Quitting Your Job to Freelance and What You Need to Know

June 15, 2015

Are you thinking about quitting your job to freelance? Just over a year ago, I quit my job as the Director of Communications at a luxury home-design retailer. I didn’t leave for another position or to travel the world—I left to freelance write, edit, and consult. At the time, my only certainties were a massive pay cut and a single client. And, oh yeah, I was moving home with my parents at the age of 28 to save money. So there was that.

My early freelancing plan wasn’t sterling, but it was ultimately successful. While freelancing, I made enough money to live comfortably (and move out of my parents’ house!), I found projects that fulfilled me, and I grew personally and professionally along the way. In fact, it was arguably one of the most formative periods of my life thus far, but it was definitely a learning process.

Here are the five things I wish someone had told me when I took the leap.

1. Do your homework ahead of time.

I made a successful transition to freelance because I did a significant amount of research ahead of time. Speaking with other freelancers (former or current) about their experiences was crucial. Some of these people didn’t even work in the same industry as me. That’s okay: A lot of the ins-and-outs of freelancing are universal, no matter what your area of expertise.

If you’re lucky enough to have people in your orbit that are freelancers, take advantage of their perspective. Ask them questions about their lifestyle; have them explain the pain points of freelancing; see what they recommend first-time freelancers invest in (a professional website, healthcare insurance, comfortable lounge clothes).

If you don’t currently know any freelancers, be bold! I emailed a very vague acquaintance (a.k.a., a stranger) that I knew was a successful freelance copywriter. She ended up being an incredibly generous resource, providing me with priceless insight that I still reference to this day. What’s more, she actually referred me to one of my most lucrative gigs.

The universe rewards the curious—seriously.

2. Line up your first client and/or gig before you leave your current job, or start saving money—now.

This is perhaps the best piece of advice I can provide. Do not quit your job without having some form of work waiting for you on the other side. Period. If this is absolutely impossible, I recommend saving enough money to live job-free for at least two months.

But let me be clear: I’m insane about this “first client” business because if you’re serious about making freelance happen, you should be able to procure work before quitting. If you can’t, there’s no guarantee you’ll be able to procure it after quitting—and then you’re up a creek. The liberties and perks of freelancing will soon feel irrelevant (and uncomfortable) without an income to support them. You won’t be able to enjoy the upsides—such as unlimited vacation—if you’re constantly worrying about being able to pay your rent. Moreover, work begets work. It’s easier to win a new client when you have a strong reference from a current client.

3. Be prepared to work your ass off.

While the joys of working in your pajamas or taking off early whenever you feel like are undeniable, freelancing—and freelancing successfully—is actually really hard. In fact, I have never worked harder than when I was a freelancer. The work was constant. I worked all day, I worked at night, and I worked on weekends.

See, when you are your own boss, running your own business, you are the sole driver of your success. It’s difficult to justify slacking when there’s no one else to pick up the slack. So if jumping on a client call on vacation or putting in three hours of work on a Saturday afternoon sounds like hell, freelance life might not be for you.

4. Say “yes” a lot. But know when to say “no.”

In the first few months of freelancing, I took on a lot of work. I blogged for a food website. I wrote SEO copy. I consulted for a friend’s fledging finance website. I conducted countless interviews. Some of it I loved. Some of it I didn’t.

In freelancing, saying “yes” to work is generally a good thing, especially early on. It means you’re staying busy, making money, and securing connections. There were times, however, when I seriously regretted taking on a project. It usually occurred when I couldn’t say “yes” to a single one of these questions:

• Does this work pay well (i.e., does it match or exceed my minimum hourly rate)?
• Does this work open up new, potentially lucrative opportunities and connections for my business?
• Does this work interest me or pose instructive challenges?
• Do I really need this work (i.e., will I not be able to pay my phone bill without it)?
• Does this work fit into my overall schedule (i.e., do I have the bandwidth to take it on)?

Use these questions as your guide. Looking back, I wish I’d had them to reference when I started out.

5. Ride the wave.

Despite having a successful run, I am no longer freelancing. That’s because one of my clients—after months of working together—offered me an incredible full-time role. Although the opportunity originally freaked me out—I loved my freedom, damn it!—I ended up accepting the job.

I had an epiphany that inspired me to take the position. It makes me sound like I’m on LSD, but I think it’s a fitting analogy:

Freelancing is sort of like catching a wave. (Note: I’ve never actually surfed, so I’m picturing a boogie-board type of situation.) You’ve got to be willing to jump on the good ones and just go with them. Sometimes the wave you’re on will run its course and you’ll head back out for a different one. Sometimes you’ll have an epic wipeout. And every once in a while, you’ll catch one that’ll take you all the way to shore. Don’t fight those. They’re usually good. And if/when the I-need-to-be-free urge strikes again, you can always paddle back out.