The Future Belongs to Generalists 2.0 [#76]

I still vividly remember my first smartphone. It was 2012, and the coolest thing on it was that you could send free text messages.

When I founded my first company in 2016 - a recruiting agency bringing nurses from Italy to Germany and teaching them German - a lot of students didn’t believe that language classes over Skype (no kidding) would work.

In 2021, several companies developed vaccines within a year that had never done before.

Today, I’m chatting with three co-workers on a digital basis. All of them are AI. 

Technological progress has been crazy fast, and there's no indication that's gonna change anytime soon:

What does the world of tomorrow look like? Honestly, I have no idea.

It’s evolving quickly. 

And that’s the point: in a world that’s evolving quickly, old jobs go away, and new ones are being created. Whatever hard skills you’re learning today might be obsolete tomorrow. (In fact, the World Economic Forum is already working on an initiative to re-skill 1 billion people by 2030.)

AI is a big culprit here: especially if your job relies on following a script or solving a well-defined problem, there’s a good chance AI will do it better, faster, and cheaper.

Doesn’t matter whether that’s accounting, law, frontend development, admin work, you name it. In 2023, Goldman Sachs estimated that AI will replace more than 300M jobs, and I think that number will only increase. 

What we do know is: change will accelerate further. And generalists are uniquely positioned to navigate this, by learning faster and having a broader, diversified skillset. Putting all your eggs into one basket without knowing whether that basket will still exist in the future would be … irrational. 

In short: it won’t pay to become a specialist anymore. And we’re not prepared for this. 

The Educational System

The roots of our current educational system trace back to the early 1800s in Prussia. It emphasized obedience, standardization, and mass instruction to serve the needs of the Industrial Revolution. It was designed to produce factory-ready workers, compliant citizens, and good soldiers. 

People who execute well. Not people who question assumptions, think creatively, and adapt quickly. 

We still see this today: 

• Choose a major at 18
• Do a master’s degree at 21 that pushes you further towards specialization 
• Do one job for the rest of your career 

This worked in a world that largely remained constant. Specialists thrive in what author David Epstein calls, “kind environments”: situations where rules are clear, patterns repeat, and feedback is immediate. Like golf. 

Take, for example, Tiger Woods. Tiger picked up a golf club at age 2. By age 3, he was on national television. For his entire life, he pursued ultimate excellence in one sport – and became the best at it by a mile. 

This worked, because in golf, there’s only a finite set of moves you have to master. It’s just you against the terrain. The more you practice, the better you’ll become. It’s a predictable, “kind” environment. 

Thing is: we don’t live in a kind environment. 

We live in a wicked environment, where there are no rules, change is unpredictable, and most of all, fast. 

A person that mastered this environment is Patrick Collison, the founder of Stripe. When Patrick started working on Stripe, he wasn't a payment expert. He didn’t come from banking. What he did have was an insanely broad set of interests.

He'd been programming since he was a teenager, taught himself design, dabbled in philosophy, and read obsessively across disciplines. He and his brother John didn’t approach Stripe like payments specialists — they approached it like generalists. They asked: “Why is accepting money on the internet still so broken?”

They didn’t just build the technology; they innovated in regulatory affairs, design, and integrability to “increase the GDP of the internet”. Today, Stripe powers payments for millions of businesses, from startups to Amazon.

What gave them an edge? It wasn’t deep specialization in finance. It was their ability to navigate complexity – across tech, UX, legal, and business – and move fast across all of them.

That’s the power of a generalist: Not mastering one domain — but moving between them. 

Now, you and I aren’t the Collison brothers. We’re far away from that. But maybe somewhere on this blog, the next great founder is reading this. Who just needs a slight nudge to build their generalist skillset. 

Let’s talk about how to do that, shall we?

How to build your generalist career

Here are the four steps to building your generalist career: building meta skills, testing different disciplines, developing T-shaped expertise, and building a portfolio career. 

[1] Meta Skills

Generalists are, fundamentally, specialists in meta skills: when you don’t have domain expertise, you need to get incredibly good at the soft, or meta, skills. I’ve clustered this into 3 tiers: 

Tier 1: Foundational Meta Skills – such as learning how to learn, critical thinking, problem solving, and communications. These come in handy everywhere, and will not be replaced by AI anytime soon.

Tier 2: Amplifiers of Impact – such as personal productivity, time management, emotional intelligence, and systems thinking. 

Tier 3: Specialized Meta Skills (for businesspeople) – tech literacy, negotiation, financial literacy, and leadership. 

Once you’ve learned these skills, you can move on to the next level: testing different disciplines. 

[2] Testing Different Disciplines

Know this guy? That’s Roger Federer. He’s the Tiger Woods of Tennis. Won all the trophies.

But he’s also very much NOT like Tiger: his path to excellence was completely different. He played squash, basketball, handball, soccer, you name it. Only in his late teens, he gravitated more towards tennis – a time in which plenty of other kids had already been working with professional coaches for more than a decade.

Tennis, unlike Golf, is a “wicked environment”: given that you have an opponent, it’s much more unpredictable. You constantly have to adapt, think outside the box, while executing the basics well. Having a more general instruction here is valuable. 

I assume many of you want to pursue a career in startups. Now that’s you’ve close to going into the working world, the best advice I can give you is to start out in a generalist position, such as a Founder’s Associate. That way, you’ll see all spaces of startups and do work in all sorts of fields. 

This will help you lay the second foundational layer after meta skills, your domain-specific skillset. And give you slight pointers to develop your T-shaped expertise: 

[3] T-Shaped Expertise

If you want to be like Tiger Woods and become the best Golf player in the world, the competition will be tough. But if you want to become the best golf player in the world who also runs a startup and speaks five languages, competition will be rare. (Not sure what you’re going to do with this specific skillset, but you get the idea.) 

It’s easier to be among the top 5% in 2-3 disciplines than the top 1% in one. 

So when you’re doing your Founder’s Associate work, sooner or later, you’ll realize that you like some parts of the work more than others. Great! Go deeper on these topics. This is the natural development of a generalist: you build deeper expertise in a few fields, simply because these are more interesting to you. 

When I joined Sdui, they had been looking for a while for someone to lead international expansion. It required a very broad skillset with spikes in entrepreneurial thinking, leadership, and intercultural ability. 

I had built an international company before. I speak five languages fluently. There was zero competition for the job. 

Now, my T’s are recruiting, writing, and international expansion – all topics I’m interested in, although not necessarily related. 

But they don’t have to be: why should you only do one job? 

[4] The Portfolio Career

Last week, I visited my grandma. She was born during WW2, grew up in the post-war era, and had her first kid at 22. She and my grandfather worked hard to provide a stable, safe environment for their children to grow up in. Job security was everything. 

Over a nice pork roast dinner, she asked me: “when will you get a proper job?” Like, as a government employee, or manager in a big corporation. Because these jobs are “safe”. 

Except … that they aren’t. Not anymore. Anyone can get fired these days (despite incredibly strict German labor laws). Mass layoffs are everywhere. 

So instead, it makes sense to diversify. If you’re investing in the stock market, you don’t only buy one stock. You buy a diversified set of stocks, maybe just ETFs that reflect the overall market. 

So why the hell do we go all-in on one stream of income? 

The answer to this is the “portfolio career”, where you set up a diverse set of income streams. It’s a career building approach tailor-made for generalists who want to do more than one thing. How to build one would bust the scope of this keynote, but let me quickly show you how I’m setting one up for myself.

Right now, I: 

• Run a recruiting business that matches early-career generalists with early-stage startups (for instance, in Founder’s Associate positions)
• Write a weekly newsletter with >750 subscribers 
• Do occasional consulting gigs on the topic of international expansion
• Sell an online course about Personal Productivity 
• Am looking to publish an e-book on international expansion for startups later this year 
• Still play Lacrosse at a high level (although I’m not getting paid for it)

I’m loving every minute of it. I work more than most full-time employees – but whenever I get bored, I can just switch tasks or take on a new project. And the best thing is: I’m not dependent on any single one of these income streams. 

I once read this quote:

“The worst human addictions are alcohol, nicotine, and a monthly salary.”

A portfolio career allows you to break that addiction to a single salary. 

But in order to build your own portfolio career, you can’t skip the steps before. You need your meta skills, general domain expertise, and 1-2 edges where you’re particularly good. But then … you won’t ever have to specialize. 

Unless, of course, you want to. 

And that’s what I want to leave you with: 

A generalist is sometimes considered a “jack-of-all-trades, master of none”. I disagree. 

I believe generalists are masters of the unknown. The only constant in our current world is change. And in a world that’s constantly changing, we need more people who embrace meta skills, bring insatiable curiosity, and see innovative paths where others see none. 

That’s why I believe the future belongs to generalists. 

And if you wanna be part of it, there are 2 things you can do:

1. apply to my company that matches top generalist talent with early stage startups, and
2. subscribe to my newsletter where I explore building a generalist career