Is It A Calling? – Jon Allegretto

May 22, 2016


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.