Dilemma

So my quarter-life-crisis is reaching decision time in the dilemma. My boyfriend, who is a musician for a living, could use some marketing to organize his strengths into a promote-able package. I want to do entertainment work, preferably in the music industry, and my degree is in marketing. We work well together, mutually motivate, and would probably be a pretty unstoppable force once we got into the swing of things. This would also not require me to move to a major city. I would be able to start locally and decide if major-city movement would ever really be necessary.

The downside: He is not in the financial shape to hire a professional to do the job (hence the only reason the opportunity is available to me.) This means I would be unpaid- basically an entertainment marketing intern- at least until I prove myself a valuable employee and succeed at making him some money. It would be motivating because if he goes down, we both go down. Compensation has not been fully discussed, but he knows he would have to cover some of my expenses.

Another concern is (obviously) that we are romantically involved, meaning that any turbulence in the relationship could lead to employment problems. Fortunately, he is professional enough that I don’t think this would be a problem and I don’t see us breaking up any time soon, but I want some kind of contingency plan for this.

The main concern, though, is the parents. His are super-religious and do not want me living with him. This is how it used to be and they were thrilled when I moved out to appease them. (This was discussed as part of the compensation- I could live there and he would pay rent and bills).

My parents are super-negative. I don’t even want to broach the subject of quitting my entry level dead-end job with benefits to “take a step backwards” as they would see it. Going from a company with a 401k plan to being an unpaid intern in an industry you know nothing about? Stupid. My argument for this is that I knew nothing about the industry I work in now when I started and now I manage quite fine- and I don’t even like it! Also, it would be better to get out now when I have nothing to lose, really, instead of staying for years, gaining nothing but wrinkles and regret for not doing something worthwhile. However, I’m sure if I were to continue living with them throughout the process, it would be an endless tirade of pessimism for my future and how I’m a failure at life because I’m still living at home and working for nothing.

I see a once in a lifetime opportunity and a possible stepping stone, but I wonder if I can overcome the inevitable negativity that will result. I wish I could just be honest with them about the ups and downs and have them say something helpful instead of voicing all the ways it’s going to go wrong. I can think of those myself!