82: Everything I Really Need to Know as an Entrepreneur, I Learned Playing Music

I’ve been a musician for longer than I can remember. I started playing trumpet 32 years ago, but music has always been in my life in some way or another. I’ve been an entrepreneur – off and on – for the last 12-13 years. In 32 years, I’ve become pretty good at the trumpet. As far as being an entrepreneur? The jury is still out, but I like to think I’ve developed some good qualities. Of course, the biggest room in anyone’s life is the room for improvement.

That being said, there are a lot of qualities in the experience of becoming a good musician I’ve found are similar in becoming a successful entrepreneur.

  • You suck when you first start. Sometimes people like to argue over which instrument is the absolute worst to listen when someone first learns to play. The clarinet and violin are the unofficial winners in this extremely unscientific poll. Regardless, they’re all pretty awful when someone is just beginning to play. It usually takes a new trumpet player at least 3-4 years before their tone quality doesn’t drive its listeners to self-immolation. But you have to start somewhere. A blogger wrote something along the lines of, “If you wait until you’re perfect to start, you’ll never start.” When Apple first introduced the iPhone, Steve Jobs said, “Don’t worry, be crappy.” Being bad at something is a good way to stay humble and develop patience. Memories of your suckitude will also bring a source of amusement when you do achieve success. Which brings me to the next point...
  • Success is a process, not an event. This is something a chiropractor told me years ago. He showed me how my back and neck were out of alignment and then explained the number of treatments it would take to get them back in shape. It had taken years for my neck to get out of alignment and I couldn’t expect it to just pop back into place with a couple of adjustments. No one becomes a great musician overnight. It takes years of trial and error, two steps forward, one step back. Any time I get frustrated with my trumpet playing, I compare where I am at that moment to where I was a year prior. If I’m further along than the year previous, I tell myself at least I’m still going in the right direction. The process includes victories and failures. It runs the full gamut of human emotion.
  • Success is not a victory. It’s the culmination of many small victories. I remember when playing anything above a middle C was extremely difficult. Then it became easy. Then playing a G on top of the staff was difficult but it too eventually became easy. Today, songs and exercises I once considered impossible to play are part of my warm-up routine. There are no gigantic leaps on the journey to success. It’s a matter of stepping from one cobblestone to the next. Sometimes the biggest breakthroughs are in overcoming the most miniscule, tedious challenges that baffle the casual onlooker as to their significance.
  • You need a clear vision of success. Otherwise, you’re like a ship lost at sea. You don’t need to envision everything you’ll do in your career. But you need to know what or who you want to sound like, what style you want to play. If you bring a crowd to their feet with your performance, what have you just done? It’s not about the style or genre, it’s about the performer who had a vision of what they wanted to do with music, made a plan according to that vision and then stuck with it come hell or high water.
  • People will think you’re totally cray-cray. Well-intentioned friends and family members of musicians who do their craft for pay are always telling them to "get a grip with reality" and get a "real job." As well-intentioned - or even right - as they may be, what these people don't understand is that for a serious musician, music isn't just something that's heard on a radio. It's something that is constantly coursing through their head. It's a part of them. It defines them. You know you're obsessed with something when you do it when others tell you're crazy for doing it.
  • Success begins with a conscious decision to be above average. This one is important because this is when you begin to separate yourself from others. You might even lose friends because of this decision. People who are average don’t like to be reminded that they’re average. They wish everyone would be average. Being average is easy. You just need to do what everyone else is doing. But being above average is a sacrifice. You win an award for being outstanding, but the people closest to you become resentful. They call you arrogant. They scrutinize your every move. Perhaps you are arrogant. Well, you need to work on that. But so are the people making that accusation. You don’t see them running to the nearest therapist to fix their problems. They want to point out your shortcomings because they don’t like to be reminded of their averageness. But that very attitude is what makes them average in the first place. When you decide to be above average, and become that, then you want to be way above average. Then, if you’re successful with that, you think, “I’ve come this far, why don’t I become a peak performer?”
  • A routine is of the utmost importance. Success as a musician happens as a result of establishing a routine and sticking with it. The routine is usually basic scales, long tones, exercises, etc. It requires discipline to do something you can do in your sleep for an hour each day. Sure, you need to maintain your skills, but you also need to maintain that regularity in your day. The person or ensemble that wows an auditorium, stadium, or church sanctuary full (or half full) of people is the person/ensemble who has a daily routine and makes it their priority for their day.
  • There’s always someone better than you. You may as well accept it. Don’t just accept it, embrace it and learn from them. Trumpet players have a bit of a reputation for being egotistical. The running joke among trumpet players is to introduce themselves and say, “Hello, I’m better than you...” It’s only a joke. It’s never sincere. Let’s turn that on its head. What if you were to approach someone far more accomplished than you in music and say, “Hello, you’re better than me. I want to learn from you.” What kind of response do you think you would get? I’ve taken that approach many times and can’t remember being turned down. Of course, I’ve at times had to pay these people for their time and insights, but that’s just what you do when it’s appropriate.
  • Failure is no one’s fault but your own. A musician’s teacher or mentor is responsible for teaching how to use the tools and develop the mentality to become successful, but ultimately the musician needs to go out and make it happen. A great way to tell if someone has a mindset to be successful is if they take responsibility for their failures. If they blame everyone for their problems, they’ll go nowhere. A person of success is willing to reflect on their their own decisions which led to a particular failure, accept responsibility for it and resolve to never make that mistake again.
  • The boring, tedious things eventually become enjoyable. I remember when practicing scales and exercises was the most boring thing imaginable. It was right up there with watching paint dry and pouring salt on a slug. At least the slug had a reaction when salt was poured on it. These days, those scales and exercises are the first thing I do when I practice. It’s actually kind of fun to reflect on the many memories from playing them: crazy things that have happened on gigs and crazy people I’ve played with over the years. Before I play a song, concerto or etude, I’ve played a lot of scales and simple exercises. Not because I feel like I have to do it, but because I want to do it.

It's funny how musicians shy away from entrepreneurship because they don't want to identify themselves as businessmen. What many of them don't realize is that all the time they've spent developing their skills as a musician, they've also been developing the qualities of an entrepreneur. Success has less to do with a great idea, or the latest internet tool to promote it than simply showing up every day, making just a little bit of progress each day, until you've eventually hit your stride, found your groove and people really see the value of what you bring to the table.

About the author, James Newcomb

I'm a full time MusicPreneur. Every now and then I play music. Send me an email at!

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