(Jun 26 2025) The Reality Of Pursuing A Life In The Arts

If you read my last entry you’ll be aware that recently I’ve been plunging myself into the world of jazz history and spending a lot of time piecing together the roots of the art form, specifically from an arranging perspective. Interestingly, just yesterday I was looking more into Duke Ellington and was reminded of the fact that while he experienced many years of financial success, ultimately as jazz lost popularity in the wake of newer styles like rock’n’roll in the 1950s and onward, even Ellington had to support his passion for music primarily from other avenues such as music publishing. As a big band arranger living in modern times, I had the strange realization that if someone like Ellington had to subsidize his band through his personal wealth, than what odds do arrangers without the clout and career of Ellington have of maintaining a career today, a time where big band music and jazz are even less relevant in the public's eye? 

The truth is that this question is something that plagues anyone interested in pursuing a career in an industry which is not valued financially by the general public. As someone who loves jazz arranging and has decided to dedicate my life (so far) to making a career out of the craft, it is a consistent battle between finance and art. Unfortunately, the reality of most jazz musicians is the same and there are only a very small number of people able to carve out a place where the music they are passionate about is valued highly enough to satisfy their financial needs. For most, they look for alternative income streams in related fields such as education or create music that is slightly more valuable in the public’s eye that they personally don’t enjoy. 

Like many, my introduction to this reality took place when I finished university. While the exact situation I found myself in was probably not one that is universally experienced, specifically finding myself moving from the USA back to my home country of Australia abruptly due to an employer ghosting me at the last second which resulted in not acquiring a much needed work visa to stay in America (and a whole lot more), the end result of having to claw myself out of debt with skills that weren’t seen as financially valuable is something everyone graduating with a music degree or wanting to pursue a career in the arts inevitably faces at some point.

With no other options I found myself taking any job that would hire me, most of which were not music related. This lasted for the better part of two years before I finally was able to lock in a small 6 hour per week bass teaching job. Due to the financial situation I was in, I didn’t really have time to think about much more than surviving, but with a slightly higher income I finally had a bit of space to look at my life and what I might want to do with it. 

Interestingly, while I see myself as a jazz musician, I believe my main skill set is music adjacent and where I feel most comfortable is as an organizer and manager. Ever since I can remember, I’ve never felt afraid to dive into hard problems because I’ve always believed that with enough organization anything is possible. Although abrupt, my transition back to Australia came immediately after the recording of my first big band album and left me with the desire to continue in that space where possible. Initially, this manifested itself with the idea of bringing my entire US based big band out to Australia alongside some sort of guest artist. With the realization that I simply didn’t have the skills or knowledge at the time to create the required capital to make it happen, that dream sat on the backburner while I slowly worked at other non-music jobs. However, in 2018 while discussing the thought to my friend and prior school band director, Dave Palmer, he mentioned how my high school had actually been communicating with my arranging professor from university, Rich DeRosa, about acquiring some charts of his. Long story short, over the span of a few weeks I had fully committed myself to organizing and sponsoring a trip for Rich to come to Australia later that year. While it wasn’t a full big band, it was close enough to my original dream and satisfied the guest artist component. More importantly I could see how it may actually be possible to achieve, even though I had less than $1000 in my bank account, was newly married and still living at my parents house at the time.

Without realizing it, I had decided to lean into my dreams, or maybe more specifically to the point of this newsletter entry, to embrace art more so than finance. I had no way of knowing if I could come up with the funds to make the trip happen, nor had I any experience in doing anything like this before. Yet, unbeknownst to me, I was breaking from the norm and not letting financial security define me. Perhaps due to not really having much money I was more comfortable taking risks, but whatever the reason, I decided to take the road less traveled. Some might say this was not a wise financial decision, and if I were to just look at the events of 2018, I would agree. I was able to successfully bring out not just Rich, but a slew of other US artists for a two week trip filled with workshops, seminars, and performances, with the artists getting to work with close to 2000 individuals over about 10 days. The project was a huge success in so many ways, except financially as I had to personally fund about $15,000 to make it happen. I’m not too sure how I found that extra cash at the time, but it definitely came out of work that I didn’t necessarily want to take on. However, while the event made no sense financially back in 2018, life works on a much larger scale than simply days, weeks, months, and even years, and often the rewards of our actions aren’t presented in such a neat time frame.

Looking back, now almost 7 years to the day where the artists descended on Melbourne, would I do it again? Absolutely. At the time I had no clue what that year would entail or what it would lead to in my future. From a financial point of view, it was a huge flop in 2018, yet in the coming years allowed me to access so many avenues I would never have come across otherwise, many of which have been profitable and have helped me have some level of financial stability. If I were to weigh up everything, the event was a huge net positive in every category, except I can only say that now having seen the cascade of events that took place in coming years.

So why spend all this time discussing this part of my life? Well as I’ve gotten older and also spent a lot of time interacting with many people who are also navigating trying to make a career out of music both young and old, I’ve seen a terrible trend. If I look at almost everyone I know, I see people burdened with the idea that money defines their life. Yes, money is essential to a capitalist system and needs to be managed well in order to thrive in our current society, however it doesn’t need to be the incentive for our actions. So many people let finance control their trajectory which then results in robbing them of the time and space they need to work out how to actually make their skillset work with the current world we live in. I think almost everyone would prefer to live a life where they spend the majority of their time on avenues they love more than by the balance of their bank account. Yet so few people are happy to compromise on their finances to pursue art. 

Now looking over that paragraph it is easy to think I’m saying to disregard finances completely but that would be unwise and probably put anyone into serious issues that they may not be able to break free from. What I’m really trying to say is that we should take a second to look at how we view our intentions and understand the true desires that are behind our actions. Somehow in the last 60 years or so, we as a western society have become increasingly comfortable, yet the very nature of life is unstable and there is no guarantee of what will happen tomorrow, let alone in years to come. We distance ourselves from discomfort and risk, often without even knowing it. We think that a music teaching job is more secure than pursuing a career built around creating our own art, yet most often we fail to realize that a job can disappear at any time, and really the feeling of security was fake to begin with. That doesn’t mean don’t take the music teaching job, just know that it may not be entirely as stable as it seems.

Unfortunately, there are many byproducts of pursuing financial stability and prioritizing work that doesn’t align with our interests. In my own experiences, it has led to fierce arguments, depression, and a whole slew of negatives that have impacted my life far worse than the discomforts of trying to pursue a dream. Even when pursuing my dream, such as right now with my arranging business, it seems that every time that I follow a financial incentive eventually it robs me of all happiness and usually also negatively affects the businesses reputation among other things. 

So where does that leave us? The older I get and the more time I battle with the reality of pursuing art in a world which doesn’t value it financially, the more I realize that to be an artist is to accept a life of compromise. Everyone who follows this path has to decide how they want to interact with money, whether it defines their view of success, and ultimately if it will define how they live their life. On one hand those who pursue their dreams take the risk that it may never work out but live with the freedom that they attempted to live the life they always wanted. Whereas on the other side, those who pursue financial stability may be able to access other avenues of the world due to the size of their bank account but be left with being unsatisfied that they didn’t utilize their time on something they loved. And of course there are the very few people who are able to weave the positives of both sides together, such as Duke Ellington in the 1930s, but even that may not last forever and eventually in almost all cases the individual will be plunged into the world of compromise once more.

Coming off the back of a recent podcast I’ve been listening to called Akimbo (thanks for the recommendation Aaron Hedenstrom!) I want to leave this entry with the same thought as one of the episodes I listened to this week. So often we look at conventional ways to live life without ever questioning whether they actually are the best for who we actually are. Whether that be working a job we hate or creating a business model around maximizing profitability, unless that truly aligns with who we are, there are often better options available. Seth Godin, the creator of the podcast, has suggested one possible alternative at least when it comes to business, and that is to focus your life around actions that benefit humanity and trust. While it probably won't yield the same financial return as other options, I think we can all agree that it is an honorable pursuit which will benefit society and is built on a more stable rock than financial incentives. 

Until next time,

Toshi