5 Things That Frustrated Me When I Started Freelancing

Oct 20, 2015

I can hardly believe it, but I’m already closing in on a year and a half of being a full-time freelancer. Somedays it feels like I’ve been doing this for two minutes, and other days it feels like I’ve been doing this for two decades. My business has come a looooong way, and I’m extremely proud of where I am today.

But, those proud moments are punctuated by a lot of reflection on where I came from. In fact, it really wasn’t that long ago that I was spinning in a panic about the decision I’d made (remember my terrifying post about losing my biggest client?!). “What the heck have I done?” I thought to myself. Along with, “How will I ever make any money doing this?”

Well, you know I love to put a positive spin on things around here. But, I also like to balance that with a healthy dose of realism. So, while starting my freelance business is the smartest decision I’ve ever made for myself both personally and professionally, that doesn’t mean it was without its fair share of struggles and annoyances. And, I never want to gloss over those pesky and all too real things in favor of making my life seem like a bed of roses.

After all, I figure the realistic insight and advice I have to offer doesn’t do anybody any good if I don’t ever actually share it. So, here are some big (and, admittedly, not so big) things that frustrated me when I was starting my freelancing career.



Perhaps one of the largest (and most surprising) frustrations was the rates that many well-known publications and websites offered writers. I was shocked to learn that many of these outlets don’t pay writers at all. And, if I was lucky enough to find one that actually offered compensation, their rates were so paltry it wasn’t even worth my time.

I promise you, there are well-paying gigs out there. You just need to find them. My suggestion? Stray away from the more “traditional” places that can get away with simply offering writers exposure, and instead put your name out there locally. Connect with some local businesses, and see how you could work together. Sure, small businesses don’t have a huge budget, and it’s not an easy way to make a quick buck. But, you’ll gain some experience, make some connections, and start making a name for yourself!


I think we’ve all done this at one point or another: I’d see a posting for a writing gig somewhere, and immediately craft the perfect pitch email. Then, I’d start having delusions of grandeur. I just knew they’d love me. They were definitely going to hire me—tomorrow.

So, imagine my surprise when over two weeks later I was still met with radio silence. Yes, you’re incredibly excited to be launching your business and finding people who actually need your services. But, it’s important to remember that they don’t share your sense of urgency. They have other priorities aside from just making your day.

It can be tempting to hound them until you get a response (which, if you do that, will likely be a “no”). But, do your best to remain patient. Craft a polite follow up response two or three weeks after initially sending your information and just wait (and hope!) for the best.


Starting freelancing is remarkably similar to starting any other career. I couldn’t land gigs until I had a portfolio of published clips to show. But, I couldn’t get those published clips if I didn’t land a gig. It was an endless loop of frustration.

This is one of the (very, very, very rare) times when I’d recommend writing for no charge—just exposure. In the beginning, I wrote for a few larger, better known sites in order to get a few published samples I could showcase. Yes, it stinks to spend time on something when you know you won’t even make a penny. But, think of it as an investment in your future. Once you build up a big enough client base, you can kiss those free projects goodbye. There’s no rule saying you need to work for them forever. I let mine go long ago.


I like to think of myself as a fairly confident person. But, we all know that starting something new and scary has the ability to drag all of those self deprecating thoughts right out of you.

That person is way better at this than me. They have way more experience. This place will never want to hire me. Why am I even doing this?

You don’t need me to tell you that those thoughts aren’t productive, and they aren’t doing you any good. So, instead of spending your energy beating yourself up and comparing your success to others, channel those efforts into actual helpful, beneficial activities. Take notes on things you love about someone else’s website or portfolio. Jot down some of the outlets they’ve written for so that you can pitch them later. Sure, you’re still a little envious. But, at least you’re using it to your advantage.


Yes, this is a small frustration. But, I couldn’t leave it off the list. When I first started freelancing, I worked at our kitchen table in our old apartment. The table was directly under a ceiling fan. And, since I started freelancing in the summer and our apartment didn’t have central air, the ceiling fan was running constantly. Which means my papers were always getting blown across the room.

It was frustrating. And, I can’t tell you how much having my own workspace has improved both my attitude and my productivity. So, even if you can’t set up an entire office when you’re just getting started, it’s important to at least designate a small corner that can act as just your workspace.

Whether you’re experiencing these right now, are worried about experiencing them in the near future, or are looking back and shaking your head like me, I hope this glance at the “not so fun to talk about” side of things helps you out.

Now, go get after it! Until next time!