My First Year Freelancing: Wins, Lessons, and What I’d Do Differently

I didn’t start as a writer.
By Sire Jeep | Philippines, 2025

My first freelance job? Technical support for a U.S. client.

I answered emails and chats, fixed basic tech issues, and worked through the night.
No training. Tight deadlines. High pressure.

I didn’t last long, but I learned something important:

Freelancing pushes you early. You either fold or figure it out fast.

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✅ Win #1: Taking the Leap

That first project made everything real. I earned money online.
It wasn’t much, but it changed what I believed was possible.

🔁 Lesson #1: Know When to Walk Away

Leaving that job wasn’t easy.
But it was the right move.

The stress, imbalance, and lack of growth showed me one thing:

Not every opportunity is worth keeping.

Sometimes, quitting is the smart call.

Source: Unsplash - Nathan Dumlao

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✅ Win #2: Getting a Client in Dubai

My next gig came from a Dubai-based e-commerce brand.
They needed help with admin work, copywriting, and operations.

We jumped in—excited for the potential.

🔁 Lesson #2: Don’t Fall for Overpromising Clients

They said:

• “We’ll increase your pay next month.”

• “You’re part of our core team.”

• “Bonuses are coming soon.”

None of it happened.

We delivered. They didn’t.

Watch patterns—not promises.

Your effort deserves fair compensation.

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✅ Win #3: My First Long-Term Client on Upwork

Then I joined Upwork and landed a Canadian client running a travel blog.
They needed a reliable editor.

I stayed on-brand, delivered on time, and earned repeat work.
That felt like real progress.

Good work travels. A client halfway across the world trusted me.

That gave me confidence and a portfolio I could grow from.

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🔁 Lesson #3: Freelancing Needs Boundaries

Early on, I said yes to everything:

• Late-night revisions

• Weekend deadlines

• No personal time

I burned out fast.

Now, I:

• Set work hours

• Schedule time off

• Say no when needed

Protecting your time isn’t selfish. It’s what keeps you going.

Source: Unsplash – Surface

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Thinking of Starting Your Freelance Journey?

Ask yourself:

• What skills can I offer right now?

• Can I work across time zones?

• Am I ready to learn fast and adapt?

Freelancing isn’t just working from home.
It’s pressure, mistakes, wins, and growth.

You don’t need a perfect plan.

You just need to start.

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🤝 Want Help Starting?

Not sure how to get your first client?

Wondering how to write a proposal or build a profile?

Let’s talk. I’m happy to share what worked for me.

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☕ Support My Writing and Pay It Forward

If this post helped you prepare for freelancing or feel more confident about your next step, you can support my work here:
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Thanks for being part of this journey.