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My Journey Through College, Design Agencies, and Freelancing

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I’ve been fortunate to have taught 3 web design and development courses at the Rochester Institute of Technology (my alma mater) as part of the New Media Design & Imaging core curriculum — in person, with about 40 students per class.

In 2016, one of my students, Lakera Davis, asked to interview me for an assignment.

Her thought-provoking and inspiring questions got at the heart of my college and career life to reveal the path that led me to where I am today. I want to share our conversation with you in hopes that it will inspire you to recognize your passions and pursue your dream career.

What made you decide to major in New Media Design? Why did you choose RIT (Rochester Institute of Technology)?

I like to think that even though I chose RIT, the New Media Design program chose me. It sounds cheesy, but it’s true. Like most students who take the SAT’s in high school, I got tons of snail mail from colleges and universities around the country.

I chose RIT over hundreds of other schools based on nothing more than the quality of their brochure, website, and geographic location. It looked like a great school with a variety of interesting majors, so I scheduled a visit.

I originally applied to RIT for Computer Science and Photography because computers and cameras were the things I loved most coming out of high school. However, when I came to RIT for a portfolio review during my junior year of high school, I accidentally got redirected to another line and found myself talking to a professor and advisor from the New Media Design & Imaging program.

After a brief conversation about my skills and interests, she determined I would be a very good fit for the program and accepted me on the spot, which is largely unheard of. Once I got into the classroom, I fell in love with the material and never looked back.

What were your goals for your future while attending RIT, if you had any? Do you believe that you’ve met those goals?

I don’t think I ever set my sights on one single goal and tried to achieve it. In my opinion, life is too unpredictable for that type of thinking. Instead, I kept broad goals in mind and ensured the decisions I made would push me in the direction I wanted to go.

For example, I knew I didn’t want to work at a big company in a big city, but wanted to make a comparable salary to those who did. I also wanted to do something I really enjoyed every day while maintaining control of the projects and clients.

Upon graduation, I got a job in Rochester, NY at a small company working with some of my best friends. We had control over the projects and I made a comparable salary to my peers who moved to NYC and San Francisco for work. 3 years later, I left that job to pursue a full-time freelancing career, which has left me in complete control of my income, projects, and clients.

How would you describe New Media Design to someone who’s never heard of it?

New Media Design is the digital, interactive version of Graphic Design. People tend to observe something created by a graphic designer, but interact with something created by a new media designer.

What made you decide to become a freelance designer? What was the transition like between leaving your day job and becoming a freelancer?

I became a freelance designer before I even understood what the term itself meant. Freshman year of college, I started to really enjoy web design and development. Before long, someone asked me if I could design a website for them. I agreed. I quickly found myself getting paid to make websites for people in my close network of family and friends.

I built my own website and used it to display my work, services, and contact information which began attracting clients from outside my network. My freelance side business slowly grew on a referral basis over the next 3 years while I finished college.

I continued to grow that side business slowly during the 3 years after graduation as well. It was just something I really enjoyed doing. The idea of maintaining control of the projects, clients, and budgets was very appealing to me.

Eventually, my frustration with the 9-5 agency life crossed paths with my growing freelance side business and it simply made sense for the career transition to happen. Practically, financially, and emotionally, it was the right fit for me.

I had a regular influx of work inquiries and made sure to line up a few clients before putting in my 2 weeks’ notice. I’ve been booked out months in advance ever since.

In your opinion, what makes a person qualified as a freelance designer?

I believe anyone who has a genuine desire for something beyond the 9-5 grind can channel that passion and motivation to become a successful freelancer. Beyond that, it’s a combination of time management, hard work, communication, and dedication that will make for a truly successful freelance career.

How would you describe the way you design for your clients? In other words, how would you describe your style in your designs?

I design for the needs of my clients and therefore I don’t have one distinct style that defines me or my work. I believe that design exists to solve problems and find solutions within constraints. If I limited myself to one style I would limit my solutions and therefore limit the clients I would be able to work with.

Having said that, I try to design in whatever “style” will encourage my clients target audience to complete the task at hand in the most simple and intuitive way possible.

Could you describe the process it takes to create designs for your clients whether it be just for desktop viewing or for responsive websites?

If design was a subjective matter, the creative process would be much more difficult. However, because I’m using design to solve real business problems for my clients, I’m able to more strategically identify what will work for my clients and what won’t. My process always starts with strategy and planning.

I ask my clients about 20 detailed questions about their business and the project. From there, I create wireframes that outline the website or application architecture and page flow. Once that is in place, I move on to the visual design which essentially paints another layer of hierarchy and detail onto the existing framework; a layer that shows what a user will interact with in the final product.

From there, the project moves on to development and implementation either through myself or a 3rd party development team.

Can you describe what it was like working for some of your clients?

I’m privileged to have worked with some of the best clients in the world. However, that wasn’t always the case. When I started freelancing, my clients were simply looking for a website or app and didn’t have a clear understanding of why they wanted it or what value it added to their business.

The clients I work with today such as TaxExact and FraudFindr have a firm grasp on the value of my work. This shifts the focus of every conversation away from subjective design critiques and onto the business goals and objectives of the project.

The result is that my clients value myself and my work more and are willing to pay not for my time, but for the value of my design solutions and expertise. They see my work as an investment in their business rather than an expense.

In addition, I screen each client thoroughly to make sure we will be a good fit to work together on the project before they sign a proposal. The clients I choose to work with make the project enjoyable and we often develop long-lasting relationships which can turn into repeat work.

How important to you are the testimonials you received from previous clients?

Testimonials are one of the most important components on my website and a cornerstone in the success of my business. It’s often not enough for a new client to see my work. They want to know that someone else has gone down the path of hiring me and come back better off than they were before.

Testimonials are a great way to reassure clients that hiring me is a good investment for their business because it was a good investment for past clients as well. The result is that more clients are willing to contact me and less resistant to pay my fees.

Lakera: How much do you think Dribbble has helped improve your business with clients?

I may not have ever been able to become a full-time freelancer if it weren’t for Dribbble. Their design platform helped me earn over $150,000 of side income in just 3 years. You can read my success story on their website.

I get constant work inquiries from Dribbble which often turn into high-paying projects and excellent portfolio pieces. As an invite-only platform, it also serves as a place of inspiration for me to see the best work being done all around the world.

Could you explain to the viewers a little bit about your book, “Kickstart Your Freelancing Career,” and your newsletter? What do you hope that people reading them will take away from them?

I think I decided to write a book for the same reason most people decide to write books. I wanted to share my story while helping others. With Kickstart Your Freelancing Career, I wanted to share what I wish someone had told me when I first started freelancing.

How do you find your first clients? How do you know what to charge? How do you write a good proposal? How do you transition from part-time to full-time freelancing? These are the questions I had to answer for myself and so my goal for KYFC was to give anyone looking to enter the freelancing market quick, actionable advice on how to succeed.

My hope for readers is that by the end of the book they can make a well-informed decision about whether or not freelancing is right for them and are well-equipped to forge a path to success in an oversaturated market.

As for my newsletter, I send my best freelancing tips and insights every Saturday morning. My goal is to help people be better off than they were before and so far I believe I’ve helped my subscribers do just that. You can sign up for my free newsletter and grab my free book here:

Last updated on March 3rd, 2023

About Matt Olpinski
I've been freelancing since 2009 and have worked with over 100+ clients including some of the biggest brands in the world. I later started my own company Matthew’s Design Co. and now teaches 50,000+ freelancers each year how to succeed through my personal blog, newsletter, and community for freelancers.