Freelancing: 4 Things to Know

Date:September 7, 2019
Time:4 min read

In September 2016, I left my stable 9-5 job and pivoted into freelancing. At the time, I had already a few freelancing gigs under my belt and was confident I could figure things out as I went. How naive I was.

I was fortunate to have the luxury of several things though that provided a decent safety net:

  • financial security (savings, rainy day fund, etc.)
  • ongoing demand for the skills I had developed throughout my career

    • I was confident if all else failed, I could find a job again

It's now 2019, and while I'm thankful and lucky for the safety net I had when I began freelancing, here's a few more things I wish I had a chance to tell young, naive me:

  1. Healthcare SUCKS as a Freelancer (in the US).

    • Access:

      Getting healthcare as a (single) freelancer [in the US] is tricky. While the Healthcare marketplace offers healthcare, these plans are quite limited and still result in a lot of out of pocket costs. I came to realize how spoiled I was as an employee when I compared plans. Do you research before making that leap. While I keep hearing there's 'group' plans you can get access to by getting a membership with various associations, I am not convinced those options are any better, as after ACA, it seems they also go through the healthcare marketplace... but it could just be I haven't found the right group.

    • Cost:

      Keep in mind to budget for healthcare. When you're an employee, your company will typically subsidize somewhere between 20-80% of the costs (and if you're lucky, you're company may even cover 100%). Depending on your plan, this can easily add up to over 1K a month in health related benefits. The lower end of that might be about $500 a month. That's at least $6-$12K a year just going towards healthcare. Make sure you budget for this when you start and include it in your costs when considering your rates. It's also just worth exploring self-pay rates for your situation. Sometimes this may be cheaper, but it won't have the out-of-pocket cap for serious situations that insurance would otherwise cover.

  2. DON'T quit your stable job. Start Part Time.

    And don't quit until you have a stable set of clients that at least make up half of what you're looking to earn. I quit relatively early in my freelance exploration, and pretty soon, the steady set of clients I thought I had dwindled to none. Then there was a period of ramping up again to find more work. Finding work is EXPENSIVE as a freelancer. It takes time and energy, and it's often one-off. It's not very sustainable, quite frankly, so you have to look at ways to hack the sustainability of it so that it takes less time and offers more return.

  3. Specialize, Even If You're a Generalist.

    In an ever-growing on-demand market, specializing helps set you apart from other freelancers. As a self-identified generalist, this was really hard for me. I liked learning a bit about everything, and even doing a bit of everything. This actually works well when you're in large companies where they have more flexibility for teaching on the job. It's much harder to find opportunities like this when you're a freelancer, where clients tend to be looking for a very specific skillset to fill out a skills gap on their teams. Find a niche or specialty within your skillset and build on that. It'll make it easier to market your skills and expertise. It will also help you narrow the search for new leads. That doesn't mean you can't continue to explore other areas - doing so gives you more breadth than your specialist peers - which can also provide a value add for your clients, but focus your marketing efforts in a specific area.

  4. Plan & Budget

    I didn't have a well-thought out plan when I started out. I might have thought I did, but it was definitely lacking. It's very important to have some plan as a freelancer, and to develop a consistent schedule for doing things. You decide what you're doing every minute of the day. If you're not working on billable hours, you should be working on getting more billable hours. This was hard to structure in the beginning, but I realized my unstructured way of doing it was not very productive. I developed a habit of using a physical planner that helped me think through the month, the week, and each day. While I still use an electronic calendar for scheduling meetings, writing things down was helpful in a different way. I noted things that were less work oriented and more personal in a physical planner - when to exercise, when to meet with friends, etc. I blocked off chunks of time for business development or skills development. Regardless of how you plan, some plan is better than no plan, and developing habits structured around your business can improve productivity in the long run.

Each of these topics likely merits a deeper dive, except healthcare. I'm not touching that one. However, I would welcome any tips and advice anyone may have to share regarding healthcare. I have not figured out an ideal solution for that yet.

On the topic of developing habits, I intend to write a blog post at least once a month. Perhaps more frequently as time permits.

Stay tuned!

If you have any questions, feel free to tweet at me (@rachel_cheuk), email me (rachel [at], or get in touch with the contact form.