I like this question!! I have a very independent/entrepreneurial career path so far. I have tried a lot of different jobs,
and so far I like it best when its my own company and/or I'm helping someone market their product or services..
At first career wise I was studying medical and socio-cultural anthropology at U of Toronto and I was going to go on and become a researcher/professor.. but then, upon graduating, I jumped ship and entered Toronto's live music scene full-time.
At one point after the MA I was studying opera singing full-time (with a private teacher), playing back-up vocals and keyboard in a Toronto pop band, and pursuing jazz singing and going to lots of open mics. I couldn't decide what genre of singing I liked best.
Meanwhile, I had to figure out a way to pay the bills, so I worked for the Ontario Ministry of Health answering their Infoline for awhile, but I was a disaster
as an employee there.. missing at least 1 day a week and often 2. I found the environment at that government office really toxic. It was in the basement and I didn't get enough sunshine and the management was very uptight. I got laid off, thankfully.. I also worked as the produce manager at a health food store, which was better, but it was hard on my voice to go in and out of the cold storage freezer so not ideal for a singer.
Then I started teaching singing lessons to adult beginners from my home, which I liked a lot better, although the income wasn't as stable and I had to do all my own advertising.. I kept on doing that, but meanwhile a friend had the idea to start a French/English translation business with me. I had been to French immersion school as a child and was in France for a year of my undergrad so I'm fairly bilingual and I like translating (its a lot of what cultural anthropology is about, translating value and meaning between cultures). It took awhile, but eventually the translation business became my main source of income and it still is now.
When I moved to Halifax, I kept the translation biz and phased out the singing lessons from my income sources because you can't charge as much for music lessons out here and there's not as much demand (because there's so many great musicians here already teaching!).
A few years before moving to Halifax I found out about an energy healing method called EFT (Emotional Freedom Techniques), and I had been doing EFT coaching sessions for people in Toronto and London Ontario, and now I've started doing that here in Halifax.
While I will never stop doing the translation business probably, I would LOVE to do more EFT sessions, because it is so incredibly effective (on depression/fears/phobias/physical ailments etc.. it is a lot like acupuncture, only without the needles, you just gently tap on meridian points with your fingertips). It would be really meaningful and lovely to have as my main job helping people feel better. I do the sessions on the phone/Skype and in person.
So, right now I'm working on my EFT website, I'm going to call my company "EFT Wellness", and I have written an e-book about "Eliminating Separation Anxiety in Dogs" (email me and I'll send you a free copy, I'm still collecting feedback about it its so new). Also if anyone is intrigued and wants a sample tapping session, PM me
Meanwhile, in addition to the above I still dream about doing music for money so I can devote more time to writing and performing. As Jemaine said once in an interview (rough paraphrasing), you mainly make art so that you can show it to your friends, but in order to have the budget for making the art you need to show it to the world at large..
I have two different projects on the go right now.. one is my "Anna Danova" jokey songs project: myspace.com/parttimemodelthat ...while I really really enjoy writing these jokey songs, heavily inspired as you can see by the guys to whom this message board is dedicated, my initial forays to comedy open mics gives me the impression that it is quite difficult to be a woman in comedy, sigh... so I dunno how intensely I'm going to pursue it. Maybe I just havn't found the right venues yet.
Then there's my 'serious' pop/rock music.. I wrote a lot of new songs this winter, and my main goal in the summer is to record some decent sounding demos and then look into recording a full album or an EP in the fall. I want to assemble a band, and some of my musician friends in Toronto may help me out in which case I would move back to T-town, though Halifax has been lovely!
Still not sure what I want to be when I grow up though. I'll be 31 later this month, and I think a lot about having a family and which aspects of my entrepreneurial life I would slow the pace on in that case.