From $0 to $2K+ in Three Months

A real Upwork case study on pricing, positioning, and confidence

A few months ago, Katerina — who hadn’t been paid for design work from late 2022 until September 2025 — saw one of my posts about my Upwork earnings.

Rather than dismissing it as luck, she thought, “If she did it, I can do it too.”

What followed unfolded faster than she expected.

You can read her version of the story → here
And below is the same journey — from my perspective. 😉

---

STEP 01: Understanding where to start

When we first spoke, Katerina wasn’t lacking skills, she was mispositioned.

• Title: Framer Expert

• Hourly rate: $25/hr

Here’s the problem:
On platforms like Upwork, “Expert” signals $80–$120/hr.
At $25/hr, it doesn’t read as a bargain, it reads as confusing, if not even scam.

So we fixed the signal first:

• Expert → Specialist

• $25/hr → $40/hr

Instantly more believable. More aligned with client expectations.

This is the part most freelancers skip — and the reason they stay stuck.

---

STEP 02: Finding what actually differentiates her

Her bio originally opened with:

“For me, design has always been about people, not just pixels…”

Nice, but generic.

Her real differentiator was hiding in plain sight:
👉 15 years of sales experience

So I told her:

Push your differentiator from line one.

She changed the opening to:

“With 15 years of sales experience behind me, I understand what actually drives business growth and how to connect that with compelling design.”

Now she wasn’t “another Framer designer.”
She was a designer with a business mind.

---

STEP 03: Letting the market shape the message

As she started getting orders, a pattern appeared.

Most clients weren’t asking for custom design.
They had bought Framer templates — and were stuck trying to customize them.

So when she later raised her rate to $60/hr, we rewrote the bio again — this time around a clear pain point:

“You bought a Framer template and now it’s a nightmare to customize and launch? I’ll populate it, create the pages you need, add CMS, forms, embeds, connect your domain, and launch your site in 4 days.”

Same skills.
Clearer problem.
Higher value.

---

STEP 04: Use the platform like it’s a platform (not just a job board)

Most freelancers treat Upwork like a place to send proposals.
That’s leaving money on the table, so we focused on using every visibility lever the platform offers.

A. Upload an introduction video

This matters more than people think. On platforms crowded with spam and low-effort profiles, letting clients see you and hear you builds trust fast.

💡Tip: Don’t mention Upwork in the video.
You’ll want to reuse it on Fiverr, your website, or LinkedIn later — and future you will thank you for not creating extra work. 😉

(Yes, I made this mistake. No, I still haven’t re-recorded mine for Fiverr.)

B. Set up fixed-price packages using “Projects”

This is one of the most underused features on Upwork.

By creating fixed-price offers:

• You show up in more places on the platform

• Upwork pushes your profile both through proposals and product-style listings

• You get analytics: impressions, clicks, and orders

Which means you’re no longer guessing.

You can see what titles work, what offers convert, and improve them over time — like a business, not a lottery.

We adjusted her thumbnails, clarified the three-tier pricing, refined the description, and added a clear upsell strategy.
That’s when her first Project order came in.

---

Where is she now (3 months later)

• 9 completed jobs

• 4 contracts in progress

• $2K+ in earnings

• Rising Talent badge

• Confidence — in her skills and her future

And yes, she would have figured this out on her own.
But it would’ve taken months — maybe years — of trial and error, self-doubt, and a real risk of giving up.

For context: my first Upwork gig was $1.
Katerina is already ahead because she skipped steps.

---

Where is she heading

You can check Katerina’s profile → here.
You’ll notice her earnings are currently set to private.

This is intentional.

Early on, she priced projects lower to build momentum.
Over time, that created a mismatch:

• Past projects at $100–$200

• Current offers at $500+

• An hourly rate that no longer matched the visible history

The signal was off. So she removed it. Within 24 hours, she already had 4 projects in discussion. Before that, clients were opening proposals and starting conversations but often hesitating.

The visible pricing history didn’t align with the offers she’s selling now.
Once the mismatch disappeared, so did the friction.

For now, she’s keeping her earnings private as an experiment, focusing on larger, better-aligned projects, and letting her positioning do the work.

---

Why I am sharing this

This his isn’t a one-time setup where you flip a switch and suddenly succeed. This is a business.

You experiment. You test. You adjust your strategy as you go. But getting your foot in the door is the most important step to focus on. Once that happens, the rest starts to unfold naturally.

I want to help you with that first step, so I’m hosting a live workshop:

The $1K/Month Micro-Gig Blueprint
How to build sellable offers on Upwork & Fiverr — and prepare for 2026
📅 Dec 17 · Live on Zoom · Recording included

If you’re tired of guessing, over-preparing, or waiting to feel “ready” —
this is for you.

Access Link → here

​Note: While this workshop is tailored primarily for illustrators, the insights and strategies will be valuable for other freelancers as well.

As a thank you for supporting this Substack space, all subscribers get a $10 discount with the code GENTLEHUSTLER.

See you there!

Adriana