I have a friend who’s worked in the entertainment business for a long time (he used to be my lawyer) and he’d often say to me: “you’re being penny smart and dollar stupid.”  He was always telling me that I needed to avoid being short sighted; life’s about playing the long game. Perspective is hard to come by, especially early in your career, before you’ve had the opportunity to make a heaping pile of your own mistakes.

Sometimes, an idea that seems positive or helpful for today hurts you down the road.

For example, when you’re interacting with promoters, you might be tempted to exaggerate your draw to get more money or a better time slot. In the short run, that seems like a great idea; you’ll get on a bill that you couldn’t otherwise touch. You figure “Why not? The other bands will sell tickets and no one will notice that I only brought four people!” Wrong answer. More often than not, the other bands won’t sell those tickets, and the promoter will lose money and get burned. Why do you care? In the future, when that promoter hears your name, he’ll say “Those guys? Not doing a show with them! They’re full of shit.” Most promoters work with a bunch of venues; even if the promoter you’re dealing with only works for one small club, you can bet your ass he has other promoter friends around town and they sit around drinking coffee bitching about bands that didn’t sell enough tickets. Don’t be that band; keep your name out of that conversation, because in the future you’re going to want to work with those promoters.

A misstep today can cost you dearly down the line.

Many years ago, a private investor tried to “partner” with me on my entire career. They offered me an enormous sum of money (many times over what I’d made in my entire life up to that point) for a 50% stake in everything I did for the next decade (records, merchandise, touring, the whole shebang). I really didn’t like the terms of the deal, but it was so much money. I was living in a four-bedroom apartment with my friends in a less than awesome neighborhood; as appetizing as it would’ve been to get a gigantic pile of money upfront, I knew that in the long term, I’d be better off without those partners. It hurt to say no to an enormous check, but with an eye on the future, I did. The next year, my career grew, and the year after that it grew some more, and the year after that it grew even more and so on and so on; at this point, I would still be locked in that onerous deal after paying them back countless times over. Sometimes you take the money and run, and sometimes you just run.

The moral of this story: don’t just think about today. It’s easy to get caught up in what’s good for you right now at the expensive of what might be good for you in the future. You want to have a long, meaningful career, so make your decisions accordingly.  

REASON TO IGNORE THIS ADVICE: It is 1969. In that case, you can make some mistakes and no one will notice. Oh, it’s 2017? You’re fucked then, because the internet…so there’s nowhere to hide from your past.