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Freelancer Spotlight: Josh Medeski

Yay! I’m super excited to have finally convinced a male freelancer to share their story with us on FTF. I know the guys are reading too, but for some reason they haven’t been as open about sharing their stuff.

So today I introduce to you Josh Medeski, web designer & developer who jumped into freelancing straight out of college.

Welcome Josh!

Josh Medeski Quote

What kind of freelancing do you do and how did you get started?

I’m a freelance web design and developer. I’ve been interested in graphic design since my freshman year in high school and knew I wanted to pursue that career by the time I graduated. I got my degree in art but knew there was more for me out there in web design. I have always been self-educated and if something interests me I put 100% into it. I decided to become a freelance designer because I wanted the freedom of picking my clients and creating my own schedule.

Are you freelancing full-time or on the side?

Fill time! Since graduating college I left my job as a barista and took on freelancing full time. It’s a lot of hard work and I have to wear a lot of hats, but I think it’s totally worth it.

How long did you freelance on the side before you made the jump?

I had a couple of part-time jobs before freelancing full time, and I’m also a professional magician (which brings in good money when I perform). Once I had the right amount of clients I took on freelancing full time.

What is your favorite part of working for yourself?

Being able to work from anywhere anytime and spend more time with my wife. I also love being able to choose what projects to take on, and I have the opportunity to set aside time to learn new things and work on personal projects.

What is the biggest challenge you’ve had to overcome in working for yourself?

Paying the bills. Freelancing can be “feast or famine”. Being able to make it through dry spells means cutting costs and sacrificing wants vs needs. When money is good, I have to choose wisely what to spend it on and how much to save (especially for taxes). Overall, money is my biggest challenge for me. I’m beginning to learn the power of products and finding ways to get more streams of income.

Walk us through your typical workday.

I wake up around 9 and have breakfast, check emails, catch up on articles, and go through my todo list. Next I start working on a project using the Pomodoro technique. I tend to stick to a single project for a couple of hours then switch to something else. I take a lunch break around 2 and watch an interview or tv show. Then I spend the rest of the day continuing work (till around 6 or 7). My evenings are spent with my wife, we usually make dinner and then watch a movie or play a board game. Sometimes I work on personal projects in the evening while watching tv. I’m usually in bed around midnight.

What advice would you give to someone a few steps behind you in their freelancing entrepreneurial journey?

Learn to say no. Work with people that share your business values and appreciate your work, otherwise you will be miserable (my personal experience).

Thanks Josh!

Josh currently runs his own freelancing business and provides front-end development, graphic design, branding, and writes for a few design websites. He also likes watching movies with his wife and doodling on the weekend. You can connect with Josh on Twitter to see his latest readings and writings.



Leah Kalamakis Leah Kalamakis is the founder of The Freelance To Freedom Project and a web designer/developer for brilliant entrepreneurs. When she’s not hanging out in the FTF Community, you can find her people watching on the streets of NYC. Come say hi on Twitter, Instagram, or Facebook.

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{ 1 comment… add one }
  • Jo

    I just have to say that I have experienced Josh’s skills first hand and am lucky enough to have him in my mastermind group. He is EXTREMELY talented and such a contributor to everyone. I highly recommend him and his work!

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