My Last Day As A Freelance Copywriter: Highs and Lows

Today’s the day!

And on my last day at the agency, the owner brought his 6-month old puppy dog, Lenny. What a perfect—yet unintentional—gift. I considered stealing her. 

Honestly, I didn’t know what I was doing when I signed on as a freelance copywriter in February 2018 (on top of working a full time job at Rapha). I knew I’d work in the office on Monday and work remotely on Fridays. I knew it would help me out financially to have a second income. And I thought my three-month contract would end after, well, three months. I thought those three months would buy me enough time to find a full-time copywriting job somewhere in Boulder or Denver. In reality, I hoped after three months of working my ass off, they would bring me on full time. I wanted them to like me and keep me, so I made myself available in the evenings as well, working on anything they needed when I got home from my other job. There were countless late nights, but it felt worth it when I didn’t have to worry about rent and when I could comfortably pay for my cyclocross race entry fees in the fall.

Those three months turned into more than a year of ongoing work, which I felt incredibly grateful for. Not only was it an extra little cushion of pay twice per month, but I got to work on my writing skills in a professional setting. My right brain was firing on all cylinders. I also think applying for jobs and jumping back into a full-time job would be much more difficult had I not found this freelance opportunity.

Overall, I had a really wonderful experience; the team was so welcoming and treated me like one of their own. They even gifted me a jacket when the company got new merch from one of their clients. I enjoyed a small team much more than I anticipated; while the process wasn’t as fluid as it would’ve been in a larger agency, everyone operated with, what felt like, a stronger sense of ownership over work, and an all-hands-on-deck approach to getting projects complete on tighter timelines. I respected that and learned a lot from the process.

Coming off this experience, I decided to put together some highs and lows. If you are a creative considering taking on freelance work (especially on top of a full-time job) I hope this helps! And of course these will differ from person to agency.

The HIGHS of freelancing:

1. Freedom: Responsibility and professionally speaking, I was treated like a full-time employee; my duties and expectations were no different than a full-time copywriter’s. But, personally, I felt like I had a bit more freedom when it came to life things. I didn’t feel any guilt when I had to work both of my days remotely, I was trusted to get work done from wherever I was, and if I had all my work done for the day and wanted to leave a few minutes early, I did.

2. Hourly pay: This is a high and a low. The more I worked, the more I got paid, so this was a driving factor when I was offered more hours per week to take on jobs in the evenings and on weekends when I wasn’t working at Rapha, my full-time job. I definitely burned the candle at both ends, but I was rewarded for that.

3. Portfolio work: While I was working at job that didn’t challenge me creatively and didn’t relate specifically to the advertising industry, I liked having a freelance job to help me stay relevant in the advertising industry, especially as I was applying to full time jobs. I’m not sure I would have gotten interviews had I had a large gap in my resume and no current work to show.

4. Potential full time: Though it didn’t work out for me, sometimes freelance work can turn into a full time job. I had discussions with the recruiter (I went through a recruiter to find this position) and the agency team and, unfortunately, there wasn’t quite enough work coming in for them to hire another full time, salaried writer. But opportunities like this open doors if you’re hoping to get a larger role down the line.

5. Working remote: Most often, freelance work is remote. AKA in your pajamas, from your bed, until you forget what day it is. I was very grateful I got to work remote one of my dedicated freelance days. I took my time in the morning, had time to fit in runs, bike rides, appointments, etc. The dream life is working remote, IMO.


The LOWS of freelancing:

1. Unsteady work/less security: Without a contract, you could be axed out of nowhere, and that’s the reality of working in the creative industry, especially advertising. I had a contract for the first three months, but after that the contract idea sort of faded away and I was working month-to-month unsure when and if I’d be cut.

2. Doing taxes: Thankfully, I just had one freelance job, which means I only had one extra I-9. The more projects that come in from different agencies and clients, the more insane taxes get AND the more you need to keep track of your expenses like driving mileage, gas, meals at work, etc. Unfortunately, I didn’t keep track of anything. I could easily go back to my bank statements and figure it out, but that’s 13 months of write-offs I should’ve kept track of and could’ve claimed this year. Paper trails, people!

3. Hourly pay: Yeah, this one is also a low, too. I had a salaried job in Florida and I remember how lovely it was to get paid on holidays and sick days and even when I was out getting an oil change in the middle of the day. With a freelance job, you’re strictly paid for the hours you’re actively working, and nothing outside of that.

4. No benefits: I’ve never heard of a freelance job including benefits, and mine certainly didn’t. I was lucky because I had them them through my full time job. This is also a reason the company can pay much higher—they aren’t footing any doctor visits or contributing to your 401k.

For me, there were more benefits when taking on freelance work, which is why I did it. The driving factor, at that point in my life when I accepted the job, was money. I listened to one of Tim Ferriss’s podcasts awhile back and his guest stressed the importance of having more than one stream of income. I didn’t realize how right that was until I was collecting two paychecks for a year.

I’m not sure if I could handle more than one when I take on this new salaried job in a couple weeks…and I’m not even sure what it would be. But we’ll find out.

Have you ever freelanced? Got any tips/advice/highs/lows?

4 Replies to “My Last Day As A Freelance Copywriter: Highs and Lows”

  1. Thank you for sharing your experiences as a freelancer. Unfortunately, I never worked as a freelancer but it’s definitely on my to-do list. All tips are very helpful 🙂

  2. I’ve worked in the graphics arts department of a small midwest manufacturer for most of my career … it’s a good gig with standard office hours and salary … but I wonder about the freedom a freelance gig would offer. Thanks for sharing.

  3. Thank you for sharing some of your highs and lows about freelancing. That’s awesome that your contract extended, but I cannot imagine the exhaustion you had to deal with!

    For me, the difficult thing is I’m agreeing to some jobs that are so low that they aren’t worth my pay or time, but it’s a client with steady articles to write, so I’m in a slow process with working on it.

    I hope you have a wonderful start at your new job soon. Best of luck to you! ♡


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