Transitioning to Full Time Freelance

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Note: this is an update to an article I wrote in 2010, when I went from college to full time freelance.

I started freelancing all the way back in 2002, when my church came to me looking for a website. As a junior in high school, I used
Frontpage, and GMail had yet to grace me with it’s presence. And this seemed like a really good opportunity for me to run
the business I always wanted. I freelanced all through high school and college. It was at the end of my senior year in 2007
that I realized I wanted to keep doing it. So I went to grad school to learn more about my trade, and better prepare myself full time freelancer. I stuck with it for a time but sought full time employment for 6 years before coming back to self-employment.

So what does it take to transition to full time freelancing (from school or employment)? Let me tell you what I’ve learned.

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Announcing the WordPress Freelance Coaching Program

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You might know my freelance origin story. It’s one I tell a lot, at WordCamps and on podcasts. I sort of fell into it when I was 15 years old. My church asked if I could make them a website. After I declined, they offered to pay me. Pay me to learn? How could I pass it up! This predates WordPress, so I did everything using Microsoft Frontpage, then moved Notepad++. In 2004, I mentioned to my friend Stephen that I was thinking of building a CMS. He showed me WordPress, and the rest is history. For over 15 years, I’ve been freelancing and have used WordPress for most of that time. I get questions about both topics regularly, and I wanted to create a program for me to help WordPress freelancers specifically. So I created the WordPress Freelance Coaching Program.

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I’m Returning to the World of Full Time Self-Employment

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Six years ago when I got a job at The University of Scranton, it was a little bittersweet. For 2 years following my Masters Degree, I was self-employed. The thing that lead me to look for a new job was that I was working out of my parents’ house, and honestly, time was running out on staying on their insurance plan. Leaving that world was sad, but I was excited at the notion of working with a team. After 3 years at the university, I felt I was ready to do something different and more challenging.

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The Great Freelancing Advice I Never Took

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This is an excerpt from my upcoming eBook, Freelance 101.

Because I started freelancing at age 15, I would often struggle with what I would do after I graduated from college. I could start my own business and freelance full time, or I could get a “real” job. At one point while I was in the throws of this existential crisis, my dad and I went to dinner with a family friend who happened to be starting his own business. This friend, who was close to my dad’s age with two kids of his own, offered me some advice. I, being the headstrong early 20-something male, promptly disregarded it. It wasn’t until I was towards the end of my 20s that I realized it was some of the best advice I never took.

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An Intro to Freelance 101

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One of my goals for 2016 is to publish a new book. I actually have 3 separate ideas, including an update to Responsive Design with WordPress. However, there is a book that I have wanted to put out for over 6 years, with a first draft already done. Originally called The Student Freelancer, it covers a lot about how to get started as a freelancer, from to setting up your business to pricing. It also covers how to make the most out of freelancing throughout school. I’ve decided to rename it Freelance 101 and release it this year.

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Why Pro Bono Work Hurts Everyone

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It’s something that has happened to everyone who’s a freelancer, or perhaps just everyone who runs a business. People will ask for things for free; I want to make it super clear now that I’m not saying never do pro bono work. I’ve done it. It just needs to be the right circumstances; asking a person you don’t know for free work is not only bad for the freelancer, it’s bad for your project in general.

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