It all began with finger painting praise in preschool and evolved into a lifelong exploration of design, apparel, branding, and entrepreneurship.
Cole shares the real journey behind becoming a full-time designer and illustrator. From selling hand drawn t-shirts in fourth grade to working with major brands, to navigating new territory with AI, his story is a reminder that careers are built through passion, persistence, skills, and believing in the value of your work.
Q: Can you take me back to the beginning of your creative journey?
I like telling this story because it brings up the question of whether you are born with artistic talent or if you learn it over time. I honestly feel like the only reason I am even in this space is because my preschool teacher told my parents my finger paintings were better than the rest of the class. Those little reinforcements like “you are good at this” were enough to propel me forward.
I was always creative as a kid. It was the only thing I was ever good at and I was very entrepreneurial. I always wanted to do art but did not know how to make it a career. The beginning of everything really started with drawing on t-shirts and realizing you could actually make designs and put them onto real shirts. That spiraled into a few apparel businesses, then working for surf and skate companies like Element, Hurley, and O’Neill. After college, I worked at a creative agency, but it was more real estate brochures than creativity. That helped me realize I did not want to do that forever and that logo and branding could be a real opportunity.
Q: Did you go to school for graphic design?
Yes. I went to the University of Arizona, which was more of a degree in partying than anything else, but I did get my fine arts degree. I used most of my time there to develop a clothing brand for fraternity and sorority apparel, which ended up being really successful.
Q: You started in apparel. What got you interested in it?
My dad was in the apparel space, so that always inspired me. But really, apparel was a means to keep making art. Being a traditional artist is a harder business and I was trying to figure out how to make art sustainable. Then I realized design is a great career path and apparel helped with that.
Q: You do apparel, branding, packaging, and illustration. What does a normal day look like for you?
Working for yourself means you make your own structure. I never know what project is coming in. One day it can be a logo, the next it can be packaging or apparel. I honestly enjoy that variety because too much of one thing eventually gets stale. A day in the life is simple. Get up, drink coffee, make art, go to sleep.
Q: What did the early days of job searching look like after college?
Relationships are huge. If I could give advice to anyone graduating, your first job will most likely come from your relationships. I would also say that social media presence matters more than having the perfect portfolio. The second I realized you should put out the work you want to receive, everything changed.
Q: When did you start growing a following on your social media?
In the beginning, you think you need the work to get the work. But it is actually the opposite. You need to create your own passion projects and put them out there because social media is your new portfolio. When I focused on the work I enjoyed most, people started asking for it. That was the lightbulb moment.
Q: What are some projects you loved working on?
Choosing a favorite project is like choosing a favorite child. One of them was an Australian beer brand, Better Beer. Another was Ripped Jerky, and they are crushing it. There are so many. But honestly, my favorite project is always the next one because it gives me an opportunity to grow and make something better than the last.
Q: Are clients finding you or are you doing outreach?
Ninety-nine percent through social media. The other one percent is random. About half of my business comes from recurring clients, and the other half is new people finding me online.
The hardest thing for a designer to do is design and brand yourself, you can no longer just be designers. You also have to be a content creator, photographer, video editor, everything. I was not comfortable with that at first but I got used to it. And I remind myself that everything I want is on the other side of cringe. Most people never start because they are afraid of looking cringe. But that is what stops people from growing.
Q: What are your thoughts on AI? Do you use it in your work?
I think AI is neutral. There is good and bad. But it has actually helped my business. Before AI, people would come to me asking for just a logo. Now with ChatGPT, the value of a logo is almost zero because anyone can create it in minutes. So now people coming to me, with an exploration of a logo but they want something better and I show them what a brand identity is. AI ends up reinforcing the value of professional design. It has been like my sales manager in a way.
Q: For someone curious about Graphic Design, where should they start?
I would ask them a lot of why questions because I need to understand what success looks like for them. Do they want to make cool art, make a lot of money, or be their own boss? Those answers change everything.
If you are just starting, I would introduce you to Adobe Illustrator. It is the leading program. And this is the easiest time in history to learn graphic design. YouTube, tutorials, creators, it is all accessible. You can sharpen your skills so fast.
Q: Are there steps Designers can take to get ahead or stand out?
I wish there was a short cut, I think the biggest reason people fail or stop is because there is a huge gap between what they know is good and what they can actually create. So when you first start, you are learning the program and it's really frustrating. Bridging that gap takes time. So I would just say don't expect those shortcuts and eventually you'll get better. I'm so much better than I was day one. I hope I'm twice as good in 10 years than I am today. As long as you give those yourself the grace to be able to start and improve, then it'll be a good path for you.
Q: Do you have advice on working with clients?
Yeah, I would say stay as curious as possible. If you go into a meeting and you ask the why and what success mean to them in the next 1-5 years, then your pitch gets 10 times better. I can talk directly to why everything I'm about to give you is going to solve those issues directly and so the communication part really has to do with understanding what their needs are and then catering your solutions to do exactly that.
Q: How should someone decide between freelance and working for a company?
I always tell people to choose the least risk option. I had external pressure telling me to get a stable job, so I did. I took a pay cut to work at an agency, but that experience helped me make the best decisions later.
My advice is to get a job first, learn, get real experience, and build your personal brand on the side. That makes for a smooth transition. I do not believe in “the leap.” I believe in building something while you still have stability. And the most important part is to just start. Make decisions. Put something out there.
Q: When did you realize art was more than a hobby?
Probably in fourth grade. I hand drew t-shirts and hats with Sharpie on my parents’ counter and sold them at school. I made a couple hundred dollars. People were stoked, I was stoked, and some of my friends still have those shirts. That was the moment I realized someone would pay for something I created. It changed everything.
I also learned Adobe Illustrator at twelve. I have almost twenty years of practice now. If you think my art looks good, it's because I have been doing it for a long time.
Q: What is your message for someone who wants to pursue this career?
I am stoked for them. This is a great career. I love my job. It can be lucrative and there is room for everyone. There is so much work to go around. If you are good at what you do, it is rewarding. If you are considering it, you should do it.
🔑 Key Takeaways
Put out the work you want to receive and let social media work for you.
Cole’s career transformed when he realized that posting passion projects leads to the clients and opportunities you actually want. Social media is a portfolio, not just a place for updates. Consistency and intention matter.
There is no shortcut, but skill grows with time and patience.
Every artist faces the gap between their taste and their current skill level. Those who push through it improve faster than they realize. Grace, repetition, and long term dedication always win.
Build stability before you take risks.
Instead of a dramatic leap into freelancing, Cole emphasizes a slow and strategic shift. Learn from full time work, earn while you grow, and transition when you have proof that your creative path is viable.
AI will change the industry, but strong creative fundamentals still matter.
AI can generate quick results, but it cannot replace intuition, taste, or brand understanding. Designers who embrace the tools and deepen their craft will stand out even more.
Start now, even if it feels cringe, because everything you want is on the other side of showing up.
Growth requires visibility. Artists who succeed are not the ones who never feel cringe. They are the ones who post anyway, share anyway, and keep improving in public.
📢 Check Out the Full Interview
Watch the full interview with Cole Friedman below or youtube @ainahcommunity
Explore Cole's work:
IG: colefdesign
