Freelancing Setbacks: Re-Evaluating and Prioritizing

Am I really doing the best I can? Couldn’t I be working harder? I’m not where I want to be financially or professionally. It’s probably my fault for not focusing.

I lack self-discipline. I’ve tried so many times to commit to certain goals, and I repeatedly fail to achieve them.

Maybe I’m not cut out for this …

As a mindful and spiritual person, I feel torn between two modes of thought: a) The “you are enough/you are perfect as you are” way of thinking, which focuses on contentment, and b) The idea of constant self-improvement and betterment.

I think the ideal mindset is probably found somewhere in the middle. The key is accepting that you have to work hard in order to improve yourself, and then loving and appreciating yourself for your hard work once you’ve accomplished something.


(Found this graphic over at Sally’s Baking Addiction)

I’ve come across a few roadblocks lately with regard to my freelancing business and globe-trotting lifestyle. Let’s review the timeline of my professional life over the past two years:

About two years ago this month, I left for New Zealand. I took a basic content writing job (a demotion at the time) so I could have the life-changing experience of living and working abroad. It was an amazing experience, and I have absolutely no regrets.

When I came back to the States the following February, I took a job with my former company in Chicago – but my new position wasn’t a great fit. My ex and I broke up, and numerous other personal turmoils ensued. I knew I had to get out of Chicago.

I was offered three-month contract position in San Francisco, and my new manager told me she planned on hiring me full-time after my contract was completed.

“So, there’s no guarantee of employment once the contract is up?” I asked.

“Technically no, but I’m telling you right now, Maggie, I really want you on our team. I think you’re an amazing writer.”

I quit my job in Chicago and spent three months working semi-remotely, living 50/50 between San Francisco and Chicago. The company in San Francisco decided not to hire me after all. I had no option but to return home to my parents’ house in Twin Lakes.

However, this proved to be an interesting opportunity. I’d always wanted to freelance. Maybe this was the perfect time to give it a real shot. About six months ago, I committed to starting my freelance business. My goal was to have the flexibility to travel indefinitely, working remotely as I explored the world. I wanted (and still want) to be a digital nomad, like so many of my peers in the writing industry.


Now here we are, six months later, and I’m still in Wisconsin. (Granted, I’ve had some amazing travels to California, Mexico City and New York in the interim.) Last week, I lost two clients (two of the three steady streams of income that I had coming in), not because of my own work, but because I took on hourly marketing jobs with fledgling companies. The companies chose to restructure, and freelancers are no longer part of the budget. I’m practically back to where I started six months ago.

When something you’re doing isn’t working, you’re forced to reexamine your approach. Should I be spending my time differently, focusing on the journalistic work I really want to do instead of the hourly marketing jobs I took to make ends meet? Should I be applying for full-time jobs instead of freelancing?


I decided to go back to the drawing board. When something isn’t going the way you want it to, ask yourself the following questions: 1. What are my priorities?, and 2. How can I best accomplish those priorities?

I narrowed down my thoughts and feelings into criteria for where I want to go from here. Here are my priorities:

  • I want to get more of my work published by major publications and websites. This will help advance my name and build my portfolio so that I can eventually secure a writing job, rather than a marketing job, which is my ultimate goal.
  • I want the flexibility to travel. I could find this in a full-time job if remote work is an option, or I could continue freelancing.
  • I want to move out of my parents’ house and into my own place. This also gives me the ability to sublet or rent out my space when I’m traveling for long stretches of time.

Based on these priorities, I’ve come up with the following game plan:

  • I’m going to focus on pitching and submitting stories, rather than applying for hourly freelance marketing jobs.
  • I’m going to consider full-time employment that suits my needs (allows remote work).
  • If I do find a full-time position, I’m going to keep freelancing on the side in order to get published more frequently.
  • I’m going to make my finances a priority. I am lucky enough to only have a small amount of debt, so I’m going to work on paying that off whenever I have extra cash flow. I won’t be traveling in the next few months unless I have a big breakthrough that allows me to finance it up-front.

This doesn’t really mean much in terms of changes to this blog (other than some new post topics, which I’ll get to in a minute), but I wanted to be completely transparent about the realities of freelancing. I don’t spend my days pitching and submitting – it’s not like I’m burning the candle at both ends and not seeing any payoff. Rather, I’ve been focusing so much on every little side job that can bring in cash, I’ve neglected to look at the big picture: finding high-quality work that accomplishes my personal goals.

And with that, I thought I’d give you guys a taste of what’s to come in terms of upcoming blog posts! Since I will be focusing on my finances for the next few months and won’t be doing much traveling, I’m going to revisit a major adventure that preceded The Olive Branch: my summer in Europe. I’ll be writing retroactive posts about my time in London, France, Switzerland and Germany. I might also do one about the time I got stranded in Hawaii for three days.

There will be other stuff interspersed with these travel posts, too. I’m thinking of creating a vision board to keep me on track, so I’ll probably write a post about that. I also really want to share some more of my favorite healthy recipes with you guys, and I’ll keep you posted about any small weekend trips or adventures. And most importantly, I’ll keep you updated on how my new approach is working, and how I help keep myself on track.

Until next time! <3

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