How I Quit My Job to Freelance: 7 Steps to Freedom

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In November 2010, I started a piddly little WordPress blog after years of ruing the fact that I never turned my English degree and lifelong love of words into anything other than a run-of-the-mill office job.

It was, at the time, just a way to vent my frustrations and maybe connect with a few people who felt the same way. I was 98% sure nothing would come of it, although 2% of me secretly hoped I might be able to pull a “Julie & Julia” and turn it into a life-changing tool.

That 2% of me was more determined than I gave it credit for, because two and a half years later, in May 2013, I gave my notice to my 9-to-5 job and launched my very own full-time freelancing business.

Here’s how I got from point A to point B.

(These tips are geared toward freelance writing since that’s the path I took, but you could easily translate them for other freelance careers.)

1. Build Skills and Hustle

My initial hurdle, and the reason I’d never tried getting paid to write, was that I’d had some health issues in college. As a result, I’d never managed to build up the experience (clubs joined, pieces published, internships completed) I needed to launch a professional writing career.

But the great thing about the internet is, you can break your way into whatever field you want if you have the skills and sheer hustle to make sure people notice you.

Since I didn’t have a resume or portfolio to show potential clients, I started treating my personal blog, Cordelia Calls It Quits, like my living portfolio. I labored over every piece until it was as close to perfect as I could get it. (In the early days, that wasn’t much, but over time I got better.)

I worked on clarifying my niche — the topics I wanted to be known as an authority on — and I developed and honed my voice into something that would stand out from all the others in the blogosphere.

I pitched guest posts to bigger bloggers to get seen by their audiences, and once I started getting paid gigs, I created a page on my blog to showcase my growing credentials.

2. Learn, Learn and Learn Some More

I didn’t know much about writing and blogging as a business, so I read everything I possibly could to get up to speed.

I followed popular bloggers in my niche, as well as bloggers whose voices I adored, to see what they were writing about and how their audiences reacted.

I devoured ebooks, courses and webinars on how to be a better copywriter, how to land freelance clients and how to use tools like SEO and Google Analytics to expand my readership.

Everything new I learned, I applied to what I was working on. And if I didn’t know something, I taught myself from the trenches. I watched what worked and what didn’t and reconfigured for the next time. Experimenting and failing can be their own valuable teachers.

This step never ends, even after you’ve “made it.” Best practices in any field constantly change and evolve, and you need to stay up to date on what works and who’s who in your industry.

3. Cultivate an Awesome Network

Writer Kelly Gurnett with her husband. Photo courtesy Kelly Gurnett

Writer Kelly Gurnett with her husband. Photo courtesy Kelly Gurnett

Who you know really is as important as what you know when it comes to getting a freelance biz off the ground.

As I was nurturing relationships with my audience and other bloggers, I was unwittingly creating the source of many of my most successful client relationships.

The day I decided to put up my first “Hire Me” page on my blog, my new online friend, J. Money of Budgets Are Sexy, happened to put a line in one of his posts telling people to check out my work. A brand manager across the country read this post, visited my hours-old services page, and became my first paid freelance client.

Over the years, I’d say more than 95% of my clients (and about 99.9% of my favorite clients) have come through word-of-mouth referrals from existing clients and fellow freelancers. Never underestimate the power of your network.

4. Keep Your Day Job

Whatever you’re doing to pay your bills, keep doing it, at least for now. It may feel like the last thing you want to do, but it will do oodles of good for your business in the long run.

Keeping my day job as a paralegal and side hustling in the evenings and weekends allowed me to be selective about how I grew my career.

I was able to take on the projects and clients that aligned with my skills and interests (and my preferred pay rate), rather than scrambling to accept anything that came in the door simply to keep paying my mortgage.

I was free to make mistakes and find my groove, as a writer and a businessperson, without the pressure of knowing that everything rode on my writing.

Side hustling was also great practice for the time- and stress-management skills I’d eventually need as a full-time freelancer. (If you can handle a full-time job and a side hustle, you’ll be better prepared for what it’s like to be your own boss.)

5. Be Prepared

Freelancing means creating a whole new relationship with Uncle Sam and the IRS, so make sure you know what you’re getting into when it comes to self-employment taxes.

I spoke with a CPA, who advised I put one-third of my freelance earnings into a savings account so I wouldn’t be caught empty-handed when hit with the fun, new quarterly tax payments I’d have to make.

Build an emergency fund to cover those inevitable months when gigs are running dry but your monthly bills are still the same.

Research the health care and retirements benefits available to you when you’re no longer a salaried employee, and take their costs into account when figuring out what your new budget will look like once you’re freelancing full time.

You may find you need to make some budget cuts, at least at first. (I sold my car, among other things).

6. Step Down Strategically

The inspirational saying “leap and the net will catch you” is, simply put, rubbish.

While it’s necessary to have a certain amount faith and guts to become a full-time freelancer, you know what’s even better? Not going broke during your first few months on your own.

That’s why, even though I was itching to break free, I took my transition from the 9-to-5 gradually and deliberately.

First, I started the side hustle.

Then, once I’d built up enough clientele and monthly revenue to justify a mini-leap, I asked my boss if I could take off one day a week (with the associated pay cut) if I still kept up with my workload. He agreed, and I started using my “Freelance Fridays” to focus on banging out more work and securing more business.

Once I’d hit my next monthly income goal, I went down to part-time work with my employer, which I did for a number of months until I finally felt secure enough in my current income and upcoming projects to make the final leap.

Granted, I had worked for this employer for over a decade by this point, and it was a very small and flexible organization. Most companies likely won’t be so agreeable to a step-down negotiation like this, so be prepared to do what you need to keep the lights on while you make your transition.

That might mean taking a part-time job (or a couple part-time jobs) with another company. It might mean cobbling together a number of other freelance gigs like dog walking or remote customer service to supplement your income.

Whatever arrangements you need to make, be sure to pay your bills and keep your finances steady as you grow your business. Starting off in the red won’t do you any good.

7. Don’t Burn Your Bridges

When you’re side hustling, don’t let your performance at your day job slip.

When it’s finally time to call it quits at the traditional workplace, you’ll want to be able to leave on good terms, with a resume that’s full of references who’d be happy to rave about your skills and work ethic.

Sometimes a freelancer has to return to the grind for a while if things get rough, and you don’t want previous employers telling stories about your epic “I quit” video.

When my family’s finances took a turn due to some medical issues, I had to return to the 9-to-5 for a period for the predictable paycheck and paid benefits — and I was actually able to get my old job back as they remembered my work ethic and we parted on good terms.

In fact, since I’m back to freelancing and my old firm has since dissolved, one of the associates reached out to see if I’d be willing to do some content creation for her new firm’s website, so the good vibes keep reverberating.

In the freelance world, reputation and word-of-mouth are a currency in themselves, and you never know where your next job lead could come from. So wherever your journey leads you, the more bridges you leave intact, the better for your bottom line.

Your Turn: Have you dreamed of becoming a full-time freelancer? What steps can you take today to start making it happen?

Kelly Gurnett is a freelance blogger, writer and editor who runs the blog Cordelia Calls It Quits, where she documents her attempts to rid her life of the things that don’t matter and focus more on the things that do. Follow her on Twitter @CordeliaCallsIt.