4 Questions I Asked Myself Before I Went Freelance


1. Are my skills relevant?

Good news! Companies, now more than ever, are turning to freelancers to fill their staffing needs. The not-so-good news: there is an unprecedented number of full-time freelancers to fill those slots. Before you make the big leap, make sure that you have a relevant skill set. Web development, for example, is a marketable skill that has been highly coveted for the past decade with the rise of startups and digital marketing platforms.

If your skill is not particularly relevant, make it relevant! Are you a passionate knitter who is looking to start her own knitwear line one day? Take cues from ethical fashion trends and source your fibers from a fair trade vendor. Target busy millennials by speaking on the therapeutic effects of knitting – maybe even host a small workshop. Create quirky knitting products aligned with modern consumer needs, like iPhone covers and laptop cases.


2. Can I meet deadlines?

Freelance work is all about self-imposed deadlines. With no one to tell you to "have x on my desk by 5pm Friday," you are now responsible for managing your own time by breaking up large projects into short-term due dates. If you are a known procrastinator, divvy up projects into even smaller pieces so that you aren't cramming two-weeks-worth of work into a single night. If you are notorious for missing deadlines, you should seriously reconsider freelancing. The "free" in freelance requires a lot of discipline, and will likely work against you.


3. Can I survive without income for eight months?

Unless you are set up with handsome retainer contracts, chances are you will be struggling financially for the first 6-8 months. Dry spells, late payments, unexpected expenses like attending networking events and lawyer fees – it's all part of the game. Even seasoned freelancers are constantly weighed down by financial uncertainty. Before you make the leap, make sure that you have a financial buffer of at least eight months in your bank account to live comfortably.  (I repeat – comfortably!) No one wants to start a business while living off ramen noodles and stressing about rent.


4. Do I have the right temperament?

Freelance work is solitary work. You spend hours alone during the week and, at times, are required to sacrifice evenings and weekends to get the work done. If you are the type of person who a) feeds off constant social stimulation, b) prioritize leisure time, or c) require external reinforcement to get work done, freelancing may not be right for you. There are many ways you can indulge your passions without becoming a full-time freelancer – doing it as a hobby or freelancing part-time, for starters – so do not be afraid to explore other options before quitting your day job.