8 things they don’t tell you about freelancing

When I decided to abandon the world of 9-5 and finally try my hand at living life as a Full-Time Writer™, I was taking a calculated risk. I knew it wouldn’t be easy. I knew money would be tight for at least a year (my planned time to test the experiment). I knew it would take a lot of work to keep myself on task.

But I did my research. Crunched the numbers, outlined my plans, set up some safety nets, crossed my fingers and made a wish to the magic wish fairy, and took my pants off as soon as humanly possible. In other words, I did it without the total recklessness that so often defines my major life decisions.

Yet there are a few things no amount of research could have prepared me for. Stuff that I didn’t consider or that otherwise took me by surprise.Stuff no one tells you about.

With that in mind, here are the eight things I discovered that no one told me about freelancing for a living — because I know someone else out there is thinking of doing this ridiculous thing, too, and that someone needs the truth:

1) You will be crushed with guilt

I was a little prepared for this because guilt is an inescapable part of my personality (thanks, Mom), but I didn’t know how much it would pervade every part of my freelancing life. Turns out that working for myself and my psyche don’t necessarily play nice together. Without that clearly defined 9-5 that validates a person’s work day, slow periods when I don’t have much work make me incredibly guilty.

“I could be doing more.”

“I should be soliciting more work.”

“I should be hunting for opportunities.”

“I should start this whole big project that might only make me $10 just to justify my existence.”

And so on. I work an honest week’s work, sometimes quite a bit more than that, but it still feels different than my days of traditional employment. There is no leaving at 5pm and forgetting about work until the next morning. I’m in my “office” 24 hours a day, and the amount I make relies entirely on my ability to create new paying work for myself.

So yeah, every hour I’m not actively working makes me feel like I should be doing more. Including making this blog post. And that’s not healthy.

2) You’ll spend a lot of time doing taxes and shuffling paperwork (aka, you are a business)

This whole freelancing thing? Turns out it’s like running a business. A very small business, yes, but a business all the same — at least, if you want to do it right and professional-like and so that the IRS doesn’t break down your door and such.

Which means I spend far more time than I imagined invoicing clients, doing accounting, signing contracts, calculating hours, tallying expenses, calculating marketing budgets (yeah), and on and on and on.

That’s not fun.

But it’s reality. Before taking the plunge, I got CREAMED in taxes because I wasn’t handling my increasingly kinda-sorta-decent freelance income properly. I gleefully wrote and got paid and thought America liked me because gosh darn in, I’m a go-getter!

Yeah, no. It doesn’t work that way. You will be over a barrel if you handle things like that. So don’t. My advice? See a tax professional and get an LLC set up right away, preferably an S-Corp (otherwise you’ll be paying double taxes, seriously), and start handling this stuff just like you would any other business. Because you are a business.

This is all stuff longtime freelancers already know, but damned if it wasn’t a kick in my newbie ass.

3) Your social skills will atrophy

Seriously, why does no one tell you this?

I work from home. Yes, it’s rad. No, I don’t wear pants all the time. Yes, I’m wearing pants right now. No, they’re not full-sized adult pants that go all the way down, they’re shorts, and that’s because I do what I want to do so leave me alone, okay?

You don’t tend to see a lot of people during your day, though. Those little office water cooler moments you take for granted (and that on many days you absolutely hate)? The little interaction you have when you’re trying to ignore the cashier and buy your morning coffee at the same time? Listening to Janice in accounting tell you about the stroke her 14-year-old Boston Terrier just had?

charlie_its_always_sunnyWhether you realize it or not, you’re flexing your social skill muscles when you engage in this stuff. You know, the same way going out to get the mail keeps your legs fit and limber. Yeah, like that, but more often and more effective.

A lot more effective, it turns out. Look, I’m no Mr. Congeniality who loves to shake hands and meet every last Joe and talk about nothing for a tightly-focused hour — in other words, I could never run for president — but I do enjoy social interactions. Those little water cooler moments? I like them, dammit. The cashier you’re trying to ignore? I love exchanging some quick pleasantries with those people! Janice in accounting?

Okay, she can go stuff it.

But otherwise, engaging with people is a skill, and it’s one that fades if you don’t use it. I’m serious. And I’ve been experiencing it firsthand. Where once small talk came easily (if painfully) and conversations with people I like and respect were as natural as passing gas (perhaps the most insulting analogy of this post, but made with good intentions), now I sometimes find myself having halting, awkward conversations and struggling to bring my text-based communication skills to the flesh-based world.

The solution? Have lunch with friends at least once a week. If you know people with flexible schedules, get together when you can. If not, take the drive and meet your 9-5 friends during their lunch break. They’ll appreciate it just as much as you will. When that stuff doesn’t work out, find an excuse to walk to the nearest store to get a glass of iced tea or buy a ballpoint pen or have your prostate examined. You need to get off your ass anyway, fatty, and that little interaction with the clerk is just what the doctor ordered.

And for god’s sake, don’t think chatting with people on Facebook counts. It doesn’t. (Besides, screw Facebook.)

4) Every client will think they’re your only client

Not all that different from everyone in the service world, actually, so enjoy your small bit of camaraderie with the people who bring you your mozzarella sticks. Yet another reason to treat them well!

This sort of goes back to #2, but explores a different angle of that weird situation. First, as a freelancer, you need to understand that you no longer have employers, you have clients. There is a subtle but important distinction there (which we’ll touch on in the next point). Remember that.

And second, know that every client will think they’re the only client you have. They’ll know you have others, sure, but in their head they are your main priority. Always. “Serve us now!” And that’s a totally fair way for them to think because why should they give a damn about your eleven other projects? That means you’d better have good prioritizing skills or, even better, good skills at setting expectations.

Because the fact of the matter is, they don’t care that you’re juggling a dozen things at once, nor should they.
No matter how much you have going on, your top priority is the person you’re speaking to at any given moment. Learn it, love it, live it.

5) You can fire your clients

I hadn’t really considered this one until I started watching Mad Men. It’s an easy one, too. Got a client you can’t stand working with and who isn’t even remotely worth your time?

You can fire them.

That’s it. It’s that simple.

Sort of. Yes, sometimes there are extenuating circumstances and bigger pictures you have to take into consideration, such as whether or not this client could ruin other business for you, if they are paying you a markedly better rate than you usually get, or if they are Kate Beckinsale.

But if you run the numbers and the Pain In Your Ass to Dolla Dolla Bill Y’all ratio is off, ditch that client. Simple as that. ‘Cause you work for yourself, and that means you can work for whoever you want and tell anyone else to take a long walk off a short playground slide.

6) You have to ask what you’re worth (and take what you can get)

When you do your first bit of paid writing, you’ll be amazed that someone is willing to pay you to do stuff  you would have done for free. My first freelance check came in 1999, and it was a revelation. You’ll give me money for this? Wow! Over the years I chased that high, rarely getting it, occasionally succeeding, and over time getting really damn good (if I do say so myself) at delivering what people want.

That first bit of “we want your writing” attention is a pretty powerful cocktail, though, so powerful that entire publications have taken advantage of it and duped people into working for free (or, in the case of listings at sites like Guru and Upwork, expect people to work for pennies an hour).

But screw that. This is a skill. It’s a vocation. It’s work. And people get paid for their work, writers included.

That’s another rant, though, and one that gets away from the point I meant to make when I first jotted down this list. What I MEANT to focus on, and what too few freelancers dishing out advice tell you, is that you’ve got to ask what you’re worth. You’re worth more than you think, too, because your skill is rare and valuable.

Not even a joke. I’ve been homeless, so screw off

Remember that. Pricing yourself down in order to get jobs backfires, not to mention it often works out to a fraction of minimum wage once you do the math. Charging your actual value results in more references, word of mouth, and business — assuming your work is up to snuff, of course.

Look at it this way: If you make a killer $10 burger and charge $3 for it, no one wants it because you can get generic salty bullshit at McDonald’s for the same or less, and what you say about yourself when you ask $3 for your burger is that it’s going to be generic salty bullshit. You’re also not asking $24 for your burger, because you’re not a pretentious asshole. You ask $10, because that’s what it’s worth.

So get your $10, or whatever the market says professionals like you should be charging.

That last part is easier said than done, though, because …

7) Settling on your rate is frickin’ tough

Do you charge by the hour? By the job? By the day?

Do you vary based on the client? Do you stay consistent? Do you stay firm? Do you negotiate?

The truth is, there is no easy answer. I’ve been doing freelance work on the side for ages, and switched to doing writing, editorial work, and social media marketing on a full-time freelance basis during the last couple of years. And while point #6 is finally settling in — it’s why I no longer do local news reporting, because despite my passion for good local journalism, when it comes to freelancing it pays like shit — the idea of establishing your own rates is tough.

It’s not like you can point to the pile of nails and screws you’re going to use and say, “It’s based on this.” You can’t tally up the ingredients in the soup, add a percentage for your employees, add a percentage that is your pay, and call it a day. It doesn’t work like that.

You have to figure out what you need to live. That’s important. You also need to know what other people are getting for similar work. And to be honest? You need to assess what your client is getting from your work. ‘Cause look, penning some content for a local non-profit group’s website and a major national tech company’s website is two different things.

No one told me that. No one told me I should charge accordingly. Took me a while not just to figure that out, but to accept that that was okay.

Thankfully, there are resources out there outlining the going rate for writers and editors, broken down by the kind of work you’re doing, and showing the high/low range for said services. Those resources are quite helpful. Find them. Use them. Cite them when necessary. They’ll help you understand that following the advice in #6 is okay.

8) You will become addicted to heroin, pornography and cats, not necessarily in that order

When I first conceived of this list, I had four items. I knew it couldn’t be four, though, because five is the magic clickbait number. So this was #5, because it was stupidly silly and because there was also a small amount of truth to it, just enough so that I could talk about eating badly, wasting time, and why my fat cat won’t get his ass off my keyboard.

I don’t have to, though, since in the writing of this post (which wasted nearly 2,500 words of my writing time, so screw me for being so stupid) many other worthwhile ideas were generated.

Which means I killed an entire afternoon on this crap.


Good luck out there, freelancers. We all need it.