Every generation tends to inherit a story about work. The question is always whether or not it still fits the world you’re working in.

Our grandparents learned loyalty. Our parents learned how to grow a career. We learned that we needed to pick an expertise.

I was told to get an education, get a good job, get good at one thing, and then work my way up the ladder.

That was the plan, and in return I would feel safe. The white picket fence and two and a half kids safe.

That advice wasn’t wrong. My father’s generation got pensions out of it. Mine got a title and maybe some budget, and you could easily explain to someone what you did for work. I’ve pretty much run that same playbook for a bit over 20 years, working in shipping, real estate, and software. I can’t say that any of it was planned from the start.

And at no point did anyone ever put an expiration date on it.

The rules changed quietly

Every week I get a few targeted ads that showcase webinars and courses for people like us. They’ll tell you that four out of five jobs will be gone inside of three years. You need to keep up and operate at the top of your field or get left behind. The threat is vivid, and the cure usually costs around €99.

It would be easy to dismiss, but it’s something so real that you can’t just wave it away. Companies and marketers that are selling panic are working with real material and raw emotions, and the reality is we do have to keep up. That reality might just be worse than the sales pages that get thrown at us.

Matt Shumer wrote a solid take on what’s happening. It’s not that AI is replacing one specific skill. It’s becoming a general substitute for all cognitive work, and it’s getting better at all of it at once.

That’s tough for us measly humans, especially since we are pretty shit at multitasking, let alone multi-learning.

If that’s right, then just getting better at your expertise is basically running a race against something getting better at everything at once. It’s Usain Bolt running against someone who is not only faster in the 100m but is essentially the ultimate decathlete.

What we’ve been taught to value about work for the past few decades is being commoditized.

PwC analyzed more than a billion job postings, and it seems that entry-level work is increasingly demanding senior judgment rather than just technical execution. The trend that they’re seeing is the real story here. If you need better judgment starting your career, we should ask what’s going to be expected of middle managers in the near future. Or maybe they don’t exist as the “super” individual contributor becomes a thing.

Why capable people freeze in the age of AI

It’s not necessarily all doom and gloom, though. The marketers can’t sell tons of courses about the world ending.

And it’s not that you are afraid of being incompetent, either. You know you can do your job, and you know that you can do it well. After all, you’ve done it for years. That’s why it might feel a tad bit insulting to feel as if you need to panic over a machine.

But the fear beneath the chaos is more subtle.

You might have an inkling that you’re becoming exceptionally good at a life you didn’t choose.

Nobody’s to blame for that feeling. Not your employer, not AI, not the economy.

It’s much more of an intrinsic mechanism. One where you ask yourself: At what point did I stop choosing? When did I slowly fall out of the driver’s seat?

According to Kevin Kelly, the most common mistake we make is to do a great job on an unimportant task. AI might make you fast at the task, but it has no opinion about whether or not the task was actually worth doing. That’s your choice, and at some point you’re going to have to ask yourself whether you are on your own path or if you’re chasing someone else’s dream.

The reaction I see most people having to the changing work field isn’t panic. It’s stillness. But not in the quiet, reflective, contemplative way. More the let’s-see-how-this-shakes-out kind of still.

It’s not that these people are lazy or behind. They’re standing still because the playbook that they got at the start of their career no longer matches the game that they feel they are playing.

It’s like watching a sport that has moved on strategically from what it looked like decades before. Which is roughly what I said about the layoff wave earlier this year.

Who picked the game

What survives is your ability to choose where to point the repertoire of skills that you’ve accumulated.

George Mack calls this high agency.

I find his definition amazingly useful. He says the idea of high agency confuses people because it isn’t a single thing. Instead, it’s three things that rarely show up together: clear thinking, a bias towards action, and disagreeability. Take one away and nothing moves.

The obvious objection is that it’s easy for me to say. I write a newsletter (thanks for reading btw). You’ve got a manager and a mortgage to pay, so you don’t want to rock the boat.

But either you do the rocking or someone else will do it for you.

Most of the people we admire are the ones we look at and wonder how they manage to do everything. Maybe they have more hours in the day than we do. But I don’t think it’s the hours. I think it’s alignment. They’re pointing their work where they actually want it to go.

I was in the audience in Hamburg in June while Moritz Petersen gave a short talk about being the unofficial communicator inside your own organization. He teaches sustainable supply chains at Kühne Logistics University. Then he briefly went through everything that he built over the last few years.

A children’s picture book explaining how ice cream gets to the shelf, which sold 20,000 copies and is now his most successful publication of any kind (a slightly complicated feeling, I imagine, for a working academic). A day where he brought 30 fifth graders onto campus to pack fragile goods, and a podcast explaining how logistics works. Then he started a weekly news show because no one else had.

None of those things fit into his job description. He does them because he feels that somebody has to explain the field (logistics, in his case) and because he finds it fun. For his closing line, he simply asked, “When do you start?”

Also, turns out the psychologists have been observing people doing this for quite a while now. Researchers studying hospital cleaners discovered that the people who found the most meaning in their work didn’t change jobs. They just quietly did things that they thought should be done. Those things just happened to be outside their job description, but ultimately improved the work they did. And isn’t that what work is actually about? Aligning what you do with how you feel that work should be done to make the biggest impact? All signs point to this being the way to a fulfilling career.

I stopped trusting the scoreboard

I didn’t set out to become a “creator”. To be honest with you, the word itself still feels a bit cringe to me.

What happened was a meeting.

Not long after the company I was working for went all-in on AI, I sat in on a call about the plan. I believed in the plan, and I think things would be a bit different if I were actually skeptical, but I wasn’t.

But somewhere within that hour, it occurred to me that it felt as if something was slowly draining away. It was hard to put a finger on. Maybe it was the culture, the soul, or the story that we were selling ourselves on. Whatever it was, I felt as if the narrative people had spent years building was being torn up and replaced by something lifeless. It’s not that anyone was doing anything wrong, but that that alignment was no longer there.

You see, this newsletter had been sitting in my head for four or five years by that point.

Collecting dust.

Helping nobody.

On that call, I asked myself: Why am I sitting here listening to something I don’t fully believe in and not pushing forward the things I do?

I felt the pull to go and tell a different story instead. One where the humans come out fine. Better even.

I checked out right then and there. Not from the job. From the story I was being asked to buy into.

What I really wanted at the time, though, was to stop having my entire sense of whether I was doing well handed to me every few quarters in some review by one organization.

So I started writing. Nobody gave me an assignment. Nobody approved it, and 41 weeks later I’m still doing it. The podcast is on the way, and there’s now plenty in my archive that I think I would write differently now.

To start, I didn’t risk anything. At that time, I still had a job. I was still busy with kids and hobbies. There was nothing dramatic that happened. I just decided to start leading myself first.

Constraint or cover

Which brings me to the question I’ve started asking myself.

Why did it take me so long?

The honest answer was procrastination and safety.

The reality is that things like money, a work visa, a family that depends on your income, or even your health are all constraints. These are real constraints that you have to design around.

On the other hand, “the timing isn’t right” is usually a cover. So is “once things settle down.”

One question can help sort this out. “Would you accept this excuse from someone you are coaching?”

If a friend you admired told you that they had been meaning to start something for two years but the timing wasn’t right, you’d know when to call bullshit on that. You might be kind about it, but you’d be totally right to call it out.

At the same event I was attending in Hamburg, Wibke Dauletiar said companies rarely get stuck because of imperfect decisions. They get stuck because of decisions that never happen.

Careers work the same way. Almost no one gets derailed by a bad decision that they made on purpose.

Make one small change this week without anyone signing off on it. You can reshape a project or write a memo that no one asked for. Do a little more of what makes you come alive.

Ready enough

Every generation eventually discovers that the story that it inherited about work no longer explains the world it lives in. Progress and innovation make sure of it.

I’ve always loved a quote that’s often attributed to Winston Churchill.

It imagines each of us being tapped on the shoulder once in our lives and offered the chance to do something uniquely suited to us.

The big tragedy isn’t missing the moment. It’s being unprepared when it arrives.

None of us will ever feel completely ready. But we can decide to be ready enough.

Ready enough to write. Ready enough to build. Ready enough to raise a hand. Ready enough to choose.

Our grandparents inherited one story about work. We inherited another. Like theirs, ours no longer fits.

AI is going to change almost everything about work, but you still get to choose the story you write next.