I'm totally up to the challenge, but I can't lead him on. Here's what I had to say:
If you're turning to music to help make ends meet.. then.. well, it's not exactly the most viable career choice. I understand that you want to express yourself and you want to do something you enjoy. These are both important things, and if you can achieve them through music, then I encourage you to do so! But if you also hope to use your music to make a living, then you'll probably have another thing coming.
I don't mean to discourage you, just giving you some real talk. I tried it for 2.5 years and only survived by the grace and provision of God and my various communities in the city (church & activist groups). At different points I became freegan, I bartered my time for a room, I took my show on the road (because it's cheaper to hitch hike around the country and play one-off shows than it is to pay rent in NYC), I shared a two bedroom apartment with 4 other people and one of those bedrooms with 2 other people (we built 3-level bunk beds); and I was always scrounging for ways to make a buck here and there - gigs and odd jobs, volunteering for medical research, etc.
Point being - it's really hard to "make it" as a musician or artist.
I'm not saying that you can't do it. I'm just saying that you'll enjoy it more if you're not counting on it to pay the bills. So. I have no advice to give you. Just reflections on my own experience. And lessons on how to play guitar, if you still want them.
I'll have more to say on this and "unjobbing" at the Matt 6:24 blog, coming soon.