I’ve always had an entrepreneurial mindset, but right after law school, I spent a year working at a law firm in Indianapolis. Early on, I realized I wanted my career to revolve around doing what I want, when I want, with whom I want, where I want and minimizing anything that doesn’t align with that. Being an employee, made the Sunday Scaries real, I didn't control my time and law firm life didn’t feel like the right fit for me.
I moved to Chicago looking for a more dynamic, worldly experience, though I was still working remotely for the same firm, before it was the cool thing to do. About a year later, COVID hit. Many businesses were closing and layoffs were happening, but at the same time, a wave of people were launching passion projects and new businesses fueled by extra down time, unemployment and stimulus checks.
It was during this time that my cousin launched a new business and kept asking me to help her file a trademark. I was hesitant at first, even though I had studied trademark law in school, I hadn’t filed one in years. Eventually, I agreed, and once I did it, I realized it wasn’t so bad, it came back like riding a bike.
I remembered that I created a Fiverr account years prior after seeing an ad while in NYC, but I never used it much. I decided to list a trademark service, thinking it might help me cover a few bills. At the time, I wasn't making much from my firm job because I worked mainly on contingency cases, and courts were closed.
Within a few months, Fiverr went from helping me pay small bills to covering all of my bills, and within six months, I was exceeding my pay at the firm. Once I saw business was sustainable, I built out my systems and transitioned into "soft quitting" the firm (only working there as of counsel). By the one-year mark, I fully left to run my own firm full-time, supported heavily by Fiverr.
Since then, freelancing has been life-changing. Fiverr gave me the stability and freedom I needed. Because of that, I’ve traveled to more than 40 additional countries, bringing my total to over 60, with a goal of reaching 100 by the end of the decade. I’ve bought a home, made major investments to build long-term financial security, including building a hotel in my favorite beach town in the world, and built a thriving law firm.
While I now run my own practice with a small team, Fiverr has been a cornerstone of my legal career’s success. It gave me the ability to build a business on my own terms, invest in my future, and live a lifestyle I never thought was possible for an attorney, nor for me.
Looking back, freelancing didn’t just change my work, it changed my entire outlook on what my career could look like. It gave me time, ownership, and opportunities I didn’t know existed coming out of law school. There are many paths to your definition of success. If you're thinking about making the leap or just want to do things your own way, I think my story is one of many that shows you can deviate from the beaten path.
A few personal highlights:
- I've been recognized as a trusted attorney by thousands of clients in over 80 countries.
- I’ve maintained over a 99% satisfaction rating across more than 2,800 orders.
- I've been able to help entrepreneurs and businesses all around the world protect their brands — many of whom are first-time business owners, just like my cousin.
- Fiverr helped me build not just a career, but a life of true freedom and ownership.
- I've sang from the rooftops to countless friends, family and social media followers how freeing freelancing can be.
A few tips I've picked up along the way:
- Set Boundaries: Even I struggle with this still, but responding to messages at midnight and working weekends might impress a few people, but it can set the wrong tone and burns you out fast. It's easier to do when business is thriving but make them clear early on and clients will respect it.
- If you're too busy, your rates are probably too low: This was one of my key lessons this year. If you're busy all the time but still stressed about money, you're probably not charging enough. Price for the value you provide, not the hours. Low rates attract high-maintenance clients.
- You can't please everyone: Some people won’t like your rates, your style, your turnaround, your process, or even your work. That’s okay. The quicker you can filter those people out, the better you'll do and feel.
- Feedback is data, not your identity: A bad review or difficult client isn't always about you. Learn from it, keep it professional and move on. Again, you can't please everyone, so if you receive one bad review but have 500 positive ones, it's likely you weren't the issue.
- You became a freelancer for a reason: Most of us didn’t choose to freelance to work more (although it can happen). Don’t forget why you started. Be mindful of protecting your time, energy, and peace.
- Don’t wait on fate: Most clients don’t know what else you offer them unless you let them know. After a successful gig, you can casually suggest an additional service: “By the way, a lot of my clients who buy X service also benefit from Y service. Let me know if that’s something you’re interested in.” Upsell without being pushy.
This article was written by Derrick, founder of Morgan Business Solutions, a law firm providing full-service trademark representation. With almost a decade of experience, Derrick empowers entrepreneurs to safeguard, defend, and commercialize their brands. Explore Derrick’s legal services on Fiverr Pro here. 
