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.)
12 Comments.
Ah yes, the horrors of having a 1099 job!
One of the first things I did when transitioning from a full-time Sys Admin to a freelance writer was to put a CPA on retainer. I took one look at the New Jersey and Federal tax sheets for self-employed folks and my eyes glazed over – I give you a ton of credit for figuring it out on your own!
If anyone’s just starting out as a freelancer, I really can’t stress the value of a CPA (or at least solid advice from a CPA) enough. It’s a bit antithetical, since you’ll have to pay them money up front to save money in the long run, but avoiding the dreaded audit is well worth the hassle.
Congratulations on becoming a full-time freelancer and a member of the Pajama Army ^^
@Matt, good advice! I really don’t want to spend money on a CPA, but you’re totally right. I’ll see how the June filing goes and reconsider.
I’ve seriously thought about starting my own web dev/computer repair business a lot of times. I think I don’t do it because of the initial stability issue. I’m sure I would do fine after getting some customers, but I’m terrified of the first 6 months to a year.
@James, I can’t say anything to make you feel better about those first six months, but I can say it worked out for me in the end. At my old job, I saved about 50 percent of my income through frugal living, and so I’ve just been living off of that. If you can save a large part of your income, then you can just chalk up a rocky start as an expected startup cost instead of an inconvenient surprise. Because there’s also the chance that you’ll make money right off the bat!
I’ve thought about being a freelancer, but I’m not so sure. I feel like if my boss treats me like a partner instead of a subordinate, then yeah, things won’t be so bad. My current job is like that even though we’re trying to get big.
Sounds like you’ve got a pretty sweet gig, Tony. I don’t know if I’d be able to leave that, either.
Hey Lauren. It’s Lauren! I just quit my job in March to do freelancing fulltime. I’m going through the invoice issues now because some use ebyline and some don’t. I like being in my pj’s all day and having time to do other stuff on the side. I may join the FT life again one day, but I really like my sweat pants right now. ;)
@Lauren girl, I love your new website! So clean and professional. Congratulations on the pajamatastic freelance life. I’m glad it’s going well.
well I’ve been a freelance website developer since about 2003, but being a “small time” freelancer, and a computer engineering student at the same time was rather tough for me. Now I’ve gotten an offer to code full time. In my experience over the years as a freelancer, there was literally no difference between work life and personal life… they were into each other. After 7+ years, i think its time to separate work life from personal life. I still get to code, and do what i love anyways, but with steady pay. let’s see how this goes
Really helpful entry – thanks, Lauren!
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