How to Thrive as a Freelancer When the System Isn’t Built for You

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Sovereign freelancers

One of the hardest lessons for freelancers to learn is that the system we’re working inside isn’t exactly optimized to help us succeed.

Platforms like Upwork or Fiverr? They’re designed to maximize their own profits, not yours. Payment processors? They’ll hold back your money if it protects them, even if it hurts you. Corporate procurement systems? They’re built to squeeze the most out of contractors while giving the least in return.

Even governments, when you think about taxes and regulations, aren’t exactly bending over backwards to make life easier for independent workers.

At first, this can feel overwhelming. Almost like the whole world is tilted against you. And in some ways, it is.

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When the AI’s story is better than your own, it’s time to spill the ketchup.

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imperfection beats AI every time

I’m working on a whole new project. Pretty much an entirely new business.

To help me build everything, I’ve been using a Custom GPT, which has a knowledge base of everything I have been doing for the project so far. In other words, it knows as much about the business as I do.

For fun, I asked it to make up an origin story for the company. Something fun, and maybe a little tongue-in-cheek.

Twenty seconds, later I had the full origin story.

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Introducing Sovereign CoPilot — An AI Assistant and Coach for the Sovereign Freelancer Course

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This isn’t like my usual posts. More like an announcement. And it’s a BIG one.

And yes, it’s a pitch too.

I just trained and integrated an AI assistant into the Sovereign Freelancer course.

Student enrollment now includes the Sovereign CoPilot — an always-on guide as you learn, build, and grow your freelance business.

Here’s what the Sovereign CoPilot does…

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Why Sovereignty Is the New Success Metric for Freelancers

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Freelancer working in her office with a poster on the wall that says "I am Sovereign"

We live in uncertain times.

Political discourse seems more divisive than ever.

Many world economies are in a state of turmoil.

And the rise of AI threatens the careers of knowledge workers everywhere.

It’s little wonder so many freelancers feel concerned about their future. How can you grow and thrive in the face of so much uncertainty?

First, let’s diagnose the underlying cause…

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As a freelancer, how much attention do you pay to your health?

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As freelancers we work alone.

Because we work alone, our health matters a lot. We don’t get paid sick days, and we don’t have any company health insurance.

And I’m not just talking about something like a case of the flu that keeps you away from your desk for a full week. You can plan for maybe a couple of weeks a year when you feel too unwell to work.

But how about the number of days when you do sit down to work, but are not feeling well enough to give 100%? Or even 50%?

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