Don’t Just Surround Yourself With Smarter People

One of the most repeated pieces of advice in business and personal development is simple enough:

“Surround yourself with smarter people.”

It sounds good. It flatters ambition. It suggests that your future depends on upgrading the average IQ or success level in your WhatsApp groups.

Over the years, though, I’ve come to realise that this advice is incomplete. Often, it pushes people deeper into the very traps they’re trying to escape: burnout, golden handcuffs, status games that leave them quietly empty.

I think there’s a better version of this advice:

Don’t just surround yourself with smarter people. Surround yourself with people who are free in different ways than you are.

This idea sits at the core of how I think about life design, and it’s also the core design principle behind The Good Life Collective (GLC), the private community I run.

Two Kinds of Freedom

When I say “free”, I’m not talking about passports, politics, or being able to work from a laptop on a beach.

I’m talking about the room you actually have to move inside your own life.

In practice, I see two very different kinds of freedom:

1. Freedom to win.

This is the one most people optimise for. You pick a game—your career, a business, a public profile, a net worth target—and you get very good at winning inside that game. You learn the rules, acquire leverage, build skills, and improve your position.

If you surround yourself with “smarter people” in the conventional sense, this is usually what you’re buying: better tactics, sharper thinking, insider knowledge. You become more effective at the current game.

2. Freedom to keep playing.

This one is quieter and more important. It’s the ability to zoom out of the current game entirely:

• to walk away from a path that no longer makes sense, even if you’re “winning” on paper
• to change countries, careers, or identities without your life collapsing
• to spot when a game is slowly destroying your health, relationships, or sanity—and actually change course

You can be highly free inside a narrow game and almost totally unfree outside it. Think of the executive who is unbeatable in meetings, but genuinely cannot imagine a life without their title. Or the entrepreneur who can pull off million-euro deals, but is incapable of slowing down long enough to actually enjoy any of it.

On paper, they’re powerful. In reality, they are trapped by their own success.

How We Fall Asleep Inside a Game

Most of us never consciously choose our main game. We slide into it.

You get good at something, opportunities appear, money and status follow, and before you know it, your entire life is organised around one scoreboard: revenue, valuation, salary, number of properties, number of followers, whatever.

At first, it’s energising. You’re progressing. The numbers are going up. People around you approve.

Then, slowly, the walls close in:

• you filter people based on whether they help or hinder that one metric
• you stop doing things that don’t “move the needle”
• you treat anything that doesn’t fit the game as a distraction or a threat

At some point, the game becomes invisible. It stops feeling like a choice and starts feeling like “just how life is”. That’s what I mean by falling asleep inside a game.

Now imagine you take the classic advice literally and “surround yourself with smarter people” who are all playing the same game as you, just a bit better.

You’ll get sharper. You’ll get richer. You’ll pick up advanced tactics. But you’ll also share the same blind spots, the same unexamined trade-offs, and the same silent fears.

You all get better at winning. None of you get better at asking whether this is a game still worth playing.

What Differently Free People Look Like

This is where the idea of differently free people comes in.

A differently free person isn’t just “smarter”. They’ve escaped a trap you’re still in, or they’re willing to pay costs you’re not yet willing to pay, in exchange for a kind of freedom you haven’t prioritised.

Their life doesn’t fit your script, and that’s the whole point.

You’ll recognise them because their choices make you pause:

• You’re obsessed with efficiency; they leave deliberate empty space in their week and guard it like a hawk.
• You’re focused on accumulating more; they walked away from “more” and are clearly lighter and happier.
• You’re chasing visibility; they choose depth over reach and are uninterested in being known at scale.

Under your current logic, some of their decisions look irrational. But you can’t dismiss them, because the results are undeniably real: they’re calm where you’re anxious, present where you’re split in ten directions, rooted where you’re constantly drifting.

This isn’t about copying their life. It’s about letting their way of living expose the invisible walls of your own.

Why I Built the GLC Around This Idea

The Good Life Collective wasn’t created as a generic “networking group” or a fan club. It’s a deliberate attempt to assemble high-agency people who are playing different games, at a similar level of seriousness, and keep them in conversation long enough for their freedoms to rub off on each other.

Within the GLC, you will find these kinds of profiles:

• someone who sold a business early, and consciously chose a slower, more grounded life instead of chasing the next big exit
• someone who optimises everything around being an involved parent, even if it means saying no to prestigious opportunities
• someone who moved countries two or three times to build a legal and lifestyle setup that actually matches their values
• someone who is “under-earning” relative to what they could command, because they refuse to sacrifice health or freedom of time

On paper, they’re all “smart”. In practice, what matters is that each of them is free in a way the others are not.

Put them in the same room, and something interesting happens:

• the entrepreneur who only thinks in terms of net worth starts to see the cost in terms of time with kids, stress, and fragility
• the person who over-indexes on safety starts to see how much opportunity and aliveness they’ve been leaving on the table
• the restless nomad sees, up close, the long-term richness of deep roots and long-standing relationships

Nobody is held up as “the correct template”. Instead, each person makes different options visible. You’re exposed to freedoms you didn’t know how to value before.

Freedom, Family, and the Long Game

A recurring theme in our conversations inside the GLC is the tension between work, family, and the long game.

Many members are in the thick of it: young kids, demanding businesses, geographical moves, ageing parents, changing tax regimes. It’s very easy to slip into a quiet story that says, “I’ll sacrifice now, and later I’ll be free.”

On a spreadsheet, that story is neat. In real life, it’s messy. Time with kids doesn’t come back. Health doesn’t magically restore itself on command. Relationships don’t pause gracefully while you chase a number.

When you sit with people at different stages of the journey, the trade-offs become more real. You hear from those who over-invested in work and now live with a sense of having missed something important. You hear from those who protected family time and see what that bought them. You hear from people who tried to do everything at once and hit a wall.

Again, there’s no single right answer. But your decisions stop being theoretical. You’re not optimising your life in isolation. You’re learning directly from the consequences other people have already lived through.

That’s what I mean by freedom to keep playing. You’re designing your life so that 10, 20, 30 years from now, you’re still in the game with your health, relationships, and sense of self intact—not just with a nice financial statement.

Beware the “I’m Above All Games” Trap

There is another pattern worth mentioning.

Once you see that any particular game can trap you, it’s tempting to swing to the other extreme and never fully commit to anything. You become a permanent observer:
always exploring, always keeping options open, never going all in.

That, too, is a game.

Refusing to choose is still a choice. Floating above the concrete realities of work, family, money, and place might feel clever, but it usually leads to drift and a low-grade dissatisfaction that never resolves into anything solid.

The goal is not to avoid all finite games. The goal is to play them deeply, but stay awake to the fact that they are games—and to maintain enough inner and outer freedom to change course without blowing up your life.

In my experience, you don’t develop that kind of awareness in isolation. You develop it in conversation with people whose games and freedoms don’t match your own.

The Upgrade: From “Smarter” to “Differently Free”

So let’s come back to that original line:

“Surround yourself with smarter people.”

It’s not wrong. But on its own, it’s shallow.

If you only follow that advice, you’ll end up extremely good at one thing and oddly fragile everywhere else. You’ll be free to win inside a narrow game and unfree everywhere outside it.

The upgrade looks like this:

Surround yourself with people who are free in ways you’re not.

People whose lives don’t fit your template. People whose choices confuse you at first, then quietly expand your idea of what’s possible.

By all means, learn from people who are “smarter” in your field. But don’t stop there. Find the ones who are calm where you’re restless, brave where you’re cautious, rooted where you’re scattered. Let their freedoms challenge your defaults.

Over time, that mix is what protects you from winning the wrong game.