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About 2 years ago, I transitioned from being self-employed in the music industry (small record label and mailorder company) to taking on a full-time job elsewhere in a completely unrelated field. My main reasons for stopping my business were a) burnout and b) a business that was failing miserably (due mainly to my burnout and lack of attention, but also to newfound competition). At the time, I was mildly in debt to credit cards and a relative (about $12K in total), and just needed to get back on my feet.

So, I sucked it up (going back to work in the corporate world after 7.5 years of being self-employed was a mild shock), put on my Dockers, and did my job, and have continued to do my job for a solid 2 years. I've now paid off all my debt, and have saved up about $20K. However, I still have that itch to get back to working for myself, for a variety of reasons: 1. That lifestyle suits me and my personality best; 2. I miss music and all that it entails; 3. I think I could be successful at it, with the experience I've gained in the 2 years since. The time off I've had from music and my business has done me good, I think. I now realize that much of my failings as a businessman before were due to not planning enough, not measuring "where I stood" financially, and not being consistent enough as far as effort. If I were to get back into it this time, I would truly treat it as a business (which I didn't before, for the most part).

I've been mulling a gradual return for quite a while now. I could do one of two things, either resign myself to the fact that it is only going to be a hobby forever (meaning I'd get some enjoyment out of it, but never make enough to sustain myself), or dig in from the start, treat it like a serious business, invest as much $ as I can now and hope that it takes off again. Every time I start to think I want to pursue the latter, though, something happens that takes the wind out of my sails and makes me reconsider the whole thing. Mainly, it's feeling like I'm just not interested enough in music in general now, whereas before I was truly rabid about it. I don't want to invest $10,000 or more in a venture that I'm not going to pursue seriously. I'm just worried that I'll back out.

Does anyone have any suggestions as far as a checklist of things to consider in deciding whether or not to make the plunge, again? Like, factors that should decide for certain whether to stay on the sidelines or jump full-steam into the water?
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