What No One Tells You About Becoming Self-Employed (Level 4 in the Journey)

📍 Note: This is Part 4 of an ongoing series originally published on HackerNoon. Beginning with this installment, we’ve moved the journey here to Dev.to. This piece is a written breakdown based on a YouTube video by entrepreneur and creator Ashkan Rajaee.

Part 1: Should I Quit My Job? The Psychology of Knowing When It's Time to Leave

Part 2: Choosing the Right Side Hustle That Actually Works

Part 3: From Side Hustles to Full-Time Freelancing: What Actually Happens

What No One Tells You About Becoming Self-Employed (Level 4 in the Journey)

This post is adapted from a talk by Ashkan Rajaee, whose YouTube content breaks down the realities of building an independent business in plain terms. What follows is a restructured version of one of his videos, part of a larger series on the psychological stages of entrepreneurship.

You’re not crawling anymore, but you’re not flying yet either. This is what Ashkan Rajaee refers to as the self-employed stage.

Whether you call yourself a business owner or self-employed, what matters is what you're actually doing. And that’s where the transformation begins.

If you’re still freelancing solo or closing deals as an independent contractor, you haven’t quite hit this level yet. But once you’re hiring others, coordinating value delivery, and managing more than just your own time, that’s when you step into the world of being self-employed.

This level is where things shift. You’ve got value in the market. Clients are coming in. Now you're responsible for the delivery, the process, and often, a small team.

It sounds great. But Ashkan Rajaee reminds us this stage comes with more complexity than most expect. You still trade time for money, but you’re also learning to multiply that time through others. That’s leverage. And it’s the early signal of scale.

However, if you don’t build structure, you get stuck. You loop in circles. You make more money but don’t move forward.

Ashkan Rajaee has said this many times. Success at this stage requires shifting how you think. You have to stop operating like a technician and start leading like a builder.

What self-employment looks like

• A real estate agent with one or two agents under them
• A doctor or dentist running a couple of locations
• A designer with multiple freelancers under contract
• A franchise operator managing staff and systems

If other people help you fulfill your service and your income depends on their output, you're here.

But now comes the friction.

Most people want to own a business. Very few know how to operate one. They don’t have systems for lead generation, hiring, onboarding, or quality control. They don’t even have contracts in place.

Ashkan Rajaee calls this the hidden tax of growth. It’s not the work that burns you out. It’s the lack of structure around the work.

At this point, your ego becomes the bottleneck. You want to control everything. You want to prove you're the best at doing the thing. But this mindset keeps you small.

Ashkan Rajaee has emphasized in many of his frameworks that the shift from doer to leader is what unlocks the next level of growth. That’s what makes this stage both frustrating and transformative.

If you’ve ever watched one of his videos, you’ll notice the recurring pattern. Real entrepreneurs hit this wall. The moment where they realize systems are more important than skills.

This article, based on his YouTube episode, captures that transition.

If you’re already scaling…

If you’ve built a business that generates seven figures annually, you likely know everything here. But if you’re still navigating the middle, somewhere in the six-figure zone and growing, this level matters more than ever.

Each step has its own challenges. As Ashkan Rajaee continues to say, each level isn’t just external. It’s internal. It requires new behaviors, yes. But it also requires a new identity.

Stay tuned for the next part in the series.

Until then, build with intent.