bring a hard project to life. To discipline a failing division into a winning one.

They’re already scanning the organization for anyone who shows the hunger they recognize in themselves. So, you just need to make yourself visible to the one person who can actually move you forward.

Ambitious people are drawn to ambitious people. If you can communicate that you see the big picture, that you understand what they’re trying to build, that you want to be part of making it happen, you’ve already separated yourself from 99% of the organization.

I also have a (open) secret for you. People at the top are lonely. If you’ve ever worn the big boy pants even once in your life, you know this in your bones.

People at the top are constantly surrounded by people, and are very busy, but they are also incredibly lonely.

The reason is simple: No one around knows the weight of bending reality to their will and shouldering the responsibility of command. These leaders can’t bitch about how they feel to anyone, because a lack of confidence from the top makes for a shaky boat.

If you can show up and appreciate their work and show that you too, can shoulder command, you may not only get noticed, but find yourself a friend.

The Political Reality

People get squeamish being political, but I’m going to tell you anyway because pretending otherwise doesn’t help.

You have no power. You’re starting from nothing. To get power, you need to be granted power by someone who already has it. This is literally THE game, and there’s no opting out if you are ambitious.

You need a sponsor. Not a mentor who offers advice, a sponsor who actively advocates for you when you’re not in the room, who assigns you to visible projects, who promotes you into bigger roles.

And sponsors don’t become sponsors just because you’re talented. Remember, that they are talented, ambitious and powerful. To continue being ambitious and powerful, they need allies too, and need to believe you will be loyal to them as they help you rise.

Think about it from their perspective. They’re taking a risk on you and spending political capital to move you to the places you want to go. More than that, they’re attaching their reputation to your success. They need to believe that you’re on their team. That your success is intertwined with their success.

That when you gain power, they gain a powerful and formidable ally, not a competitor.

This isn’t cynical. This is how humans work. Everyone needs people they can count on. The person at the top is no different. When you prove that you’re in it with them, that you’ll work like a zealot for their vision, that you’ll be loyal when things get hard, you become someone worth investing in.

I’m not saying to be sycophantic. That’s transparent and off-putting. I’m saying to genuinely align yourself with what they’re trying to accomplish. Make their priorities your priorities. Make their wins your wins. Be the person they can trust absolutely.

Working Like Your Career Depends On It

Now comes the part nobody wants to hear.

You have to work. Not normal amounts. Not “sustainable” amounts. Not whatever your peers are doing. You have to work with an intensity that matches your ambition.

Think about how long a reasonable person would take to complete a task. If the answer is a day, finish it in an hour. If the answer is a week, finish it in two days. Sacrifice sleep, sacrifice weekends, sacrifice whatever you need to sacrifice in the short term.

You are building a reputation, and the reputation you want is “unreasonably effective.”

This sounds brutal, and it is. But here’s why it’s worth it: reputations are sticky. Once people believe you have an ungodly work ethic, that’s how they interpret everything you do going forward. When you eventually slow down, they don’t think “this person is slacking.” They think “this task must be genuinely hard if even they can’t knock it out in two days.”

The opposite is also true. If you establish yourself as someone who works at a normal pace, that’s how you’ll be seen forever. That’s how you become invisible.

This reputation compounds. Early intensity buys you permanent credibility. It changes how your work is perceived, how your opinions are weighted, how your potential is evaluated. The more you reinforce this, the more you become a legend.

When to Walk Away

And here’s the most controversial part that everyone gets wrong. You are going to need to leave, and you are likely going to need to do it often.

You might need to change 3 jobs in 3 years, and that’s perfectly okay. There is ALWAYS a job for someone with high agency.

Sometimes the person at the top isn’t as ambitious as you thought he was, or that he just isn’t taking to you. Maybe you didn’t convey your ambition clearly enough. You hedged. You minced words. You were afraid of seeming too aggressive, so you came across as just another reliable person. You didn’t commit to the bit that you are genuinely exceptional. Or it could simply be that they’re not receptive to you specifically, for whatever reason. Chemistry matters, and sometimes it’s just not there.

Or maybe you didn’t convey your loyalty clearly enough. The person at the top didn’t trust that you were on their side. They saw your ambition as potential competition rather than potential alliance.

Sometimes you might have misjudged how much “white space” is available in an environment for you to stretch into. Or maybe your read on the person in charge was wrong from the start. They’re less ambitious than they appeared. That big change isn’t coming.

If any of these are true, staying longer won’t fix it. You will not convince someone to see you differently after they’ve already formed an opinion. You will not create chaos in an organization that wants stability. You will not make an unambitious leader suddenly hungry.

Leave. Find the next environment. Try again with what you’ve learned.

The Real Timeline

You absolutely do not need twenty years to reach the top. Every organization has someone in their late twenties or early thirties near the C-suite, someone who got there impossibly fast by conventional standards.

They’re not geniuses, they’re mostly people who found the right environment, made themselves visible to the right person, proved themselves invaluable, and worked with the intensity the situation demanded. I would know, I was that person.

You could be too.

This is the career advice that matters.