Maybe You’re Not Ready for Self-Employment

January 5, 2017
This is something I have really been struggling with lately. I haven’t wanted to admit it to myself, but I also know that we learn from our experiences, both good and bad. I’ve been self-employed as a freelance jane-of-all-trades business developer on and off for the last 7 years. And while there have been periods of sufficient income, there are the low periods as well where I was scraping by. I’m at a point right now where I’ve decided that 100% self-employment probably isn’t the best fit for me at this point in my life. Queue the search for a complimentary career that will allow me to continue pursuing my passions (helping businesses grow) and afford me the freedom and flexibility I need in a job to maintain my sanity.

I believe that it’s possible to find a J.O.B. that will allow me to continue using my entrepreneurial spirit. Here are some of the benefits I see to putting full-time self-employment aside (until you’re really ready)


It can be challenging for some to be self-motivated to go out and prospect or to focus on developing that next piece of content to sell. Working from home, I have found it way too easy to get distracted by the pile of laundry or the dishes in the sink. I also live in a gorgeous part of the world and am constantly tempted by all the outdoor (and indoor) fun there is to be had here.

Aerial View of Kelowna, British Columbia, just after sunset on Knox Mountain, Canada.

By working with a company, you don’t only have yourself to answer to. One thing I’ve also discovered about myself is that I’m much more driven when I have an inspiring leader at the helm. This also goes for business partnerships. I’m very thankful to get to grow this blog with someone who inspires me and we encourage each other to be better. In fact, we have a slack channel dedicated to daily accountability.

Professional Growth

One of my personal values is to Never. Stop. Learning. And while there is a wealth of free information and training available online, there is nothing quite as valuable as learning and growing with a company. Many organizations also offer paid training to their employees which is something that I definitely look for in a potential job.


I’m inspired by ambitious, smart and adventurous people. This is my tribe and I believe this is a definite benefit to traditional employment. Co-working spaces have also been a good way to collaborate with interesting and like-minded people. Some of my more personally defining moments have been formed with people I’ve collaborated with while at a career.

Consistent Income

This is a no-brainer. If you’re in a place in your life where you need the stable income then it seems like a pretty clear choice to stick it out in traditional employment a bit longer. I’m not ready to give up on my side hustle but I believe it’s possible to restructure your work day to accommodate your passion projects by setting realistic goals and having an accountability buddy to help make sure you realize them. When that passion project has replaced your employment income consistently for a few months (or you find some deep pockets to rely on…) then consider making the jump!

What I’m not willing to sacrifice for a career:

Remote Working/Flexible Schedule

If there’s one thing I’ve learned from my years in traditional employment it’s that I’m not the type who can sit at the same desk for 8 hours a day/5 days a week (or do the same repetitive task over and over). It has taken a lot of soul searching to figure this out, but I know myself enough now to avoid burnout and keep my leadership happy. I will only work for companies that afford me this very important luxury. Do you already work for a company but wish they would be a bit more progressive in this department? We’ll send you Peta’s post on approaching your boss about more flexible working arrangements when you subscribe to our weekly feed of our newest posts.
My path to self-employment and entrepreneurialism all started back in 2009 when I read two life-changing books: The 4-Hour Work Week by Tim Ferris and Rework by Jason Fried. Both books fueled the budding ideas of self-employment and doing things differently and they set the tone for the next few years. Through my experiences I also learned that actually working 4-hours a week is not realistic (and later learned that this was not really Tim’s intended take-away from the book) but it opened my eyes to outsourcing tasks that I struggled with and Jason’s book gave me ideas on how to work more productively and adopt a less-is-more mentality. These are lessons that will stick with me even through my entry back into traditional employment while I continue to build upon my passion projects.
After a lot of soul searching, I can now say that I’m ready to rejoin the ranks of traditional (with some conditions) employment while not losing focus on my long-term goals. I’d love to hear your thoughts on the subject! Feel free to comment below.
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