How bad do you want it? – Damon

May 3, 2016

Here is my question to you:

How bad do you want it?

Whatever it is that you want. Exactly how bad do you want it?

But wait. Read this first, then you can answer that question for yourself.


Meet Damon. He is a musician and songwriter. He majored in music in college. He got his start as a classically trained horn player (his primary instrument was the trumpet). When he finished undergrad, his intent was to go to graduate school for music performance. But to do that, he knew he needed to elevate his game when it came to his playing. He wasn’t to that level yet. What that meant was that he needed a couple of years of extremely dedicated practice.

Of course there was also that pesky need to get a job.

But he knew himself well, and if he went and got a full-time job, he’d come home every day and the last thing he’d be able to do would be to practice at a high level. He needed more focus than that.

So he started architecting a work schedule around practicing his music. He took a couple of seasonal jobs working with kids and coaching youth sports—one of the jobs left him the entire morning to practice before he had to start work, and another only required full-time hours part of the year before ramping down to part-time.

And then there was the band. In college, Damon was part of a pop band that practiced a couple times a week and played shows on the weekend. Graduation killed the momentum with the core group of band members, so Damon grabbed the shell of the band (along with its original set of music) and rebuilt the band with some new members.

The guiding principle for his life was simple—“How am I going to make it work around my music? Because that’s where my heart is.”

He did all of this for a couple of years—the seasonal jobs, practicing in the mornings, and playing with the band in the evenings and on weekends.

And then something shifted.

As he put it, he found himself in a phase that looked sort of like a rut, but it turned out to be beneficial. The truth was that he enjoyed what he was doing so much that he didn’t want to give it up. He loved his seasonal jobs working with kids. He loved his band. He no longer felt the need to go to grad school for music.

All of a sudden, this weight of pursuing grad school had been lifted, and this freed him up to pursue things in a different way. He continued working his part-time jobs and putting more of himself into the band. Over time, the band matured musically, they recorded albums, and they toured.


And then they were signed by a label.

Many people think being signed by a label means you’ve suddenly made it as a musician or a band. But the reality is pretty different. It’s like being published as a writer. It’s great—now your stuff is out there as a product and it has some distribution—but there’s no guarantee it will sell.

And until it’s selling, you aren’t really making any money. (Even advances—which are usually smaller than people anticipate, especially for anyone new to the game—are just prepayment on potential future royalties that ultimately may or may not come). That means you still have to promote the hell out of your stuff and people still have to want to buy it for you to ever financially sustain yourself with your craft.

Getting signed is the beginning of the journey, not the end.

But with this beginning, Damon began to see a new possibility. The band, the music, the thing he loved most, it had a chance at becoming a full-time, self-sustaining thing. No longer did it feel like the barrier standing in the way was making better music—now it felt like the barrier was getting that music heard by people.

In music, there’s really one proven way to do that. You have to play more shows.

But there are some problems.

First of all, let’s talk about what “play more shows” actually means. It generally means playing at least a hundred shows a year—or a show about every three days—on top of practicing and any administrative work. Playing that many shows requires hitting up a lot of different cities, since you can only do so much in any given city. And playing in lots of cities means you really don’t have time to do much else.

Second of all, let’s talk about the financial reality of this picture. When you’re just starting out and you’re somewhere between an amateur and a professional pop band, venues typically guarantee between $150 and $300 a night. Damon’s band has 6 members in it. Get your calculator out and tell me if it’s possible for those 6 people to feed themselves and pay rent on one hundred shows a year at that level of guaranteed pay. (That’s $15,000 to $30,000 a year, divided by 6, and that’s ignoring all the other costs like gas money for your van/bus/cars.)

Obviously you hope that things start to click, the shows get bigger, the money improves, and you’re making some meaningful money selling your recordings on top of what you’re bringing in from the shows. But that takes time and good fortune. The question is—for how much time can you make that situation work?

In a typical scenario, a band gets signed in their late teens or early twenties, before they’ve had time to build up much in the way of responsibilities. They can go on tour, eat street food, crash on people’s floors, and get by until they get traction or they get burned out. Even then, the runway isn’t usually all that long before the moment of liftoff or the moment of crash-and-burn. That’s why most bands, even those with real promise, don’t ever bridge the gap from amateur to sustainably pro.

But by this point, Damon’s band was made up of 30-year-olds. They had 9-to-5 jobs, they were in committed relationships, and were living a so-called “regular American life.” So a typical situation for them went something like this:

“Can we play in Boston next week?”

“Well, Rob can’t do it because he has a work thing he can’t miss.”

Game over.

Damon saw the writing on the wall. The only way his band even had a shot of going for it was if people could shed their day jobs. And the only way he could possibly get them to shed their day jobs was if he could find a way to pay them some guaranteed salary they could live on.

Here’s where things get interesting.

Damon’s life savings consisted of the money he was able to scrape together and set aside over the previous ten years of stringing together his part-time work, along with some inheritance money left to him when a family member died.

Around this time, Damon and his girlfriend had made the decision not to have kids, which meant they would be two working adults with nobody to provide for other than themselves.

So as he looked at his situation and his life savings, he began to consider a radical idea:

I can hang onto this money and use it for things people usually do, like a down payment on a house and a car. Or I can invest it into turning this band into a full-time, self-sustaining business.

If you wanted to start up a business selling widgets, you would need capital. That capital would be used to make the widgets, to pay any employees, and to cover your operating expenses.

If Damon wanted to turn his band into a full-time business, the formula would be the same.

First and foremost, he would have to “hire” his band members as employees as a way of buying their schedules. No more “Sorry, can’t go to Boston because of [fill in the blank]…” Now they would be employees and it would be their job to go to Boston.

Second, he would be covering the costs of producing and selling the music itself (the widgets).

And third, he would be covering the business’ operating expenses (website, gas money for touring, etc.).

There was no denying it. It would be a huge risk. But this was what he loved. If he could find a way to get them across that chasm from amateur to self-sustaining professional band, it would all be worth it.

Damon decided to roll the dice.

He began taking his band members out to lunch one-on-one to pitch them on the idea. The essence of his pitch was this:

If we want to take this thing further, we have to do it now. If we wait any longer, there will be kids and commitments and people’s priorities will have changed beyond the point of no return. We’ve proven to ourselves that what stands in the way for us is not ‘becoming a better band’ or ‘making better music.’ It’s getting our music heard by enough people and by the right people. And we can do that, that’s in our power.

Not all of them were willing to take the leap, even with some level of guaranteed income. The guitar player didn’t go for it—he didn’t want to risk giving up his day job. But when all was said and done, Damon had something very few bands in his situation have—a committed group of musicians who were willing to make this their one and only job, along with enough cash infused into the business to give them a little bit of runway to give the dream a real shot.

Taking the leap is a risk for anyone. But most people’s leaps do not entail taking the entirety of their life savings and using that to help support five other band members as they get the band off the ground. So I assumed the leap itself was probably the time Damon felt the most fear.

It turns out I was wrong. But I’ll come back to that. First, I want to share what might seem like a tangential story of Damon’s around risk-taking and connecting with what’s most important to you.

When Damon was first out of college and in his early days of intense practice in preparation for applying to graduate programs in music performance, he was faced with a dilemma.

Damon’s teacher told him that he would always be limited as a musician if he didn’t make a complete and total change to his embouchure (which is the way musicians shape their lips and mouth on the mouthpiece of an instrument—it affects a lot of things like tone, pitch, a musician’s versatility…). When Damon first learned how to play, he adopted a technique that wasn’t technically correct, but he was able to get pretty damn good over the next fifteen years in spite of it. But the issue with technique was catching up with him, and he was plateauing because of it.

His teacher’s basic message to him was—if you want to be a weekend warrior in a pop band, then you’re probably fine as-is and we’ll work with what you’ve got to make some incremental improvements to your playing. But if you want to be able to play at the next level—good enough to get into music school, good enough to play in a symphony, good enough to break through the barriers you’re up against—then you have to start from scratch, adopt the perfect embouchure, and relearn how to play your instrument from first principles. And it may take you years to get back to the level you are at right now.

Holy shit.

It reminded me of the story of when Tiger Woods was at the top of his game, winning tournament after tournament, and he took this crazy risk to reinvent his golf swing. He was the best golfer in the world at the time. But changing his swing was the only way he could keep getting better. It was the ultimate gamble—things would have to get worse before they could get better, and there was no guarantee of ever even getting back to the same level. It was the epitome of messing with the golden goose.

Damon had the same choice to make:  Am I willing to move significantly backward for some unknown period of time in order to move forward?

But to answer a question like that, a person has to look many levels deeper, and ask themselves things like:  Why do I want this? How important is this to me, really?

But you have to pass through that level and go even further, until you get all the way to The Question. There is really no other way to answer the earlier questions honestly and authentically without answering The Question, which is this:

In the end, what do I really want?

When you are up against it like this, you have to get in touch with what matters most to you. It’s the only guidance you can trust.

Damon decided to make the change.

So the advanced musician, the guy who majored in music in college and performed semi-professionally for a number of years, decided to take the backwards step all the way to becoming a beginner again. He literally had to take out his old books from when he first learned to play his instrument and relearn how to play from the absolute basics. He deconstructed everything and rebuilt his playing back up block by block.

It took about four years before he reached the level he was at when he made the change. Four years.

I can only imagine the temptation to throw in the towel and revert back to the old way. People give up on diets after a few days. Four years!

Here’s the thing. The teacher was right. Not just about the “it might take years” part, but about the other part too. After those four years, Damon broke through his previous plateau, which has even opened up the possibility of being able to play professionally at the highest level.

I took a lot away from this story. But I won’t hit you over the head with it. For once, I’ll let something speak for itself.

Instead, let’s get back to the scariest time for Damon.

Because as you’ll recall, the scariest time was not the point at which he bet his life savings on this dream. This surprised me at first, but it was because of how he viewed that bet. His primary aim was not to recoup that money. He saw it as having funded a “grant” for the band. He was ready to accept the possibility that he may never see those life savings again. The goal of the grant period was to get them through the ramp-up from amateur band to self-sustaining professional band that could fund itself.

So the scariest time for him was not the leap itself—it has actually been the past few months of the journey. For the last few months, he has been staring down the barrel of the end of the grant period, wishing the band was further along, but having to come to grips with the fact that he might be losing the gamble.

The band isn’t making enough money to reach the holy grail of self-sustainment. The growth trajectory isn’t steep enough to get there by the time the grant money runs out. And on top of that, the band was dropped by its label and is back to shopping itself to other labels, which means they aren’t getting any of the promotional support that a record label would provide.

Barring a buzzer-beating miracle, it looks like they are going to run out of time.

Damon’s fear comes from the prospect of having to go back to life before this amazing but brief period of pursuing the dream full-time. The fear comes from those moments where the self-sabotaging voice in the head is allowed into the conversation so it can vomit the kinds of questions that make you want to punch it in the face: Was this all just a waste of time? What did I handicap by giving up my life savings—am I not going to buy a house until I’m fifty?

The thing is, technically the show ain’t over and the fat lady hasn’t sung. There are still ten seconds on the clock.

But I still wanted to know if there was any regret. And here is what Damon shared with me:

“Honestly, it’s been worth it. Even with all those concerns. I didn’t want to have to look back and think, ‘Man, we were so good, if only we had gone full-time, we had a chance.’ Obviously I can’t make people like my music. But I wanted people to be able to hear it and make their own decision. Torture for me would’ve been ‘I wish we had tried.’”

So what now?

Well, the clock might say there are only ten seconds left, but the game isn’t over even if those ten seconds run out. There’s still the second half of the game to play.

The rules change in the second half, and the game may get tougher in certain ways, but fundamentally it’s the same game.

It’s still about making music. It’s still about playing shows. It’s still about shopping to labels and getting the music out there in other ways. It may go back to being a part-time thing, but the fundamentals don’t change.

As the band members have been contemplating what they’ll do after the grant period, Damon has been doing the same for himself. He is exploring auditioning for symphonies, which of course wouldn’t have even been possible had he not taken four years to tear himself down to the studs and rebuild himself as a classical musician. He’s also kicking around the concept of going back to grad school, opening a studio, and teaching private music lessons.

And he will continue to be the driving force behind the band’s part-time efforts if that’s where things end up. If anything blips on the radar and they start to gain traction, they could find themselves heading back into full-time mode. Not all the band members would be up for coming back. But in his words, Damon and a couple of the guys will be “in this until we die.”

So let’s come back to the original question I asked you earlier about your thing, whatever that thing may be.

How bad do you want it?

Not a lot of people are willing to put as much of themselves on the line as Damon. And I don’t just mean money, either. You could substitute money with something else; it’s just a symbol for whatever it is that you have to put on the line.

Lots of people looking to go out on their own or start a business get hung up on money. Well if I had resources…

But everyone’s situation has its advantages and disadvantages.

Damon told me how fortunate he was that when he graduated from college, he didn’t have to go get a full-time job like so many others. He found a way to string together part-time work. In his words, not mine: “Most people don’t get that choice. They have to go into a 50 or 60 hour a week job and get abused. I was lucky.”

He told me how much his practical reality would have been altered if he and his girlfriend had decided to have children. He quoted a statistic of it costing many parents a million dollars to raise children, and how not providing for another human being significantly changes the math.

He also told me about how he was fortunate to have built up some savings to give the band some runway to go for it.

He was fortunate, but he also made choices. Lots of people have savings. Not that many use their savings to take a risk and do something remarkable.

But in the end, it’s never really about money anyway. It’s about something else entirely.

It’s about that thing that allows a person to bet whatever they have of value on a bunch of their fellow artists and a dream. It’s about that thing that compels a person to take four years of their artistic life to move backwards so they might someday be able to reach a new level. It’s about that thing that allows somebody to say, come hell or high water, they’ll be doing it ‘til the day they die.

So what is that thing exactly? Because it’s really fucking important. Do you have it?

♦ ♦ ♦

Sometimes reading about other people makes it seem easy. But what if you don’t even know what you want to do? Read the next story about how sometimes, you have to find yourself first.

Ali Painting - Face



Thank you Damon. This may have been the trigger.