Blogging Til I Win a Grammy: Day 539

Post #28 of ANNIE B.’s D.I.Y. MAGAZINE: Bogging ‘Til I Win a Grammy

Today’s Topic: Making a Living as a Successful Touring Singer/Songwriter
“I promise to post blogs here, sharing some daily activities & the work I do to achieve my career goals, and when I do win that Grammy, YOU can say you followed me all the way! I also hope to give inspiration, information, & advice to indie artists, and I hope you take a little something away with you when you read my posts, whether or not you are yourself an artist!”

If you ever have ANYTHING you’d like to respond to in my blog, PLEASE find me at

There is a really cool online community of female artists called GoGirls Music. They have a yahoo group and one of the posts was: “Acoustic tour advice”. I figured, “I can offer a lot of good advice…. I think I’ll respond to this.”

I am also posting it here in case you are interested in finding out more about how I got to where I am today. This would be of particular interest to you if you are thinking about going on tour as a solo artist yourself! I hope you enjoy, and pass it on to a friend who is a singer/songwriter!!!

I have added two things to this list… in the DON’Ts list… the last two were added as I posted it to my blog here.


I lived in my car for a year in 2006 and that’s when I and learned how to make a living playing music… on the road. And now I make a living playing mostly in WI & Northern IL. The first time you do it, just plan ahead as many dates as you can, and DON’T be afraid to call venues a few days before or even the DAY OF your arrival in any given town.


1. Learn plenty of cover songs in addition to REALLY OWNING your originals… have as much music to perform as possible. I’ve already had a guy give me a $100 tip to “Keep playing” after I had played for 4 hours that evening…. he just got there and wanted me to keep going with the live music. I played for 2 more hours, playing every single song I knew that evening, only repeating about 3 or 4 songs. After tips & CD sales, I made about $300 that night. People who you play for your first time out will not be familiar with your originals, so you need to entice them with some covers that will blend in with your originals. They will put money in your tip jar asking for a certain song or a certain artist, and if you can “sell them” a different song from that artist, or a song from a similar artist, they’ll be happy.

2. THIS IS HUGE, ESPECIALLY FOR YOUR FIRST TIME OUT: DO NOT rely on making money in big cities or even medium-sized towns. Stay with the small towns to rely on making money… bars & restaurants in these towns will most likely NOT already have music booked, and they are much happier to have you come down and play, and they might even pay you if you end up keeping people there who would not normally hang out late. They might just do it for the heck of it, since many bar owners are often open to trying something new, or they like to help the “little guy” since they are one of the “little guys”. If you call a bar/restaurant (non-corporate… avoid Applebees and the like, of course!) in a small town, you’re more likely to get the owner or the manager who can make that decision last-minute…. making it easier for you to get last-minute gigs. DO play some opening slots in big cities but do not expect to make much money. It’s good exposure, though, to play a reputable venue in a big city, so find a good BALANCE between money-making gigs, and “exposure” gigs.

3. Book as many gigs as you possibly can while you’re “on tour”, leaving zero to to two nights off per week. This will keep you MOTIVATED to make some more calls that next morning when you wake up.

4. When booking, ask the bar owner if you can crash on one of the bartenders’ couches. More than likely, they will be able to hook you up (and may feel especially obligated if you are playing for tips only). I can’t tell you how many perfect strangers’ couches I have slept on and was treated like gold, sometimes even the bar owner, but usually someone who worked at the bar… these people are trustworthy, or the bar owner would not have hooked you up to crash with them.

5. DO NOT BE AFRAID to HUSTLE THE CRAP OUT OF YOUR CDs AND YOUR TIP JAR (if the bar owner does not mind)!!!!!!!! This saved my ass…. I went up to every single person during my break and told them, “I’m working for tips tonight… I’m worth a buck, right???” Or, “You are REALLY gonna love my CD… I promise… it’s just like what you’ve been listening to tonight!” VERY IMPORTANT INFORMATION = Artists at the level we are at will sell most of their CDs at live shows, NOT online, NOT in record stores, and NOT out of their trunks, unless you’re a hip-hop artist. My band in Los Angeles sold less than 100 CDs in 2005 (when our CD came out), and when I left L.A. to live out on the road, I sold the rest of those 800+ CDs (we gave lots away for promotional purposes, but I had about 800 left when I left to hit the road in 2006) in about 15 months. At $10 per CD, that’s $8,000+ in 15 months = $533+ per month in CD sales alone. My mistake is that I did not re-order more CDs when I sold out. I could have easily made another $10,000 in another year.

6. The more merch you have to sell = THE MORE MERCH YOU WILL SELL. Purchases of CDs or other merch from the person playing at the bar/festival/restaurant/coffeehouse are ALWAYS IMPULSE purchases. This means they like you, and they want to have something to remember you by, and it’s totally on a whim. If you have a CD, they may or may not buy it, depending on if they want to spend that extra $10 they may need for beer. If you have CHOICES for them, they feel like they’re “going shopping” (which is soooooooo much more fun, especially for girls…. we LOVE to shop) like a keychain for $2, a sticker for $1, or even a Tshirt for $15 or ball cap for $20 (in addition to those CDs,) they might just buy that $15 Tshirt instead of your CD (which is fine… take it!), OR you can do a special deal… CDs are $10 but a CD AND A Tshirt is $20……….. get it? Or, with any purchase, you’ll get a free sticker!!!!

7. BE SURE to be a part of the CDBaby Credit Card Swiper Program, so you can accept credit cards!!!!!!!!! YOU WILL SELL MORE IF YOU CAN TAKE CREDIT CARDS. I have found that about 1/10 of every credit card sale does not go through. This is due to the fact that you cannot actually run the card at the time of purchase… you have to mail in the carbon slip to CDBaby and track the sale on CDBaby. If you do not have your CDs for sale on CDBaby, you are MISSING OUT ON A LOT OF TOOLS to help you. GO TO: and get your CD on there!!!!!

8. CREATE An 8 1/2 x 11 POSTER on your photo editing software on your computer for EVERY GIG and e-mail it to the talent buyer (owner/manager) and ask him/her to post it as far ahead of time as possible. Even if you book something the day before… it might spark the interest of a few of the patrons who go there every day after work.

9. Bring a pillow and blanket for those “sleep in your car” nights. Investigate where to stay, like truck stops that are OPEN & LIGHTED all night long. DO NOT STAY IN REST AREAS… THEY ARE UNSAFE. You should take the key out of your ignition since it’s actually illegal to have your key in your ignition, or be sitting in the driver’s seat (even with no key in the ignition) if you are sleeping in your car.

10. Eliminate bringing a huge P.A…. you can easily get away with a head and two speakers for almost any venue. I rarely use monitors. Those new BOSE towers are really nice and easily portable. MAKE THE INVESTMENT FOR SMALLER/LIGHTER EQUIPMENT NOW. YOU WILL MAKE YOUR MONEY BACK IF YOU WORK AT IT, and you will save your back, and LOTS of gas money, by avoiding using a trailer. Get good at “playing Tetris” in the packing your gear. Invest in those wonderful bags for your stands… they will make all your gigs and your life so much easier!

11. EAT AS HEALTHY AS YOU CAN. Bring a small cooler and stock it with tortillas, cold cuts, and cheese. You’ll save $$$ on food, you’ll eat healthier, and YOU’LL FEEL BETTER! Grab an apple, banana, and orange at the truck stop rather than a Snickers bar & a bag of chips. Look for the package of 2 Pop Tarts, the Nature Valley Granola bars, the vanilla ice cream bar, instead of the cookies or M&Ms. They have fruit at lots of gas stations, believe it or not!

12. KEEP A RUNNING DATABASE of ALL venues contacted, all communications & dates of communications, all agreements and dates booked, guarantees paid, tips made, CD/other merch sales, and contact people’s names/phone numbers/e-mails addresses.

13. JUST LIKE YOU HUSTLE CDs & merch, HUSTLE to collect e-mail addresses of every person in that bar. Keep a good list of e-mail contacts according to city.

14. BE SURE TO ASK THE TALENT BUYER/OWNER: Can I have a tip jar? Do you mind if I go table-to-table during my breaks to collect e-mail addresses and tell people about my CDs? If you prefer I don’t, do you mind if I leave a card on every table asking people to fill out their e-mail address? GET A BOX OF THOSE LITTLE GOLF PENCILS and create cards to put on every table for every gig, even if you end up going table-to-table. BUT ALWAYS ASK THE BAR OWNER/MAGANER permission for anything you want to sell or do in addition to performing at their venue.

15. NETWORK WITH OTHER BANDS/ARTISTS!!!!!!! This will help you in finding a place to crash, in getting a better gig in that town, and in getting people to that gig! Gig-swapping is HUGE and a great way to build your fanbase… when you open for a band/artist in their town, they are more likely to tell their friends & fans about you. BE SURE to do the same for them when they are ready to play a gig in YOUR town.

16. Bring your computer and make sure you have somewhere to log on every day… there’s so many free wi-fi spots even in small towns, you should be able to log on every day… check your e-mail to make sure your poster went through, book another gig for those open slots you still have in your schedule, log on to FACEBOOK and create an event page for EVERY GIG, and invite your friend(s) who live in that area and ASK THEM TO INVITE ALL THEIR FRIENDS!!!!!!!! KEEP EVERYONE ON A LIST on Facebook, according to what city/town (or state?) they live in.


1. DON’T invite all your Facebook friends to all your gigs while on tour, asking them to invite their friends who live in those cities. They will stop opening your invites.

2. DON’T set yourself up to have to drive more than 6 hours in one day, unless you DO NOT have a gig that night. It will exhaust you and you will not be able to perform at your best that night.

3. DON’T be afraid to call and ask to play at a bar at the last minute. Call & ask for the owner or manager and WITH A POSITIVE ATTITUDE, tell them you’re traveling and you have an opening, and you’d rather work for tips than not work at all.

4. DON’T get offended when someone turns you down for a gig. BE POLITE and STAY POSITIVE, and tell them you appreciate their time & consideration, and maybe you can work something out next time you are in town.

5. DON’T get drunk every night after or during (or especially, before) your gigs!!! This will KILL you and you might even end up canceling gigs due to your hangovers!!!

6. If this is your first tour, DON’T ASSUME YOU ARE AN ARTIST WHO IS TOUR-READY. Prepare for this tour physically… if you are a singer, your body & your vocal cords are your instruments, and you need to TAKE VERY GOOD CARE OF THEM!! You will find that unless you are used to performing 3, 4, 5, 6, or 7 nights in a row, your voice will get tired very quickly unless you have learned how to sing properly for several hours, and for several days in a row. The best advice I have for someone who’s never done it before is to start small… start with no more than 3 gigs in a row, no more than 2-3 hours per night, and then have a night off. You will learn what your limitations are, and you will learn what to do and what not to do (like drinking heavily at gigs!) as you go. I also advise that your learn how to strengthen your voice with voice lessons. Take some voice lessons before your tour, and spend good money for the RIGHT vocal coach for YOU. Many voice teachers don’t tour, they teach a few days per week, and they can’t advise you on how to strengthen your voice so it’s tour-ready. Look for a voice teacher that can advise you on how to become tour-ready. This is KEY to the success of your tour. You want to KICK ASS every night of your tour. You don’t want your voice to be weak, you want it to be STRONG at every gig, for the duration of the entire evening. I’ve had pop, blues & jazz, and operatic vocal instruction, and the operatic training was the best instruction for vocal strengthening, in my experience. Opera singers need to be able to sing with amazing power & endurance, or they don’t make the cut. The best rock singers have had operatic training, including Pat Benatar, Ann Wilson, and Steve Perry.

I hope that helps!!!!!!!!!!

PLEASE feel free to visit my blog to find out more about my experiences MAKING A LIVING AS A SINGER/SONGWRITER: – – Scroll down to the bottom and start with “DAY 1” and read on until you just don’t want to read anymore!!!

I learned how to make a living as a singer/songwriter in 2006, when I left L.A. to live in my car, and I did that for about a year. I then moved to Austin, TX, and still traveled/toured a lot, then back to my hometown of Milwaukee, WI in 2008 when my mom went into the hospital. Now that it’s been 4 years, I still schedule a tour about once a year, and I’ve built up a good database of gigs that pay well, and a whole lot of other contacts and opportunities for future tours.

I still make a living as a singer/songwriter today, and my current goals for this year are to (1) make a BETTER living as a singer/songwriter, and (2) to get more recognition as an original artist and to sell more CDs and get better gigs opening for bigger acts.

My name is Annie B.
Thanks for reading, and ENJOY THE JOURNEY!!!!!!!!!!!!!!!!!!!
Annie B.

VCT: Walker’s Pint, Milwaukee Ale House, Martyrs’ (Chicago), Cooler Near the Lake (Kenosha), Goose Island (Chicago)

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