The Pitfalls of Self-Employment

For this Friday Fun-Day, I’ve decided to post a more serious topic alongside the weekly writing prompt. Mainly, I want to talk about my experiences with self-employment and use my mistakes thus far as a horrible warning for those who are looking to work for themselves. Mind you, the experience has been great for me; I’m making some money, meeting new people, and getting to read some interesting books and short stories I otherwise wouldn’t have come across. Still, I’ve made enough mistakes these past 3-5 months to share nuggets of wisdom with my readers.

You can’t take self-employment lightly. Even if it’s just a side gig, there’s a lot to it: pricing, customer service, taxes, schedules, just to name a few. There are many materials across the web and in print about this subject, but none of them can fully prepare you for the reality. Some things you have to learn first-hand.

I don’t have any big “this mistake could’ve ruined my financial life and career” stories. Instead, I have a few smaller, more general pieces of advice that I think can help others looking to start self-employment:

  • Find the appropriate platform to promote your services. When talking about side jobs for struggling writers, I mentioned Fiverr,, and Upwork. I’ve heard that more options exist, but I’ve only tried these. It took trying each one for me to realize that Fiverr is the best option for me. Because customers come to me primarily, I’ve been able to get many more orders at better prices. Fiverr is also more understanding when people make mistakes, usually removing gigs rather than users unless there’s a clear scam, trolling, or abuse. never yielded any jobs; Upwork gave me one good connection, one unprofessional experience, and multiple scam attempts before I made a mistake and they deactivated my account. You can’t take my word for it, though. Fiverr works best for my freelancing efforts but that won’t be true for everyone. You just have to try each one on for size. Heck, you may find that your best option is to use as many as you can handle.
  • Word your gig postings appropriately. One of the biggest problems I’ve had on Fiverr has been writing the descriptions for each gig. If you’re not careful, one word or phrase can be misinterpreted as breaking a rule and be removed. Fortunately, Fiverr only removes them. Other similar sites aren’t so lenient. You must also make sure to read the site’s rules for gig postings carefully as well as the rules for any other website you may mention within the gig posting. Some don’t actually allow the service you’re offering or otherwise don’t want to be associated with certain gigs. If you’re not sure about your posting, save a draft and ask the website customer service or admin to look it over. They don’t want to spend time removing gigs any more than we want our gigs removed, so they’ll most likely not have a problem with letting you know about any issues.
  • Price your gigs fairly. I’m not only talking about fair prices for your customers; the prices have to work for you, too. I’ve been horrible about underselling my skills. Two different customers have suggested that I raise my prices. When your customers, without consulting each other, tell you that, you should probably listen. You can’t gouge your clients but you can’t rip yourself off, either. Your time and effort are valuable. If your skills are worth paying for, they’re worth paying a fair price.

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  • Set a schedule. It’s so easy for your personal life to invade your work life and vice versa, even more so when you’re self-employed. Setting a schedule helps to separate these aspects a little better. The line still blurs but at least you can tell your loved ones that you have to work and then you can tell yourself that you’re off the clock with minimal guilt. I’m still working on this lesson, along with fair pricing. Modern culture, at least in the U.S., encourages people to take their work home with them and essentially become workaholics. Writers and other freelancers know this all too well, especially since we usually love our work. For our mental health, we have to force the separation. Writers often have to separate regular work from writing as well, and that’s what I’m most struggling with right now.
  • Remember it’s a learning process. As a perfectionist, I have a hard time accepting this fact. Self-employment is a matter of trial and error. You learn something new every day and you can’t beat yourself up for every tiny mistake. Learn from it and move on. Don’t stop the process at your own experiences, either; search out resources talking about self-employment and learn some tricks from seasoned veterans. It may seem like a lot of extra work but you’ll be glad you did it.

Writing and self-employment can be very similar. They can both take over other aspects of your life and require a lot of trial-and-error before you feel comfortable with your work. You have to remain resilient and never give up. You know what they say: if at first you don’t succeed, try, try again.

What are your experiences with self-employment, both as a writer and in other areas? Any advice I forgot to mention? Leave your thoughts in the comments so others may benefit from your wisdom.


Designed by Stephanie Hoogstad circa 2011

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