By Joe Dyton
Hello! Thank you for visiting the Dyton’s Words blog. This is Part Two of my introductory post. If you missed Part One, you can find it here.
My early days as full-time freelance writer
“Living the Dream?”
My early days as a freelance writer were as great as I imagined they would be. I was operating on my own schedule for the first time in my life: waking up without an alarm clock, going to the gym and starting work as I saw fit. I was writing for the clients I had picked up when I was working full-time and used my “free time” to pitch new clients. All was good—until it wasn’t.
One of the first hiccups I encountered was with one of the clients I got right before I left my job. It was a daily online publication, so the client had my attention Monday through Friday. I wasn’t 100 percent familiar with the industry or the client’s process, so I was spending more time on this particular client’s work than I wanted to. The pay was decent, but not enough to justify how much time and effort I was giving the work at the expense of growing my business. This was not a full-time job, but it began to feel like one—exactly what I’d spent the last 14 years trying to escape.
I knew I was not interested enough in this particular industry to learn enough to get through the work faster. I also realized that I did not want clients that I reported to every day. We mutually decided to part ways. I did not necessarily want to give up the steady pay, but I was grateful for the time back so I could find (hopefully) higher-paying clients that would not require as much of my attention.
I started to use that extra time more wisely and landed a few more clients—that was the good news. The bad news was a lot of these clients were “ad hoc” and I never knew when they’d need me or how much money I could count on them every month.
I know what you’re thinking, “Joe, didn’t you just give up a client where you knew how much you’d get paid each month?” Yes, but I believe there’s a happy medium where a client can be counted on for steady work and not feel like a full-time employer. At least that’s what I had hoped was the case at time!
The “ad hoc” client base was OK in the beginning because I had savings to supplement my income during the slower times, but that was only meant to be a short-term solution. Eventually, I wanted to land more work, earn more money and those savings would go back to being a safety net. Unfortunately, at some point my savings were covering my expenses more than my income was. This model was not sustainable—my savings were going to eventually run out unless I started to get some steady work—fast. Something had to give.
Freelance—fun while it lasted?
Approximately 20 percent of new businesses fail during the first year of being open, according to the U.S. Bureau of Labor Statistics. That was a stat I remember seeing often as embraced this freelance journey. No one said it to me or anything like that; I just recall seeing it a lot as I researched starting my own business. It’s like when you never notice a certain car before, then someone you know gets one and suddenly you see it all over the road.
As my financial safety net dwindled and I could not replenish it fast enough, I realized I was likely to become a part of that tragic statistic. I can remember saying something to my girlfriend one night at dinner that I never thought I’d have to:
“I’m thinking about going back to work.”
I explained to her what I was going through. I was tired: tired of pitching, tired of wondering when the next check would arrive, tired of worrying about money in general. A little more than a year into my new venture and I was ready to throw in the towel; I hated the idea of being a quitter, but I had to be realistic.
So I started looking into full-time gigs, but I made a compromise with myself. I’d only apply for remote full-time jobs. If I could still work from home, I would not feel like I had failed completely. Plus, working from home would allow me to still do some freelance work and hopefully continue to build my business with less pressure because I’d be earning a paycheck as I did it.
I secured three interviews, but none of them panned out. I was so bummed out about my situation I remember just lying on the couch and taking an afternoon-long nap—something I never do. I’ve been known to take a power nap, but a multi-hour nap was a new one. I woke up and said that could never happen again. I was not going to pull myself out of this hole by lying around and feeling sorry for myself.
The turnaround
As I pursued more full-time job opportunities, I was talking to one my clients about an upcoming interview (I don’t remember how the subject came up). I told him how I was looking for something more steady. He said something unexpected that changed my fate in a major way:
“We can bring you on full-time.”
He did not mean full-time as in the 40 hours per week sense, but in the monthly retainer sense. It was that “happy medium” I mentioned earlier—a reliable income stream from a source that would not need me every day. Our agreed upon rate was more than enough to cover my monthly obligations and suddenly I had a lot more peace of mind.
Not too longer after that, an organization I had tried to get a freelance copywriting gig with previously reached out to me. They had a year-long project they needed writers for and asked if I was interested. Another monthly retainer? Of course I was interested! I went from no recurring gigs to two to go along with my “ad hoc” work, which was beginning to pickup. I felt like I was finally “set” and have not applied for a full-time job since. Some clients have come and gone since that dark period in my freelance writing career, but I continue to have work in the pipeline.
So that is my story, and I’m sticking to it.
There you have it—my journey from wannabe freelance writer, to part-time freelance writer to full-scale freelancer. It has been a bumpy road and I’m sure there will be more bumps along the way, but I would not trade this life for anything.
I know I asked you to bear with me for this initial post and the rest would be more educational and less about me, but I’d be remiss if there was not at least some kind of value here. So, here are a few takeaways from my darker days as a freelance writer.
• I still feel I made the right move of leaving my full-time job when I did. I had a few clients in tow and was mentally ready for a new challenge. I would have done a few things differently though. First I would have taken more time to develop a strategy to build my business before I went to full-time freelance. When I was freelancing on side the process was simple: find clients, write for clients, rinse, lather repeat. I didn’t have any targets in place because it was a side hustle—a chance to earn extra money to put towards the business I’d eventually build.
I carried that mentality into my full-time freelance writing career and that was a big mistake. I should have had more details buttoned up earlier in the process such as:
• How much money I was making from my clients while I was freelancing part-time
• How much more I’d need to make to match my full-time income
• How many clients I’d need to make up the difference
• How much time I’d dedicate towards writing, pitching and promoting my business
• Marketing strategies
Get the picture? I flew by the seat of my pants a bit in the beginning, which ended up almost derailing my business before it could get started. I know the best time to start is right now, but it does not hurt to have plan when you do start.
• My other big takeaway was if you need more work, don’t hesitate to ask your current clients. It’s easier than pitching because you already have the relationship in place and the client knows your work. I could have saved months of headaches if I’d proposed a retainer agreement with the one client I mentioned earlier.
My hope is this blog will continue to educate anyone who is interest in freelance writing. I’m still figuring things out with how this blog will go (format, post frequency, etc.). The process might change, but my dedication to helping aspiring and current freelance writers go from here to there will not.
Thanks for reading.
–Joe
Joe Dyton (@JoeDyton) is the President and Founder of Dyton Writing and Editing, and a freelance insurance, real estate and personal freelance writer. He’s written for Connected Real Estate Magazine, GEICO and Student Loan Planner. He can be reached at joe@dytonswords.com.