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Adventures in Freelancing (Pants Optional)

I never thought I’d miss desk chairs.

I was fortunate enough to be one of those people who started working immediately after college. A yearlong internship panned out—the television company with which I’d been interning took on a $45 million project during my last semester, and rather than train new coordinators, they just started paying me once I graduated. I started at $500 a week, which at the time felt like legit riches, and then got bumped up to $600 a few months later.

Although I was only supposed to contract for about 5 months, I ended up staying as an employee for more than a year, during which time my incredible boss/mentor rallied tirelessly to get me put on salary, but to no avail. I tried to move laterally in the company, toward one of the creative jobs that were more along the lines of my degree, but nepotism reared its fugly head and I was passed over for any new positions.

So, I found myself with no chances to move within the company and no full-time prospects elsewhere. I did cry, once—in the comfort of my own breakfast burrito—and no one noticed except the waiter, who (bless him) wordlessly handed me a mimosa. After a few sips, I pulled myself together, considered my skills and connections, and shifted my mindset to freelancing. Fortunately, thanks to the proactive work of my now-former boss, I spent almost no time searching for jobs. She put me in contact with a few company connections, all of whom I reached out to immediately and pushed to set meetings up with. During these meetings, if there were even an inkling of a suggestion of a task mentioned, I said yes. Always yes. I agreed to everything from working a private school charity function for a producer to managing the marketing for an upcoming indie film. I can’t stress enough how important it is to say yes. If the task is basic enough that they’re asking a relative stranger to do it, and it doesn’t involve a Hazmat suit, it’s probably something you can figure out how to do. I consider myself a lifetime double student at the universities of Google and Your Local Public Library.

So I got a backup laptop battery, switched out my unlimited MetroCard for a pay-per-ride and, before I could put on my comfy slippers, I was juggling five different freelance gigs. And I do mean different. I spent my days alternating between cutting Flavor of Love highlights (yes, the VH-1 masterpiece), to pulling stills and sound bites for a TV show’s digital board game, to frantically researching Photoshop layer-masking for a website’s design after having promised I had the adequate skills to do it.

The Money

Let’s talk about the fun part of freelancing: getting paid!!! Negotiating a pay rate is not as tricky or as terrifying as you’d expect. Before that process begins for you, ask someone in a similar field about the rates they charge, both when they started and now. When you go back to the employer, don’t be afraid to aim higher than you think you should. If you’ve gotten this far in setting up a freelance position, they’re unlikely to slam the (e-)door in your face. They’ll either say yes, or they’ll counter with a lower rate. From there, feel free to negotiate away; I found that agreeing on a rate within a couple of emails saved both of us from any potential resentment.

Here’s another thing about quoting a rate for your work. Come on—lean in for this one—I’m going to type in italics to invoke whispering: If they’re hiring you to do some extra work, eight times out of ten they don’t know how to do it themselves. They probably don’t even know what the typical rate is. Don’t take advantage of people, obviously, but don’t be afraid to upcharge based on your own experience (whatever that may be) and to make it worth your while. Like I said, I promise that an employer won’t turn down your services, then tell all his/her friends not to hire you, and then hack into your OKCupid account to declare you a huge, pompous, money-grubbing asshole if you quote a rate that’s too high.

What’s less fun than negotiating a rate is chasing after employers for money. It’s not necessarily that you didn’t do a great job, or that the employer is a bad person, or that the project is necessarily a total go-nowhere scam running out of the back of a souvenir shop. (I repeatedly stress not taking this stuff personally, because it’s very easy to let happen, especially if you’re working alone most of the time and away from the regular, conversational feedback of office life. A year of freelancing left me more sensitive to criticism than Joffrey Lannister-Baratheon.) It is simply not your clients’ top priority to give you their money, regardless of the job you did. So don’t be afraid to bring it up kindly in an email or make a phone call, regularly, to make sure it happens. No one is going to worry themselves as much about your payment as you are. Be your own #1 get-money-get-paid advocate.

The Routine

Throughout my time freelancing, it was hard to regulate some semblance of a routine. I would work late until I fell asleep with my computer in my lap, and then I would wake up the next morning, grab my computer from my bedside, and start working again. The sheer number of deadlines made self-motivation easy; the trickier task was turning my brain off from “work mode.” Imagine getting to your office at 8 am and leaving after midnight every day. Even if you’re only committed to eight hours, you’ll probably find yourself working ahead just because you’re in that environment. When I was working from home, there was no differentiator, especially when “home” was a teeny tenement apartment with no common spaces.

But there were numerous advantages! I could work in my pajamas (although to avoid the inevitable self-disgrace, I usually didn’t), I could do my laundry and grocery shopping in the middle of the day when there were no lines. I worked my gym schedule around the TV Guide for the channels I could watch on the treadmill. My conversational skills didn’t exactly flourish, but my work and home lives were the most efficient they’d ever been.

The Location

At one point, I decided to take the phrase “working remotely” to heart. With some extra cash from one particularly lucrative job, I moved to an apartment two blocks from the Mediterranean Sea for a few months while I continued to cut, edit, and write content for various clients. Wake up, work over breakfast, bring lunch and write on the beach before it got too hot, come home, work through dinner, go out with new roommates. And, of course, go on the occasional adventure. I realize that not every freelance job can be done from across the globe, but if the stars align accordingly for you, then get your ass out there.

Hanging Up The Slippers

Before I knew it, a year of freelancing had passed. By then, I was working part-time in the office of a client, a social media/entertainment startup, who now needed me on-hand for a few hours a week. I was also bartending a couple times a week, more for the social interaction than anything else. I felt both exhausted and also, strangely, unaccomplished; unless you’re looking at freelance gigs cumulatively, it’s easy to feel like you didn’t contribute greatly to any one project.

Not long after that, the part-time office job asked me to come onboard full-time. After weighing the decision, I decided to hang up my slippers and come back to office life. I would miss the freedom of scheduling my day, and I would miss indulging the weird idiosyncrasies I had developed from being alone most of the time for 15 months (like talking to myself excessively and eating certain foods with a knife only). Ultimately, the most alluring prospects were the regular, decent salary, a stake of equity in the company, the comfort of a desk chair (so much more ergonomic than the headboard of my bed), and the chance to interact all day with humans who weren’t appearing on a daytime talk show.

Am I glad I made the switch back to a one-job-only, 9-to-5 life? Yes. Do I miss the flexibility? Yes, every time I get a low-airfare alert for some exotic city, or try and elbow my way to the only rust-stain-free dryer at the laundromat at 7:30 in the evening. On the plus side, I have more regular in-person human interaction; I’m finally starting to get out of the habit of what I call ‘speaking in email,’ ending all spoken office conversations with “Best, Alyssa.” And I don’t have to chase anyone for a paycheck—it lands nicely into my checking account twice a month.

Is It For You?

I don’t know that I would recommend freelancing as a full-time job to everyone. I think it’s worth trying, especially if any of the above perks seem attractive to you. And oftentimes, they can lead to a steadier position, as in my case.

If you’re thinking about jumping on the freelance train, it’s worth having some money saved up, in case the jobs dry up or in case an employer is dragging their feet to give you your first paycheck. There’s always going to be some lingering awareness (and there should be, if you’re responsible about your bank account) that there will be periods of low income in addition to times where you’re flush with cash. Retail copywriting, for example, is heavily sought after from October to December, but unsurprisingly, work dries up after the holidays. So as tempting as it is after a well-paid gig to head to Serendipity 3 for a celebratory Frrozen Haute Chocolate, it might be worth saving some of that cheddar for a rainy day. If managing your money with some Scroogery isn’t something you think you’re capable of, then maybe freelancing isn’t for you.

Of course, starting to freelance isn’t always an all-or-nothing decision. You might be working one full-time position when someone asks you to take on a project. Then that may lead to other projects, some concurrently, until you have to consider whether it’s enough money and consistent work to quit your day job for. If so, and if you don’t LOVE your day job, then I say get out of there! Be free! Spread your self-sufficient wings! And when that day comes when you’re called back down to Earth for another permanent position, you have to make the decision for yourself: Just how much do you love eating oatmeal with a knife?

Photo by Meaghan Morrison

Photo by Meaghan Morrison

Not Going Broke, A How-To

After vacationing in Japan, visiting New York, and moving in with my boyfriend, all within three months, I had a lot of debt and needed to have a plan to get rid of it. I have a decent job that sort of allows me to live comfortably, but the reality is that I needed to budget my spending and hold myself to it. Budgeting my way out of debt and into better savings sucks. It really does, but it’s part of being a responsible adult who maybe wants to buy a house, or get married, or take another big vacation abroad.

Photo by Meaghan Morrison

Photo by Meaghan Morrison

Let’s take a look at how I try to set up my budget, which is generally applicable for a young working professional living in the major Bay Area. Please note that the cost of living can be scaled down (or up) depending on where you live.

How Much Money You Make

For salaried workers, this is pretty simple. How much do you get paid? How often do you get paid? Multiply accordingly to figure out about how much you make each month. For example, let’s say my annual income is $40,000–after taxes. It comes out to about $1,200 per paycheck twice a month. We’ll work with a baseline of $2,400 dollars each month, subtracting as we count our expenses.

Cash Flow: $2,400

How Much You Have to Spend

Car payments, rent, and insurance are some typical costs. These are required for not losing your car, your home, and your health (or maintaining any of the above), and as such, these are your priority payments each month. In addition, since you have to buy gas for your car, you should estimate the average cost of a tank and the number of times you fill up in a month. I generally go to a gas station about three times a month, give or take a week. There’s not really an opportunity for cost savings here, barring trading down your current car and moving back and forth.

Cash Flow: $2,400

Rent: -$700

Car Payment: -$306

Gasoline: -$120

Car / Renter’s Insurance: -$110

Cash Flow after Necessities: $1,164

How Much You Have for Food

Barring rent, food is where I spend the majority of my money each month. Cutting back from having sushi two to three times a week sucked, but I had to devise a plan for saving money where I usually spend the most.

First, I accounted for breakfast and work lunches. I normally don’t eat breakfast, but sometimes I do get coffee. Paying $4 three times a week for a coffee and snack comes to $12 per week for breakfast. For lunch, the cafeteria at my work tends to charge about $6 per meal, but I want a little breathing room to eat out with my co-workers once a week at about $15. A $6 cafeteria lunch four times a week, plus $15 for eating out once a week, comes to $39 per week for lunch. Next, we should account for dinners, desserts, and other snacks you would normally eat at home. I try to eat something of moderate size and of moderate price from the grocery store most nights of the week. This usually comes out to about $10 a day, sometimes serving for two or more.

To account for eating out, I let the cost savings roll over, and try to not binge on alcohol or appetizers. In order to calculate how much you’d spend each month, multiply your weekly costs for breakfast, lunch, and dinner by about 4.3 (the average number of weeks in a month). It isn’t an exact number, but it generally works out to be fairly accurate (and then I round up to the nearest whole dollar).

This part of the budget varies greatly from person to person, as some people care more about what they’re eating, how often they’re eating it, and if they can stand leftovers. I for one don’t mind leftovers, but hate monotony in the variety of my overall meals, so I spend a little more on some meals for bigger tastier foods.

Cash Flow after Necessities: $1,164

Breakfast: -$51

Lunch: -$168

Dinner: -$300

Cash Flow after Food: $645

How Much You Have for Fun

Shit gets tricky here. You have a finite amount of money left this month. You could spend it on drinking, a new pair of shoes, or a coffee table. I like all of these things, but my savings are more important to me. If you don’t have any, what happens when you run into trouble? I’m a bit proud and don’t really want to ask my mom and dad for help, so I put a small, but decent chunk directly into savings.

After that, it’s sort of like juggling. You can revise how much you spend each month on entertainment, such as movies or small trips. Or maybe, you want to spend more money on material things, and go shopping more often. These budgets are flexible because you still have money left over. I recommend that you put anything remaining from your cash flow into savings.

Cash Flow after Food: $645

Savings: -$200

Entertainment: -$120

Shopping: -$200

Cash Flow after Fun: $125

Getting Out of Debt

Above, there’s the basic outline of a budget, but you can see that at the end, there’s not a lot to pay back toward existing bills. Here’s where you look at all the things you’re spending money on and figure out where you can afford to cut back. For example, you don’t really need to spend $200 a month on shopping for new things. This could be cut down to $50 for new games or some new makeup, bringing your debt repayment funds up to $275. Furthermore, not everyone is like me and spends a lot of money on food. Some folks I know spend less than $200 a month on food, and that could be you too! Saving money to pay debt sucks, but it needs to be done if you want to be a financially responsible adult. Just learn to cut where it doesn’t hurt as bad.

Note that if you have long-standing credit card debt, you should try to pay it off first before putting a lot into savings. Your savings doesn’t accrue interest, while owing money to credit card companies costs you more in the long run. You should also aim to pay off your credit cards every month, making the bills in the long term much more manageable.

Making Everything Easier

Finally, work out your budget in Microsoft Excel or Google Spreadsheets: it’s an excellent way to have a copy that you can manipulate and track your progress. Alternatively, you can use a site such as Mint to have them track your spending. Such websites can pull records from your credit cards, bank statements, and other bills to better show much you’ve been spending, and usually they have great ways to analyze your spending or track your goals. You can use these to see where you’ve been putting all your hard-earned cash, so you can decide where you need to cut back.

Good luck with the budgets and the savings!