8 Unexpected Lessons I’ve Learned as a Freelance Writer
Going freelance may seem like the dream, but it’s not for everyone.
You know that interview question everyone hates: “Where do you see yourself in 10 years?” Well, throughout my 20s, I always had an answer ready: I wanted to be a freelance writer.
From afar, it seems like an absolute dream. You get to work from home, take amazing trips (no vacation day limit!), and you never have to deal with office politics.
Earlier this year, I had the opportunity to make my dream a reality. I decided to leave a corporate job that wasn’t right for me. I’d recently moved to a new city, so without a big professional network or a lot of opportunities in media, I forged my own path as a freelancer.
After about six months of freelancing, I’ve realized it isn’t for me (at least at this point in my life), but I’m grateful for the lessons it taught me about my work, my personality, and what I really want to do in my career. I think these lessons may be helpful for anyone else thinking about making the leap. Below, a few of my biggest takeaways from my six months of freelance life.
1. Working from home is pretty awesome.
OK, I’m not gonna lie: After 7+ years of working a 9-to-5, not having to go into an office felt ridiculously luxurious. I could wake up leisurely, make eggs (or whatever else I wanted!) for breakfast, and decide to work out at any point of the day. (ClassPass is much less competitive when you’re freelance.) And I definitely did not miss getting on the subway in rush hour.
2. But having a routine is underrated.
A few people warned me about making sure I created a daily routine as a freelancer. At first I shrugged it off, thinking I was decent at managing my time. But after just a couple weeks, I started sleeping in later, procrastinating with chores and errands, and generally wasting more and more time. I started to feel anxious when I saw a completely blank G-cal for the following day, wondering how the hell I should structure my schedule without having any place to be. I even started to feel envious of people I’d see leaving my apartment building all dressed up and heading to work in the mornings, while I wandered out for coffee in workout clothes. (Yes, wearing athleisure every day does get boring after a while.)
3. Being your own boss is super empowering.
This was probably the biggest benefit for me: It was incredibly rewarding to realize I can not only make rent, but make a viable living off my own talents, skills, and connections. Yes, I realize being a freelance writer isn’t nearly like being a startup founder or small business owner. But from hustling to find new clients to creating an invoicing tracking system, I felt a little like an entrepreneur — and I liked it. Plus, without having a “boss” to answer to, it was so freeing to choose which projects to say yes to, and which to turn down.
4. It’s lonely AF.
Now back to the cons. Like the whole having-a-routine thing, I started to seriously miss talking to co-workers — or really, anyone — during the days. Sure, I could go to a coffee shop, but I still wouldn’t interact with anyone except the barista. As anyone who works in a creative field knows, brilliant ideas usually come from brainstorms with other creative minds — not from chilling solo on your couch. I started to feel creatively stunted as well as socially isolated after just a couple months of freelancing.
5. You need to know *a lot* of editors to make it work.
I know there are tons of online courses out there that ostensibly “teach” you how to become a freelance writer. But here’s a little secret. There’s only one step to becoming a freelance writer: Know people who work at the publications you want to write for — and know them well.
I couldn’t have gone freelance (let alone in Atlanta) had I not spend 6 years in the media industry in NYC. During my on-staff years, I worked with or crossed paths with a number of editors who have now spread out to a huge number of publications, so I felt confident I had enough connections to work for as a freelancer. Still, it wasn’t always easy for me to get a response from people I even have personal connections with.
A friend and former colleague once gave me the advice that before going freelance, you should know at least 10 editors who you can pitch — and who will respond. That second part is key. I easily know at least 30 editors at various websites and magazines who I can email — but getting them to respond is trickier. Editors are busier than ever these days (I’ve been there), so they may not have time to read or respond to emails. I also think they get a little lazy, because let’s be real: It’s much easier to keep assigning to the same people than take a chance on someone new — let alone work with someone new on crafting a pitch into a story.
I’m not blaming them; it’s just a fact of the media industry these days that everyone is stretched thin. Taking the path of least resistance makes sense; it just makes it exponentially more difficult for freelancers to break into new publications.
6. Getting paid is extremely frustrating.
To say the least. This morning, I followed up with three different clients who have yet to pay me for work I completed this summer. (It’s November.) Many of my invoices have been “lost” in the system, or a company switches payment processors which holds up payment for months. I’ve been shocked at the number of big-name media companies that use archaic and inadequate payment systems, sending out live checks via mail months after your work is completed. You definitely need to have a cushion in your bank account before going freelance, and don’t expect to get paid on time — ever.
7. For me, doing purposeful work means more than just receiving a check.
Obviously, checks are important — no matter how late they are. But when payment is the only feedback you receive on your work, it’s a little demotivating. I’ve found I personally require more than just a check in the mail or money appearing in my bank account to feel like my work has purpose or meaning.
What I loved about working at a publication is that you get lots of feedback, like page views and analytics and reach on social. In other words, you what’s working and what’s not. And you learn from both. As a freelancer, occasionally I’ll hear that a story performed well, or an editor will thank me for my “great writing” — but that sort of feedback is rare. While I don’t need pats on the back, I miss that feeling of making an impact that’s measurable. Which brings me to the final point…
8. I want to be a part of something bigger.
In the end, I have to thank freelancing for helping me figure out what I truly what to do in my career. Contributing articles on a variety of topics to a bunch of different brands is certainly one way to earn a living (and not a bad way at all!). But I feel like I’ve learned a little about a lot of topics, while not becoming deeply knowledgeable in any.
I’ve realized I want to help create something tangible, build something from the ground up, and most of all, have an overarching goal for my work. Words and information will always play a part in whatever I do next — I strongly believe quality content is king, especially in today’s digital age — but I want to do more than just write one-off articles. I want to help a brand grow, and make a quantifiable impact through content, whether that’s B2B or B2C. I have a whole list of thinkers, influencers, and podcasts to thank for helping me come to this conclusion, but that’s another article altogether (shout out to Gary Vee). For now, I’m taking some time off from freelancing to figure out my next step—and I’m excited to see where I end up.