What’s It Like to Freelance?
Myths vs. Real Talk
PIPER HICKMAN / WNW Member & Group Creative Director at 360i
It usually happens a couple weeks into a new gig. A full-timer will come up and start asking pointed questions about freelancing. If it’s an ‘older’ person (re: mid-30s, because advertising) they’ll wonder what it’s like, poking around topics like stress-level and money. If it’s someone younger, they’ll ask about the freedom of it all.
Whoever’s inquiring, I’m honest. If they’re encroaching on 40, I tell them they better have the inner constitution to weather uncertainty while adulting. I ask if they have kids. A mortgage? A pre-existing condition? If so, I assure them they’ll need to seriously save up before crossing the freelance threshold. If they’re younger and serious about being in this business for the long haul, I tell them to tweak their definition of freedom. More on that in a bit.
When I made the transition to freelance in 2011, leaving a full-time job I’d outgrown, I had expectations about what it would be like. I had heard a lot about freelancing, I made certain assumptions and I went into it a little naïve. Turns out, it was very different than I had anticipated. So now, having just ended a seven-year freelance career to go back to a full-time staff position, I’d like to help anyone considering making the same leap I did years ago. When it comes to freelancing, here are the myths and here’s some real talk.
MYTH: There’s freedom
The perception of freelancing seems to be: you work a few weeks, then take a month off tra-la-la’ing around town visiting museums or jetting off to Tulum. Not so. When you’re freelance, you have the illusion of freedom and when you’re full-time you have the illusion of security. It’s just two different ways of basically telling yourself the same lie—that it’s all good.
Either way, you’re hustling. And if you’re a freelancer, you’re constantly hustling. In my case, my husband and I have a kid, a mortgage and a dog that challenges his digestive system to the tune of a few hundred dollars in vet bills on a quarterly basis. School, food, new carpets—it all adds up. So I took all the work I could get. And so do most freelancers I know.
Now, while you don’t have freedom per se, you can create a little more control of your time and schedule. Just a little. If you want to go to Cuba in May for ten days, and you plan ahead, you don’t have to get your direct report’s approval, and that is all kinds of amazing.
MYTH: It’s all fun and good vibes
Another misconception is freelancing is fun and relatively easy. Well, not really.
Sometimes you’re brought in on an assignment that an agency hasn’t been able to crack for months, and it just has bad juju attached to it. You’ll slog your way through to a solution, but it won’t be easy or fun. Or, you’ll be partnered with someone you just don’t vibe with. Or, you’ll get a broken chair and a crappy desk next to the men’s room in a section of the office that still feels and smells like 1993.
Freelancing is a continual leap into the unknown. You never know what you’re really getting into until Day 1. Sometimes it’s awesome. Sometimes it’s hell. Regardless, it’s temporary. So you just have to suck it up, do your job and earn your day rate.
“I’ve seen other freelancers maximize their coin by double dipping, but again, you make more by working more. So, yeah, you can make really good money, but you will definitely have to put in the work to earn it.”
MYTH: Dolla, dolla bills
Those crazy day rates, right? Well, yes, you can make a lot of money freelancing. But…
To make a lot you have to work a lot. And as your own entity, you’ll need to provide your own health insurance (if you can’t go on a partner’s), your own life insurance (if appropriate) and your own disability insurance (yes, you really should get some). And then there are taxes. Whether you LLC or not, you’ll need to sock some of the earnings away to pay Uncle Sam and hopefully your future self’s IRA.
I’ve seen other freelancers maximize their coin by double dipping, but again, you make more by working more. So, yeah, you can make really good money, but you will definitely have to put in the work to earn it.
MYTH: It won’t be that different than full-time
A lot of people come to freelancing with a full-time mentality. This doesn’t work. The parameters are different and to succeed, you have to work differently. You can’t get proprietary about your work. You can’t get political. It’s best to assume a kind of transactional approach, quickly figuring out what the people who called you in want, and delivering it. This is a distinctly contrary mind-set to what makes for full-time success—you aren’t trying to get promoted, you aren’t trying to get sent to Cannes. What you are trying to do is solve a problem and validate your day rate. Period.
And then there’s production. As a freelancer you may not actually make work for a while. Or, you might see someone else produce your idea. This is one of the biggest differences between being a freelancer and a full-timer. If you aren’t okay with this, then freelancing might not be for you.
“A lot of people come to freelancing with a full-time mentality. This doesn’t work. The parameters are different and to succeed, you have to work differently.”
MYTH: You get to give zero f*cks
Lots of people think that freelancers are just for-hire a-holes who don’t care. But the good ones do…a lot.
I know this is contrary to some of what I wrote above, but you can be a transactional-minded freelancer and still care about the work. I got into advertising because I love writing, I love stories, I love film, I love photography, I love design. And I love the creative minds I meet a result of working in this industry. And even though advertising is based on capitalism, I love that it allows for some artistry. So, as a freelancer, I still cared. Most of the freelancers I know are just as passionate about their craft. You can’t do this day in and day out and not care. But there are people in the industry who don’t seem to get this. They treat freelancers as tertiary to the business. So there’s that. Sometimes as a freelancer you can feel like an outsider looking in at advertising through a glass wall.
REAL TALK: It’s like a mid-career internship
I learned a lot during my seven years of freelancing—much more than I think I would have had I stayed full-time. But I had to; my livelihood literally depended on it. The pressure to stay knowledgeable, topical and relevant will keep you up on your creative game.
And then there’s the exposure. Getting to be a fly on the wall in all kinds of situations—seeing how different agencies work, pitch, strategize, produce, etc. This can make you a better creative, too.
Also, freelancing can increase your network exponentially. You meet new people with every gig. The more people you know, the more opportunity you may have to work with or for them in the future.
REAL TALK: It’ll make a businessperson out of you
I’m a writer. I used to say I wasn’t good with numbers. But I am now. What changed? I had to start calculating day rates and IRA contributions while also juggling tax bracket knowledge and write offs. The minute the numbers were about my money and my business I was suddenly able to get all ‘Beautiful Mind’ about my finances. I can quickly tell you what an extra hundy on your day rate will net you in a three-month gig and how it will affect your tax return, or lack thereof. The longer you freelance, the better your math acumen will be.
“You have no idea how amazing it is to watch a turtle at 2:15 on a Tuesday when you know somewhere in Midtown some poor CDs are grappling with a nine-page packaged goods brief with 15 RTBs and 25 deliverables. It’s sublime.”
REAL TALK: Eternal sunshine of the jobless brain
Being in-between gigs can be nerve-wracking for sure. It took me a few years (and many assurances from my husband) to not worry so much about when the next job was coming. But once you relax and let yourself experience the high of ‘in-between-gig-brain’, you’ll never want to go back. Never.
You’ve been there before. You know that feeling of levity when you quit a full-time job and haven’t started the next one yet? Imagine having that feeling several times a year instead of once every few years. Imagine going on vacation and not checking your work email because there IS NO WORK EMAIL.
This is when I would do all the things that replenish the creative reserve like see movies or go to museums or take classes or work on a personal project. Or, I’d just hang out with my kid. Or, actually cook dinner. Or, just sit in the Brooklyn Botanic Garden and look at turtles. You have no idea how amazing it is to watch a turtle at 2:15 on a Tuesday when you know somewhere in Midtown some poor CDs are grappling with a nine-page packaged goods brief with 15 RTBs and 25 deliverables. It’s sublime.
REAL TALK: European-ish maternity leaves
While six-months pregnant and definitely showing, the place I was freelancing for offered me a full-time job. I considered it, but when we discussed my maternity leave I knew it wouldn’t work out. I don’t remember the details but, because this is America, it was something like: some fraction of pay, go on disability, then come back in 8 weeks or we can fire you if you want more time and rehire you later. I had never been fired before and I didn’t want to have it happen for the first time because of my kid.
So, I passed, and they kept me on. I freelance waddled my way into the office until the very end of my pregnancy. Then I took five months off and didn’t go back to work until I was ready. I finally knew it was time when I realized I was spending more time on ad blogs than mommy blogs. But, it was a real relief to return on my schedule instead of someone else’s.
When it comes to going it on your own, there’s no knowing exactly what it’s going to be like until you actually do it. If you decide to go for it, just save up 3-6 months living expenses and expect it to be everything and nothing like you expect and you’ll be just fine.
Header Illustration by WNW Member Aaron Kemnitzer