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.

♦  ♦  ♦


There is always a price to pursuing your passion. 

There is always a price to not pursuing your passion.

Which of those do you think is more true? In this final profile, it’s time to look at one of the biggest assumptions we make about doing something you love. Let me cut right to introducing you to Edward Daniels.


Edward grew up in a small town in Virginia. Anyone tagged as an intelligent kid in his hometown had a career path to follow. You became a doctor. Or you became a lawyer. Take your pick.

Okay, doctor it is. So Edward shuffled off to college on the pre-med track. That is, until he got bitten by the acting bug and started questioning everything. Science just didn’t seem to fit. He wasn’t interested by the labs. The first thing he dissected he didn’t care about one bit.

But the entertainment industry, well that was something that had never even been on his radar coming from that small town in Virginia. Yet after doing some acting in college and winning an oratory competition, he discovered not only did he have some talent, this was a real passion.

So he ditched pre-med, graduated with a degree in Philosophy, and moved to Washington D.C. to pursue his acting passion. And almost immediately he started enjoying success. He was doing theater and was cast in a show at the Kennedy Center. There were movies and shows being filmed in D.C. and he picked up various roles and gigs along the way.

Actors are usually waiting for their big break. But the dirty little secret is that 9 out of 10 actors who commit to acting as a career can’t even make it work, let alone make it big. Forget your big break, can you put food on your table? Can you pay your bills?

Edward was walking the line. From an artistic perspective, he was pretty satisfied with the successes he was having. He was working a lot and being cast in roles he was satisfied with, so the trajectory felt good.

But he was living paycheck to paycheck in a house with a bunch of other people, he was frequently behind in rent and bills, he would have the utility company shut off his power… basically, he was the quintessential starving artist.

Yet everywhere around him were friends of his who lived in their own apartment, or were getting married, buying homes, having children.

“When are you going to get a normal job?” his friends would ask him. It’s hard for people to wrap their head around an intelligent, well-educated person choosing to live with such financial instability in the name of what they perceive to be some acting fantasy.

And truth be told, there was a piece of Edward that even felt like he was living in a fantasy world. After you’re questioned like that by the people closest to you, of course you’re going to doubt yourself.

But just because his friends didn’t understand, didn’t mean they were right, right? After all this was his passion. His break would come some day, wouldn’t it?

Well, a break of sorts did come. One day he was driving home and his car broke down. Stuck on the side of the road, he didn’t know where to turn. So he called his mother for help.

“You need to figure this out,” she said, and they hung up the phone.

There Edward was, stranded on the side of the road, unable to get home, rebuffed by his own mother. So he started calling friends until he found someone who was willing to help. And of course he had to borrow some money. That experience left a mark.

A few months later Edward went to his hometown to visit his family for a holiday. At the end of his visit when he was saying goodbye and getting ready to get on the road back to D.C. before nightfall, his father pulled him aside.

“Your mother and I want to talk to you.”

Edward knew immediately something had to be wrong, since his parents never pulled him aside. And out flowed the disapproval of Edward’s life decisions…

When are you going to get a real job? We sent you to college to become a doctor, and you graduate with a degree in philosophy of all things. Look at your friends and what they’re doing, and how successful they are.

“But I am successful,” Edward said, pointing to all the shows he was booking.

“No you’re not,” his mom said.


A moment of my own editorial…

It seems almost commonplace for people who choose to go their own way to be met with lack of acceptance and understanding somewhere along the way. But until you’ve actually experienced it, it can be hard to understand just how isolating it can be. And it can be difficult to know the pain of the internal conflict it feeds… you feel like you can’t win, you’re caught in the catch 22, you’re damned if you do, damned if you don’t. How you respond to this is usually the real moment of making it or breaking it, not some external moment of “catching a break.”

Edward left that conversation with his parents with a mix of emotions. His life didn’t make sense to his parents. They clearly didn’t understand him. And that’s indescribably painful.

But here was his response:  He took that as fuel for his journey. He came away from it motivated to prove to them that this was what he was doing with his life.

Except he didn’t outright reject his parents’ message either. It wasn’t a self-righteous “I’ll show you…” Edward also internalized the truth of their message as well as the importance to himself of having his parents’ understanding. And even more importantly, he took that message on board and realized that he himself could no longer tolerate being a starving artist.

This was a huge turning point for him. It wasn’t the “big break” everyone hopes for… that magical moment that almost never actually comes when some external event frees you from your current situation and catapults you into sustained success.

This was a personal breakthrough.

At this point Edward started looking at his life through a different lens. He looked at what his friends and peers had that he wanted… but not for the sake of comparing or judging himself. He was taking an honest inventory of his life. “I can’t do that, but why not?” And then an answer would come: “Because you’re doing 6 theater shows a year and you’re hardly getting paid for them.”

This honest inventory kicked off a series of life changes, the first of which was where Edward chose to focus his time and energy.

Most actors wait tables to make ends meet. Edward’s side job was DJing. It started with hosting a karaoke night at a bar where bachelorette parties were frequently held. Some of those brides-to-be would ask him if he did weddings and private events, which led him to starting his own small side business as a DJ.

Edward could see he wasn’t making the most of DJing. It was a unique opportunity. The pay was good. The flexibility of working from home and setting his own schedule allowed him to focus on auditions. He enjoyed being a DJ. And it helped him as an actor. Every event is a creative production, weaving together music, lights, special effects, and interaction with the crowd into an experience. It provided creative juice that he could pour right back into both acting and DJing.

So Edward decided to put significant focus on growing his DJ business. And the more energy he poured into it, the more he was getting booked. He told the story of a wedding where the bride was given golden tennis shoes, so for the first song, he had the crowd going crazy as he mixed Footloose and Boogie Shoes together. Perhaps that’s a memory from her wedding night she’ll remember forever. After the event he received positive reviews. Positive reviews from experiences like that turned into referrals and more opportunities.

He also shifted his focus with respect to the acting opportunities he pursued. The simple fact was film was much more lucrative than theater. One day on a television or movie set provided the financial equivalent of one week of doing theater. So Edward began turning down many theater opportunities in favor of film, and became more selective in the film and theater opportunities he pursued in general.

The second big shift was in the value he placed on himself as an actor and the corresponding expectations he had for doing a gig.

Actors often fall into the trap of not valuing themselves. As an actor, you’re constantly chasing jobs and experiencing rejection more than success. When you do land a role, it’s easy to fall into the trap of feeling lucky to have any role, even if the pay is crap and the perks are non-existent.

For the new Edward, there would be no more “Okay, I’ll do $75 background work.” Making 2 or 3 dollars an hour for 20 hours? Not a chance. Now it was What am I getting paid per gig? What am I charging? What does the contract look like? He raised his DJ rates to align with the local market and the true value he was bringing. He wouldn’t take an acting job if it didn’t meet his financial standards or meaningfully progress him in his career.

Changing his sights from “surviving” or even “getting by” to “thriving” made a huge difference in Edward’s life. There was an immediate shift in the growth of his roles, his business, and his personal fulfillment.

Quick side bar:  When Edward agreed to have me interview him for this little side project of mine, I believe it was for two reasons.

First, he is an enormous advocate of following your passion in life. He is a living example of somebody who has chosen to go his own way, even when it was counter to all the pressures of society, friends and family. He enthusiastically rattled off similar examples, like Compass Coffee across the street from him in D.C., started by two ex-Marines who knew nothing about coffee and have brought an incredibly authentic local and growing business to life. Or another guy he knows who opened a late night snack delivery business in a college town. Or another woman who has taken her one little story global headlining her own one-woman show.

But I think there is another reason Edward joined this conversation with me. And it brings me back to where we started. There is always a price to pursuing your passion.

I, like many others, focus on the sacrifice of pursuing a dream or a calling. “Go for it at all costs!” I might say (but might not actually do in my own life). In fact I almost included “Starving Artist” in the title of this series.

It turns out Edward hates the term “starving artist.” (It’s similar to how I went ahead and titled this series of posts Dream Followers and then Ross Dettman threw up all over my notion of “following your dream.”)

Edward’s point is that “starving artist” legitimizes the idea of being broke in the name of your passion, which doesn’t have to be a necessity. It may be a romantic notion to be willing to sacrifice so much to follow an inner calling, but it fosters a limiting mindset and limiting behaviors.

“There are things we do in our twenties that result in us being a starving artist in our forties.” – Edward Daniels

To illustrate, Edward recalls a time a friend said something he has never forgotten. Sure you’re doing shows, you’re getting good roles, but at the end of it, what do you have to show for all of this? Those words sunk in deeply. At the time, Edward was living in a house with a group of random people. He had gone from being in a relationship and when the breakup happened, he realized “I literally can’t make it on my own.” He had no sense of freedom. And it was a miserable feeling.

Maybe it was his friend’s powerful words, maybe it was his parents’ penetrating message, maybe it was his own internal drive and aspirations, or most likely it was a combination of all three, but Edward made a deliberate change:  He went from financially unstable and accepting that as the reality of pursuing an acting career to systematically overhauling his life so he could pursue his passion and afford a basic lifestyle he deserved.

Today, Edward has taken those hard-earned lessons and uses them to coach actors on his practical philosophy of living the artist life on your terms.

Figure out the salary you need. Broaden your available opportunities by getting your portfolio in the hands of every casting agency. Register in other cities. When an opportunity comes, just like a normal job you should negotiate. You should understand the time commitment, the pay and any other details and determine if it meets your expectations and can be used to progress your career. Don’t fall into the trap of the “I’m in it for the experience” mindset. Too many artists adopt an unspoken belief that, “Well, I’m an artist, at some point in the future the value I bring will be valued financially.” 

But more generally, he gives advice that applies to anyone pursuing a goal, and it’s advice he himself followed to change his life and make pursuing a career in entertainment a sustainable reality.

Make a plan and get it on paper… ‘this is what I want over the next year of my life,’ and the little steps that get you there. You don’t have to lose 100 pounds in the next month. You just have to begin. I make a lot of lists… lists in my opinion are so simple. Just moments of setting goals on the paper and checking them off. Plot it out and let that motivate you to make it happen. And surround yourself with people who are doing it and are successful, so you can ask what they are doing and how they are making it work.

There may be a price to pay when pursuing a passion, but don’t assume that price has to be financial instability.

But how about the other statement?

There is always a price to not pursuing your passion. 

This is the aspect of Edward’s story that resonates with me on the deepest level. It comes back to the essential reason I took on this project of profiling all of these people.

Ultimately, pursuing one’s calling is about being yourself. And Edward never gave up on being himself.

Even as he struggled to make ends meet, even when he felt like he was letting his parents down or like he was letting himself down, he still knew he had to find a way to make this life work. He chose authenticity over caving to external pressures time and time again. He persevered and followed what was true to him.

I want to illustrate what can happen when you do this by sharing a couple brief stories Edward shared with me.

In the early days of acting, Edward described a time when he would see other actors and wanted to change his style to be like them. Or how before his DJ gigs, he would think “What am I going to do, what am I going to wear…” In essence, he felt he needed to be somebody.

But his DJ clients would keep coming back to him, saying “We love you, we love your voice, the crowd response differently when it’s you.” And he was securing acting roles just the same. In his words, he began brushing away the idea of having to be “the thing that’s not quite you,” and in turn he was able to let loose and discover a new confidence and sense of self-value, and a new freedom. He shed inauthenticity and discovered the joy and fulfillment that comes with doing so.

Edward also recounted a time when he was in a relationship with someone whose friends were all in accounting, law, and government. Every time he went out, he felt like “I’m an actor an a DJ” was a conversation killer. He felt awkward and often edited himself.

But one time he was at an event and said “I’m an actor,” and a guy turned around and said, “Hey, you were in Rent… you were amazing!” That was a moment of self-realization for Edward… Yes, I don’t need to be ashamed. I’m an actor and I can say that with confidence.

And even with respect to his family, there was the day his mother came to watch him perform in Rent. Edward recalls how she was crying after the show. She could see that this was who he was, and she finally understood how happy he was doing his thing.

In spite of immense external pressure that was consistently trying to push Edward to head down other paths that didn’t feel like they were him, he managed to hold onto what he knew to be true for himself the entire way. And by pursuing his truth, he grew to become even more authentic and free. More than any other lesson I have taken from Edward, this has influenced me the most.

So, when all is said and done, which is the heavier price to pay, the one you pay by pursuing your passion or the one you pay by not pursuing it?

♦  ♦  ♦

So what does all of this mean? These six inspiring individuals have opened my eyes to many things. In the Finale, I share some of my thoughts about finding a higher purpose, following your dream, and living a life without regret:

Finale: Follow Your Truth

Artist by Maggie Smith - Duo Tone


My sincerest thanks to Edward Daniels. From traversing that big river to today, I am inspired and in awe.

You can find more about what Edward is up to at



This was the day. It was five years in the making, but also a lifetime in the making.

For the past five years, Jon Allegretto had been working at the auction house. It was fine work. There were good people there and they were generous to him. But the work was repetitive and time moved much slower while he was there. It wasn’t the kind of slow that makes you stop and appreciate things, it was a different kind of slow—the kind that makes it feel like a part of your spirit is slowly draining through a tiny hole in a bucket one drop at a time.

Every drop was another reminder of how he wasn’t serving his purpose. Whenever you slow the frames down enough, this kind of thing tends to stare you right in the face.

Drip.    Drip.

For all of those five years, and a bunch of years prior to that, Jon had been nurturing his calling on the side. But let’s be honest—who the hell actually makes rock musician their life?

Not many. Not that many really even try. Most of those who try get swallowed up by late nights, by long stints on the road, by the music industry, by the lifestyle, by not achieving the success they want, by running out of money, by burnout.

But here’s the thing with a calling—it doesn’t really listen to all of that. It just keeps calling. You can try to push it to the back of your mind or ignore it, but it doesn’t go away. It might go dormant, but whenever things get quiet enough, there it is again, calling, patiently waiting for you to pay attention.

Until you’ve listened and you find yourself at a pivotal moment.

Jon’s moment was at the auction house, there for the last time in his life, about to cut the cord and leap into the unknown. No more relying on it for safety. This was it.

He walked out of there one final time. As he got outside, he balled up the pair of pants he had worn as part of his “uniform” for the job and tossed them in the dumpster.

At this point of his story, I cut in—“So what was going through your mind at that moment?”

“It was… Fuck. Now what?”

“Why the pants in the dumpster?”

He looked under the table to see what kind of pants I was wearing.

“Okay phew,” he said, “Because I hate khakis. I vowed I would never wear them again in my life. I still haven’t.”

Good thing I didn’t show up wearing my Bonobos. I proceeded to have an imaginary debate with him that he didn’t know about, but lost anyway. They’re not really khakis, they’re chinos … plaid pockets… whole different ballgame here.

(He’s not the only guy I know who has a distaste for some form of pants. But I digress.)

Jon and I met up at a bar in Wicker Park on a cold-ish February night.


The fact that we both live in Chicago is a testament to the different forces that guide our lives. Years ago, I had moved down south to the mid-Atlantic to escape northern winters, only to get married and move to where my wife grew up just outside of Chicago. Ten years ago, Jon followed an inner urge to move away from his home town of Williamsburg, VA to a big city that wasn’t New York or Los Angeles. As he contemplated it, all kinds of signs started pointing him toward the Windy City until he was sufficiently convinced the universe was conspiring to get him there. Then he knew he had to go.

In other words, there we were, two people who had no logical reason for crossing paths in life, one of us having bounced haphazardly toward this moment, the other having followed his vision and his intuition. It was apparent to me that this was how Jon approached all of his life.

“If I’m doing the wrong thing, I know it.” – J.A.

Jon knew when it came to something else too. He remembers being two or three years old when it started. He begged his parents for something over and over again, and it wasn’t a puppy or a pony. It was a guitar.

His parents resisted. He asked them for a guitar for years. It wasn’t until he was twelve years old that his parents finally caved in and bought him one. It took Jon falling deathly ill to the point of hospitalization before something in them softened up about the idea.

Since that time, music has always been his thing. Sometimes you get a glimpse into how deep something runs in a person. At one point in our conversation, Jon dropped a bomb on me about how, recently, three of his friends had tragically passed away. But almost in mid-sentence a song came on and he said, “Holy shit this is Henry Rollins band!” And he abandoned the story about his friends in favor of some air drumming. (Henry Rollins was a huge musical influence for him.)

Jon has been writing music since the minute he started playing, has recorded everything he has ever written—songs, short little riffs, anything he wanted to remember—and still has the cassettes from his earliest days of composing.

This love for music brought him to solo music, to his band A Friend Called Fire, to a series of self-organized national tours, even to playing on one of the stages at Madison Square Garden.

For years, Jon was able to pursue all of this while working at the auction house, including touring with the band. It was one of the unique aspects of his job and the people there—they gave him the flexibility to take a bunch of weeks off at a time for a tour. Not many jobs would still be there waiting for someone after a national tour. So why quit?

Something inside of Jon was telling him he was becoming too reliant on it and it was time to move on. So he listened.

But things rarely move as quickly as you want them to, and there are bills to pay from Day One. So Jon started stringing together various sources of income. There were a bunch of different odd jobs. He spent some time working from home for a tech company. He taught guitar lessons. He also taught a higher education class at an art school.

This is often the hardest part of one’s journey, and not just for the practical, financial reasons. This is usually when one feels most on an island. This is when self-doubt is the strongest. This is when fear starts seeping in.

The price of being a sheep is boredom. The price of being a wolf is loneliness. Choose one or the other with great care. – Hugh MacLeod

This was the case for Jon. And it could have been a much more potent force. But he was in a relationship with somebody at the time who was an incredible support for him. She consistently encouraged him that he’d be alright. Looking back on that, he now realized how important that encouragement and support had been for him.

There is one other thing I neglected to mention about Jon. He also has a background in photography and journalism. (It’s an interesting experience to interview somebody with more experience than you as an interviewer.) Here are a couple of his photos:



(You can check out his galleries at

It turns out he’s no chump. He once did photos and editing for live events like Zac Brown Band shows.

So he has dialed up his focus on photography, doing weddings and other live events. The bad news is both music and photography peak in the summer and are “like tumbleweed” in the winter. The good news is photography pays pretty well and also provides some balance to his life. That balance helps offset the potential for burnout he might feel if he was focused exclusively on music.

Jon has also done other music-related side jobs, like commercials. If you’ve ever seen the Taste the Feeling campaign from Coca Cola, Jon’s voice is in the chorus.

I asked Jon about doing commercials because a lot of musicians and music fans have this thing about “selling out.” I share the (paraphrased) gist of Jon’s thoughts here because I think it’s important for anyone pursuing art professionally:

“If you’re doing music professionally, you are providing a product to people, and part of that needs to be kept in mind. There are lots of ways to monetize your art without compromising your integrity and beliefs. You also have to survive. I’ve heard people say things like, ‘Talk about selling out, I heard Led Zeppelin in a car commercial…’ But for me, if they wanted to use my song in a car commercial and they’re reasonable about it, I’d be like, hell yeah, let’s go.”

Whatever it takes. You do your art for you, but if you choose to survive off of it, you have to be realistic about how much it’s just for you and how much it’s for others too. Others may disagree, but for me, that resonates.

So then what’s next for Jon?

When I asked him where he ultimately wants to go, he said, “I’d like to be doing what I’m doing right now, only at a higher level.”

He has aspirations. He wants growth. But he wants to be doing exactly what he’s doing right now. That is an amazingly rare thing.

There’s a reason I wanted to share Jon’s story. It started with him telling me this about his music:

“I don’t have a choice not to do it.” – J.A.

I immediately recognized him as belonging to what I referred to as “group 1” in Living Your Dreams: Always Moving Closer (the group of people I have always envied most). But it goes beyond that. So many people know that their art is their passion. But meeting Jon drove something home for me that I hadn’t fully understood until that day:

There is a huge difference between passion and purpose. 

People pay a lot of attention to whether or not something is their passion, myself included. And there is a lot of debate about how important passion is. Now, contrast that with something Jon said to me:

“I have the belief that music is somewhat divine, like I have a responsibility to do it.” – J.A.

What struck me most was the word responsibility. Passion is how something makes you feel. But responsibility, in the way Jon used it, is an entirely different thing. It’s similar to how I feel about my sense of responsibility to be the best parent I can be. It’s as though you’ve been given this gift that you have to care for and honor, and you know you would not be living your best life if you fail to follow through on it.

That’s what separates a calling from an ordinary desire. It’s that clarity of purpose. On a practical level, it feeds this incredible persistence, this attitude of I will go through, over, around… whatever it takes to get to the other side of these mountains.

That’s something Jon has that not everyone has. Not everyone has the will to traverse the ravines of adversity. And passion alone can only take you so far. It becomes an entirely different journey when it’s about fulfilling your purpose.

I have no doubts about Jon’s ability to make it work over the long haul. Because he has given himself no other options but to make it work.

But that doesn’t mean the journey is any easier. You still have the same work to do to get to the other side of those mountains. It takes the same amount of patience. It takes the same amount of grinding it out. And it takes the same amount of sacrifice.

Jon has made many sacrifices along the way. He gave up the security of steady employment. He had to make all the adjustments to his life to make ends meet. He went against the grain, choosing not to take the safe route in life, even if others in his life would have preferred he do just that. He could have listened to his parents’ anxieties. He could have listened to that voice of Resistance that says things like “you’ll end up starving on the streets.”

There were also the sacrifices we didn’t talk about, the ones he chose to keep close to the vest. He vaguely mentioned “knowing at one point that it was not the right time for certain changes in [his] life,” and then shared no more. I imagined a relationship on the verge of moving to a deeper level of commitment, but ultimately ending in separation because it would go against this path he had chosen to take. I may never know. But I’ve learned that the sacrifices a person doesn’t want to talk about tend to be the ones surrounded by the most pain—whether that’s one’s own pain or someone else’s. (And the two tend to overlap for compassionate people.)

Having a clear sense of purpose also doesn’t mean that you always know exactly what to do. This was one of the things Jon said he struggles with most. Should I spend my time doing this or that? There are so many possible directions he can go. He can go all-in on one thing, or half-in on a couple things, or a little less on three things, and there usually aren’t clear signs about which approach is best. Purpose doesn’t give you an answer for how to handle all of those decisions.

So when do you know what’s right? When do you know you’ve veered off track?

My own way of describing this is always moving closer. Jon described it as a constant process of honing and redirecting—of looking at things and saying “What will I do of the things I enjoy, and how do I cut off more of the fat?”

When talking with Jon, at times I felt like I could’ve been sitting across from somebody twenty or thirty years older sharing their life wisdom with me. You have to be patient. It’s so much more gradual of a process for most people than they realize. But there really is no other way. 

Jon’s advice, which wasn’t really offered as advice but I took it as such anyway, was this:

“If you don’t pursue your goal one hundred percent of the way your way…”

And he left it at that. We’re left to fill in the blanks ourselves. My question is, how does it finish for you?

♦  ♦  ♦


But what if we can’t risk it all? Some of us have families. Some of us don’t want to risk not being able to pay the bills to pursue a passion or a calling whether it’s in art, business, or life in general. Is taking that kind of risk a must? Read about that in the next story, Food for a Starving Artist.



Sincerest thanks go to Jon Allegretto for some good laughs and a dose of the Wisdom. Check more of him out at and and


If you have you’re own story to share and are willing to be profiled, contact me here.