The trap that looks like freedom

A few weeks ago, I scrolled through LinkedIn and saw a post from a founder that hit me hard. He said: I don't care if my employees watch Netflix, shop on Amazon, or work four hours a week. As long as they deliver what we agreed on, on time, at the expected level. If I need more, I ask for it or pay for it. If they consistently don't deliver, they're out.

He made it sound clean. Simple. Fair exchange of value.

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I left a comment because I had to — I used to say almost the exact same words to my team. I don't care when you do this or how you do this. We have two metrics: client satisfaction and quality. Everything delivered on time, everything done well, client always knows what's happening. And it was. People would come to me asking, "Can I take Friday off?" My answer was always the same: "Sure. Is your work on track? Is the client informed? No open questions? Then yes." Same with vacations. Same with showing up to the office. In team meetups, one-on-ones, casual chats — that was the operating principle. Results over hours. Trust over surveillance.

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It sounded right. It felt right. In a small team, it was right.

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Then I closed LinkedIn and got back to work. But the post kept coming back over the next couple of weeks. Not dramatically — just quietly returning while I was deep in something else. He's right. But he's only half-right. And I already knew exactly why.

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Because I've lived this from every angle. Freelancer. Founder of a tight team. Then a bigger team, more offices, more countries. The post wasn't a revelation — it was a clean frame around something I've watched play out in dozens of founder conversations this year alone.

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What "pay for results" doesn't tell you

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Here's what I've noticed: I ask founders all the time how many people are actually on salary. When they say they have ten people, maybe twelve, I ask: How many are actually employees? Usually the answer is three. Maybe five. The rest are contractors or freelancers. That's a normal phase. When you're growing, you can't carry a full team through slow months without bleeding margin.

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Freelancers give you flexibility. They bring specialists you couldn't afford full-time. They make the math work. So far, so good. But here's what the LinkedIn post doesn't say. Most people don't come to work to think like entrepreneurs. They come because they want stability. A salary. Benefits. The guarantee — even if it's conditional — that they can plan their lives. And, at the end, they treat the company as “theirs”.

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But freelancers and contractors are wired differently. They don't see your business as theirs. They've got other clients, their own timelines, their own lives. They deliver what you agreed on. But they don't really care what happens to that deliverable once it leaves their hands. They give you pieces. Not pictures, not direction, not "hey, maybe we should approach this differently because it'll actually help the client more." Just pieces. And why would they?

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And someone has to take those pieces and make them into something. Someone has to notice when one doesn't fit. Someone has to feel what the client actually needs and connect that back to what the freelancer is building. Someone has to hold the picture in their head, week after week. That someone is you. And the longer you do that, the harder it becomes to stop.

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That's the glue.

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The other half of the trap is the people who are on payroll. Without clearly defined roles, without expected outcomes attached to each role, without a system that rewards actual contribution, they slowly become passengers. They stretch estimates. They pad timelines. Anyone inside a system without real expectations eventually drifts toward "less effort, same paycheck." It's not malicious. It's human. They started in “their” company and eventually ended up careless. So the founder ends up in this strange place. Freelancers who deliver pieces but don't push the business. Employees who collect a paycheck but don't drive it. And in the middle of all of it — the founder, holding the picture, connecting the pieces, catching what falls. Making every real decision. Every day. But…

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What the culture is really is

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I remember being terrified of hiring my first person. It was a programmer. Young guy. I didn't know how to manage. I'd been doing everything myself, and hiring someone felt like putting my name on a guarantee. My personal responsibility. What if I made the wrong call? I sat with that fear for a long time. But eventually I did it. And then I did it again. And again. And the more I hired — real employees, with salaries and benefits and office space — the more I realized I wasn't building a company to work more. I was building a place I actually wanted to come to.

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Because when I worked for other people, that's what I wanted. A place with respect. Honest conversations. Where your ideas mattered. Where the founder actually gave a shit about whether you showed up or not.

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Three weddings happened in my company. Between employees who met there. We sent gifts when their kids were born. On birthdays — the kids' birthdays — the team would gather and give presents. One PM told me that what she valued wasn't the salary. It was that she could get on my calendar whenever she needed. That we did weekly updates about where the company was going. That she felt like she was building something that mattered.

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That's culture.

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Not ping-pong tables. Not free snacks. The feeling that you're not just trading hours for money — you're building something with people. And that’s what works with five people. Then starts breaking at fifteen. And what quietly destroys you at fifty.

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What I actually built

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I had freelancers. I had contractors. I had partner agencies. A lot of them, at peak. But in my company, all the key things lived inside.

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Documentation, tools, processes, knowledge, client relationships, the actual thinking about strategy and direction — all of it stayed on our side. The freelancers and partner agencies were the final layer of execution, plugged into a system we owned, not the other way around. And the contractors weren't really "contractors" in the cold transactional sense. Most of them got paid vacations, gifts on birthdays, invitations to company events, sometimes training paid for by the company. The line between contractor and team member was blurred on purpose, because, for me, the culture mattered more than the paperwork.

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None of that worked just because we paid people. It worked because we built around them. Clearly defined roles. Expected outcomes for each role. A system of bonuses tied to real results — personal and company — transparent enough that people could see how their work moved revenue, and how that moved their own paycheck. All tied to a strong culture.

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Here's a small example of what that gets you. When one of our in-house designers got faster — because briefs got tighter, templates got better, review got cleaner — that gain was ours. It went into margin or back into the business. With a freelancer, that gain disappears. They charge per deliverable. Faster means earning less, so they don't get faster. The compounding lives with them, not with you.

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That's the hybrid. Key people inside, on payroll, with clarity and real skin in the game. External execution plugged into your system, not running parallel to it. Knowledge, relationships, and direction — all yours. It's not glamorous. It doesn't fit in a LinkedIn post.

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But it's the version that lets you stop being the glue.

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The LinkedIn founder isn't wrong. Paying for outcomes is smart. But that's only part of the picture. The other part is the structure underneath, and the human investment underneath that — the things that make results actually reproducible without you sitting in the middle of every decision. Rebuilding while keeping clients happy and revenue coming in simultaneously isn't easy. But if you don’t, you stay in the current phase. You're the glue in 2026. You're the glue in 2027. You're the glue in 2028.

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The question isn't whether you can hold it together — you've proven you can. The question is how long your version of holding it together still works, with everything coming: AI reshuffling delivery, clients squeezing prices, the market getting noisier, your own energy being a finite thing. The real risk isn't that you can't hold it. It's that something gives sooner than you planned for.

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You started alone. You got clients. You delivered. You built something out of nothing. That deserves real respect. The next move is admitting the first version of your business was always supposed to fall apart — so you could build the second one.

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One thing you can do this week:

Open your team list. Don't think about loyalty, don't think about how long they've been with you. Just look at the structure.

For each person, ask two questions:

• Are they an employee with clearly defined outcomes? Or someone you're holding together with your attention?
• If they made a wrong decision tomorrow, would your business absorb it, or would you have to fix it personally?

Be honest. The pattern jumps off the page. Because that answer tells you everything about which phase you're actually trying to build.

Hit reply and tell me. I read every response.

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P.S. After I left that comment, another founder jumped into the thread and said something I've also lived: at five people, freedom and trust are enough — feedback loops are too tight to hide anything. At thirty or fifty, freedom without real structure turns into chaos that hides for months before you see it. "Pay for outcomes" is right. The question is whether the outcomes themselves are clear, the handoffs are clean, the quality is repeatable, and the work is actually moving the business forward. Freedom and structure have to grow together. He nailed it.