I've never been a contractor per se but I've been working in tech for decades, so this is just a bunch of random thoughts.<p>You say you don't interview well and this could very well be a deal-breaker as a contractor. As a contractor, you are part salescritter as well. You are selling yourself. As in all things, these are skills that come more naturally to some than others, but can still be learned by anyone given the motivation.<p>How is your resume? If you don't have a strong resume, website proving your experience, or portfolio, most companies are going to shy away from you as an unknown quantity. It's REALLY hard (maybe impossible) to spin up a contracting business without some documented or word-of-mouth history of being a sharp cookie.<p>Are you utilizing your network? Maintaining connections with co-workers and friends is extremely important when W-2 job hopping, and I suspect it's even more important in contracting. If you are targeting small to mid size businesses, most decent-sized cities have regular meetups for local business professionals that are literally just for networking. They don't even have to be tech focused events. Just go and meet people. Ask them what they do and pretend to be interested in their work. Tell them what you do and notice that they are pretending to be interested in what you do. It sounds stupid, but one day someone will call you out of the blue and say, "So-and-so said you know X, and can I throw money at you to solve my problem?" Print business cards. Attend conferences that are tied to your field.<p>IME, successful contractors specialize in a fairly specific niche, like embedded design, or Postgres performance tuning, or storage buildouts. Generalist contractors can do well too, but there are a lot of them, so you have to stand out above them somehow, whether that's better marketing, networking, and/or experience.<p>Your last three paragraphs speak to job dissatisfaction. I have to take a page from Mike Rowe here and suggest not looking for the perfect job that sparks your passion. Instead, bring your passion to the job. It's always hard to tell from the outside whether a job will be fun and uplifting or a soul-crushing experience. It's not the work that matters, it's the mindset you carry with you throughout the day. Optimism is also a learned skill, and one that definitely did not come naturally to me. But one embraced, it opens up So. Many. Doors.