Dear Teenage Self... (4 Things I Would Tell Teenage-Jesse About Music Careers)

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Do you ever look back to High School and wonder how much time you spent doing ridiculous things? I’ve probably amassed literal days of crafting the perfect AOL Instant Messenger “away status” or walking around video rental stores looking at the covers of DVDs I would never watch (although, I still do this with Netflix…).

In the midst of all of the ridiculous posts on and youth group movie nights I remember developing a very serious passion for music. There was a lot of stuff to navigate and I wish I could go back and encourage my teenage self with a few things about my “future career". I figured I’d list them here in case any of you could use some encouragement as well!

  1. Music as a career is possible, but it looks different than everyone thinks. Not everyone who makes at a living doing music will be a household name. So many of the people I admire now are people who do their work behind the scenes and crush it.
  2. Find good community and dig in with them. The “staying power” I have in music now is directly proportional to the community that I’m in and the woman I am married to. Without their continued encouragement and support to pursue it, I would’ve stopped a long time ago. Find those people who will push you and keep you lifted.
  3. Being the best musician in the room is neither important or possible. Everyone has something different to bring to the table. Just because you study for 4-6 hours each day, know your modes, and how to construct atonal matrixes doesn’t make you the best musician in the room. Sometimes people without a formal education in music can hear things that you can’t because you have “rules” so deeply ingrained into you. (*Note: music theory and practicing your chops is great, but the importance of that has rarely ever shown itself in my career thus far.)
  4. Gear is cool, but don’t let envy of other people’s gear consume you. Seeing friends with pedalboards filled with $400 Strymon reverbs and delays, hundreds of dollars of overdrives, and every mod available is certainly something to want, but find what sounds great and don’t worry about having everything. You’ll never be satisfied with your pedalboard when you’re constantly trying to innovate and create different sounds.

I’m sure I can think of hundreds of other things to tell the teenage version of myself, but I’ll start with those 4. What would you tell the teenage version of yourself? What is some advice that you’ve been given that’s been helpful to you?

Musicians Vs. Taxes

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It's that time of year again... every commercial on TV is for tax software, every artist you played with last year is reaching out for a W9, and every expense receipt you have is being tracked down. Taxes are not sexy, but I had a couple of thoughts I figured I'd share to help out my friends who constantly struggle with tax season.

1) What should you write off?
When I first came to Nashville in 2011 I was told to save every receipt and write off anything I could possibly write off: car trips to coffee meet ups, snacks from the road, instrument purchases, etc. This helps alleviate some of the tax burden for the year but could actually be hurting you if you're looking to get a loan in the next couple of years (house loan, car loan, business loan). Whatever you write off comes out of your "provable income", so if you're asking a bank for a house loan and you've written off half of the $40,000 you made last year with things like guitars, gas reimbursement, coffee, etc. then you'll look like you make a lot less each year than you actually do. If you're not looking at taking out a loan for a few years, write off as much as you can, but just tuck that nugget away for when you start to look at a business or home loan.

2) Stay organized for next year
Although filing taxes for this year is still happening, it's important that you start keeping records for next year to make the process less painful! Go out and get a binder with some dividers and keep a log of your miles, tuck away your expense receipts (including the receipt for buying the binder), and track your income as well. If you do this for every gig this year, next years taxes are going to be a breeze. You don't have to write off everything, but it's a lot easier to choose what to write off than to wish you had kept a receipt for something.

3) Know what you need to charge
Being a full-time musician is tough because so much of the industry is based on verbal agreements and going with the flow. But something that I've found very useful is deciding what you need to charge in order to make a gig possible. It doesn't have to be extravagant, but know your minimum threshold for being asked to play a gig. It might hurt to say no to something that pays $50 when you're hurting for cash, but if it's going to require you to drive your own car and potentially get a flat tire on the way, you'll wind up saving money in the long run.
For the married folks, talk with your spouse and see what that number might look like. It could be playing for free for someone you really want to get connected with, but just know what you're willing to accept in order to sacrifice that time at home with family.

Money conversations can be weird, but for the sake of your future self it's good to start thinking about how to handle it now. Taxes might be daunting, but they don't have to be that way next year. And if you need help, I'm happy to talk through stuff with you (for a fee... wink wink).

If you want more tips about money in the music industry (and 9 other topics), I still have a free eBook that's available! Check it out:

Thanks for reading!

Coffeeshop Musicians

Nashville is littered with musicians. Your barista is a songwriter. Your Uber driver is on the radio. Your waitress probably won The Voice three years ago. There is certainly no shortage of skinny jean-wearing, essential oil-sniffing, kombucha-drinking musicians in this city.

Something that was staggering to me when I first moved here is just how many of them there are hanging out in coffee shops all day. It can be hard at 10:40am to find a seat in some of these places. My first thought was "why are all these people here?" and then it hit me that I was there for the same reason: e-mails and coffee.

The coffee shop is the millennial office space. Wifi? Caffeine? Semi-clean bathrooms? It's a perfect environment to think up Instagram posts to look busier than you actually are. "It's my 5th latte this week, so I'm obviously pretty well off... right?"

I released an eBook last Friday called "100 Tips For Session & Touring Musicians" that was basically aimed at the 2011 version of myself because I was a little intimidated by the coffee shop musicians. Everyone seemed to be doing something, everyone seemed to know everyone else, and everyone seemed to have enough money to buy crazy expensive drinks. I realize now that many of those people felt the same way I did and didn't have a clue of how to start off their music careers. The eBook is kind of a way for me to help out fellow musicians who might feel the same way now that I did then.

Here are 3 of the 100 tips in the book:

Tip 58: Download the Right Apps To Get Paid - When you do get a gig, make it easy for people to pay you. Cash App, Venmo, and PayPal are 3 quick apps that many people use to pay their players.

Tip 77: E-mails & Coffee -  E-mailing can be extremely frustrating, but it’s something to develop as a skill. Find people you want to work with and contact them. See if they’re available for coffee or to hang out and then BUY THEM COFFEE. 

Tip 28: Learn from the Producers & Engineers - This was one of the hardest things for me to get used to. Producers and engineers have a wealth of knowledge that they can share with you to make you better at your craft so take notes!

For those of you who make the coffee shop your office, I do have one tip that wasn't in the book. This is super practical and may hurt a little, but: get a Starbucks gift card and start working towards a gold membership. If you schedule your meetings at Starbucks, they have free refills for gold members (maybe even green members) so you can stay and just refill your coffee before your next meeting. I used to line up 3-4 different meetings on a $2.50 cup of coffee (+ tips...). "Meetings" can be expensive and this can be a great way to save some money and still be able to buy coffee for those you're asking to meet with.

If you're at a coffee shop right now and want to read the eBook click here. Or you could just text me and we could meet in person like people used to do in the 90's (or so I hear).