Things nobody told me about becoming a freelancer


It’s been four months since I quit my job, but I’ve reached the point where I’m able to pay my bills with just my freelance gigs. I think that finally qualifies me as a professional freelance writer.

I decided to become a freelancer for pretty typical reasons. I wanted to be my own boss. I wanted to build my own schedule. I wanted to work in my pajamas and never sit through another boring meeting again. I wanted to flex my writing muscles by writing for a variety of places including a tech blog, a women’s career advice blog, and even a print magazine.

That’s basically what my life has become over the last few months, and it’s awesome. But—and you knew this was coming—it’s not ALL awesome. There’s a lot of work associated with freelancing that I kind of skimmed over when choosing this career path. Here’s what I’ve learned only by doing:

It doesn’t happen overnight

In the state of Virginia, where I live, you don’t become self-employed by filling out a form or acquiring a license. You simply start working and voila: you’re a sole proprietorship.

The trick is coming by that work in the first place.

In December, I wrote a list of 30 media outlets where I’d love to see my byline. But when I pitched all of them and didn’t hear back from most, I started to get discouraged. It was only when I started leveraging my connections—with colleagues from previous reporting jobs, writing mentors, and LinkedIn—that I started getting promising responses.

Really, I should have known this already. When I set out to apply to 30 jobs in 30 days in 2010, I heard back from 40 percent of companies where I had a recommendation from an employee.

It takes forever to get paid

By February, I was working for three different publications. However, I only made $300 that entire month. What happened?

It wasn’t that I’d only done $300 worth of work. It was that I was invoicing—AKA requesting to be paid for my work—in a way that was slowing down the process. I was waiting to charge for my work until stories were published, which could be weeks after I’d written them. Soon I got smart and learned to invoice as soon as I’d completed my part of the bargain.

Now, I’m on retainer for a few different places, which means I don’t have to invoice every time I write an article. I either invoice just once a month, or they direct deposit. It’s closer to what it feels like when you have a regular paycheck.

Your taxes are the length and time commitment of a short novel

How did you spend last Friday night? In my case, my supportive fiancé and I watched video tutorials on the IRS website. Starting this June, I begin paying my taxes four times a year, a process that’s called paying estimated taxes.

Why pay estimated taxes? As a freelancer, my employers don’t withhold any of my income like they would if I were full time. I’m also unsure how much income I’m going to earn this year. So instead of guessing wrong and ending up owing $10,000 to the IRS next April, I’m paying as I go.

Self employed people are at an elevated risk of getting audited, since the IRS claims most tax fraud occurs within the ranks of self employed people. If you ask me, I’d wager that many self employed people just don’t understand how the tax code works. For example, I have to fill out the deceivingly similarly named forms 1040 ES and 1040 SE. And that’s just the beginning!

All in all, I never realized how similar freelancing is to entrepreneurship. You have to be your own publicity agent and your own financial bookkeeper. I don’t spend more time writing than I used to, but I do spend more time working—on these related tasks. It’s hard, but energizing to realize that I’m better at math and administration than I thought.

This isn’t a rags to riches story. I’m not more financially successful than I used to be. (If anything, things are about the same.) But I feel like a more fully realized person now for proving to myself that I can do this.

Would you ever consider a career as a freelancer? Why or why not?

(Photo by Philip Taylor.)