I was hanging out in the Multithreaded Income podcast‘s Discord server, and a conversation about staying freelance versus working for “the man” an employer got me thinking. I have been bouncing around between working for myself and working for employers since 2011, after solely working for employers since the late 90s.

Working for an Employer

When I go back to working for an employer, it’s usually for one of many reasons:

  • I get tired of the administrivia and just want to focus on sharpening my tech skills.
  • I get tired of working by myself and want to work with awesome people again.
  • I find the right opportunity at the right moment for me to make that jump.

Working for Myself

When I quit my job in 2011, it was because I felt stagnant where I was. I kept getting the same types of projects and felt like I wasn’t growing enough. I also had a mentor outside of the company I worked for who reminded me of my potential, so I knew I had to get out.

If I am going back to working for myself, it’s typically one of these reasons:

  • I’m leaving an unhealthy work environment. Micromanagers, toxic teammates, toxic clients, and a team getting let go have been past reasons.
  • The company I’m working for is going one direction, and I am not interested in going that direction. This happens often when I’m in a smaller company that is growing, when I don’t feel like the transitions headed my way will be a good fit for me.
  • I want to grow skills that need more time and focus to grow, and my work doesn’t align with those skills.

Current State of Employment

In my current state:

  • I’m working for an employer, with it being finding the right opportunity at the right moment. I’ve wanted to work with this crew for awhile, and everything finally lined up.
  • I’ve got an employer that supports what I need at this time – the ability to bring all of me to the table, doing what I enjoy, and still having the flexibility where I can step away to deal with family stuff and self-care without feeling guilty. I can’t commit to a 9-5 role since I have parental obligations. And I recently stepped my hours back because it’s a struggle to push for 40 hours with the chaos of life around me.
  • I’m in a role where I also need to keep growing my skills, in addition to helping others grow.


In case it isn’t clear, I’ve realized that the only one responsible for my career is me! So many of the reasons for choosing one side or another are selfish. Does this make it risky to hire me? Perhaps. However, in the right environment with the right supports, I’m content with staying where I am. And that… that’s where I am today!

By sadukie

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