The Ups and Downs of Freelance (& Important Lessons I Learned in 2023)

Wednesday, November 22, 2023
A visual representation of me freelancing.

We are coming to the end of another year. This time last year, I had stopped getting assignments from a well-paying writing gig and considered pursuing another direction entirely. As 2023 began, I accepted some freelance public relations work and quickly accepted the challenges that went with it. Now, this year, things have ended far differently for me than when I started. I'm now writing for some pretty popular magazines and public relations is now a soon-to-be distant memory.

For anyone who does freelance, you know there are major hills and valleys to this type of work. And I have faced some significant lessons this year that I wanted to share with you:

1. Freelance work doesn't come with a guarantee. 

I guess this is a pretty obvious one, and I don't just mean the certainty of the workflow. I also mean the guarantee that it's right for you. I've always done (and enjoyed) freelance writing. However, this particular lesson came around when I started doing public relations. I thought I'd love it when I started. While I enjoyed it at times, I quickly realized it wasn't right for me. There were countless aspects I hadn't considered before I started. You have to invest in a lot of resources. You have to always be on top of potential opportunities, leaving me with the feeling I couldn't turn off my brain. And more.

The grass is always greener on the other side, as the saying goes. What looks appealing and works well for one freelancer, may not work out the same way for you.

2. There are plenty of things you'll do without any pay at all.

I can't tell you how many meetings I had this year to discuss possible freelance opportunities. Or to discuss how I could potentially represent someone in PR freelance work. I kept telling myself it was a fantastic way of learning how to talk about my strengths. However, many of those opportunities didn't pan out. Sometimes I was ghosted. Other times I realized it just wasn't a good fit for me. The sad thing is these meetings were all unpaid, of course. The mental energy, the preparation, and my insights were all given for free.

I think this is common in freelance work and I've read many articles from fellow freelancers on how to address the whole meetings-that-go-nowhere thing. My best tip? Try to do as much as you can via email before doing a meeting. It will help you understand far better whether an opportunity is right for you.

3. Contracts are really important.

It doesn't matter if this potential client is your best friend. Or a referral from a family member. The moment you begin to do freelance work for someone, you need to have a contract in place. One that outlines your payment terms, what happens if things are unpaid, what happens when you want to end the business relationship, and other things that protect you (and the client).

My freelance writing has been straightforward with this, and for that, I'm grateful. I ran into a situation this year where I attempted to work for someone without a contract and all I can say is how glad I am that I didn't do much for this person. So create a contract. There are some templates available on a variety of sites you can use (Hello Bonsai is one).

4. Keep trying. You just never know.

If you had told me I would have started writing for some major media outlets this year, I wouldn't have believed you. Not really, anyway. However, I've always been pulled towards commerce writing (i.e. those are those articles that discuss gift ideas, deals available, etc). And I wanted to do that kind of writing. With just a few of those samples under my belt and some others that came about thanks to my work with Mental Floss, I started cold-pitching editors to consider me for assignments. That's been a fruitful endeavor that has led to many opportunities.

I think what helped is I had a specific niche in mind and a goal. I'd recommend the same depending on your freelance endeavors. 

5. Cutting things out is hard.

Because of the rises and falls of freelance work, I am slow to cut things away. But thanks to a fairly recent opportunity, I have taken the brave step forward of trimming my freelance activities. I'm thankful for it. I admire those who can do that kind of work as their full-time career. Truly, I think it's incredibly brave and takes a lot of energy, time, and a multitude of resources. 

Sometimes as a freelancer, you do need to cut back. It's also hard to say no to anything. However, saying yes to everything is impossible. If an opportunity has come around and you aren't sure you want to say no but you aren't sure about saying yes, give it time. Tell the prospect you need a few weeks and you'd like to check back. I did this and came to realize I didn't need the work after all.

As I look ahead to 2024, I'm intrigued to see how my skills and efforts will play out this time. Freelancing comes with some rough waters, but there are plenty of benefits. 

What insights can you share about your experience with freelancing? 

Nicole Pyles is a writer living in Portland, Oregon. Her writing has appeared in Sky Island Journal, Arlington Literary Journal, The Voices Project, The Ocotillo Review, and The Gold Man Review. A poem of hers was also featured in the anthology DEAR LEADERS TALES. You can read her other writing on Mental Floss, Better Homes and Gardens, Tom's Guide, and in at least one issue so far in Woman's World. Say hi to her on Twitter or Threads under @BeingTheWriter.


Sue Bradford Edwards said...

Yes, yes, and yes! Just because you can do something, doesn't mean you should. I used to do a lot of test passage writing, but as I learned more about state testing and how it is impacting education, I stepped away from it. What a relief! It is hard to say "no" to a check, but you have to say yes to your integrity. If you aren't good at something or you really, Really, REALLY dislike it, it is okay to say no.

Angela Mackintosh said...

Nicole, this is a fantastic post full of reflection, and I'm so thrilled and proud to watch your career grow! :)

When I freelanced full time, I absolutely loved it, but I came to the same conclusion as you did about all those unpaid initial meetings. Finding clients and securing the contract was a huge time suck and a problem for me. I worked in the extreme sports industry; so for one, I was a woman in a male-dominated industry, and one who looked young and wasn't great at talking herself up. So I hired someone as a liaison. My liaison was a hype man who bragged about my work up and would secure the job by showing the potential client my portfolio and setting up the terms. He was well-connected in the sports industry, which was important, and knew who to approach to secure the contract. He wasn't great at paperwork, so I'd create all the contracts, but he was a people person. Then I'd go to the meeting as the talent to discuss the job that was already set in place. This was for my design agency (which comprised of just me and some contractors) and the contracts were for my graphic design, writing, magazine ads, trade show booths, full-length promotional films, etc., but I'm sure it could be for straight writing as well. These were bigger contracts, like 30k+ projects. And honestly, it would've done more detriment if I went to those initial meetings by myself, because I'm not a great speaker, but with him, I could walk in the room and everything was ready to go. It was a stress reliever because the men I met with weren't judging me because they'd already agreed to the project and were excited to move forward. My liaison received a commission off the job, and it worked out really well. So my biggest insight is to be flexible, know your strengths and weaknesses, and don't be afraid to try out big ideas!

Another thing I did--and I know this may be unpopular to say because cutting work and saying no is about empowerment--but on any job I didn't want to do, I never cut it out or turned it down; instead, I subcontracted someone to do it, ran it through my agency, and took a percentage.

Nicole Pyles said...

@Sue - Oh I can only imagine how hard that type of writing would be! I can imagine there's so many restrictions. And knowing it's okay to say no is such an important lesson! One I have definitely learned this year.

@Angela- Oh that is a VERY smart idea to subcontract work out. Good grief though I think my anxiety would be through the roof for so many reasons if I tried that haahaha. I'd be "what if-ing" just about every scenario and I have a hard time letting go of the reigns on things haha. But what a smart thing that you had someone be your hype person! I could see that working in that kind of industry! Great insights!

Ann Kathryn Kelly said...

Nicole -- I dipped my toe into freelancing only this past August, after having worked for companies as a FTer for decades. Already, I've learned so much ... like understanding that 90% is good enough if a project has already taken more hours than I budgeted for. I need to be better at stopping, instead of continuing to work for what will essentially be free hours to finish the project. This is a struggle for me, as I'm a perfectionist ... but it does me no good to continue working if I miscalculated the upfront cost. That's my second lesson: I need to learn how to quote better!

Nicole Pyles said...

@Ann - oh that is SO hard to do, knowing how much a project will take and then realizing you may need to work for free to get it done. I think that's why hourly can work but at the same time, I find that certain clients are more....particular when you do hourly work then say this is the total budget (that's what I ran into with the person I attempted to work for without the contract).

My other challenge this year is knowing when I need to take a break!

Powered by Blogger.
Back to Top