The Pros and Cons of Being a Freelancer

Pros & Cons of Being A Freelancer

Well, it’s been a while, hasn’t it? Contrary to what it may seem, I haven’t given up on this here blog. Rather, I let wedding planning (3 weeks to go!) and freelancing get the best of me and my time. I can’t say how much I admire bloggers who publish beautiful, entertaining, and consistent content, all while managing full-time jobs, families, and whole lot of other stuff. It’s no easy task, and one I haven’t quite mastered yet—but I will keep trying. Starting now.

I can hardly believe it, but it’s been eight months since I quit my job and went full-time freelance. It’s been a challenging and amazing experience thus far, and I couldn’t be happier. Every day brings something different, but in a nutshell, here are some pros and cons of this new career path I’ve chosen:

Pro: I make my own schedule. There’s no doubt about it: The flexibility of being a freelancer is amazing. Ultimately, I have to get my work done and put in tons of hours pitching, writing, editing, and networking. But how I arrange those hours is mostly up to me. I can sleep later in the morning and make up for it by working later into the night. I can go grocery shopping at 2PM when the Iines are nonexistent. I can go to master’s swimming practices at noon on Thursdays. I can take a Friday off if I plan ahead and front-load my work for the week. It’s nice.

Con: No one keeps tabs on me but me. It’s certainly liberating being my own boss, but it also means the motivating, decision-making, and scheduling falls squarely on my shoulders. No one is going to tell me it’s a bad idea to take that Friday off. No one is going to tell me whether or not to accept an assignment, and how much I should get paid for it. No one is going make me sit down and send pitches until 5PM. And no one is going to stop me when I take on too many projects, or help me with the work when I’m scrambling to get them all done.

Pro: I get to change it up. Because I’m not tied to any one company or publication, I’m able to keep my work varied and explore all different opportunities. One day I may be writing an article about wedding planning, and the next I’m interviewing a singer on tour or researching beauty trends. Some days I write all day, while others are more editing-heavy. The variety keeps me motivated and inspired.

Con: I have to keep track of it all. Once upon a time, I completed one W9 and watched money appear in my bank account twice a month, and that was that. Not so much with freelancing. Every time I add a new company to my roster—even if just for a small, one-off project—I have to submit a new W9, and sign a new contract. I have an insane spreadsheet of all my assignments, and it’s up to me to adhere to the deadlines, send invoices (per each company’s guidelines) in a timely manner, and keep track of if and when the checks roll in. I’ll spare you any discussion of tax season.

Pro: I don’t have to leave home to work. I can wake up in the morning and five minutes later be sending emails on my computer while eating cereal, still in my pajamas—and I often do. If it’s freezing outside, I may just spend the whole work day in an oversized hoodie and slippers. And if it’s hot, I may throw on a bathing suit and bring my computer out to my back deck for simultaneous working and sunning. No commute necessary.

Pros & Cons of Being A Freelancer

My only coworkers can get a little creepy.

Con: I don’t have to leave home to work. Working from home is awesome, but it can also get lonely. Without the camaraderie of an office (and I had the best coworkers in my old office), it’s not unusual for me to go an entire workday without speaking out loud (or only speaking out loud to my cats, which is probably not better…). Though it’s easier for me to just sit down in my makeshift home office and get crackin, I sometimes make myself go to coffee shops, or buy lunch somewhere, just to get some human interaction.

Pro: Every dollar I make feels like success. I’m not saying I didn’t earn my salary when I was working for another company; I did, and I know everyone else does, too. But there’s an extra special sweetness to cashing my checks now, knowing each one of them is a direct result of something I did: an article I wrote, a blog post I edited, an idea I pitched. It feels good.

Con: There’s no such thing as paid time off. Or paid “lazy days,” for that matter. When I had a salary and I was having an off day—maybe I was up late the night before, maybe last week was insane and I was burnt out, or maybe it was the third Polar Vortex of the year and I was just over it—I could sometimes get away with slacking off just a tad, or doing the minimum for that day, and still get paid just the same. Sure, if I’m not on deadline, I can take some easy days for myself (Yes, I love what I’m doing, but there are days when even work I love is still just work)…it just directly affects my paycheck. Case in point: I’m taking a couple weeks off for my wedding in July, which means turning down some assignments, in turn minimizing my income for the month. If I want to make up that lost cash, I’m going to have to really hustle in August. 

Pro: I’m doing what I want to do. Even on the days so busy I feel like pulling out my hair; even on the days so dead I feel like I’ve hit a wall; even when I’m agonizing over tough assignments; even when I go weeks without getting a check in the mail…it’s worth it, because I’m in the career I want, and doing something I love.

Fellow freelancers: Anything to add?

I quit my job and started a blog.

It’s going to be a pivotal year. Yesterday, I turned 29. Today, I started my blog. And a few days ago, I quit my full-time job in advertising. Now, before you start to think I’m some insanely delusional millennial (that’s only partially true), let me do some explaining. I like to think of myself as a bit of a mind-reader (okay, not really–but today, go with it), so I’m just going to go ahead and answer the questions you’re probably thinking.

1. So you quit your job to start a blog? 
No. Er, not quite. I quit my job because it no longer made sense for me. Long story short (ish): My passion has always been writing. I went to school for it, did some awesome internships at some awesome magazines & websites, and got some fantastic freelance gigs. I moved to New York four years ago with only a freelance writing and editing job to support me, and a cooler as my desk chair and a yoga mat as my office. But I wanted (and needed–see previous sentence about the cooler & yoga mat) a full-time job, and decided to try my hand at advertising. I got a job at an agency doing media planning and buying and, well, hated it.The people were amazing; the work itself was too much business and too little creativity. Less than a year later, I made the move to a digital publisher, in an Account Manager role.

During my three years at that company (partially in New York and partially in Chicago, after I moved back), I managed lots of cool, custom campaigns. I went to shoots, worked with designers and was there when our websites launched some pretty amazing things (like this, this & this). I gained invaluable knowledge and became friends with amazing people (Really, one thing I’ve always loved about the ad industry is that it’s full of outrageous-in-a-good-way, bold and hilarious people. Some of my best friends now are ones I met through both of my ad jobs.) The problem was I wasn’t being creative; I was a liaison, and a manager, but not a writer, or an editor, or a producer. Throughout my time in advertising, I also freelanced on the side, and it was the perfect creative outlet. And over time, it became clear that I needed to turn that creative outlet into my full-time career. So, here I am. Out of advertising and corporate America, and into the life of full-time freelancing. And because sometimes, websites don’t want to buy random articles I write about myself and my oft-eccentric life, I’m also blogging.

Never underestimate the power of a cooler chair. Photo Credit: Mallory Kinley

Never underestimate the power of a cooler chair.

2. If you just started the blog, why are there already a bunch of old posts on here? 
I’ve had a website for several months now, but it was purely a home for my professional portfolio. Rather than create an entirely new site for the blog, I just gave this one a face-lift, shifted some things around, and now is a home for both my blog, Sarrandipity, and my portfolio.

3. Why Sarrandipity? 
I can’t take credit for this one. I tried for ages to think of the perfect blog name: something catchy, easy to remember, and fitting for me, and what this blog would represent. But I came up short. Insert my lovely friend, Lauren. I exasperatedly shared with her my lack of ideas and, within minutes, she said the magic word: Sarrandipity. I’ve always loved ‘serendipity’—and not just the movie. The word, defined by Merriam Webster, means ‘luck that takes the form of finding valuable or pleasant things that are not looked for,’ is such a great reminder that goodness and good things are everywhere, and we just need to keep our eyes open. And the fact that my last name, Sarran, fits so perfectly into the word? That, in itself, is serendipitous.

Serendipity really is an awesome movie.

Serendipity really is an awesome movie.

4. So what is this blog going to be about? 
It’s going to be eclectic, that’s for sure. I don’t want to limit myself to writing about just one thing. I have such varied interests, from style, to music, to fitness, traveling, cats, and more—and all of that will be represented here. The blog itself is a work in progress. I spent so much time not creating this blog because I wanted to wait until I had everything perfectly figured out: the right name, the right categories, the right design. But, I got tired of waiting for perfection and instead decided to take a leap of faith and start this damn thing. Probably related to that leap of faith I took to quit my job.

5. Why should I follow you? 
If the promise of cat photos and Friends references (if you recognize the gif at the top of my post, you have my heart) isn’t enough, I hope to provide you with entertainment, inspiration, and the occasional laugh (at my own expense, of course).

gif via; photo by mallory kinley

Clip: “What is Fred Savage’s Advice to Young Filmmakers?”

Fred SavageI had the opportunity to interview child actor-turned-director/producer/Hollywood every-man at the CineYouth Film Festival in Chicago. The festival featured filmmakers all under the age of 21–talk about inspiring. Savage hosted opening night of the festival, walking the red carpet to kick things off. He was super-friendly, and had some great things to say. What, you ask? Read on to find out.