10 Years Since I Started Freelancing Full-Time (My Story and What I Learned Along the Way)

Ten years ago, on May 15, 2015, I left my job to start freelancing full-time.

Over the past decade, I’ve led high-impact design projects for some of the world’s most recognizable brands, including Marriott International, Bloomberg, DHL, Porsche, American Express, and most recently, Instacart.

Along the way, my work and insights have been featured in major publications like The Wall Street Journal, Adobe, Dribbble, Freelancers Union, WeWork, Honeybook, GoDaddy, and more — helping me share what I’ve learned with a broader audience of freelancers and creative professionals.

I built a six-figure freelance business from scratch, started my own company, and helped thousands of freelancers grow careers they actually enjoy.

But my story doesn’t start there — and none of that happened overnight.

Freelancing success isn’t found. It’s forged by consistently making smart decisions at the intersection of discipline, determination, and discernment. I had a willingness and determination to figure things out as I went and it worked.

This milestone isn’t about “making it.” It’s about celebrating the day I chose to bet on myself, the years before, and everything that followed. This is my story, with the level of detail you rarely hear from experts — so I hope you enjoy it.

✨ Freelance Insight

Freelancing success isn’t found. It’s forged by consistently making smart decisions at the intersection of discipline, determination, and discernment.

How It All Began (2008)

I studied New Media Design & Imaging at R.I.T. from 2008 to 2012. During those first few semesters, I started using what I was learning to design websites for real people — mostly friends, family, and classmates. These projects were either free or a few hundred dollars. I had no experience and barely any skills.

My first client was a non-profit who gave me a small grant. Then it was a classmate who needed a portfolio website. Then the family lawyer needed a new business website. My first clients came from my immediate network.

I didn’t realize it at the time, but I was already freelancing.

Almost immediately, I realized these clients didn’t want Photoshop files, they wanted working websites. So, out of necessity, I taught myself how to code.

Lets not gloss over that sentence too quickly.

This was a formidable challenge. I learned how to code my designs while the projects were happening. I can’t endorse this strategy, but it underscores how much fun I was having. Paying clients are also highly motivating, so I worked long days doing anything I could to bring those Photoshop files to life.

I quickly fell in love with the entire process: finding clients, negotiating pricing, sending contracts, designing and coding, collecting testimonial, and adding the project to my own portfolio website when I was done.

And being in control of it all? I had never experienced anything quite like it.

In the early days, I said yes to anyone who would hire me. I took on small projects for little or no money just to learn and have fun.

Getting someone to hire me for my skills and expertise was just as exhilarating as collecting the paycheck. I wasn’t thinking in business terms, I just really enjoyed the process. Sometimes the projects worked out, and sometimes they didn’t. But I kept going and learned from every experience.

Much to my parents dismay, I never got a job in college. The available on-campus jobs felt like such a waste of time when I was so captivated by the new skills I was learning. I was determined to make money freelancing instead.

By the time I graduated, I had made about $10,000 over four years. That’s not enough to live on. In fact, that’s only $2,500 per year or $67 per school week. Looking back, I’m not quite sure how I survived. I had summer jobs and internships, but my freelancing journey was hardly a success.

My biggest projects to date were $500-$1,500 and my rate was somewhere in the $20-$30 per hour range.

If freelancing full-time was my goal, I probably would have given up at this point. Thankfully, I never thought about it this way at the time. I was having fun, learning a lot, and making extra money on the side.

Full-Time Employment (2012)

From 2012 to 2015, I worked full-time at a design agency like most of my peers, but I kept freelancing nights and weekends. I spent the majority of my free time on my freelance projects and frequently worked late into the night. It wasn’t because I had to, it was because I was having fun!

Freelancing full-time was never a consideration at this point. I loved my job. It was a small web design and development company and I had a lot of influence. Every day I learned more about the business side of web design, but I frequently questioned why we pitched projects the way we did and why we couldn’t raise our rates.

✨ Freelance Insight

I wasn’t freelancing full-time yet, but I was learning how to run a business without realizing it.

I wanted more control over the process, the pricing, and my own income. After a while, I started to realize the company wasn’t on a growth trajectory. My instincts were sound because sadly, the company closed for good several years later.

So I started leaning into freelancing even more. After all, what’s the risk? I had a full-time job if I ever messed up a project pitch or had a client refuse to pay me. This was the perfect time to experiment and figure things out.

My Lightbulb Moment (2014)

I think we all have our lightbulb moments — when we see something from a different perspective that changes the way we think or approach a problem.

For me, that moment was when I heard Brennan Dunn talk about positioning for the first time. Up until that point, my freelance website was little more than a student design portfolio. All throughout college I had kept updating it when most of my peers didn’t. I redesigned it once or twice a year as I learned more about design and prepared for graduation.

It was all about me, my work, and my successes (which is ideal when you’re a student looking for a job). But after learning about positioning, I realized how backwards this approach was for a freelancer looking for a client.

My portfolio website was my only sales tool — and I’d been using it to talk about myself instead of focusing on my clients. So I redesigned it (again) and re-wrote all the copy to speak directly to their goals, challenges, and outcomes. I positioned myself as a designer who could help them solve a business need, not just a designer who could make pretty graphics.

That single shift changed everything.

New to freelancing? Start here with my FREE 100+ tip guide.

Price your services, find better clients, and avoid beginner mistakes all in one clear, practical book.

Get the free book

My freelance clients got better. The projects got bigger. I raised my rates slowly and intentionally. Eventually, I landed a couple of long-term, high-value retainers with early-stage startups — and 7 years into freelancing, I finally hit a crossroads.

Leaving My Full-Time Job (2015)

I couldn’t take on more freelance work without burning out. My nights and weekends were at full capacity. I had a choice to make: stay at my job and turn down freelance work, go part-time, or transition to full-time freelancing.

My risk-averse plan was to go part-time at my job, but then something unexpected happened. Two clients I had been negotiating with said yes on the same day. Combined, their projects were worth more than my annual salary, but there was no way I could do it all.

At the time, I was planning to get married and buy a house, so this was not the ideal time to be making potentially risky, life-altering decisions. But I knew it was the right thing to do. I had a healthy savings and worst case scenario I knew I was more than qualified for another full-time job.

May 15, 2015 was my last day of employment. It wasn’t impulsive. It was a strategic, well-planned transition backed by experience, savings, and signed contracts. That decision marked the beginning of a new season — one that would shape the next decade of my life and career.

✨ Freelance Insight

The decision wasn’t impulsive. It was a strategic, well-planned transition backed by experience, savings, and signed contracts.

Full-Time Freelancing (2015-2021)

From there, I kept refining my positioning, improving my website, and landing higher-quality work. My portfolio did most of the heavy lifting, bringing me bigger and better projects on a regular basis. During these years, I did freelance design work for Bloomberg, Marriott International, American Express, DHL, Facebook, and Instacart — all of which were leads brought in through my website.

I also did design and development projects for many early-stage startups. Some of these turned into ongoing retainers lasting months or even years, which provided long-term predictable income — the holy grail of freelancing.

My success was starting to get recognized. I was featured in major publications like The Wall Street Journal, Adobe, Dribbble, and GoDaddy, appearing on podcasts, and doing guest interviews. I started this blog, sent my first newsletter, and began creating products and resources for freelancers.

My client work won 5 international design awards. I hit my stride and had real momentum. Over the next few years, I worked harder than ever.

New to freelancing? Start here with my FREE 100+ tip guide.

Price your services, find better clients, and avoid beginner mistakes all in one clear, practical book.

Get the free book

In 2018, I formed my S-Corp and officially launched Matthew’s Design Co. to better position myself as a business, not just a solo freelancer. That shift helped me land the two largest non-retainer projects of my entire career — both 12-month contracts well into the six-figure range.

I outsourced all of the development to two trusted developers and personal friends while I handled the client interactions, project management, and design work. This was my first experience with subcontracting and it went quite well.

The growth was steady and sustainable, but over time, I realized I had hit an income ceiling. I was earning about the same amount every year and couldn’t earn more without expanding my team.

I was at another crossroads: scale my business or stay solo and maintain my current income level.

Joining Instacart Full-Time (2021)

In 2021, Instacart hired me as a freelance product designer for a 6-month engagement. They wanted me 40-hours a week. Normally I’d never agree to that. I only worked a max of 20 hours per week for a single freelance client to ensure I had multiple income sources.

But as fate would have it, I just fired another client so my schedule was clear for the next few months. During those 6 months working for Instacart, my design manager asked me (gently, but persistently) if I’d consider joining full-time.

I had to be honest — I had no intention of going back to full-time employment. I just spend the last 7 years building my own company. But I genuinely enjoyed the team, the work, and the income. It took a little time to see it, but this became a third option I hadn’t considered yet.

By now I had been freelancing (at least part-time) for about 12 years. I knew I had hit a ceiling both financially and mentally. Maintaining a high freelance income took a lot of effort. My wife and I were planning to start a family. For the first time in years, stability felt like freedom.

✨ Freelance Insight

For the first time in years, stability felt like freedom.

The thought of a stable paycheck, company equity, working with a team, signing off at 5pm, never working nights or weekends, and subsidized health insurance was compelling. It felt like what I needed in the next season of life.

So in November 2021, I joined Instacart full-time and continued freelancing on the side for two more years before tapering it off entirely.

Present Day (2025)

As of May 15, 2025, I work full-time as a Senior Product Designer on the Instacart Business team. I have a beautiful life with my family, and a quiet sense of gratitude for the road behind me. I’m not freelancing right now — and that’s okay. I will again someday. But for now, I get to look back and reflect on everything that decision taught me.

What’s really stayed with me after 15+ years freelancing?

Looking back on 15+ years of freelancing, it’s easy to focus on the big milestones — quitting my job, landing big clients, and starting my company.

But the real growth happened in the quiet moments.

The client calls that didn’t go as planned. The proposals I rewrote ten times. The risks that paid off (and the ones that didn’t). The lessons that stuck with me weren’t always obvious at the time. They revealed themselves slowly through experience, reflection, and repetition.

New to freelancing? Start here with my FREE 100+ tip guide.

Price your services, find better clients, and avoid beginner mistakes all in one clear, practical book.

Get the free book

Here are 10 lessons I’d like to share from my experience as a freelancer:

1. Build before you leap
Full-time freelancing doesn’t require a dramatic exit or perfect timing — it just needs a solid foundation. I made my mistakes when the stakes were low, and that made all the difference when it was time to go all in.

2. Treat your website like your best client
Every redesign brought more clarity — not just to how I looked, but to how I talked about the value I provided. My site didn’t just show off my work. It sold it for me, over and over again.

3. Price reflects confidence, not just skill
Higher rates don’t come from a calculator. They come from knowing your worth and communicating it clearly. I raised my prices when I started believing in the outcomes I could deliver — not just the hours I put in.

4. Opportunities come from being visible, not pushy
Some of my best projects came from casual conversations, not sales pitches. When you’re generous with your work and clear about how you help, the right people start finding you.

5. Process is what makes your business sustainable
Good design isn’t enough. I needed structure (proposals, timelines, expectations) to stay sane and serve clients well. Once I built systems, everything got easier.

6. Great clients give you more than money
The biggest check doesn’t always mean the best project. A client who trusts your process, respects your boundaries, and values your input is worth more than any one-time payday.

7. Freelancing has seasons — and that’s healthy
Some months I sprinted. Other times I rested. Learning to embrace those cycles (instead of feeling guilty) kept me from burning out and helped me build a business I could actually enjoy. Growth doesn’t mean constantly accelerating. Sometimes it just means staying aligned with your life goals.

8. You can outgrow a great season
Freelancing full-time was a season of growth, freedom, and success — but even great seasons have an end. Walking away wasn’t giving up. It meant I recognized what I needed next — and had the freedom to choose it.

9. Thinking like a business changes everything
Forming an S-Corp didn’t just change my tax structure — it changed how I saw myself. I wasn’t “just a freelancer.” I was running a company, and my clients responded accordingly.

10. Consistency is more powerful than any hack
There’s no secret formula. The most valuable thing I did was keep showing up, refining my process, and trusting that small improvements would add up over time. And they did.

Ten years later, I still believe freelancing was one of the best decisions I’ve ever made. Not because it was easy — but because it gave me the freedom, skills, and clarity I needed to build a business on my own terms.

The point of this story isn’t that you should freelance full-time. It’s that you don’t need to wait for permission. You don’t need to hit a magic number of years, followers, or income before you take your next step.

You definitely don’t need the perfect portfolio website.

Freelancing is rarely about “making it.” It’s about designing a career that supports your life — not the other way around. If you’re standing at a crossroads like I was in 2015, I hope this gives you the clarity and courage to move forward. Not with panic, but with purpose.

Start where you are. Build on what you know. Stack your wins. Then make the decision that’s right for you — not for Instagram, not for your peers, and not for the version of you from three years ago.

You might surprised how far that one smart, strategic decision can take you.