I thought about it, but contracting just isn't for me. I was definitely looking at incorporating according to whatever my tax attorney suggested. My anchor client ghosted me and I took that as a sign I am not yet ready to contract.
Sorry to hear what happened. Losing existing clients definitely sucks (especially if you had a longer working relationship with them). On the other hand, it could also allow you to seek out different opportunities. What aspect of contracting makes you feel you are not ready?
More than anything else, it came down to finances. Running off on my own was sort of an impulsive decision after getting very dissatisfied and disillusioned with the practices of another firm I was working for; I wanted to do honest work and be able to pursue my responsibilities without constantly being micromanaged. I didn't have many savings built up, so I had nothing to carry me through until I found more clients. I also didn't have a portfolio published, kept finding better things to do besides make my website, spent very little time networking, and overall just didn't take things as seriously as I needed to.
If/when I get my finances together and have some money saved up, I'd love to try it again. I need to improve my focus (might be time to go back on ADD meds) and would probably want the guidance of a mentor before I attempted the process again.
Health is really important! Hope you get to try it again, Freelancing/contracting comes with a whole new set of challenges, but it might be worth it.
For me, I got tired of the unpaid overtime nonsense and started to feel used. I understand that deployments sometimes must happen on weekends to reduce business impact, but years of weekend work started to wear on me. I also felt I was dependent on my employer to provide a career path, but it didn't match what I wanted to do. So I decided to become a contractor, but I stayed at the my employer, just converted over to a contractor.
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