Non-Patronizing Advice for Gen Zs Who Want to Make More Money

Part 1: Playing the invisible game

At Christmas I reconnected with a cousin who is 23 and stuck in a low-paying dead-end job doing customer service at an ecommerce company that sells lotions for babies or something.

This job was a godsend when she got it, because she’d spent the prior 9 months depressed, applying everywhere she could and student debt bills for “business administration” degrees don’t pay themselves.

But even though the job wasn’t bad, it wasn’t going anywhere. She could feel it and wasn’t sure what to do. She told me a better role had opened up in a different department and she wanted it badly but she really wasn’t qualified. Before she could talk herself into applying anyway, the posting came down.

Oh well, back to fielding unhinged complaints from incoherent middle aged white women who thought they ordered 2 bottles but got them in separate packages and so wanted a freebie.

It was Chistmas though, so I told her as a gift I’d help her get the job. She laughed, because I am known in my family for being hilarious.

I wasn’t joking. Recently, I am on a holy crusade to help interesting people make more money because I’ve decided that’s good and apparently, I’m good at it.

A month later, after a few conversations and a competently written letter to the midwits in charge of hiring, she had the job, with a tidy raise in a job much less likely to be automated away in 6 months.

An invisible game

She told me afterwards that nobody had ever walked her through any of what we’d talked about. She’d been working since she was 18 and the entire game was invisible to her.

I get the sense that this is common. Young people get trash advice about anything to do with jobs, economy, etc. Their parents’ advice is terminally outdated. The internet is trying to sell you a $997 course on garbage side hustles. And everyone else is too busy managing their own quiet panic about AI, recession, whatever, to give a single fuck.

Meanwhile, as is obvious to everyone, the economy itself really has done Gen Z’s dirty. I don’t need to belabor this because the stats are out there. The math of starting a career doesn’t math like it used to.

So the economy is broken for young people, sure, but they have to figure it out anyway.

Ultimately, the advice I gave her was just a grab-bag of practical tactics that apply to many situations, drawn from my experience mostly failing to start companies, selling things and helping people sell things, and negotiating my way through various sectors and jobs.

So, this is the first piece in a series I’m writing, specifically for the youth, about how to actually make more money, get ahead, and make it through this shitstorm.

This first piece is about how to play the invisible game when you’re already inside a company, get your manager’s job, and do it all while “acting your wage”.

Lfg fam. (sorry I couldn’t resist)

Nobody wants to do work, and you can use this to your advantage

The single most useful career skill I’ve ever developed is figuring out what the person across from me actually wants. Not the corporate-approved nonsense they say they want in meetings. Once you know what they’re actually stressed about, actually measured on, actually afraid of, actually motivated by, everything else is simple.

If you help them get what they want, you become the person they can’t do without.

Everybody at every level of every organization is mostly consumed with their own problems, while trying to do as little work as possible. This is great news, because it means the bar for standing out is comically low.

When my cousin and I wrote that letter, we didn’t write about what she wanted. We spent most of our time figuring out what the people reading it cared about. We talked through the owners’ priorities, what the hiring manager’s team looked like, what problems they had that weren’t in the job description. Then we wrote a letter that made hiring her look like an obvious solution to their problems.

It worked because it was aimed correctly at their weak point: they really did not want to have to deal with hiring and training someone new while whats-her-name went on maternity leave.

You can imagine them reading that letter and thinking: “Fuck, well, this person over in customer service doesn’t really have the qualifications but hiring her anyways would save me some headache” before reopening a tab with 5000 Ai-generated resumes they have to click through.

This applies to literally every professional interaction you will ever have. If you have really thought about what the most important person every room is trying to accomplish, and how you might help them get it, you have a crazy advantage because literally no one else even tried.

Be the most prepared person in the room (this is actually so easy)

Five minutes of preparation before a meeting makes you the most prepared person in the room. Which, to be clear, is a laughably easy title to hold. Many people walk into meetings having thought about the topic for approximately zero seconds. They’re reacting in real time. You, having spent five whole minutes preparing, will seem like you have preternatural insight into the situation. It’s fine if you don’t. You just did the bare minimum thing needed to stand out.

I cannot overstate how much of a multiplier this is. Just giving slightly more of a shit than the next person about what’s actually going on, and casually mentioning “when I prepared for this meeting”, makes most people notice and feel like you’re making a big effort.

Make your work visible or it doesn’t exist

There’s this belief, especially among people who are actually good at their jobs, that your work speaks for itself. It does not.

Nobody is going to notice that you quietly solved a problem, streamlined a process, or saved a teammate three hours a week unless you tell them. And I don’t mean in a cringy, self-promotional way. I mean in a “hey, I finished that thing, here’s what I found” way. A very small update email. A quick message in the team channel. A one-liner in your next 1:1.

The people who get promoted are often not the people who do the best work. They are, with unsettling consistency, the people whose work is most visible to the person making the promotion decision. This is annoying if you’re someone who does great work quietly. It is also just how it works and you should stop being annoyed about it and start sending update emails because they are probably higher ROI than your actual todo.

Do things fast

Related: do things fast. Speed is a reputation hack that almost nobody talks about. When someone asks you for something and you get it back to them in two hours instead of two days, it creates a wildly disproportionate impression of competence. The work doesn’t have to be perfect. It has to be fast and just good enough and visible. People are often slow mostly because they overthink it, they context-switch, they put it off. Being the person who just does the thing quickly is, in my experience, worth more than being the person who does the thing perfectly three days later.

Keep track of your achievements

For the love of god, log your achievements. Keep a running document. Date, what you did, what the outcome people cared about was. At some point, you will be called into a pathetically poorly-organized performance review run by a middle manager who literally could not care less about your performance.

Saying “I feel like I’ve been doing a good job” or even improvising a reasonably good set of arguments is 10x less useful than coming in with twelve specific things you achieved and why they mattered.

If you’re want to successfully negotiate hard on salary, you gotta out-prepare the person trying to argue for why your salary shouldn’t go up. If you’re more prepared than the interviewer, it’s easy to win the interview.

The letter we wrote for my cousin worked because we had receipts. We could point to specific things she’d done and map them to specific things the specific people involved cared about.

She actually didn’t have a list, and I had to grill her for an hour about everything she “sort of” remembered achieving and tell her why the hiring manager probably cared about it in the first place. But if you don’t have a money-saint in your corner willing to do some thinking for you, it’s on you. Without this, the letter would have been vibes.

Vibes don’t get you 38% raises in 30 days.

Be likeable as if your fucking life depends on it

On the topic of vibes, I should be clear that vibes DO matter. They really matter.

As an odious and dislikable jag, I hate to admit this, but the people who get ahead are, overwhelmingly, people that other people like being around.

You don’t have to be the life of the party. You don’t even have to be particularly charismatic, funny, or charming. But you do have to be noticeably pleasant. This should be easy but giving your manager, who is emailing you after hours because they’re worried about getting fired, a professional but curt update on your work life boundaries is a morally right, but strategically idiotic move.

To be clear: you can and should say no, set boundaries, give feedback. But you can do that while still being likeable.

This is not a personality trait. I don’t want you to read “be likeable” and think it means “be someone you’re not” or “be fake” or “be an extrovert.”

It doesn’t. It means making a series of small, boring, repeatable choices every day that make the people around you feel like working with you is easy rather than hard. This is not a young people thing either. In every professional situation I’ve ever been in, I have been shocked at how rare the little things are.

The bar, as always, is on the floor.

When decisions are made about who gets the promotion, the project, the raise, the opportunity, those decisions are made by people, in rooms, about other people. And when two candidates are roughly equal on paper, which they almost always are, because both their resumes were written by AIs, the tiebreaker is always “who do I want to hang out with more?”

Your boss is not going to go to bat for you if they find you even a little annoying. They’re just not. They might respect your work, they might know you’re technically the best person for the role, and they will still advocate for the person who is 80% as good but who they enjoy talking to. This is deeply unfair and completely universal and you should plan for it because it’s not going away anytime soon.

Also, for what it’s worth, this gets MORE true the higher up you get. People at the top tend to be likeable, at minimum to the people who affect their goals, for a good reason.

Likeability compounds in a way that almost nothing else does. Every easy interaction, every small moment where you made someone’s day slightly less annoying, every time you were the person who didn’t create a problem when you could have adds up. That reputation enters rooms before you do.

This is the thing that makes your eventual ask, be it for promotion or salary or whatever feel like a formality rather than a negotiation. People want to say yes to people they like.

My cousin is, for the record, extremely likeable. I don’t think the letter works without that. You can have the best-aimed, most tactically brilliant ask in the world and it will bounce right off if the person reading it thinks you’re a pain in the ass. The letter got her in the door. Being someone people actually wanted to talk to every day is what closed the deal.

Becoming a person that’s annoying to lose

There’s a thing in companies that nobody talks about openly but everyone instinctively understands, which is that some people are load-bearing and some people are decorative. Load-bearing people, if they left tomorrow, would cause real, visible problems. Decorative people could vanish and things would basically be fine within a week.

Because no one actually wants to do work, being load bearing makes you untouchable.

The fastest way to do this is to pick one specific thing that no one wants to do and become the person everybody comes to for it. Become the go-to for something useful and visible even if it’s small. DO NOT become the the go-to for invisible things unless you can make them visible.

Once you’re the go-to for something visible, you have leverage whether anyone acknowledges it or not. Your name comes up in rooms you’re not in. People route decisions through you. And when it’s time for raises or promotions, the calculation shifts from “does this person deserve it” to “what happens if we lose them.”

I have hired and fired lots of people. If you are asking “what happens if we lose them”, it means you’re going to try to avoid losing them if possible.

That’s a much better calculation to be on the right side of.

Ask for things

This is the part that ties everything else together, and it’s the easiest to skip.

You can be prepared, fast, visible, load-bearing, and liked by everyone in the building. And none of it converts to money unless you ask. Organizations do not simply hand out opportunities, raises and promotions to people who deserve them. They hand them out to people who ask for them and make the ask easy to say yes to.

It’s often easy not to ask, or to feel like you can only ask for something obviously on offer. It might feel risky. It might feel like if you were really going to get it, someone would just offer. This is completely wrong, of course. I have never once, across many companies, seen someone get a raise just because they deserved it. I have seen it happen many times because they asked.

The mechanics of asking well are not complicated. Frame it around their goals, not yours. “I want to take on X because I know the team needs to hit Y” lands differently than “I feel like I deserve more”, or god forbid “living costs have increased”. Have your receipts ready. This is why you’ve been logging your achievements. Be specific about what you’re asking for.

Also, look for opportunities to ask for things that are not on offer. Technically, speaking, my cousins new position was no longer accepting applicants. You can construct asks that further your interests (and again, tell a story about how it furthers the interests of the other party) probably more often than you’d expect.

And if you can, make your ask low-pressure. You can ask for a lot without making it feel like a random if you’re clever. My cousin’s letter worked partly because we told them she wouldn’t be heartbroken if it didn’t happen. She just wanted to put it out there. In the letter, we even floated the idea of doing a “work trial” to let the company see if it’s a good fit.

Counterintuitively, in some cases when you make an ask easy to say no to, you make it much easier to say yes to. People freeze up when they feel cornered by someone else’s expectations.

Everything in this piece from preparation, to speed, to visibility, the receipts, the relationship-building, it’s all infrastructure for the moment when you open your mouth and ask for the thing you want. You’re building up ammunition before you know what you’re going to use it for. And when the moment comes, you want the answer to feel obvious, not generous.

Let’s make some money

That’s the invisible game. Or at least the part of the game that’s played inside the building you’re already standing in. Many people will go their entire careers without playing it on purpose, or just get mad about it being unfair.

But it’s more fun to win a game than be stuck at a table you hate.

None of it is rocket science. Model what people want. Prepare more than everyone else, which is to say, prepare at all. Be fast. Make sure the right people see you doing stuff. Keep receipts. Be easy to work with. Pick a thing and own it. And when you’ve built the case, ask for the thing well.

Go forth and make some money.