How One Ends Up Self-Employed - Elizabeth Stapleton
Elizabeth Stapleton
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How One Ends Up Self-Employed

If you told me just two years ago that I would be self-employed I would’ve thought you were crazy. If you told me four years ago, I would’ve told you to stop smoking crack. 

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Four years ago my mindset was not in any place where I could imagine being self-employed. Still my journey to self-employment really started back then.

Back when I started reading books like 4 Hour Work Week and finding blogs like Making Sense of Cents or Budgets Are Sexy. There were tons of other fantastic books and blogs that showed me that it was possible to make a living working full-time on your own terms.  

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Before then I had no clue this world or this opportunity existed. Had I known I probably would’ve tried starting to pursue it a lot sooner.

Coming to the End of My Rope at my 9-5

About a year and a half before I got laid off (more on this in just a second) the company I had been working at started making some changes. These changes really negatively impacted the company culture. I slowly became really unhappy with my job.

It wasn’t that I didn’t like the work, there were parts of the work I absolutely loved. However, the office politics which still existed, even though I was home-based just got terrible. I was unhappy and it kept spiraling down until I was absolutely miserable.

I'd been Side Hustling as a Freelance Writer

While I had been blogging for a while, because I had no clue what I was doing when I started blogging I was a long way off from making any money from my blog.

I also knew that given my work schedule, I had very limited time. And sporadic burst of work on a blog do not really help it grow. So I turned to freelance writing. Ultimately, I ended up buying Gina Horkey's 30 Days or Less to Freelance Writing Success to help me get started. 

Recommended Course

30 Days or Less to Freelance Writing Success: Personally, I found the course, 30 Days or Less to Freelance Writing Success extremely helpful to get me started. It breaks everything you need to do, step by step so that by the time you get to pitching for jobs you are prepared and successful. For me, the course paid for itself when I got my first freelance writing job. I now earn between $2,000-$4,000 per month (check out my income reports) with freelance writing.

Though it did not take me 30 days to get through the course. I’d say maybe took a couple weeks including setting up my website. Which is ElizabethStapleton.com, though the site you are looking at now is approximately the fifth version of this site.

Back when I started my freelance writing work, I had just a very basic Squarespace site. It included my information and a very small portfolio.

The Course Helped Me Make the Leap

After taking the course I felt confident pitching and I actually had all the tools that I needed to successfully pitch freelance writing jobs. Sure enough I got freelance writing jobs. 

I did use Contena at the beginning to help me find jobs to pitch because I was limited on time. Frankly, I couldn’t spend all day looking for freelance jobs, so Contena proved to be an excellent investment.

Recommended Job Board

I used Contena when I was working my 9-5 and getting started freelance writing. It made it easy to find freelance writing jobs to pitch. While it's not a cheap Contena it is definitely worth it if you don't have a ton of time to spend looking for freelance writing jobs to pitch. 

Contena pulls together pretty much all of the available freelance writing jobs out there into one place and will even notify you via email of ones in your niche. They also provide an estimate of how much you will make with each job.

Finding Freelance Writing Work

I can’t say I was super consistent when it came to finding and working on my freelance writing as a side hustle. My job had me traveling a lot. So much so that my dream plan of traveling permanently went bye bye. 

However, even sporadically pitching freelance jobs made me realize that I could make real money from that side hustle and I could get out of the job that I was making me miserable. 

I worked at it and I made a goal that in January 2017, I would be self-employed. Now there’s one caveat, part of that goal was hoping that I get laid off. I know it probably sounds really weird but stick with with me for a second.  Every year my company goes through a reorganization where people got laid off, it pretty much sucked. 

Getting Laid Off

They had been steadily cutting down the number of people in my role over the last two years. I kind of figured they would be doing it again. So there was a good chance my role was going to be cut and I hoped I’d be on the chopping block because I wanted the severance.

I knew that extra bit of cash would really help me in pursuing my self-employment goals. Now, to be clear I was not fired and did not get laid off because I didn’t do my job, I did my job to my best ability until my last day. 

Truth be told, I was pretty happy when I got the call about being laid off. Once I found out that’s what was happening, I started kicking my freelance writing into high gear. I mean working it! It was exhausting, but I wanted as much money saved as possible so I could pursue working for myself in 2017.

I Started 2017 Self-Employed

So I start 2017 self-employed and I promptly got sick with viral bronchitis, which I then again got two months later. A lesson in working for yourself, make sure you take care of yourself.

Now, it’s been almost a year and I’m still working for myself. Admittedly, how I make money has shifted and my goals have shifted but I’m still not a 9-to-5. 

Who knows, maybe I will go back to a 9-5 someday, but right now I’m really loving the freedom flexibility that working for myself has given me. And while I am still very focused on growing my business, I’m also slowly working towards trying to take better care of myself.

So what about you? Are you working for a 9-5 or are you already self-employed? Was your story similar to mine? Let me know in the comments I’d love to hear from you!

Freelance Writing Tools & Resources I Recommend

Grammarly (personal editor): I use Grammarly as a second pair of eyes to help me clean up and proofread my writing/typing. The best part is that it is free to use. You can install an extension on your web browser and it will check any writing you do online. While there is a paid premium version, you can get by with the free version for a long time. I only recently upgraded. If you want to know more about Grammarly, you can read my review.

30 Days or Less to Freelance Writing Success (course): Personally, I found the course, 30 Days or Less to Freelance Writing Success extremely helpful to get me started. It breaks everything you need to do, step by step so that by the time you get to pitching for jobs you are prepared and successful. For me, the course paid for itself when I got my first freelance writing job. I now earn between $2,000-$4,000 per month (check out my income reports) with freelance writing.

Contena (Job Board): I used Contena when I was working my 9-5 and getting started freelance writing. It made it easy to find freelance writing jobs to pitch. While it's not a cheap Contena it is definitely worth it if you don't have a ton of time to spend looking for freelance writing jobs to pitch. 

Contena pulls together pretty much all of the available freelance writing jobs out there into one place and will even notify you via email of ones in your niche. They also provide an estimate of how much you will make with each job.

About the Author Elizabeth Stapleton

Elizabeth Stapleton is the founder and voice behind Less Debt More Wine and ElizabethStapleton.com. She is a Pinterest marketer, online entrepreneur, and recovering attorney whose writing has been featured on Entrepreneur.com, The Huffington Post, The Penny Hoarder, Budgets Are Sexy, Credit Sesame, and Magnify Money. Additionally, she has been quoted in articles on Business Insider, Student Loan Hero, and Nerd Wallet.

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