Archives For Dream Followers

Finale: Follow Your Truth

August 21, 2017

How important is it to love what you do for work? Should you pursue your passion as your career? When should you go for it? When is it better to keep your hobby as just a hobby? Should you go all in and risk everything? Should you nurture it on the side?

These were some of the questions I began with at the start of this little project.

Fast forward to today, over a year later, and while I’ve learned more, it seems I know even less. But I’ll share some of what I’ve learned on this journey nonetheless.

It’s no secret, my inspiration for interviewing a bunch of people who are doing what they love in life comes from my own personal struggles with this issue. There are certain recurring themes in anyone’s life… patterns that replay themselves over and over… and this one has been one of my biggest repeating loops.

I am not somebody who can just punch a clock while really living for my evenings and weekends. I seem to be wired to need to be doing something for work that I find meaningful. Yet time and again I’ve found it difficult to figure out what that thing should be or how to make it a reality.

I’m not exactly sure why. Maybe it’s that I got somewhat of a late start to this reflection, dropping out of a Ph.D. program and realizing my entire education had sent me down “the wrong path.” Maybe it’s that I have too many interests, and each time I start to progress down a path I feel some other passion is neglected and find myself pulled off course. Maybe I just haven’t found my calling yet. Maybe I’m overly idealistic and my expectations are too high. Maybe all the things that give me a sense of purpose are too difficult to rely on for income when I have a family to support. Maybe I haven’t been patient enough. Maybe I’ve been too much of a sissy and haven’t been willing to really take a risk.

Living in a “land of opportunity,” it has been instilled in me from very early on just how lucky I am. Not only am I not going hungry, I even have a choice when it comes to livelihood. Not everyone does. Many people are born to different circumstances. Sometimes one can’t help but feel selfish in having a desire for more meaningful work. After all, even in a land of opportunity there are a ton of people who have to clean toilets to support themselves. Hell even I’ve had a job where I cleaned toilets.

But where has this gift of choice gotten me? Usually it’s put me in situations where I have a great job, but something feels missing, I feel drawn to finding something that aligns more with a sense of purpose, yet I’m beating myself up for not feeling more grateful for something so many people would be lucky to have.

So that’s the loop. Fifteen years after dropping out of a Ph.D. program, that same loop is still playing.

Which brings us to these posts about real artists pursuing their passion…

I decided on the name “Dream Followers” and immediately regretted it, but I’ve learned that when I insist on perfection, nothing gets done, so I decided to let it stand. This inquiry wasn’t about following a dream, which is often mixed up with people pursuing goals that may be whimsical, petty, or self-centered. Even a noble “dream” connotes some lofty ideal that one would be lucky to have come true. But this inquiry was not about finding people who have made their dreams come true, as in “gotten what they wanted.”

No, I was after something much more grounded, much less self-centered, and far more profound.

Just about all of us have probably at one point or another found ourselves doing something in school or work that misses the mark for us somehow. Something in us tells us “this feels off.” Sometimes it is a subtle feeling, sometimes it is painful. It is a sense of lack, a sense that something is missing.

And my strong view, which has only grown in strength after pursuing this project, is that this feeling is an indicator that you should be doing something else, not for your own self-interest, but for other reasons entirely. It’s almost like a message from the universe that something is out of alignment.

There is a difference between passion and purpose, even though I’ve used “passion,” “calling,” “what you love,” and even “following a dream” somewhat interchangeably. I explored one side of this distinction in Jon Allegretto’s story. And to me, it boils down to the difference between “what I want to be doing” and “what I should be doing.”

“What I want to be doing” is an ordinary desire. If we are chasing some life situation to make us happy or fulfilled, we’re doomed from the start. If we haven’t noticed already, no external situation will ever give us happiness or a sense of peace or fulfillment except maybe for a short while. It doesn’t matter whether that’s some job, or getting married, or having kids, or anything we might happen to want in life. If we want it and think we need it to be happy, we will suffer, to use the term attributed to my good friend the Buddha.

“What I should be doing” is a way of describing the process of following your own inner authenticity. Jon Allegretto said it really well when he referred to his calling as “almost like a responsibility.” Forget the specific outcome, that’s for the universe to decide. But in any moment, you can be acting in alignment or out of alignment with what is true for you.

Out of alignment hurts. That’s the universe’s way of nudging you to get back in alignment. You can be in alignment even if at the moment your job is to clean a toilet when your real heart’s desire is to paint vistas or write the next great American novel.

That’s because it’s not about what you’re doing. It’s about who you are.

What most of us actually want, whether we realize it or not, is not a more fulfilling job, or a relationship, or more money. We want what we think those things will give us… a sense of happiness, a sense of fulfillment, a sense of existential satisfaction. We want inner freedom. We want inner peace, love, gratitude, an open heart, a sense of alignment with what is.

And those are byproducts of waking up and being our true self.

The artists I interviewed all share something really important in common. They are all in touch with this authenticity when it comes to pursuing an inner calling. That’s how they have been able to do what they do. Whether they’ve always realized it or not, it’s about something bigger than them. If it were just about chasing a personal desire, most of them would’ve given up by now. Personal will isn’t a powerful enough force. It always dries up eventually.

How else would Ross have been able to shoot photography for ten years as a side job on top of a full time job and having twins? How else would Jon have demonstrated a similar level of hustle for so long? Where does someone find the strength to hustle that much?

How else would Jen have been able to overcome her almost daily encounters with fear and uncertainty after she leapt into the unknown? How else would Damon have been able to summon the courage to put every last dollar he had into sharing his music with the world, or to take years to move backward in his music ability so someday he could reach new levels?

How would Ali have found her way out of her Dark Period, how would Ross have withstood depleting his retirement account, how would Edward have dealt with his parents’ consistent rejection of his choice of career?

How would just about every artist I profiled happen to have stumbled into a unique combination of professions that allowed each of them to financially provide for themselves while pursuing their soul’s craft, whether that was Jon’s photography enabling his music, Edward’s DJing enabling his acting, Damon’s youth sports enabling his music, Ali’s work in autism enabling her art, or Jen’s graphic design enabling her studio art?

No, personal will couldn’t have accomplished one-tenth of that.

We find strength like this from being authentic and true to ourselves. We listen to a still, small voice inside that impels us to pursue a path. It doesn’t matter if someone does that full time or on the side. It doesn’t matter if they make money from it or not. It doesn’t matter if it’s met with wild cheers and approval or it’s lost in relative obscurity. It’s not about the outcome.

In my own small way, this project has been a microcosm of following that small voice. It began over ten years ago when I first reached the height of confusion about what to do with my life, a confusion that returned over and over again over the years. Even in the middle of the project, I set things aside for over a year without finishing it. I beat myself up for that a number of times, not because anyone else necessarily cared, but because I was attributing it to a lack of follow-through. But the truth was that life had its own course to chart, and in the end things came full circle anyway.

I wish I had done a better job on these amazing people’s stories. I did my best, but I still feel like I came up short and didn’t do the stories enough justice. But again, it’s not about the outcome. Perhaps my intention and effort is enough.

And it’s certainly not about me anyway. All I’m doing is giving voice to something you already know anyway. I’m just reminding you.

Reminding you of what?

Listen to that still, small voice inside. Follow your truth. Not just for your own sake either, but for all of us. Because everyone who discovers the sense of alignment that comes from doing what you love is a living example of the natural freedom that comes from being yourself.

Every individual who shares themselves authentically is a gift to the rest of us.

♦  ♦  ♦


Wherever you look, if you look closely enough, you just might find yourself.

Ali Painting - Face

I’d like to introduce you to Alison Hardy (the one who painted the picture above). Ali is a self-described 21st century muthatruckin’ Renaissance woman. If you’ve read some other things I’ve written, then you know I have both mad respect and deep empathy for Renaissance people. Respect might be self-explanatory. But empathy, you ask?

Well here’s what the world basically tells us:

Find your one and only calling in life and make that your career. And find your one and only soul mate and make that person your spouse. Then you’ll be happy.

The problem is… that formula (and I’ll focus on the career part) just doesn’t work for everyone. Because, some people are 21st century Renaissance people dammit. (A.K.A. multipotentialites).

This specific group of people tends to have spotted resumes and when viewed through the eyes of conventional wisdom, they often look like they are lost in life or unable to focus. People tell them nobody will want to hire them because their resumes are so damn eclectic. (My former boss recently told me I was “unemployable”). And if these people listen to what society or their former bosses tell them, they can be made to feel as though they are defective in some way. What was once a virtue back in the Renaissance period has become a liability in this age of super-specialization. And I think it’s a pity, because Renaissance people are totally awesome. But I digress, as usual.

Alison Hardy grew up in Jackson, Michigan. She was a piano player from the age of 4, as well as a saxophone and French horn player. In her freshman year of high school, she discovered she had a propensity for learning languages, and became fluent in German. She went on to study foreign languages and international relations and was on the edge of settling in Germany, but met her future husband (a Brit bound for the U.S. of A.) and decided living abroad didn’t feel like the right move.

So, newly U.S.-bound herself, she became a federal IT consultant, working in supply chain consulting for IBM. She did this for seven years before pivoting and going back to school for speech pathology. She now works in behavior analysis with a focus on autism.

Oh and did I mention she’s a mom too? Or should I say, she’s a mom and she’s all this other stuff on the side.

So what about the art?

Well that’s a pretty recent thing. Or that’s the case with the latest manifestation of her creative side.

About a year ago, Ali started going to “wine and painting” social events with her friends. (Quick side note—I recently went to my first one of these. I don’t want this article about Ali to get cluttered with the first “piece” I’ve attempted since basically failing my elementary school studio art class and never touching the visual arts again, so instead, here’s a link to my painting: Bird With Fat Thighs. I am currently auctioning this piece off. If you are interested, please contact me. The suggested opening bid is $250,000.)

Ali found these social painting events to be really fun, but she also found it to be a bit uninspiring in terms of what you could paint. Around the same time, she and her husband had bought a fire damaged home. There was a rooster emblazoned on the wall, left there by the previous owners. Then, something clicked.

Ali’s first piece was born.

It’s not often you get to see somebody’s “first.” But lucky for you and lucky for me… boom. You’re welcome.

Ali Painting - Rooster

What happened next is that she shared this piece on the social medias, and received warm responses about it. So she did a little more art and more positive feedback flooded in.

And almost overnight (which are my words, chosen by comparing this to the gradual process that happens for so many others), Ali was doing commissioned artwork on the side. Here is an example of a recent commissioned piece of hers:

Ali Painting - Commissioned

Ali went from zero to making a fair bit of money from her newly discovered artistic talents in less than one year. Someone once said “the internet is an amazing thing.” That someone was Ali.

Ali currently works four days a week at her job in behavior analysis, which she loves; she spends one full day a week doing the artwork that seems to have fallen into her lap, which she loves (some of the art is for herself, some of it is working on her growing base of commissioned work); and she spends the weekend with her family, who she loves—a perfectly balanced life for a mom and a Renaissance woman.

And she lived happily ever after.

The End.

Whoa whoa whoa… that’s it?

But what about the struggle? The strife? The sacrifice? What about the gradual and grueling process of building up a portfolio, a client base, an audience? What about putting in crazy hours stringing together multiple sources of income while tirelessly pursuing art on the side in the hopes that one day you can move from ramen noodles to rice and beans and maybe even somewhere beyond that?

Too embarrassed to admit this to Ali at the time, those were some of the thoughts that first went through my mind when she shared with me this story of the last year of her life. I think I even felt some disappointment. It was like there was a part of me that was rejecting it because it felt too picture-perfect, too easy. Or it didn’t fit some preconceived notion I had of how this kind of thing typically progresses for people.

The next thoughts that came up for me went something like this: Is there something wrong with me? Do I want people to struggle? Is someone’s creative success less valid when there isn’t pain and heartache and a slog through huge mounds of shit before having one’s passion finally bear some fruit?

And then…

Ali Painting - Rooster - thumbnail



I had my own Rooster moment. ‘Twas a wake-up call.



I realized some part of me hadn’t even really been internalizing Ali’s journey. For some reason, my brain conceived of it starting with wine and painting with friends, followed by things magically falling into place in a matter of weeks.

So allow me to back up and tell you what really happened (according to me… always good to remember that).

Ali was a multi-faceted, highly talented overachiever who had a picture in her mind of what her life would look like and hundreds of pounds of expectations she placed onto herself to go along with it. She expected herself to have a big corporate job. Her parents had been in the business world and she grew up thinking of her creative passions as hobbies, not as something you pursue for real.

After making a pretty radical switch away from the notion of living abroad in Germany, she landed in just that type of big corporate job she envisioned—working for IBM. And she was damn good at that too. And along with being damn good at a big corporate consulting job came all of the trappings—like the outstanding pay (which easily becomes a shiny pair of golden handcuffs) and a wonderful self-image you get to portray to your friends, your family, and anyone else you meet.

The problem was that the job began sucking her soul. The hours were brutal, the travel was intense, it was definitely not a calling for her, and it even made her feel like an outright fraud. For years, she would express this overwhelm and emotion to her husband, and he actively encouraged her to leave – “You don’t need to do this, do something you love,” he would say. But for some reason, she kept with it.

But why?

The golden handcuffs may have played a role, but the real reason was tied more to self-image. (Identity almost always plays a role. Pay attention to it.)

Ali was proud of her self-image of being an IBMer and having this big corporate job. She was proud enough of that to put herself through a significant amount of hardship. Even when it wasn’t working for her, she clung to it. And doing so led to a ton of self-loathing. She couldn’t understand what she was doing or why she was doing it, yet in many ways she was stuck and couldn’t seem to free herself. She was in a very not-good place.

And then, just a few years ago, when she first became a mom, she was dealt another hardship—postpartum depression.

Corporate hell.

Emotional hell.

This was the Dark Period for her. Not only was there no creative energy, there wasn’t much energy in general. Just soul-sucking job followed by depression. Yay.

There was a small silver lining though. It probably went unnoticed at first. Silver linings usually do. Something about this Dark Period triggered a change deep inside Ali’s heart. Something in her broke down. Something finally shifted.

What shifted was this:  No longer did she feel the need to fit into this idea that society placed on her, or that other people placed on her, or that she was placing on herself through her own expectations. No longer was she handcuffed by her own sense of pride. Instead, she got in touch with a glimmer inside that led her to pursue a very different form of livelihood, one that felt meaningful and fulfilling. This was when she decided to enroll in school for speech pathology. This was the first significant domino to fall.

Make no mistake. Even with all the pain and angst that was being caused by the trajectory she was on, it was not easy for Ali to give up her career and all of the things she had thought were so important to her. It was incredibly difficult, and it took a lot of time.

And during that Dark Period, there was a really important part of Ali that also went completely dark. She had completely lost her creative and artistic spark. She had no urge or energy to do anything artistic whatsoever. After fourteen years of music lessons and all the years after that of playing, she didn’t even have the desire to sit down and play the piano.

And this is purely my own editorial, not hers, but it takes an immense amount of psychic energy to live a life that is not authentic to you. So I am not the least bit surprised that between that and the postpartum depression, there was literally nothing left in her for the creative energy to flower.

Meeting Ali has opened my eyes to a number of things. But there is one thing her story has taught me most, and it is this:

Find yourself, and your art will find you.

Or your passion will find you, if art isn’t your thing. But you have to find yourself first. That’s the lead domino.

Had Ali not gone through her painful process of self-discovery—almost a form of rebirth—she never would have opened the door for these amazing talents to flourish.

I know there is a lot more to it than that, but I see it as the essence. And it’s undeniable that things are better because of it. The world probably didn’t need Ali the consultant. We’re a lot better off having her art, and the work she does in autism, and I’m guessing she’s a better mother because of all of this too.

Ali being a Renaissance woman, she also happens to have a black belt in dropping some wisdom on people. I share this philosophical nugget with you because it would be selfish to keep it all for myself in my own private notebook.

To all people with a passion to pursue:

“Let go of expectations. Let go of what you think everyone thinks you should be doing. Just let it go and follow that little voice inside of you. If every free minute you have, you’re looking at art on the internet, or you’re listening to music, that should tell you something. You have to listen to what it is that you feel passionate about. And don’t worry about the money because the money will come if you’re really good at something or you love something. Because that shows through in what you do.” –A.H.

♦ ♦ ♦

Many of us feel the need for what we do to be aligned with a greater sense of purpose. But how do you figure that out? How do you know? Read the next story about a guy whose story can help you figure out, is it a calling?




Feeling generous? Consider sharing this post and let’s push some more people to do what they love.

Thank you Ali, for the contagious positive energy and the reminder of what can happen when you follow what you love. 

Visit Alison Hardy and see more of her awesome work at Follow her at Instagram: @alisonkhardy and Twitter: alisonkhardy.

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.