I differentiate this from TOUR (which is what is the ultimate plan). The idea is build a HEADLINING (with smart opening slots also) following in each city which will show that you can sell tickets, give you the opportunity to become excellent at ENTERTAINING your audience, pay for the expansion into neighboring regions and to have some proof of your value for fickle promoters/ club owners and ultimately a booking agent (you should NOT plan on having success finding an agent until you can sell 250+ tickets locally). Play shows locally (all the towns within a 3 hour drive) frequently (but no more than 10-15 shows/year until you are selling approx 250-400 headlining tickets, then phase down to 3-4 times per year as you sell 400-1000 headlining tickets). Once you are selling 250 +/- tickets (more if you are a larger band with higher touring costs) expand regionally, then multiple regions until you can cover the whole country and ultimately other countries. Getting to a modest National stature (500-1000 tickets across the country) should take 4-7 YEARS of VERY hard work! Oh, and be professional: Advance the show, promote your own shows (digitally and physically) wherever possible, show up on time, and be NICE to everyone (no attitude when problems occur, and they WILL), respect the venue, make friends with all other bands on the bill, etc. Booking yourself WILL be frustrating. Be pleasantly persistent. Ask to play appropriate sized rooms and nights.
- Rob Gordon
www.whatarerecords.com
October 26, 2009 
You are a songwriter/recording artist and need to record and release compelling music regularly (without fail). 2) You are an entertainer / performer. Your show MUST COMPEL those in the audience (no matter how few) to come to the next show with all their friends. On stage you are an actor. Your character may be yourself. But the character usually needs to be an amplified version of your normal self. Alternately, create characters.