Keeping your head down and working hard is the most dangerous move you could make right now.
The advice that made prior generations successful will slowly kill the modern career.
“Keep your head down and work hard” used to increase your security. Now, it means only the small group of people you work with regularly know your value.
“Being loyal” used to get you a pension and retirement. Now it gets you a layoff call and a severance package (a month for every year of service, if you’re lucky. Most aren’t.).
“Top performers are rewarded” now means top performers get the added work of incompetent or downsized (and not backfilled) employees. Who’s tired of hearing we need to “do more with less?” And who do you think is doing all this fucking more?
Whether we like to think about it or not, there’s an ugly truth to the whole thing.
We all know the deal we signed.
Here in America, we’re especially expendable: a phone call, a PTO payout, and a final paycheck can change your entire world in a morning.
We’ve all seen stability evaporate over the last few decades, the amount of time I’ve been in Talent Acquisition (formerly known as Recruiting, currently rebranding to Talent, and yes, it’s a dirty field that needs the constant handle changes).
I cut my teeth in agencies for almost a decade before moving in-house, clocked over 12k interviews. I’ve led teams of stone-cold killers around the globe for most of the last decade, high-octane professionals with S-tier standards who deliver.
And I still had to lay off 75% of my team in a 14-month period before being shown the door myself.
In 2023, I was the norm, not the exception. Companies looked at frozen hiring and no backfills for the next few years and cut their recruiting teams. Anywhere from 70% to 80% of these departments were cut in a lot of companies.
The market was not flooded with recruiting talent. It was hit with a fucking tsunami. Every open job immediately became 3 to 5 times more competitive.
The same thing is happening now as AI comes in and takes work away from people who have been doing it for their entire professional lives. Whole functions are being cut like dead tree branches as fewer humans are needed to manage a workforce of agents and chatbots.
From my seat at the center of organizational hiring, here’s what I see: nobody knows what the next few years will look like. CEOs are figuring out how to balance AI automation with human capital. Department heads are trying to see if employees need to be backfilled when they leave. Can they replace that person with AI tokens that cost a fraction of a salary? No benefits, either…
If you wait for your employer to protect you, you’re betting your family’s future on people who are just as lost as you are. A cycle of layoffs, a strategy shift, an AI tool that replaces half of your work: any of those can blindside you. All of them are in motion right now.
Our options feel limited. We can wait around to see what happens with AI, or we can frantically re-skill ourselves in hopes that what we learn today will keep us relevant for the next 5 years. But there’s a third option that doesn’t require betting on a target nobody can see.
THE DEAL CHANGED
Plenty of people complain about their jobs, but maybe you’re not one of them. You might like your boss, your team, or even the whole company. That’s no trivial thing these days, and it’s where I am fortunate enough to be right now. I have the fewest professional complaints I’ve ever had: great boss, amazing team, and an organization I really want to see win.
But we can like our jobs and still refuse to bet everything on them. Those don’t have to be opposites. Holding both in your mind is the key.
Because for me, it’s not the job, the leadership, or the company that concerns me.
It’s the system that I don’t trust.
Our generation marched into the workforce thinking we had the same deal we saw work for our parents.
But the deal quietly changed.
I’m a 41-year-old millennial. We heard about pensions but were handed 401ks (often without a match). We were teenagers for Y2K and everything that followed. The deal was already shifting when I got my first taxes taken out of my Subway paycheck (and yes, I made killer sandwiches).
Since I was old enough to understand the economy, I’ve seen three recessions: the dot-com bust of 2001, the Great Recession from 2007 to 2009, and the COVID recession.
Every economic downturn, I saw the job market flooded with quality talent: hardworking, honest people who did everything right and still got fucked over.
Through the downturns, I felt like a cross between an unqualified therapist and a “career” paramedic. I’ve spent thousands of hours talking to scared, desperate people, helping them navigate the market and get back to work. I couldn’t always help.
And I know it’s going to get worse before it gets better.
If it gets better.
THE GAME
Now in 2026, as I look across the landscape, the job market is as stagnant as it’s ever been.
Tech layoffs aren’t even news anymore. Like all other modern-day horrors, they register on the feed for a day or two, then the news cycle moves on to the next tragedy.
Even people who hate their jobs are holding on to them tightly for fear they won’t be able to find another one.
For most of us millennials, our careers have felt like a game we all grew up with: Frogger.
For the uninitiated, Frogger is a game where (surprise) you’re a frog. You’re on one side of the road. The goal is to make it across the highway without getting squashed by a car. We hop, we wait, a car passes, we hop again. Oh shit, a car’s coming fast in my lane. Hop again.
Road after road, level after level, we hop, all the while hoping we don’t get hit by a car or, as was my case at the end of 2023, a bus: 2 layoffs in 5 days with a 23-day-old newborn and two toddlers at home.
If you’re staying in the system, that’s the game you’re playing. Doesn’t matter if you’re an entry-level accountant or a seasoned CFO. We’re all hopping to avoid becoming roadkill. That’s a different deal from what our parents had. It’s a shittier deal.
So no, if you like your job, wanting more doesn’t mean you’re ungrateful. It just means you want a life where dodging traffic isn’t baked into the . Wanting more is a sane response when you realize the game can’t be won by playing harder.
THE THREE OPTIONS
The way I see it, high performers have three options:
Option 1: Hunker Down (and Panic). Watch the news, see the world changing around you, and hold on to your job as it exists today and hope for the best. (More Xanax, anyone?)
Option 2: Re-skill Based on Future Projections. Definitely better than standing still, but with how fast the technology is evolving, the target moves faster than you can retrain. (More Adderall, anyone?)
Option 3: Learn Skills That Allow You to Become a Free Agent. Find the crossover of skills that allow you to keep up with change but position yourself to earn without a company, so you can be self-reliant.
Most people who are good at what they do are currently somewhere between Option 1 and Option 2. They know standing still is likely a death sentence, but they’re re-skilling based on the possible needs of someone else. That’s scary too because the people setting the target can’t see the target either.
Nobody is talking about Option 3 in the company all-hands or the team Slack channels.
AI: YOUR EXECUTIONER, OR YOUR LEVERAGE?
AI will disrupt careers. It’s already started. Ask people in customer service how it’s going. More and more fields are being impacted with each new frontier model release. There are freshmen in college studying for jobs that will be automated by the time they graduate. Meanwhile, companies are leaning into leadership development programs (even though the future will need fewer managers) and creating career paths for jobs that will be replaced by agents and tokens before they’re backfilled. They’re just as lost as the rest of us.
The system isn’t malicious. It just doesn’t have a map anymore.
The flip side of the AI coin is leverage. High-agency people can use AI to learn skills, automate tasks, and run one-person businesses with a handful of agents and a few trusted advisors.
There’s never been a better time to bootstrap a business. You can vibe code a prototype instead of hiring engineers who don’t see your vision. You can have agents write your ad copy, manage your finances, and monitor your competitors.
THE FREE AGENT
The term floating around for people who are employed and have other hustles is “portfolio career.”
As a sports fan, I like to think of us as “free agents.” Free agents are people who own their value and sell their services, either to a company or directly to customers. These are not “quit your job, burn the fucking boats” people because they have families and responsibilities. They’re also over being a draft pick, hoping to get selected and developed by a great coach on a great team.
These are people who like their work but refuse to bet their family’s future on their job.
They have stopped looking at their job as their identity.
Instead, they view their time with companies like a professional athlete: a 3-year deal here, a 4-year deal there, a 1-year “prove-it” deal they have to take when the market is tight.
The day job is part of their portfolio. The rest? Investment properties, a side business, the book they’re writing. Some other method of bringing in extra cash.
Portfolio careers are a mental pivot for most. We’ve spent so much of our lives chasing a great job at name-brand companies, like it will raise our status, secure our future, or even make us fulfilled.
But we’re old enough to know the truth: a job is a job. It pays the bills.
Getting your badge and email address with a household brand feels awesome for a few weeks. Then it wears off. Then, it becomes the job you commute to, the meetings that could have been emails, the emails that shouldn’t have ever been sent, and the colleague who heats up fish leftovers and eats at their desk.
This is the mindset shift. You’re no longer a loyal employee, wanting more, hoping a company will give it to you. You’re a free agent evaluating your options, looking for the situation that’s best for you.
COMING UP
This isn’t one letter meant to flip you from employee to free agent. It’s a season. Becoming a free agent is a build that takes time.
We’re going to build these capabilities in upcoming letters.
Because the best time to switch from employee to free agent is right now while you have a paycheck and, if you’re fortunate, a job you like. Whether you know it or not, these are the perfect conditions to start building.
Let me know with a reply or in the comments: What are you building? If you haven’t started yet, what’s the idea? What’s in the way of you starting?
I read every reply. I connect people with opportunities for a living. Now my goal is to connect builders with each other. Let’s create as many free agents as possible. Find and link builders so we can all help each other on the journey.