An Unexpected Journey to Freelance


July marked a whole year of freelancing full-time and I want to share some thoughts I’ve had ever since the jump. To give context, I’ll go into a little backstory on how a corporate tech job and a small design studio shaped my decision. This is less about the struggles of freelance over the past year and more about what motivated me to become independent.

Back when I was at IBM, we worked in small teams collaborating on app ideas that would showcase IBM technology. Designers were able to do anything and everything, from detailed product design to playful illustration. Going into the job I knew what areas of design excited me the most but was eager try them all. In the process, there was a healthy balance of collaboration with teammates and owning specific aspects of each project. Months flew by, I learned a ton and enjoyed the team around me.

About a year into the job, our mission evolved past mobile, and eventually into enterprise projects. It was a big transition for the team in a short amount of time, resulting in coworkers looking for new opportunities. Going forward, I wanted to focus mostly on branding and illustration, which would require a change of scenery. After giving it some thought, I began to apply to design studios and ad agencies around town. I had a handful of interviews and met with a bunch of industry folks, but nothing materialized. I had a relentless feeling of being stuck, having a tough time finding that new opportunity.

Looking back, I realize that we had a special group of people. It was a supportive environment and we collaborated well with one another, even when our mission changed the people were the glue that held it together. I took that for granted when searching for the next opportunity. I was so eager to work on projects I was passionate about I overlooked the environment I thrived in. Over the past year, it’s been a challenge working by myself from the home office. I miss collaborating, asking for quick design feedback, and the lighthearted goofs with coworkers. That’s something I think about regularly and I’m looking to improve that in year two somehow.

After about six months of searching, I interviewed for a position as a Design Intern at Helms Workshop. At first, I was hesitant considering an intern position, I already had a good amount of experience under my belt and was looking for something more permanent. When learning about the role, I was told there was the potential to be taken on as a Junior Designer after the internship. I was willing to sacrifice a few months to get my foot in the door, so I accepted.

I was ready for the new challenge and was stoked on the work I’d be doing. The next four months I split my time between design tasks and the usual intern duties, taking on more of a Junior role as I was taking out the trash and making the team coffee. It was refreshing that my design contributions no matter how big or small would be a part of the final product, which was a huge motivator for me. After the internship came to a close, without much of a backup plan I was excited when I was offered the Junior Design position.

I had been told there would be a six-month trial period to determine if it was a good fit. I agreed to the terms but remember it feeling bittersweet, I thought I’d proven my worth already. The following months were a rollercoaster of personal highs and lows with design wins and losses. It was a stressful situation, I felt a lot of pressure not knowing whether I’ll have a job at the end of it. Coming up to the last month, I was weighing my options if I were to fall short. I debated on taking some time off afterward then applying to a bunch of new opportunities. My other option was to give freelancing a shot, something I’ve contemplated down the road after gaining more experience. After poor communication and lack of face time with my boss, I had received one week's notice of not making the team.

I remember it being an emotional time but was lucky to have a support system of friends to soften the blow. I reached out to designers getting any advice and insight on what I should do next. After weeks of downtime and a ton of deliberation, I decided to go freelance. Ultimately I realized that the hard work I put in at IBM and Helm’s was being overlooked, leaving me unsatisfied and me wanting to go out on my own.

In retrospect, there was a lot of positives from my experience at the Workshop. I was able to switch gears and pursue what I’m passionate about. Not only that, but I was able to work directly with clients and learn some vital communication skills, helping prepare me for the freelance world. Most of those clients had cool businesses, it was fun working within their design system and helping out where I could. Now that I have the control, I can decide what clients I want to work for and the projects I want to take on, which is the ultimate perk.

When it came down to going independent, I was confident enough in my skill set but also a bit stubborn about trying something familiar again. I rationalized it, “I experienced a corporate tech job then made the leap to a small design studio, two opposite sides of the spectrum.” Freelance would give me an entirely new perspective on what design as a career could be, even if it lasted a short while. There would be no ceiling to hit, I could shape and build it how I want with fewer politics getting in the way.

Freelance was the healthy change of pace I needed, it has challenged me in so many ways even outside of design. Instead of making coffee for the team, I’m responding to client emails, leading meetings, and blocking out time in my schedule. Rather than taking out the trash, I’m invoicing clients, keeping track of all my expenses, and paying those quarterly taxes. These were hurdles starting out but they feel like second nature now, and to be honest I never anticipated enjoying some of those things, but I do.

In the past year, the formula I’ve had for surviving the growing pains of freelance has been fairly simple. Take things month by month, keep reasonable goals you can reevaluate along the way, and appreciate the progress you do make. Just like at IBM and Helm’s, you can’t plan for everything, you can only do your best and roll with it. Looking ahead in year two, that remains the same. I just need to remember what got me stoked about graphic design in the first place and continue to stay motivated, who knows what’s next.


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FreelanceJacob Cummings