Based on my experience I actually wouldn’t say that you need to be highly specialized to work as a contractor. It certainly helps to have credible and targeted

Based on my experience I actually wouldn’t say that you need to be highly specialized to work as a contractor. It certainly helps to have credible and targeted experience in areas clients want. It doesn’t necessarily need to be technology-specific, it can be business domains: e.g. customer billing, medical records, or inventory management. You may be detecting a theme in those examples: stuff that isn’t trendy or cool, but things lot’s of companies need. IMO, that’s the path of least resistance. Another very helpful thing to break into contracting is building a reputation for great work as well as a large professional network. When former coworkers become managers and need help they’ll know they can count on you. And may be willing to bring you in as a non-FTE. Lastly, I’d say work to be a desirable candidate in general. I had a multi-year engagement that came out of an interview after which the company enthusiastically wanted to hire me. I turned them down, but said I could contract 20 hours a week. They accepted.