Recap: Five Years of Full-time Freelance Writing

Five years ago this month, I left my full-time job in PR to try freelancing.

I gave myself 18 months to see if I could (in the words of Tim Gunn) MAKE IT WORK.

Long story short: It’s still working. I’m still out here, freelancin’ it up.

I feel like this is a big deal. I’ve officially been freelancing longer than I’ve been doing any other job. It’s also longer than I’ve ever kept a pair of shoes.

But the thing is...when you work alone, from home...largely by feels like there’s no one to celebrate these milestones with you. Ya know?

If I worked in an office, we’d at least go out to lunch to celebrate or eat some crappy ice cream cake. (Ice cream cake is gross. Just saying.)

So, I decided I’m going to reflect on the past five years with you guys. Okay? You don’t even have to buy me lunch.

Let’s start with a quick recap of some highlights.


  • Started with 2 contract clients for social media management

  • Tried a lot of different types of writing work for about 234,135 different industries

  • Made more than I had been making in the PR job (whew!)

  • DIDN’T QUIT (first year was so intimidating/challenging)


  • Spoke at local conferences/associations on social media

  • Started to realize I didn’t love social media management

  • Took the Creative Class and decided to niche down, focusing on blog content for SaaS/eCommerce companies

  • Outsourced taxes/financials to a real life accountant and set up a retirement plan


  • Spent part of the year traveling, presenting, and teaching social media (only to definitively realize I don’t like doing that)

  • Introduced the site (shoutout to my husband/biz partner Brandon for building that for me)

  • Launched THIS NEWSLETTER shortly thereafter

  • Went to my first conference as a freelancer and met up with my pal Emma for some co-working in Austin


  • Formed a business LLC

  • Got real comfy in the SaaS niche

  • Finally learned to say no to projects that weren’t a good fit

  • Took some amazing trips

  • Introduced one-on-one coaching for freelance writers


What’s been great vs. what’s been sucky so far...


  1. Freedom and flexibility. Holy crap do I love choosing when I get up in the morning. And wearing whatever I want all day (ahem, pajamas). And being able to take my dog on a walk when I feel like it. That is a major perk that I still pinch myself over every day.

  1. Opportunities galore. I’ve found that if you’re a do-er and are good at the thing you do, freelancing presents so. much. opportunity. You can earn a lot, work with amazing clients around the world, and if you’re efficient, not be chained to a desk for eight hours a day.

  1. The people. I’ve been fortunate to get to know some very smart and interesting freelancers over the past five years (who I wouldn’t have known if I weren’t freelancing.) So thankful for a handful of friends who “get it” and can relate with this type of work, who act as a sounding board, and who occasionally serve as co-workers when I need to vent.


  1. It can be lonely. I’ve talked about this a lot before. The bottom line is I never realized how important human interaction was for me until I didn’t have it anymore. I’ve found some ways to circumvent this and am feeling a lot less isolated these days, but it’s something I have to be mindful of so it doesn’t sneak up on me and give me the sads.

  1. No guarantees. I’ve been fortunate to have a freelance career that’s progressively grown over the past five years, which I think is thanks to hard work and a lot of luck. However, there are no guarantees that this will keep up. I never know how much I’m going to make each month, for example. Sometimes I do miss having some certainty, but so far, I’ve been able to leverage the uncertainty as fear...and that fear keeps me working hard and pushing forward.

  1. It’s hard to explain freelancing to other people. Five years in and I still haven’t figured out how to tell other people what I do (in a way they’ll understand.) It’s frustrating when people associate freelancing with scraping by, ‘not real work’, etc. Still working on this one.

The big picture

I think, looking back, there are a few big things I’ve learned over the past five years of freelancing.

For one thing, I’ve learned a lot about myself. I spend a lot of time in my own head. There are pros and cons to that, just like with anything else, but it’s given me the time and space to figure out what’s important to me, what I do and don’t like, and what ‘works’ for me as a person and as a business owner.

I’ve learned things like:

  • I have to build group activities into my life. Be it yoga class, Skype chats, brain is healthier when I make it a priority to be sociable.

  • I have a tendency to over-work. Building boundaries into my process (like office hours, restricted phone time, etc.) helps keep me from being “on” all the time.

  • I don’t enjoy speaking to large groups. Talking to a big room of people makes me SO nervous that I can hardly eat or sleep in the days leading up to the event. Not cool.

  • Conferences aren’t really my jam, either. I don’t like having to be in a certain place at a certain time. I’d rather just meet up with people afterwards for dinner.

  • I’m very into collaborative efforts. I do well in a setting where not all of the responsibility for a project is on my shoulders and like a small team environment (largely in the world of things like ‘let’s make a thing!’ or ‘let’s plan an event!’)

I’ve also learned that I am not great at thinking about the future. Give me a to-do list and I’ll knock it out right away...but ask me where I see myself a year from now and I’m all ¯\_(ツ)_/¯

That’s where I’ve been really fortunate to have a partner who is good at future-thinking. I’ve never had a formal business coach before, but Brandon (husband) has filled that role for me. Over the past five years, he’s encouraged me to do important growth-related things, like setting goals for myself (Ex: Try to get three bylines in major publications by X date), learning (he told me about Creative Class), and sticking with long-term this newsletter.

I think it’s important to find someone like that who can help you work through those important questions, like:

  • What kind of work do you actually enjoy doing (and want to do more of in the future?)

  • What steps do you need to take to get to that point?

  • What things are you not doing right now that maybe you should be?

  • Are you challenging yourself?

  • Are you taking care of yourself outside of work?

In general, having someone who keeps you accountable and forward-thinking means you’re building in sustainability to your business. It’s helped save me from burnout and motivates me to try new things.

Will I still be freelancing five years from today? I dunno. But I’m happy with how things have gone up to this point.

It’s hard work, but it’s also rewarding.

Speaking of rewards...I think I’ll treat myself to a spa day now. 💆

P.S. S3 of Creative Class podcast is live! YAY!

This article originally appeared in my newsletter, A Cup of Copy. Sign up and get these free tips sent right to your inbox every other Wednesday.