When people tell me they admire my freelance career, when they tell me it must be nice to sleep in, when they then break eye contact when I tell them how much I am paid, when I am sending a fourth follow-up email to an editor regarding that check, you know, that one you said was in the mail a month ago, this is what I think about:

Almost eight years ago, a week after my 22nd birthday, I graduated with a master’s degree from Columbia’s journalism school. I didn’t know what having an Ivy League master’s degree in journalism meant, besides an overinflated sense of young self-worth and a collection of very expensive bills. I was about to find out: nothing.

I wanted to write about politics but soon found myself applying for entry level editorial jobs at Conde Nast teen magazines, at Daily Candy, at Babble. I pretended to be a college student and blogged for $10 an hour for a shady start-up. I blogged for pennies. I blogged for free. I filled out dozens of job applications a day. I was one of thousands.

In journalism school, professors had told us to never write for less than $1 a word, but we didn’t spend much time learning how to pitch. My parents, who had fostered creative careers in New York in the ‘70s and ‘80s, encouraged it all. “Don’t take those unpaid internships, you’re worth more than that!” But I wasn’t.

I did apply for those unpaid internships. I didn’t get them.

I didn’t ask for help. I didn’t think I really needed it. I survived, and I felt lucky. Despite the rejections, I was still young and privileged and ahead of the game. Something would work out.

In 2008 I decided to move to the Bay Area, a smaller pond flush with tech money. The assignments came easier — $25 to $50 for short reviews for a local alternative weekly, $200 for longer articles. Within a few months I landed a job as the editor of Curbed San Francisco, a relatively new real estate blog. I posted ten times a day. I developed excruciating carpal tunnel in both hands. I bought wrist braces and posted some more.

A week after I was hired, the stock market crashed spectacularly. Two months later, I was laid off. Two months after that, I was sleeping on my parents’ couch.

These were, objectively, strange times for media; they still are. Tens of thousands of staff writing jobs disappeared in journalism over the last couple decades, replaced by freelance gigs that pay a fraction of what they used to. But the pool of available talent only seems to grow wider and deeper.

I read this piece by Richard Morgan in 2010, a few months after McSweeney’s had hired me to write a 3,000-word investigative article about San Francisco real estate for $250.

It seemed in my best interest to diversify my skill-set and differentiate myself from the pack.

And so I learned to draw. In between applying for quota blogging and copyediting gigs across Northern California, I filled sketchbooks with hand and drapery studies. Every other out-of-work journalist is learning Javascript, I figured, but I’ll be the only one who can draw.

While 2,000-word reported stories earned me $200 from national news and magazine sites — less self-employment taxes— some small illustrations could earn me $200 each.

But while it filled my bank account and raised my profile, my drawing seemed to ultimately devalue my journalism. Readers presumed that if my work was illustrated, it was not fact-checked; that quotes were fabricated, statistics rounded off to whatever.

I footnote everything now. It matters about as much as my masters degree.

“It looks like she’s a cartoonist first,” a journalist said about me the other day, not bothering to, I guess, look.

I was arrested and jailed while reporting on Occupy in Oakland because the police didn’t recognize the outlets for which I freelanced. Some media blogs speculated that it was because I was really a cartoonist and not a reporter at all. When I reached out to Columbia for guidance on facing the resulting criminal charges, the dean wrote a Tumblr post about it.

As I’ve established myself as an independent journalist, I’ve received more inquiries for free labor than for the paid stuff. Writers for local newspapers, for Salon, for the Huffington Post, for the New York Times magazine, for media around the world send emails complimenting my reportage and then asking me to help them with their articles about the Bay Area for free.

More newspapers and magazines want to profile me and the strange work I do than hire me to actually do it. Other writers and illustrators chastise, how can you complain about getting that kind of promotion? The year I got the most TV and radio spots and magazine write-ups, I made about $17,000.

The economic world is structured for people with jobs. Yet the self-employed population is growing by leaps and bounds — more and more people each year are paying higher taxes and buying their own insurance. We have no institutional protections, no security, no unemployment benefits when our contracts run out.

I know I’m far from alone — freelance journalists quietly, privately lament our low, late pay, our inherent insecurity, and the dual pressure to appear productive and successful while also available for hire.

During my relatively brief stint as a staff writer, I saw the wide discrepancy between labor and payment for staffers versus the freelance work our site and many others rely on to fill content columns and drive traffic.

I felt guilty. And then I cashed my checks.

I’ve cultivated relationships with great editors, and learned which ones to avoid. I have an impressive resume, from some angles. People tell me it’s the resume of someone who picks and chooses for success, a stack of interesting stories for national outlets with good reputations. I see it as a list of struggles, of hustles, of all-nighters and four-month-overdue paychecks, of $20 an hour work done for $4, of an unreasonable and naive optimism.

But each new published piece is a chance that a hiring editor might see my work, reach out, offer something. It keeps me chasing $4 an hour assignments. I’m terrified that if I don’t publish an article one week, I might be forgotten altogether, losing out on the hypothetical opportunities I’ve been working toward for the better part of these last eight years.

Media companies often make hiring choices by skimming the cream off other, competing media companies; it’s easiest to get a job if you’ve already got one. Everyone knows you’re most attractive when you’re already in a relationship. Freelancing becomes an easy place to get stuck on the low side of this employment gap. You seem great, but there must be something wrong with you.

Maybe I never should’ve left New York. Maybe I never should’ve started drawing. It feels too late to turn back now. I did not plan to make this my career. I still don’t. But here I am.

I’m currently waiting on $1,200 in outstanding payments from editors. And my degree is still in storage.

Now I have to get back to work.