A lot of people get down about Mondays. Sadly, there is a negative connotation around the first weekday while Friday and Saturday get all the hype and the glory.
I’m not going to make things better by starting off this week with today’s insights, but then again, I don’t want to mislead anyone or sugarcoat things. At the end of the day, I want to help people, even if that means having to serve up a dose of reality. After all, there are lots of lessons to be learned out of adversity.
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I’m three-quarters of the way through watching the Billy Joel “And So It Goes” documentary, and the superstar singer, songwriter, piano (and guitar) player had to learn a lot of lessons the hard way too. Yes, he was in a motorcycle accident (and so was I), but I’m writing about show business lessons – tales from the inside of the entertainment industry.
I’m going to point to Billy Joel having to find out from Christie Brinkley that his own ex-brother-in-law was allegedly ripping him off. As his manager, he – according to the documentary – was keeping lots and lots and lots of money while the ‘piano man’ ended up finding out that he had very little money to show from all his touring and hit songs and record sales.
If you’re thinking that that won’t apply to you because you’re not going to sell millions of records and do tours in arenas across the country, then you aren’t setting your sights high enough.
At the same time, while you are at the stage of your career where that all can only feel like a dream, I owe it to you to prepare you for the times you’re going to get up on stage and it will just be you, the bartender, and, well, sometimes that’s it. Okay, maybe a server or a manager will be there too.
There are also going to be releases you get super excited about and then you put that music out but torture yourself by looking and looking at Spotify and there aren’t even a thousand streams on it – two weeks after it has been out.
My dad used to tell us about a guy he worked with who would always tell him, “It doesn’t say Heaven over these doors.”

As someone who has been working with indie music artists for more than twenty years, I’ve had a front row seat to working (myself) at 11:55pm – when everyone else has gone to sleep. And I don’t mean just one time. It’s something you can plan on being a regular occurrence.
This is where I’m obligated to drop in the “everyone sees all the glamorous stuff on social media” disclaimer. It’s why I posted a photo on Instagram during one of my many business trips last year, where I showed myself standing in the room at the hotel where the washers and dryers are – yes, doing my laundry. That’s one of the parts no one tells you about.
Get used to traveling in your car, and traveling in your car, and traveling in your car (wait for it) alone. Or eating your meals alone. Or wishing you had longer arms because you don’t feel like plunking down the money for a selfie stick since you’re creating most of that social media content alone. Perhaps you’re fortunate to not have to go by car, yet you’re still going to be sitting in airports and on airplanes alone.
This is where mental health comes into play. Manage your expectations. Keep your ego in check. And always remember The Golden Rule.
Remind yourself that there are people sitting in traffic every day as they go back and forth to a job that they can’t stand but have to do. Meanwhile, they’re looking at you chasing your dream. You get to be an entertainer. (Not, “I have to go play this gig,” but rather, “I get to go play this gig.”)

You’ll be in your bedroom, another room in your house, your backyard, a hotel room, and a variety of other places, talking at your phone, all with the hope that people will see your content and it will lead to them buying your music, tickets to your live shows, joining your Patreon, buying your merch, and so on.
Ultimately Billy Joel decided that since he couldn’t trust his ex-brother-in-law he just had to manage himself. It can be oh so helpful to your career to start to put people around you that can help, like a booking agent, a publicist, a radio promoter, and so on. But you’ve got to have the personal infrastructure that you can do okay alone. When it’s 11:55pm and you’re sitting and working on your artist website, you want to be joyful, not resentful.
Now a Member of the Recording Academy, for more than twenty years I have been helping indie music artists, authors, actors, entrepreneurs, podcasters, filmmakers, small business owners, and more. What challenges are you having in your creator career that I can lend some insight to? Connect with me so you can take advantage of all my experience, and I can help and keep you moving forward.