14 Years of Freelancing: The Good, The Bad & The Ugly

How I went from $1 gigs to Fortune 100 clients, two burnouts, and a business that finally works for me.

When I created my first freelance profile on Upwork back in 2010, I had no idea it would lead me into a life I’d only seen in American movies.

I didn’t start out of passion, first it was curiosity, then necessity.
I thought success meant constant growth. Every year should be bigger, right?

Well, actually some years teach you how to earn, and some teach you how to live.
Here’s what 14 years of freelancing really looked like: the good, the bad and the lessons I learned the hard way.

---

Illustration by Adriana Danaila

---

The Baby Years (2010–2013)

Curiosity > Confidence
I was just figuring out what freelancing even was.
Experimenting. Guessing. Making $1 gigs baby steps.

2010 — $0
Created my Upwork profile. Landed zero gigs.

2011 — $200
First freelance gig ($1!). Proof that someone would pay me.

2012 — $2,000
Still figuring out the platform while working full-time.

2013 — $12,250
Started outearning my salary, so I quit my job.
Had no plan, just momentum and the gut feeling this was going to work.

💡 Lesson: Start before you’re ready. Curiosity pays better than waiting for “perfect.”

---

The Toddler Years (2014–2016)

Chaos > Boundaries
I was walking on my own, but with zero direction.
Tried to say yes to everything. Learned what burnout smells like.

2014 — $16,500
Said yes to every project (terrified to lose momentum) → burnout #1.

2015 — $14,700
Raised prices → fewer hours. Still afraid to slow down.

2016 — $12,600
Same rhythm. Steady but flat.

💡 Lesson: Overbooking isn’t ambition, it’s fear disguised as productivity.

---

The Teen Years (2017–2021)

Experimentation > Identity
This was my “Who am I even?” phase — acting, traveling, freelancing half-time, getting a taste of my independence.

2017 — $6,700 (+$5,000 from acting)
Creative detour: switched focus to acting. Put freelancing on pause.

2018 — $13,300
Back to design gigs. Slower rhythm. Lived two months in Bali.

2019 — $11,200
Started pet sitting and traveling around Europe. Work wasn’t the focus.

2020 — $21,600
Felt guilty for the “chill” years → worked my ass off → burnout #2.

💡 Lesson: Don’t cage yourself in 5-year plans. Life and career should flow together — giving each other space to shape what your path becomes. Creative careers need creative lives. Otherwise, what would you even be drawing from?

---

The Adult Years (2021–2025)

Systems > Survival

Finally learned to run a business and how to laverage all my experience and side hobbies. I learned what to say no to, how to build income streams, and how to rest without guilt.

2021 — $25,400
Registered as a business (up until now, I was just an individual professional).
Started studying the things no one teaches creatives: money, value, and positioning.

2022 — $106,500
BOOM!! Upwork + Fiverr + first Fortune 100 client + first off-platform client.
All that learning and investing in myself finally paid off.

2023 — $66,200
Post-COVID freedom. Traveled more, worked less.

2024 — $54,500
Bought my apartment. Took a break to focus on renovations, no guilt this time. It was an investment in future creativity.

💡 Lesson: Take yourself seriously as a business. Stop working out of passion alone — start working out of usefulness. And remember: to make money, you need to spend money: on your education, your mindset, your wellbeing, and on creating a space that fuels your creativity.

---

The Wise Elder Years (2025 and beyond)

Freedom > Growth

This next phase is about building assets, so the business grows even when I take a step back.

2025 — $47,700 (so far)
Working half-time hours on commissions. Building my personal brand, sharing what I know and creating content on LinkedIn and Substack.

Goal for 2026:
Build 6 new income streams as a creative:

• Brand Sponsorships

• Affiliate Links

• Merch

• YouTube

• Speaking Gigs

• Newsletter

💡 Lesson: Freedom comes from multiple safety nets.
The goal isn’t to escape work, it’s to make it work for you.

---

Why do I think I can pull it off?

Because I’ve seen others do it.

If there’s one thing I want you to take from this, it’s this:

If I could do it, you can too.

I’m not more talented or special, just stubborn enough to keep showing up.
The work is hard. No sugarcoating it.

But that’s a good thing. It means less competition for the ones who stay consistent and think long-term.

So take your time. Enjoy the ride. Appreciate where you are, because every step counts. You’re already closer to your dreams than you think.

I trust you,
Adriana