I started working full-time when I was 19, first as a marketing associate and then as a product manager when I transferred departments. Getting to work on a product I believed in with a fun and talented team was very fulfilling, and I enjoyed my time there a lot, but I found myself completely drained every day when I got home.
There were a lot of things that made working full-time difficult for me. My sleeping disorder impeded my ability to get up on time every day, and I would often have to stay a little later to make up for sleeping in. I also had no time for creative projects and found it difficult to focus on work for hours and hours at a time.
I started fantasizing about what it would be like to work from home and sleep in, take breaks to watch TV, and do things on my own time.
Despite my self-employment ambitions, I took another full-time position when I moved to New York, so that I could pay rent. I would think and talk a lot about becoming a freelancer, but I was terrified that I wouldn’t find any work if I left my job to freelance.
Getting laid off was the straw that broke the camel’s back. Suddenly, I had no job to fall back on and no safety net. I had never freelanced before, but I promised myself I’d never work full-time again.
Over that next year, I worked hard at finding new clients, branding myself, and finding a balance of life and work that made sense for me. Here’s what I learned.
Getting work is hard, but not impossible
Before officially becoming a freelancer, I had eyed freelance job postings occasionally. I noticed that in the full-time job market, companies tend to look for UX designers, whereas in the freelancing world, clients were mostly looking for one person to work on both UI and UX.
Having worked with UI designers in what was essentially an unofficial art director position for six years, I had already started dabbling in UI, but, when I decided to become a freelancer, I bit the bullet and invested in a graphic design course. While looking for work, I also continued practicing my UI design skills by doing the DailyUI Challenge and getting involved with the design community on Dribbble.
Since I wouldn’t be able to share specs I wrote for my previous jobs, I made up an app for which I wrote a job application-friendly dummy specification document detailing its functionality.
I checked a few different freelancing sites, but the clear choice for me was Upwork. They tend to list longer term jobs and have higher quality clients, unlike other sites that focus more on one-off projects and attract lower paying clients due to their branding and business model.
The great thing about freelancing sites is that they list your profile and help clients find you for free, but the trade-off is that they will take a cut of your income for using their platform. While their fee may be a turn off, it’s worth noting that they provide other services that can make it worthwhile; while freelancing on your own can lead to contentious disagreements with clients, Upwork has hour tracking and mediation in place. Upwork also uses an automatic billing system that makes sure you get paid on time and verifies prospective clients’ ability to pay you.
The catch-22 I found myself in when getting started on Upwork was that it was extremely difficult to get work because I didn’t have any logged hours or reviews on my profile, but I couldn’t get reviews or log hours without getting work.
After a few weeks of applying to jobs with no traction, I decided that I would need to become much more competitive to get my first job, which would mean temporarily lowering my freelance design rate. I started sorting posts by number of proposals, so that I’d only focus on projects with fewer submissions that other designers with more work experience weren’t applying to.
I had been on the hiring end of Upwork for previous jobs, so I knew what it looked like to receive submissions and what stood out to me. A lot of freelancers don’t invest in a cover letter (no one likes writing them, but they do make a difference), so I knew that, by putting some effort into mine, I’d stand out.
I always used optimistic language, even going so far as to sign off every letter with “Looking forward to working with you!” While somewhat presumptuous, it made me seem excited and ready to get started. I would also try to pick out parts of the job that I have experience with and explain my expertise and why I’d be a good fit.
After a lot of submissions and cover letters, I finally managed to secure my first gig at my lower rate. I made sure to work fast and communicate often and clearly–two important things to do while freelancing. After having a completed gig and a positive rating under my belt, I was able to raise my price to the hourly rate I wanted. While jobs were still h