I've taken 4 pay cuts in my career.
Each one made me richer.
Not immediately. Not on paper. And definitely not in the eyes of my family or friends, who thought I'd lost my mind - especially the time I left a fat commission check to join a company that was perceived to be illegal in Brazil back then (Uber).
But every single one of those "stupid" decisions compounded into the solid business we have now.
I've spent 13+ years recruiting. I've watched thousands of careers play out from the inside - at Uber, Nubank, Noom, AI labs, tier-1 funds. I've hired C-level executives, 100x engineers, and first employees for companies that became giants. I've also watched brilliant people with perfect resumes stall out at 35 and never understand why.
Here's what I'm now convinced of:
Most smart people are playing the career game wrong.
They optimize for salary. Title. Promotion. Brand. Remote work. The next job.
That's how you build a safe career.
Not an exceptional one.
The difference between the two isn't talent. It isn't luck. It isn't even hard work — the stalled-out people sometimes work hard too.
It's the decision framework running underneath every career choice they make.
And here's the good news: you don't need 5 years to change your career.
You need about a day to change how you make career decisions. The career follows.
Steve Jobs said you can't connect the dots looking forward - only backward. Fine. I've spent 13 years looking backward at thousands of careers. These are the dots that keep connecting.
1. Stop optimizing for salary. Optimize for slope.
Your career is a curve, not a number.
Most people manage the y-axis - how much they make today. Exceptional people manage the slope - how fast they're becoming more valuable.
A $200K job where you learn nothing is one of the most expensive things you can buy. A $150K job that changes your trajectory is one of the cheapest.
I learned this with my own money.
Early in my career I was at Hays, a massive global recruiting firm. Safe. Established. A name I could repeat at dinner parties. Then some partners left to build a new agency from scratch, and I followed them - for less money.
Everyone told me I was crazy.
Within a couple of years I was earning multiples of my old salary, because I wasn't a cog anymore. I was closer to learning how a business actually gets built from scratch.
Then I did something worse. I left that agency - where the strong commissions were pouring in - to join Uber. In Brazil. When Uber was still not fully regulated Brazil.
Drivers were getting their cars impounded. Regulators wanted us dead. Almost everyone I knew thought I was insane. My mom was afraid I was going to be beaten by taxi drivers.
It was the single best career decision I've ever made. I became one of the first recruiters in Latin America for what became a generational company.
The pattern, once you see it, is everywhere:
- Early career: optimize for learning.
- Mid career: optimize for leverage.
- Later: optimize for ownership.
Most people run this exact sequence in reverse. They maximize cash in their twenties, get comfortable in their thirties, and then wonder why their career stopped compounding in their forties.
Salary is what they pay you to stay the same.
Slope is what makes them pay you more forever.
2. Stop joining companies. Join people.
Nobody tells you this, so I will:
Your manager matters more than the logo. Your founder matters more than the title. The five people you work closest with matter more than the entire rest of the org chart.
After Uber and Nubank, I had my pick of established, prestigious companies. I chose Noom - and honestly, a huge part of that decision was one person: my future manager Mark Horton and the team.
Before hiring me, he asked for five references.
Five. For a recruiting manager. Most companies check zero. He personally spoke with 3 past managers and 2 senior hiring stakeholders.
Some people would read that as red-tape paranoia. I read it as the highest-bar hiring process I'd ever been on the receiving end of - and I wanted to work for the person holding that bar.
That one decision kept compounding for years. The standards I absorbed. The founder I got to work alongside, Artem Petakov , whose new venture I am working with. The network that eventually became the client base of my own company.
One exceptional boss will change your career more than three promotions.
So flip the interview. Do references on them:
- Talk to 2-3 people who worked for your future manager. Ask: "Would you work for them again?" Listen for hesitation.
- Ask the founder what they've changed their mind about in the last year. No answer = no learning culture.
- Find the best person who ever quit that team. Ask them why.
Naval Ravikant says to play long-term games with long-term people. The corollary nobody mentions: you have to pick the people before you can play the game.
I later discovered that Mark Horton was the reason our team got the opportunity to work inside a top AI lab in SF for about a year and that changed the trajectory of our company.
Great people compound great people. Choose accordingly.
3. Stop protecting your CV.
Here's a recruiting industry secret:
Perfect CV's are boring. And boring is invisible.
When I'm hiring for founders and top funds, the profiles that make everyone lean in are never the flawless ones. They're the ones with something weird in the story:
They moved countries. Quit the prestigious company at its peak. Joined something nobody understood yet. Changed industries. Started a company. Failed. Started again.
The weird thing isn't a bug in their story. It's the proof of agency - evidence that this person makes their own decisions instead of following the script.
My resume is a graveyard of decisions that made no sense at the time:
Left the global firm for a no-name startup. Left the money to join Uber early on. Left Amsterdam - an incredible quality of life, at a lower salary I happily accepted - to move back to Brazil and grind through Nubank's pre-IPO chaos. Left Nubank right before it got comfortable.
Every one of those looked like a mistake for the first 6 months and a masterstroke after 3 years.
Here's the test:
If every career decision you've made makes perfect sense to your parents and friends, you're not taking enough risk.
Consensus decisions produce consensus outcomes. The exceptional stuff lives outside the script.
4. Prestige is a tool. Comfort is a trap.
Let me be clear, because people get this wrong in both directions:
Yes - get the great logo. Google, Uber, Nubank, Stripe, OpenAI, Anthropic. Prestige is real. It compounds trust. It opens doors that stay closed to everyone else. I've seen a single brand name on a resume 100x someone's inbound opportunities.
But understand what prestige is for.
Prestige is a tool for earning the right to make increasingly interesting bets. It is not the scoreboard.
The logo collector spends 20 years accumulating impressive names and retires as a footnote in someone else's story. The logo user spends 3-4 years extracting everything - skills, network, credibility - then spends that credibility on a bet nobody else can make.
I stayed at Uber for four years. After the IPO, something subtle happened: it got boring. The problems got smaller. The learning curve flattened. The salary was great.
That's exactly the moment most people sign up for four more years.
The most dangerous moment in your career is the day it gets comfortable. Comfort feels like success. It's actually the interest payment on a debt called stagnation - and the balance grows every month you stay.
Use prestige. Never let it use you.
5. Get closer to the chaos.
Careers accelerate near the center of gravity.
Founders. Customers. Revenue. Product. Capital. Hard problems with no owner. Decisions that could actually go wrong.
The further you sit from those things, the more replaceable you become - no matter how good you are. You can be a world-class operator in a role that's three layers removed from anything that matters, and the market will price you like furniture.
My own path:
Recruiting inside big companies → recruiting next to founders → building my own firm working directly with founders, backed companies, and funds.
Each step meant more uncertainty. Less structure. Fewer people to hide behind.
And each step meant dramatically more learning, more equity in outcomes, and more surface area for luck.
Not a coincidence. That's the trade: certainty for slope.
Here's the one-day version: look at your calendar from last week. Count the hours you spent within one degree of a customer, a founder/CEO, revenue, or the product itself.
If the answer is close to zero, you don't have a performance problem. You have a positioning problem. Same talent, wrong coordinates.
6. Become difficult to categorize.
The future belongs to weird combinations.
Engineer + product taste. Recruiter + distribution. Designer + founder. Researcher + builder. Operator + closer.
Scott Adams called it the talent stack: it's easier to become top-25% at two or three things than top-1% at one - and the combination can make you one of one.
AI is pouring gasoline on this. Execution is getting cheap. Any single skill, in isolation, is getting cheaper by the quarter. But judgment across domains - the person who can recruit and build an audience, engineer and feel what users want - is getting more expensive, because AI can't be the intersection. It can only be the ingredients.
This article is me doing exactly this, in public. Recruiter + distribution. There are recruiters with more years than me and writers with more talent.
The combination is the moat.
Don't become the 10,000th best person at one thing.
Become one of the only people who can do your combination of things.
7. Work with people who make you feel behind.
If you're always the smartest person in the room, you haven't won.
You've designed a room that protects your ego.
Leave.
Find the cracked engineers. The obsessive founders. The operators who move 100x faster than you. The people whose "quick draft" embarrasses your best work.
The discomfort you feel around them isn't a threat. It's information - the exact measurement of the gap between who you are and who you could be.
Here's why this matters more than any course, book, or mentor you'll ever pay for:
Your standards are not chosen. They're absorbed.
You will unconsciously calibrate "good enough" to whatever the five people around you consider good enough. Sit among people with insane standards and your floor rises without you noticing. Sit among the comfortable and your ceiling drops the same way.
At Noom, my manager's bar reset what I considered acceptable work.
Working alongside the founder reset what I considered acceptable ambition. I didn't take notes. I just marinated. It was transferred anyway.
That's the mechanism. Choose your rooms like your career depends on it.
It does.
8. Stop chasing promotions. Chase responsibility.
Titles are lagging indicators. Scope is the leading indicator.
The promotion you want is a receipt for the value you already demonstrated. Chasing the receipt before creating the value is why so many careers feel stuck - you're standing at the cashier with an empty cart.
The fastest careers I've watched in 13 years all ran the same play:
- Ask for the impossible project.
- Take the problem nobody owns (there's always one - it's usually the one everyone complains about in Slack).
- Run something before you feel ready.
- Operate at the next level until promoting you becomes the obvious move - until NOT promoting you would embarrass your manager.
At Nubank pre-IPO, nobody handed out clean job descriptions. There was just an ocean of problems and whoever grabbed them. The people who grabbed the scariest ones are running companies now.
Meanwhile, the people who waited to be asked are still waiting.
Responsibility is the only promotion that can't be taken away from you. It travels with you to every future job, negotiation, and company you start.
9. Eventually, own something.
Equity. A business. Distribution. An audience. A product. A P&L. Intellectual property.
Anything.
Just don't spend your entire career renting out your time - because rented time has a ceiling, and you will hit it precisely when you have the least energy left to do anything about it.
Naval said it best: you're not going to get rich renting out your time. You need to own equity - a piece of a business.
I'd add the career version: you're not going to get free renting out your time. Even at a great salary. Especially at a great salary - golden handcuffs are still handcuffs.
Everything I did for 13 years - the logos, the pay cuts, the high-bar managers, the pre-IPO chaos - was, in hindsight, an apprenticeship for ownership. When I finally started my own company, the network did the heavy lifting: former Noom/Nubank colleagues, the founders I'd worked with, ex-Uber people scattered across every company on the continent.
Clients showed up before the website did.
Salary can make you rich.
Ownership can change your life - and your kids' lives, and what your name means after you're gone.
Start smaller than you think you need to. A side project. An audience of 100 true fans. 0.1% of something real. Ownership is a muscle, and almost nobody starts training it until it's late.
10. Delete your 5-year plan.
I know. Every career book tells you to have one.
Here's what 13 years of watching real careers taught me: the best ones are never linear, and almost none of them followed a plan.
Technology changes. Industries change. Companies die. New ones appear from nowhere - the job title "Forward Deployed Engineer" barely existed 3 years ago, and now labs fight wars over them.
And the biggest variable of all: people you haven't met yet will create opportunities you can't currently imagine. My entire company exists because of people I met through jobs I almost didn't take.
A 5-year plan is you, at your least informed, dictating decisions to a future version of you who will know 100x more. It optimizes for the world staying still. The world has never once agreed to that.
So don't optimize for predicting the next 5 years.
Optimize for being the person with incredible options 5 years from now.
High slope. Rare skill combination. Exceptional people around you. Growing scope. Something owned.
That person doesn't need a plan.
Every version of the future arrives carrying opportunities for them.
The 1-Day Career Audit
Here's the "one day" part. This works best if you actually write it down - thinking about it in the shower doesn't count.
Block 2 hours. Forget your CV. Answer these on paper:
- Who am I learning from? Name actual humans. If you can't, that's the finding.
- What am I becoming unusually good at? Not good - unusually good. What's the combination?
- Am I surrounded by people who make me feel behind? Or did I build a comfortable room?
- Is my responsibility bigger than it was 12 months ago? Not the title. The scope.
- Am I closer to the center of gravity than 2 years ago? Founders, customers, revenue, product - or further away?
- What am I starting to own? Anything at all?
And then the only question that actually matters:
If I stay exactly where I am for another 3 years, will I become dramatically more valuable?
Sit with it. Don't negotiate with it.
If the answer is yes - ignore everything, including this article. You're rare. Keep going.
If the answer is no, understand what that means:
You don't have a career problem. Your salary is fine. Your title is fine. Your company is fine.
You have a trajectory problem.
And trajectory problems are invisible precisely because everything looks fine - right up until the decade is gone.
Every valuable thing in my career came from a decision that looked wrong at the time: the pay cuts, the “illegal” company, the manager who demanded five references, leaving "fine" on the table four separate times.
Careers don't change in 5 years.
They change in one honest day - followed by one uncomfortable decision.
Fix the trajectory.
The career follows.
