How I Turned My Freelance Gig Into A Full-Time Job

How did you get enough freelance work to quit your job and become self-employed? How much did you charge when you first started? How much do you charge now? Do you still have enough clients? Do you actually work?

These are just some of the questions I have gotten over the last two years. October 2014 was both exciting and terrifying for me. Just a month prior I had officially decided to give my one month notice at my full-time job in order to take my freelance business to the next level (and to move to Grand Cayman). Well, I had decided some months before that but it took some strategy and courage to make it official with my then boss.

Join An Outsourcing Website

I had originally started picking up freelance gigs in 2012 because I was working at a non-profit and needed to make some extra cash. Outsourcing websites are a place for people to hire contract talent for long-term and short-term tasks; there are fixed-price, one time only projects and long-term hourly jobs. Writers, editors, web developers, administrative assistants, data entry specialists, transcriptionists, you name it. There are millions of people readily available to help you with whatever virtual project you may have.

As a freelancer, you can tailor your profile to your specialty and apply for work on a bid-style basis. I started with Elance.com (now Upwork).

Apply For Jobs With A Plan

When I joined Elance, I just applied for any type of writing or editing job that I could find.  No strategy whatsoever; just a shot in the dark. The problem with outsourcing websites like Upwork is that you are only allotted a certain number of application points a month under a free membership. I hadn’t taken that into account when I started and quickly ran out of points within the first few days. I realized that I needed to be more strategic by really going through the job postings with a fine-tooth comb.

I gradually began picking up small jobs but realized rather quickly that in order to grow my portfolio and prove my value, I unfortunately needed to low-ball myself in the rate department. This is something none of us want to do; of course we want to get paid our worth. However, oftentimes clients will not hire someone new to an outsourcing website; they are more inclined to choose an applicant with plenty of work history and positive reviews from previous clients. A bit disheartening, I know… but it makes sense and you’ve got to start somewhere, right? You can’t expect to go in and suddenly be making major cash without any proof of your value. Remember, these are mostly virtual jobs and the only thing clients have to gauge your potential is what you have in your profile and how you sell yourself in your cover letter.

Anyway, I didn’t have an impressive Elance portfolio as a newcomer, so I had to take the cheap route in order to get clients that didn’t necessarily care about paying for value. I had to write some really impressive cover letters, take the cut in pay and hope that my hard work paid off in the long run.

Grow With Your Experience & Consider Investing

Over time, my portfolio grew and I was averaging 5 star ratings with loads of accolades on my testimonial board. My cover letters were professional and answered any and all questions and comments presented in the job description, and my rate proposals started to grow. I was pitching 2-4x the rate I was able to when I started. I also decided to invest in myself by purchasing a membership that gave me more application points each month. This definitely helped because you are going up against a lot talented people, and need to apply, apply, apply. However, over time I didn’t really need the extra points because I was getting invited to jobs (which requires no points). As you become more of a stand-out player in the freelance community, you start getting recommended based on work history, reviews, hours put in and rate.

A year later, I was basically working two full-time jobs. I worked a 9 to 5, went to the gym, had dinner, and then hopped right back onto my computer and worked into the wee hours of the morning. It was tiring and difficult, but the extra income was so worth it. When my then boyfriend (now fiance, yay!) found out that his company was relocating to the Cayman Islands, we immediately started brainstorming about how it would be possible for me to join. I applied to a handful of local jobs but that was quite difficult because I am an expat. Then, lightbulb!

Take The Leap

Why not go full-time with the freelance gig, as it wasn’t really a “gig” anymore… but an actual job? I had a good handful of long-term (no better feeling than an old client coming back for more!), regular clients, and got one-off projects on a regular basis. There was PLENTY of work to be had. It made total sense!

So, I took the risk, registered my business, streamlined my existing work, utilized new connections and hit the ground running. Fortunately, the work environment that I entered was a special economic zone that specifically catered to new business in Cayman. There were loads of other small businesses in the flex work space; a wealth of information, connections and future job opportunities. Many would use other businesses as resources, making for a very versatile and unique place to begin my journey of self-employment.

“The only joy in the world is to begin.”  – Cesare Pavese

I am still working for myself full-time and have experienced the ups and downs that is being your own boss. Clients come and clients go, and sometimes it seems that everything good and bad happens all at once. However, I am fortunate enough in that I have been able to maintain enough work to make more than I ever did or would have at my previous job. I am also gaining opportunities that I never would have had I not made the leap. Not to mention, I am a whole lot happier. I honestly have a hard time picturing being an employee ever again.

It hasn’t been all rainbows and butterflies, but I still stand by the fact that it was the best life decision I have ever made, and I constantly remind myself that if I hadn’t made the bold move, I wouldn’t be as happy or successful as I am today.