The Artist is Dead , Long Live the Artist!

A Career Change in Two Acts

18 min readApr 2, 2021

Act II — Seven Lessons from the Other Side

1. GRIEF IS REAL: Be prepared to do the interior work.

You’ve spent years — maybe decades — honing your craft. You don’t just have a set of skills, or a job, or even just a profession — you have a vocation, which comes from the Latin word for “calling.” You are called to do this thing. Drawn inexorably toward it by some external power.

But even beyond your vocation, your craft is not just something you do, it’s something you are. You don’t sing because you like to, you sing because you must. You’ve worked in the arts or humanities or the nonprofit world because it was satisfying on a deeply spiritual level. Because nothing else made sense for years and years. And trying to change something about who you are is far more profound than just changing what it is that you do.

That kind of change always comes at a cost.

If you haven’t already done so, make time to do the emotional, intellectual, and spiritual work to process the grief that may result from a career shift this big. In many respects, it’s like a death: death of self, death of identity, death of at least some of your dreams. And your response to this loss may need to be just as robust as when someone you love actually dies.

For some, finally moving from the Sisyphean task of building a solo opera career in 21st-century America to “just working” in the private sector may come as an enormous relief, requiring little emotional or professional adjustment; for others — and I put myself in this category — it may be its own kind of long slog of a mountain ascent verging on trauma.

When I started down this path and began to grasp the enormity of what I was going to have to do both in terms of building a relevant business and technological skill set and processing the grief that would come from completely rewiring my identity as it relates to music, it became clear that this was going to take me at least 18 months to two years.

Now, that’s just my number, but I think Elisabeth Kübler-Ross would’ve been proud of me — two years was a pretty solid guess on my part. The work is ongoing, but the time and effort I’ve already put in have given me the headspace I’ve needed in order to mourn and begin to move on.

2. YOU ARE YOUR OWN WORST ENEMY: Not an exaggeration.

Since there is rarely anything easy about making a change this big, it’s then worth asking what actually makes it hard. And while there are undoubtedly some substantial external challenges which I’ll address later, you may find that your biggest stumbling blocks lie within.

A prime example: as “all or nothing” types who regularly commit ourselves body and soul to our work on a daily basis, stigma, whether real or perceived (or both), can indeed be a powerful blocker to making major changes to your career.

Seasoned by surviving years of soul-crushing challenges, we singers often take to heart the most important piece of advice given to us (if we were lucky) by our mentors and teachers over the years: “If there’s anything else you’d rather do than sing, do it. Otherwise this business is too hard.”

And while you may know and respect that on a gut level, you may have also internalized that that truism surely applies to everyone else except you.

Whether it’s because you knew you had what it takes to have a lasting arts career, outlasting the majority of your colleagues, or because you just knew on a gut level that those difficult choices belonged to a distant future which might never actually arrive, you really didn’t think that you were ever going to be the one to actually quit.

That kind of cognitive dissonance is extremely difficult to wrap your head or your heart around.

Case in point: I’m an out and proud gay man, but I was so terrified at the prospect of having basically a second “coming out” experience — this time as an opera singer who (gasp!) “left the biz” — that I actually spent the majority of my first year talking about a career change with everyone except those in the arts.

Product Managers, UX Designers, C-Suite types, software engineers, hiring managers, entrepreneurs, lawyers, scientists, tech support specialists, general corporate types — you name it, I told them my story and asked for advice.

And what I learned is that, by and large, they really, really want to help; in fact, I’ve been continually blown away by how generous people can be with their time. Many have either themselves transitioned into tech from a different industry, or perhaps are keenly aware of the enormous advantages their income and job security afford them, and so want to pay it forward.

In any case, you’ll find that most people in tech find it deeply rewarding to lift others up along the way.

Finally, when I circled back to my artist friends, mentors, and colleagues and told them my dark and horrible secret, their responses were universally supportive. ALL of them. It’s amazing how effectively we convince ourselves of all the bad things that will happen if we make a change by repeating the same stories in our heads over and over again.

It’s also amazing how often those stories are usually completely wrong.

3. START SHOWING UP: Whether in person or online.

If there’s one thing that we performers bring to the table, it’s fearlessness.

Well, okay, maybe not total fearlessness.

In fact, many of us become artists precisely because we have been deeply broken or hurt by life in one way or another. Art becomes a way of coping, a uniquely powerful and effective survival and recovery tool. Many of us never get over the fear of performing (or having our work judged by others), but rather learn to ride the fear. In fact, that fear-riding is often what gives our performances such fearsome intensity.

Well, guess what, my fearless performers? Here’s your chance to shine: you need to start showing up.

Here in sunny Colorado, which has one of the largest and fastest growing concentrations of tech jobs in the United States, there are literally hundreds of events each year, large and small, which are all about professional development and/or networking From huge, multiday, convention-style events with thousands of attendees like Denver Startup Week or Boulder Startup Week, to extremely discipline-focused midsize events like Rocky Mountain Product Camp or Mile High Agile, to countless smaller seminars and happy hours and book clubs of only a few attendees at a time. There are so many things happening here you literally cannot attend them all.

At weekly or monthly events sponsored by nonprofits, for-profit bootcamps, or other companies, you may find yourself sharing Zoom breakout rooms with five people on four continents and as many time zones. The vast majority of them are free, and there are seldom any particular professional prerequisites needed to attend.

Of course, not all markets are nearly as robust as Colorado or the Bay Area, but now that essentially the entire software development industry has moved online, there’s no reason you couldn’t do the same, as well.

Interestingly, you may find that many people who work in software development would rather swallow a nest of centipedes than mingle at an industry happy hour, introduce themselves to strangers, or speak at a TED Talk — let alone present in a weekly meeting to a group of a half-dozen colleagues they already know well.

For many non-performers, such situations aren’t just fear-filled, they’re absolutely terrifying.

Singers, think of the countless opening night parties and donor events you attended — whether you actually liked mingling with patrons or no, many of you got really good at it. Think of fearlessly diving into these situations as your superpower, and know that it would be extremely useful at a technology company.

Whether it’s in person or online, tap into that mastery of fear you’ve got and start showing up to tech events — and begin to build your network.

4. LEARN TO TELL YOUR STORY: You will be a stranger in a strange land.

“Oh wow, you’re an opera singer, I’ve never met an opera singer before!”

Singers know these conversations oh so well. Then it’s, “Wait, you have a degree in that?” and, “Are you with a… troupe or something?” and then the final indignity, “Is that actually even a job?”

They happen at donor events, audience meet and greets, but certainly also while being in any social situation — with family, friends, acquaintances, in a bar — or even at a tech conference — where you are often the only person who does what you do in the room.

The thing is, that wow factor, that spike of wonder you cause in the other person suddenly looking at you either like you have a super power or you just grew six arms, has a very limited shelf life outside of your natural habitat.

This is one of the hardest truths for any artist trying to move into tech — and one of the most desperately important things I want to communicate in all of this: people in the business world usually have no idea who you are or what you can do (or have done). They often just can’t relate.

Even worse: sometimes they just don’t care.

They don’t know what it means to have a music degree (let alone two or three). They don’t know what it means to spend two years memorizing and working and reworking a score in advance of a role debut. The don’t know how hard anyone in theater works, the long hours, late nights, 6-day workweeks for what sometimes amounts to non-money. They can’t even begin to imagine how pitiful the “team player” corporate-speak sounds to anyone who’s ever played in an orchestra or sung in an ensemble masterpiece like Le Nozze di Figaro. They don’t get that this isn’t a hobby, or that it’s something in which your multi-year (often multi-decade) commitment frankly rises to the level of religious devotion. They have utterly no idea how hard you work, nor can they even begin to imagine what you’re capable of.

So what does this mean?

Not only do most people who work in tech have absolutely no context for your potential, but with an arts or humanities background, you absolutely cannot bullshit your way into a high-paying, highly technical or pivotal business role at a software company. Perhaps once upon a time, but the industry has matured and multiplied exponentially — and so has your competition.

You can be sad about this. Or angry or baffled or depressed or any number of things. But while you’re still feeling all of those things, it’s time to get to work.

At a networking event or conference with hundreds of people in the room, you as the would-be technologist with an arts background will often only have someone’s undivided attention for approximately 60 seconds. Maybe three minutes, if you’re lucky. And then they’ll want to know why you’re at this tech conference with them — and then you get to tell them.

For starters, craft (and practice) your elevator speech. Figure out how to communicate the absolute heart of who you are, what you’ve been doing professionally, and what you’d like to do next — all in such a way that someone with no background in the arts will truly understand. Think carefully about it. Write it down. Brainstorm it if you have to. Rehearse it with one or more friends.

Mine goes something like this:

“I was in the performing arts for about 15 years. I was a working opera singer, had a nice career, sang all over the U.S. But after a time, I just wasn’t getting everything I needed to out of it, whether personally, financially, or spiritually. I just wasn’t being used enough either as an artist or as a person. And as a person, I really need to feel useful. I didn’t know what I was going to do next, but I’ve always been good with computers, so I knew a career in tech was likely the next step. A few key conversations later and down the tech rabbit hole I went.”

That’s the heart of my story in 30 seconds. Most of the time you’ll find that you don’t need more than that to really connect with someone who otherwise has no clue about your world.

But however you do it, you have to learn how to very quickly tell a very compelling story. You must tell your story. Make it count — work to really connect with people in a meaningful way. As an artist, you are (or you should be) used to doing that already, anyway. But learn to make it quick.

And then? You must begin to know what you don’t know.

5. CULTIVATE A BEGINNER’S MINDSET: Understanding the implications of learning by doing — forever.

Agile. Scrum. Lean. Kanban. Roadmaps. Sprints. UX. Regression. A/B Testing. Jira. Confluence. Backlogs. Personas. APIs. Usability testing. Cross-functional teams. Python. CX. DevOps. C. C+. C++. C#. Technical debt. KPIs. Wireframes. MVPs. OKRs. Refactoring. Waterfall. Repos. Story Mapping. Java. Javascript.

This is just a tiny, mashed-up handful of the tools, concepts, and methodologies of which, depending on your path, you may need to be able to demonstrate your knowledge expertly and intimately — on a daily basis. Out of context they are all simply trivia, and being able to rattle them off by having memorized them will never be enough. Like all professions, no single practitioner is good at all of them; tightly focused expertise is a thing in tech, too. But it gives you a foretaste of the whole universe of new things out there just waiting to be learned.

But just being a “quick study” and having “potential” is not enough. You have to be able to care about the things that they care about, and you have to be able to deliver results.

You need to learn. You need to like learning. And you need to learn by doing.

You have to show them, all these lovely people in tech whom you want to be your future employers and colleagues and customers, just what you can do. You have to demonstrate to them in no uncertain terms that you are an eminently capable, intelligent, and analytical human being who works your ass off, and who can effectively become a subject matter expert on any number of topics in depth.

And you have to do it in such a way that they understand, which means learning the language of the business into which you want to go, learning who does what, and why particular things are important to them.

When you first decide to move from the arts into a full-time role in technology, there will be a significant skills and knowledge gap — maybe a chasm, even — which you and you alone are responsible for closing.

You need to be willing to fail and get egg on your proverbial face — frequently. Just as in the daily life of an opera singer, you can be at the absolute top of your game and most people will still turn you down at auditions.

When I was a full-time job seeker, I put out well over 200 applications in seven months. I had a not-insignificant handicap in the form of my arts-and-side-hustle-heavy resume, and it meant that I had to work and re-work and re-re-work my materials endlessly to get them to a point where they made sense to tech and business people. And I had to get through a whole lotta “no’s” before I finally received a single “yes.” Sometimes learning the hard way really, really sucks — yet learn I did.

And as someone who will have chosen to love learning, you will need to be okay with all of that.

6. TO CAMP OR NOT TO CAMP? Degrees, bootcamps, and the practicalities of all that learning.

Do I need an MBA? A BS in computer science? Project management certifications? A bootcamp or two?

The short answer is (probably) no. The longer answer is “your mileage may vary.”

Just as in singing, where opera companies are way more interested in what you can do rather than where you went to school, so also in tech: while hiring managers may perk up at certain items in the education and training section of your profile, they ultimately want to know just two things:

1) Can you deliver what they need? and
2) Will people actually like working with you?

Everything else is just details.

But as I said, you can’t just tell them, you to have to show them.

Many people making career transitions like this consider bootcamps like General Assembly, Hack Reactor, Product School, or the Turing Institute. Essentially the fast-track, 21st-century version of trade schools for people looking to break into tech, these programs can last anywhere from a few days to many months at a time. Costs can vary from free to a few hundred bucks to tens of thousands of dollars.

Whether (or how much) bootcamps are ultimately worth it at this point is a topic of continual, exhaustive — and sometimes exhausting — discussion elsewhere, so mostly I’d recommend you deep dive into the interwebs to see what others have said and written in depth.

That said, it’s generally acknowledged that they can be of wildly varying quality or value, sometimes lacking skilled instructors, up-to-date curriculum, or making job placement claims unsupported by the evidence. There are many in the field for whom they have been valuable, however, so I’d say it’s at least worth investigating each one that interests you if for nothing else but for a process of elimination as you find your way.

Ask yourself how much debt you are willing to incur, look very carefully at the pros and cons of financing options like income share agreements (ISAs), and take all promises made by bootcamps and their recruiters and instructors with a gigantic grain of salt to be weighed against your personal risk tolerance.

Don’t limit your homework to just reading online reviews or the company’s own promotional materials, either; find and speak to both bootcamp grads as well as former instructors (LinkedIn is a great resource for finding people by their work/education history and asking for advice) — people who will be willing to give you their unvarnished takeaways, and their personal cost-benefit ratio.

Very importantly, also speak to recruiters and hiring managers at companies where you might want to work — they often work through hundreds of resumes a week. They can sometimes be very hard to pin down and get responses from, but the best ones will be brutally (and quite helpfully) honest.

For me personally, the best piece of advice I was given was to just go out and “build something — a website, a tool, an app; basically, a solution — and build something that ties into your existing domain expertise,” which for me was the performing arts more generally, but the opera biz in particular. So, for the centerpiece of my portfolio, I chose to create a web-based community development space for a storied American opera company with which I’d had a long, personal history. (It’s been in development for well over a year now and will launch very soon.)

I made many, many mistakes along the way, but learned much in the process. And in the end I had something to show for it when it came time to start asking people to hire me.

So, ultimately I decided against formal bootcamps and did most of my education via a mishmash of online coursework (or inexpensive, mini-bootcamps online), certifications, reading, research, finding and utilizing mentors and mentorship programs — and by building something about which I already knew a lot. It was a perfect choice for me — and hopefully it has (or will have) delivered something meaningful to the people for whom I built it.

Once the portfolio and a couple of key certifications fell into place, I was no longer seen by tech recruiters and hiring managers as just “an eminently capable person with an interesting background,” but now I also had become something else entirely: employable.

Lastly, you should know that this will all likely take longer than you think. From the time I first seriously considered making a change to when I finally landed my first paying job in tech was about two-and-a-half-years.

And, for all the aforementioned reasons, that number both matched the expectations I set for myself but was also quite simply the correct timeline. I had lots and lots of work to do, not only of the logistical and educational sort, but also of the interior emotional and spiritual kind, too.

Again, your mileage will undoubtedly vary, but to really identify the path forward that makes the most sense for you demands doing so with a deep sense of care. Take your time and you’ll get it right — for you.

7. YOU WILL ALWAYS BE AN ARTIST. Ditch the all-or-nothing thinking and embrace your paradox.

When you change something so profound about yourself, what remains? What is left?

Well, you remain.

Indeed, after all that work and grief and learning and journeying, you may be surprised to find that, yep — there you still are. That which makes you you didn’t go anywhere. Your heart, your passion, your hurts, your loves, your history — everything that inspired you to sing and write and paint and sculpt with all your being in the first place — all of it will have carried you to a new place, and you will have carried it, too. You will indeed have changed, but some things about you are eternal.

Artists of all kinds are usually especially good at understanding that last bit, but sometimes they need to be reminded, as well. So consider this your reminder:

You will always be an artist.

In the end, the artist is only in the art, and the art is only in the art-making: the sacred act of putting pen to page, of giving life to music in your breath, in the strike of a bow on a violin, transforming your pain and your storytelling into glorious beauty — all of these things matter infinitely more than a job title. When you change careers or resumes or paychecks, the degree to which the you as art-maker becomes history or identity or side hustle or endless new possibility — that is entirely up to you.

Artists changing careers are of course not the only ones who have had to embrace the paradoxical in the course of major change. In fact, the history of ancient monarchies has much to teach us, as well.

Beginning centuries ago it became customary in various European countries to, upon the death of a monarch, proclaim,

“The King is dead, long live the king!”

Wikipedia describes this as a “seemingly contradictory phrase simultaneously announc[ing] the death of the previous monarch and assur[ing] the public of continuity by saluting the new monarch.”

Variations of the phrase appear over the centuries in a number of places. In England, the tradition has its roots in a 13th-century law that states, “The throne shall never be empty; the country shall never be without a monarch.” The logic was that it was vital to assure the people that the most important role in the life of their country would never be vacant; though one person dies, another assumes the crown in their place.

Remember that, though a big part of your identity may have changed, there the kernel of your artistry shall nonetheless still be; or to borrow the title of a famous book, “Wherever you go, there you are.” Embrace that paradox and see where it leads you. “You” as artist and art-maker never actually go away, if you don’t actually want it to.

And just as with monarchs, so also with artists: there is death, there is change — and yet there is a thread of unbroken continuity, too.

Are you ready to show the world what that means for you?

Tell us. Show us. Climb the castle towers, and from the highest rooftops, shout: