How to Quit the Shitty Job You Hate and Transition Into Freelancing

Step 1: Make time while you’re working your regular job.

The key to going from office to home office is transitioning slowly, which means holding your god-awful job and progressively adding freelance gigs on your own time. I started out by taking on low-involvement editing jobs one at a time and worked on them on weekends or in the evenings. Just be upfront with your clients about your situation so they don’t expect you to turn the work around immediately.

Sleep, video games, books, fun, and relationships can come later; staying sane despite your job is the priority.

Step 2: Test the market.

When I decided I wanted to be a freelance writer, part of why I took on those paltry jobs was to see if I even enjoyed the work. This showed me there was not only a demand for my kind of work, but a chance for me to exist in the world of freelancing.

You have to test this yourself, as not everyone is wired to work without a boss’s direction, and not everyone is willing or able to live below the legal poverty line (no joke — you might be making less than minimum wage at first).

Step 3: Find a transitional job.

For me, this was substitute teaching. Subbing is flexible, and the pay is alright. If I got a call in the morning and had a lot of freelance work to do, I turned it down. If I’d committed to a teaching gig, I turned down freelance offers. I also did work at school during plan periods and lunch (including ghostwriting erotica in an elementary school classroom).

If you hate kids or can’t find subbing jobs, try a lower-paying job that has tons of down-time. I have a friend who night-audited at a hotel after we graduated high school; he watched animal fights on YouTube and checked Myspace all night. Minimum-wage employment and under-the-table jobs are replete with autopilot positions if you’re willing to give them a go; it just depends on where you’re at in your career/life.

Step 4: Build yourself up.

While it’s beneficial enough just to make money from your work, it’s also imperative that you gain confidence from the work you do. There will be a lot of uncertainty once you transition into freelancing; for me, making money to write changed everything. I thought, People are actually giving me money for this? Like, real money? I bet I can fool more people into thinking what I do is actually worth something!

Aside from that, make sure you’re collecting clients (preferably returning ones) and building an online reputation. Trust for freelancers is built on quantitative proof of your expertise, not just your actual skill.

Step 5: Transition from the transitional job into freelancing.

Hopefully you can work out a combination of a transitional job and freelancing to have a full work week, while gradually minimizing that transitional job. If not, you’ll know that maybe you don’t quite fit with freelancing yet (based on your skill set, work ethic, crowded market, not enough access to clients, etc.). Either way you win — unless you want your old job back.

Step 6: Take the plunge.

Once you’ve established a place in your market and are fairly confident you can get a steady flow of income, dropping the transition job is all that’s left. Officially taking on full-time freelancing is going to be trepidatious, but the only way to do it is to give yourself the time you need to devote yourself to it, even if you don’t have enough work at first to make a real living.

Hopefully you’ve socked away a good bit of money, because at the beginning there’ll be a lot of low- or non-paying work as you search for clients and make a name for yourself. But if you keep freelancing as a part-time job, it’ll never become a full-time one; you have to make it into one even before it is one.

The caveat

I can’t quite recommend just dropping your old job and having a crack at freelancing, no matter how tempting that is. The biggest variable, in my experience, isn’t whether there’s a market for it — there is, depending on your willingness to at least temporarily compromise on things like pay, work-week length, resume-building, lifestyle, morals, sound judgment, sunlight, social interaction, submitting to people who know less about what you do than you do, and so on in that manner.

The biggest variable is your ability to make it in that increasingly crowding market. Are you good enough and disciplined enough? Are you personable enough? Can you market yourself well enough? Those are the unknowns most of us will have to deal with before leaping off the cliff of employment into complete darkness, hoping there’s water at the end of the ensuing free fall. * For more on how to break free, check out the curriculum of the MatadorU Travel Writing program.