I didn't learn how to drive until I was 39, left NYC and moved to the Bay Area. In the early 90s, I took a Greyhound bus to most gigs. Before digipacks and cardboard jackets, I hauled a hundred jewel cased CDs in an aluminum-framed back-pack, along with a few toiletries, a shoebox full of clothing and my guitar. One frigid night at 2am in the Chicago depot, the bad-hound bus drove away with all my gear, including my guitar, which was never recovered.
I think I'm clear of ever being accused of not paying my dues, although I still look back fondly on that time. I wrote a lot of songs on the bus. I enjoyed the sense of freedom I had going from place to place, and having intimate conversations with strangers. The only part I did not like about the early days as a solo female singer/songwriter on the road was trying to get paid.
A lot of time was spent booking gigs, promoting gigs, getting to gigs, practicing in order to be good for gigs. At too many venues, I brought in a hundred people who paid a door charge (and bought food and beverages), waited hours till the end of a night (midnight, 1am), and was given $50, and once only $20. I was perpetually ripped off. It wasn't sustainable. I stopped touring for a while.
Then a friend asked me to come play and I said, "I'll play in your living room, but I can't play that club again."
"Bet," my friend said.
I had done some house-concerts before, but they were established venues I had found through houseconcerts.com. This was different; this was closer to a basement show (a punk trend that came out of necessity, as well). It felt kinda bad-ass in its own way. A few people got together, one had a small living room, we were supposed to have about 20-30 people. We were 60. Every body was touching at least 2-3 other bodies. People brought food. I played for an hour. We broke, ate, went outside to cool off. I played for another hour. For the third set everyone started singing along -- I scoured my brain for every cover I knew. I made friends. People threw $10 in the hat. I sold 60 CDs. It was almost $1200. The atmosphere was welcoming and kind. Everybody listened. At the end of night, six people asked if I would come play at their house.
A light went on in my head. I would never take shit from a random asshole at a club venue again. I would do LRCs (living room concerts) all over the world. I have done approximately 1,000 LRCs. Each one is different and reflects the style of the host(s). House concerts are responsible for most of the joy I have had performing in my life and for many of my closest friends.
Playing house concerts is an excellent way to develop your career as well as you skills as a live performer and songwriter. Send out an email, get on Facebook, call your friends, write hand written letters and announce that you are doing a living room concert tour -- invite anyone interested to host. Encourage those hosts to reach out to their friends who love music to bring other friends. Book ten or more of these shows over the next few months (even if they're for family). At each one of these shows -- in which you give outstanding performances, and tell a few good stories (if you are not good at an off-the-cuff approach, prepare and rehearse a few short anecdotes). Tell the audience you love doing living room concerts and you're coming back soon, in case they know anyone who might enjoy hosting. After you play, take down names and numbers, and addresses. Call within a week, thank them and make a date or discuss tentative dates.
Your living room concert host takes care of you. Take care of your host. Give music. Call the next day. Send a card. Be gracious.
Playing living room concerts will make you grateful for everyone in the room, especially the hosts who go out of their way to plan the event. (I will post a "How To Host Living Room Concerts" to help planning.)
It may take 1-3 years. If you can play good shows, you'll be able to do 100 house concerts a year on a steady basis. It is perhaps the most rewarding way to make a living as a musician -- and with how much it pays, you can usually fly.
* Safety note -- make sure you know or you know someone who knows your host well. Work with and invite friends and friends of friends.