Six Lessons I Learned After Becoming a Full-time Freelancer

by Jamie Wiebe

I’ve been putting off writing this article. I’ve been putting off writing anything, really: I quit my salaried job and went full-time freelance with the idea that I’d work a few hourly jobs fact-checking, researching and editing from home, which would clear up time to write.

That plan proved to be more than a little idealistic. Writing is so nebulous: How many hours will an article take me to write? If it takes two hours and pays $50, I make $25 an hour — respectable. But what if it takes three? What if it takes five, and I wasted all the time I could have spent doing work where I could have been paid hourly? What if I decide to work on something I want that pays little or nothing, like this essay? How do I fit it in then?

I’m lucky: Right off the bat, I’ve got a growing collection of hourly jobs that will, with due diligence and some hard work, keep me fed and pay the rent. But I’ve never thought so much about time, money, and what my hours are worth than I have since leaving the structure of a salaried job.

I don’t get paid to pee anymore. It’s a very stressful thing.

Let’s take a step back: I’ve been freelancing for a month and a half now, but I’ve been thinking about it for almost a year. Or forever, really — I always dreamed of working from home, freelancing for a living, just like any good journalism grad does (at least those not angling to edit magazines or work as bureau chief for the New York Times). I started with spreadsheets, as I always do, figuring out how much I spent each bi-weekly paycheck on groceries, restaurants, bars and everything else, then dividing it by 14 to figure out how much I spent each day.

After adding in rent, loan and credit card payments and savings goals, I plugged all my numbers into one of those online calculator things and it spit out the hourly fee I should charge. I almost vomited. I didn’t deserve that! No one would pay me that. Right then, I saw my future pretty clearly, still unhappy in the same job, and figured, well, that’s it. That’s all I’ll get.

But as is often the case, a series of quite-fortunate events pushed me out of the office and into my living room. One job offered me an hourly rate only a few dollars less than the calculators told me I needed; another offered almost double. I would be okay! I’d quit my job, I’d live my dreams, I’d do all the writing I never did before.

Lesson 1: Freelancing doesn’t cure procrastination

Quite the opposite, in fact, especially if you’re lucky enough to have hourly work to fall back on. On the surface, working for yourself, from home, opens up endless free time for all those projects and articles you’ve always wanted to write.

But no one told me the dirty little secret of freelancing: All those hourly wage calculators, the ones where you input your rent, your expenses, how much you want to save, etc.? They assume you’ll be working at least six (and more likely seven or eight) hours per day. Not working-in-an-office working, but billing working. Actual work hours you won’t feel guilty to put down on a timesheet.

My mom laughed when I told her I wanted to work at least eight hours a day: Allocate 20 percent of your time for goofing off or whatever, she said. But I can’t afford to do that. I have rent to pay and food to eat and cats to cuddle.

Most days, I bill eight hours of client work, which adds up to much more actual time. Making and eating lunch? Can’t bill that. Afternoon break to play Candy Crush on my iPad? Can’t bill that. Quick mid-day gym excursion? Can’t bill that. Not to mention that working eight hours — actually working — can be really exhausting. Salaried, there’s some built-in luxury: Your employer won’t dock your pay if you accidentally fall down a Wikipedia hole. It’s okay to let your mind check out every once in awhile. When that happens now, I don’t get paid.

I enjoy my work. I’m working with great people on fun, interesting projects. But work can be exhausting.

So the procrastination I thought would be cured by all the ~*~ magical freelance free time ~*~ is still hanging around.

“I’ll write this article after I’ve built up a good money base for the month,” I say. The spreadsheet I built says I need to work at least 7.5 hours a day for the rest of the month to break even; another hour a day to have some money for savings and extra credit card payments. I like watching that number drop — it’s automatically calculated based on how much I’ve worked already, so if I put in a really long day, it’ll decrease to 7.25, 7.14, or 7 hours per day still needed. “Later in the month, I can afford to squeeze in personal writing.”

But later in the month comes and even if I can afford to focus on personal projects for a while, at that point I’m so enticed by the idea that more hours equals more moneys forever and ever that it’s hard to put hourly work aside. In my salaried job, extra work meant nothing. I didn’t get paid more if I stayed late. But once I reach my “pay the rent and bills” benchmark now, I can keep going. Hello, alumni ski trip! Hi there, paid-off credit card! I can see you all down the road!

I’ve got a few articles that have been sitting in my to-do inbox for weeks and weeks now, for people and websites I really admire (like this one!) and who I don’t want to think less of me because I’m prone to procrastination.

I’ve been trying to think of a good way to explain just what it is about freelancing that makes these promised, unfinished projects weigh more heavily, and I suppose I can sum it up as such: I’m still a procrastinator, but now there’s the added pressure of this is what I want to do, and I quit my job so I could, and now I can — if I just do it. And what if I fail?

The concerns about money, about budgeting, about allocating my hours to my clients and my personal projects are just a veneer and an excuse. But they sure do make it easier to push off something that terrifies me.

Lesson 2: Health insurance is impossible and seriously, what do you guys do?

My company health insurance expired the day I quit. Luckily, I live in the great United States of America, where our government ensures no one will die in a manner preventable by proper health care, or be buried under mounds of debt because they broke a finger, or … oh wait.

I first turned to Freelancer’s Union. Through them, health insurance costs $345 per month ($225 for the step-down, crazy-high-deductible plan), plus $35 per month for a totally mediocre dental plan. Yearly, that’s $4,560 (though I hear that the self-employed qualify for health insurance tax breaks). Compared to some plans, that’s pretty cheap (and that in and of itself is bullshit); for me, it’s just at the edge of what I can conceivably afford.

Not that it matters: Freelancer’s Union requires eight weeks of proven, full-time freelance work to enroll. And even then, your coverage won’t kick in for a month, meaning I’d spend the entire month of August uninsured. Maybe that’s OK for some people with a high risk tolerance, but my risk tolerance is itsy-bitsy. Instead, after a bit of research, I went with the Empire BlueCross TraditionPLUS plan. It’s only $184 a month — a little more than $2,200 yearly — and it only covers hospital visits (plus some preventative services, although I haven’t exactly figured out which ones). But it’s cheap. I need cheap.

I still don’t have dental, and I have a cavity, which I was informed about at my last check-up before the doctor asked for $200 I didn’t have to fix it. That’s something to worry about every time I get an achy jaw. My plan doesn’t cover prescriptions; before going off my old insurance, I tried to get three months of Zoloft at once, but my prescribing doctor wouldn’t allow it without a $180 trip to see her. I didn’t have $180. I had two refills left, so I’ve been self-medicating, splitting my doses in half to make them last longer before I have to find a new doctor and get a new prescription. Without Rx insurance, the medication costs $45 each month; my new insurance doesn’t pay for doctor’s visits, so that cost could vary widely. I have no clue. Thank you, America.

Lesson 3: Life without reliability

I got pretty good at budgeting my bi-weekly paycheck back in the salaried days: half of the rent came out of one, half out of the other. Bills from one, fun from the other. And twice a year, the magical extra paycheck arrived, all $1,000+ of fun money or debt-paying money. Now, five-week months are stressful, not exciting: since how much I have to spend depends on how many eight-hour days I worked the previous month, long months that follow short months are particularly trying, budget-wise. Or, conversely, short months that precede long months require more hours each day.

Not to mention the stability of the paycheck disappears. Now I get paid in several lump sums at the beginning of the month. Ish. If I’m lucky. Right now I’m waiting for a paycheck from last month that’s three weeks late — $800. Maybe not much for some, but that’s my rent money. It’s not just the reliability of individual clients that’s up for debate. This check was mailed on time, but somehow disappeared en route, possibly due to our crazy mail-tossing landlady. Or possibly due to the interminable vagaries of the U.S. Postal Service. I don’t know.

So budgeting’s a little different. I’ve switched to using a rewards credit card exclusively, because I can never be sure if my money will come in on the 1st or the 4th or the 11th, and I’ve got three mouths to feed (me and my cats!). I stick obsessively to my YNAB budget — the program is by far the best $60 I’ve ever spent (and its $20 off right now so RUN DON’T WALK to buy it). Since I invoice all of my clients at the end of the month, I know what’s coming in; I add it to my budget before it clears, or is even mailed or Paypal-ed, and spend accordingly on my credit card. And I get reward cash! A whole one cent per dollar I spend! My strategy is a little risky: What if I don’t get paid in full before my credit card bill is due on the 19th? Then I’m on the hook, and have to dip into either my tax savings or my emergency fund to avoid interest.

Lesson 4: Umm, so about that whole “going to the gym” thing…

I live two blocks from the gym. Before, I had a handy excuse for skipping: I get out of work late/I have to eat dinner, guys/all of the evening classes are so full it’s like squeezing into a toothpaste tube. Now, there’s nothing: I’m home for the mid-morning classes. I can start work whenever I want. And dinner isn’t for eight hours.

I had this utopian ideal of my future health and fitness when I quit my job: going to the gym each morning; cooking healthy, happy desk lunches; afternoon yoga and daily meditation.


Yes, you will find ways to justify skipping the gym even though it’s a three-minute walk away. And the days I do get there (I try to go Mondays, Wednesdays, and Fridays), it totally screws up my whole day. Start work whenever I want? Sure, but that means I’ve gotta work until at least 8 p.m., and that’s if I take no breaks. Today is a Wednesday. I left the gym at noon, and I’ve been working on this article for almost an hour. To fill today’s hours, I’ve got to work until 10, at least, and probably later. Wednesday date nights are no longer as exciting, that’s for sure.

And that healthy food thing? I mean, sure, it’s a little easier to cook healthy lunches for myself. But I’m at home, where there are snacks, and where (thanks to a recent testing assignment) there are popsicles aplenty. And I find myself antsier in the evenings, ready to get out of the house, prone to begging to go to a bar or restaurant — anywhere with people! — the second my boyfriend shows up. There go healthy dates with popcorn and a movie, replaced with expensive and unhealthy nights at dive bars and sushi restaurants. I just spent the whole day on my couch. It’s a work couch. I use it for working. It’s not a fun couch.

Lesson 5: Death and taxes. Mostly taxes.

HOW MUCH SHOULD I PUT ASIDE FOR TAXES? I don’t know. I’ve looked here, but I don’t know how to account for taxes I already paid through my salaried job. I’m putting aside 25 percent of my income. Is that enough? Probably not? I don’t know! I don’t know if I owe quarterly taxes, or even when quarterly taxes are due, and I’m sure getting an accountant on the phone could answer all these questions but accountants cost money.

So I guess for the first year I’m just winging it, and if it comes out at the end I owe, like, $6,000 or something I will cry and hate myself forever.

Lesson 6: Some things are cheaper!

There are some good things that happen when you work from home. (Well, a lot of good things: I like my job 10,000 times more. I get to play with my cats all day. I watched all of Scandal in a three-day binge.) I spend less on transportation. Living in NYC, I used to buy an MTA pass tax-free through my job, but it still cost about $90 each month. Now, I just don’t go anywhere! I use the bus sometimes to get from my boyfriend’s place to my own, and if I’m feeling adventurous, I’ll go out on the weekends, but I’ve only been on the subway maybe twice in the last month and a half. It’s a nice life. Saved: $70 each month.

I spend way less on snacks, mostly because I’ve always got chips stashed around my house and there’s no longer a vending machine downstairs and a Duane Reade down the street for outrageously expensive Diet Cokes on days when I didn’t have cash. Now, I store my change in a pink piggy bank. Literally. I’d count up what I’ve saved, but I’d rather it be a surprise when the bank fills up and I dump it in a CoinStar. Saved: $25 each month.

Laundry costs less — I’m not dropping it off at the laundromat anymore, because I can go in at midday and do it myself. Granted, drop-off service was a bit of an indulgence, but it’s one I no longer need. I’m really bad at laundry (“throw it all in together in a giant heap” is my general strategy), so it’s not as neatly folded and organized, but it’s clean. Saved: $15 each month.

Despite my moaning, freelancing is awesome. I don’t spend an hour and a half on the subway every day; I do chores during little breaks in the workday, creating less of a tragic mess in the evenings. I eat better. Sometimes. I work out more. Sometimes. Everyone should live like this. But I do live in fear: of an accident, illness, or injury; of a delayed payment; of success or failure. It’s all on me, now, not a corporation, not my boss, not on anyone or anything else.

And just for reference, it took me three and a half hours to write this article — almost $100 in lost opportunity cost. I think it was worth it.

Jamie Wiebe lives in Astoria. Here is her Twitter.

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