The Road to Freelancing

Making the move to full-time freelancing was a big step and I find that almost every day presents a new set of challenges and rewards for me. As part of my journey to successful self-employment I have decided to chronicle as many of the major milestones as I can not only for my own records but also to hopefully give insight to others who are looking to follow a similar path.

Starting with the process I went through in evaluating freelancing as a career move, I plan to also discuss various other aspects of the freelance lifestyle from purchasing hardware to balancing the books.

The Beginning

'Road to Utopia' is copyright Paramount Pictures 1946.

My road to freelancing started almost by accident in July of 2009. At the time I was working for a small startup in the west end of Toronto and maintaining this website out of personal interest. One day I received an e-mail regarding some of the topics I had discussed and my experience with WordPress. The sender mentioned that he was currently involved with a project that he felt I could be of benefit to and asked if I would be willing to have a conversation with him regarding it. I agreed not knowing what to expect and after some discussion I was offered work on a WordPress powered site that needed some custom template development. To be honest, I didn’t expect much to come from it but figured a few hundred bucks for my time wasn’t a bad idea. Upon completing the work, the site administrator thanked me and mentioned that if I was interested he had some contacts who could potentially give me more work along the same lines.

Over the next 6 weeks or so, I slowly pursued the opportunity and eventually was given the chance to meet a few companies that expressed some interest in having me work for them. By this point I had thought about the idea of freelancing but considered more of a pipe dream than something I could actually pull off. To my surprise however, the contacts I had made slowly began calling upon me to take part in small projects and before I knew it, I was moonlighting as a freelance web-developer.

Starting with smaller projects and working up to full scale site development, I spent roughly 4 months developing up my business while still working 9-5. Those 4 months were incredibly exciting and full of potential, but they weren’t easy to get through. I found life became a constant battle to try and impress new clients without neglecting my existing responsibilities. In order to make both work I decided to live by 2 rules:

1. Every client I had as a freelancer knew up front that I had a day job and that I was strictly unavailable from 9:00 am to 5:00 pm.
2. The second my work responsibilities had been met, I worked tirelessly to provide less than a 24 hour turn around for everything I possibly could.

Time to Jump Ship?

As freelancing began to show more and more promise it also began to take more of my focus. I began spending 8 or 12 hours on weekends on projects as well as 1 to 2 hours every weeknight in addition to 40 hours at my day job. By early December of 2009 I had decided that it was time for me to either leave my job and give freelancing a shot or leave freelancing behind to save my sanity.

Making the decision was not easy. Was I going to be able to keep paying my bills on freelance income? Did I enjoy the work enough to take it on as an individual? I wrestled with a lot of scenarios, comparisons and debates before ultimately deciding that yes, it was the right time to take on this challenge and risk failure.

On December 28th, 2009 I gave my resignation letter to my boss and indicated that in 4 weeks time I would be leaving the company to pursue a career in freelancing. I’m not going to lie, every late night and all of the lost sleep became worth it the second I gave my notice. The realization that I might actually be onto something with this freelance nonsense was an incredible rush and I couldn’t wait to dive in.

As of this writing, I have been freelancing full-time for 7 weeks, 4 days, 2 hours and about 15 minutes. As an obvious rookie I’ve taken in an awful lot in the past month and a half and even if I should end up flat on my face, it will have totally been worth it.

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