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‘Should I Leave My Good Job to Pursue My Artistic Dreams?’

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Dear Polly,

I’ve loved reading your letters about people leaving their shitty, dead-end jobs to go make art. What happens, though, when your job is nominally what you want but you still feel dissatisfied?

I was an extremely sensitive child with artistic aspirations, a theater kid and a prolific writer of bad poetry. But I literally thought the moon would explode if I didn’t get a steady, “respectable” job. My parents encouraged me to pursue my interests, but also made me feel that quitting was shameful and weak, that only difficult things were worth doing, and that self-sacrifice for a higher purpose was the noblest calling.

In college, I had dreams of becoming a writer, but I ended up applying for a teaching fellowship instead. I got in and quickly realized it wasn’t for me, but instead of quitting like a normal person, I started speaking out against the flaws of the organization. I think I subconsciously wanted to get fired, which I did. Then I moved to a fun city and got a random job that required very little effort and left me a lot of time to read for pleasure and write more bad poetry (and drink and go to jazz clubs and make out with strangers). I was shocked to find that the moon did not explode and that I actually loved my life. It wouldn’t have been enjoyable living that way forever, but it might’ve been enjoyable for a little longer than I let myself live it.

After several months, I completed grad school, then started teaching high school English in a rural town. I was sad and exhausted all the time. Still a sensitive introvert, I hated having to create a persona that was other than my quiet, kind of crotchety self, plus grueling work and self-sacrifice was baked into the culture of the school. I left after two years to teach at a small, more relaxed hippie school with an ethos of honoring individual needs. I started deliberately doing as little work as possible as a kind of rebellion against this career that felt wrong, but I finally found my passion when I developed an after-school theater program that became a haven where the weird, sensitive kids could find joy and acceptance and purpose. It honestly felt magical. I feel so energized by this work, and I still can’t believe someone is paying me to do it.

Unfortunately, the school has become much more college-prep focused, so now we have lots of anxious kids whose parents have unreasonable expectations for them. Many students either don’t have time for theater in between their academic coaching/therapy sessions or have such bad anxiety that the idea of performing gives them hives. There are fewer theater kids at the school, and last year, there was so little interest in my drama elective that it got canceled. I am constantly stressed and waiting for the program to fizzle out completely. More importantly, I feel like the skills and passions I bring are less useful and less valued than I had thought.

Part of me knows my current situation is not sustainable; I cry often and get panicky when I think about what is happening. The fact that I’ve been teaching on Zoom for the past year has not helped. And I feel like my own learning has plateaued. But I feel panicky when I think of leaving, too! I have dreams of going back to school for theater education, but that feels crazy when I think of the expense and the move. My partner has been very supportive and is encouraging me to pursue my passions, but we live in a very expensive city, a life we could not afford without a consistent income from me. What if I realize it’s not what I want? Maybe I think the only way I can make a life as an artist is by teaching, and I’m selling my dreams short. Sometimes I just want to live in a van while I write my novel (I know, I know!).

Most of all, I fear that I will leave this job searching for something better and will end up with something worse. Sometimes I get so angry at how whiny I am, and I tell myself a real artist would literally die just to do what they love, so I should just be grateful for the scraps. When is a job “good enough”? And how does anyone ever know if they’re making the right decisions?

Terrified Teacher
Dear Terrified Teacher,

There are so many oppressive belief systems at play here that it’s hard to know which one to tackle first! Let’s start with the illusion that so-called real artists are some heroic but rare breed of self-sacrificing Über-humans who remain firmly committed to their art no matter what happens. Every time someone makes this claim, I imagine a ferocious tribe of older artists who hold forth at great length on how they’d lay down their lives for their art, thereby terrifying and discouraging every aspiring artist in earshot. Do you know who makes those sounds, though? People who are secretly very competitive and therefore don’t want other people doing what they do.

Artists aren’t like The Velveteen Rabbit: You don’t wake up on the day of your first gallery show and suddenly feel real. You have to do the hard work of creating and commit to a belief in whatever you make. It’s like building your own religion. God never appears in the clouds and consecrates all of your choices. That’s why the one thing you need to understand, as you’re moving into a creative career, is how important it is to keep the faith, trust yourself, notice what you love (and don’t love), and adjust your path as conditions change. Sacrifice and suffering and walking over hot coals isn’t what makes you a real artist. Trusting yourself and believing that art matters the most to you is what makes you a real artist.

You’re already a real artist, because you know exactly how to teach your drama students what’s so invigorating and delicious about acting. You know how to explain why drama matters, even when everyone else in their lives is telling them otherwise. Whether or not you believe that the people at your school recognize what an asset you are doesn’t matter that much, compared to your passionate belief. I mean, this is a crazy moment! You’re trying to get kids to act over Zoom! It makes sense that way fewer kids would be into that — my daughter took drama last semester and it was pretty awkward. You have to look at the big picture. What’s important is that you know what a glorious gift drama can be to that so-called weird kid who needs a way to express themselves, outside of their anxious or stressful or conventional family and outside of their friendships and outside of their more regimented classwork. You understand that art is precious and exciting and it matters so much, on so many levels, that it makes you want to cry when you really focus on it.

What you love about teaching drama is that it’s all about following the feeling, not the neurotic thought. So what do you need to do at this point in your life? Follow the feeling, not the neurotic thought. Silence the circular second-guessing and the worries and the voice that says you’re selfish and whiny and making bad choices and that YOU’RE NOT EVEN REAL. 

Say hell no to that noise, and make a commitment to continue saying hell no every time you start worrying about it again. Isn’t that what you’d tell one of your students? Give yourself the same advice. Tell yourself: I have so much potential. I need to love my job. That’s just who I am. Because look, you’ve never really believed in teaching just for teaching’s sake. You care about what you’re teaching a lot. And if you’re not teaching something that gives you shivers, you don’t care.

I’m the same way about writing. I used to take whichever assignments people gave me. At first it was about the money, but once I was financially stable, I still had this knee-jerk thing where I’d say yes to any piece on any topic, even if I wasn’t that interested. Living that way as a writer takes a toll on your creative energy. It’s not that inspiring to experience a huge chunk of your writing as onerous homework! Even though it can be hard to say no to comfort and solid pay, the overall cost to your creative energy matters. It’s hard to excel at your career once you start doing the bare minimum and don’t feel inspired anymore.

As an artist, it’s so important to do regular audits of your career in order to assess the big picture. You have to notice when you start to take on a persona that feels dishonest (like you did with your first job). You also have to notice when you’re anxious, discouraged, or doing the bare minimum. Even though it’s natural to be in that state during a pandemic, this is a rare opportunity to slow down and take your truest desires seriously and recalibrate based on those desires.

You have to remember how much you love (and have always loved) expressing your real self. This is a core value of yours. You don’t want to be in any situation that includes pretending to be someone you’re not. This is crucial to your productivity and your identity and your self-confidence. You want some way to show the real curmudgeonly you to others. And you also love to coax young, passionate kids who maybe don’t fit in that easily into showing their true selves, too.

Your needs aren’t selfish or unrealistic. Everything good you’ve done in your life, everything that inspired you and gave you chills and made you cry tears of joy, came from a place where you were acknowledging and honoring your truest desires and sharing that good energy with others.

So claim the title of REAL ARTIST and INSPIRED DRAMA TEACHER right now. Everything else should get phased out as you move forward. I wouldn’t give up on teaching drama as a career trajectory, because you already know it’s something you love and could get paid to do. This is a good time to take a leap: You have a supportive partner who’s open to downsizing and moving. Look for some combination of work that blends writing as much as you possibly can with teaching drama to the kinds of kids you’ll enjoy the most.

If more grad school is the ideal way to pursue that balance of goals, so be it. If you can dive back into your current job and promote and advocate more vocally for your program, then do that. But ultimately, it sounds like you don’t want to teach English that much, so respect that and adjust your career plans accordingly.

Don’t worry about whether or not you can 100 percent guarantee that what comes next will be much better than what you’re doing now. Real artists understand that there are no perfect, victorious trajectories in the arts. It’s the nature of the beast. Every career leap I’ve ever taken has been a risk, and even though some risks looked like mistakes at first, they always led to new opportunities and a deeper understanding of what I wanted.

You have to experiment. Some choices will look ill-considered at times. Accept that now and try to relax into it. Talk to your partner about it. Stop trying to control what happens next. You could pursue theater education and then decide it was a mistake. You could get your van and write your novel and then decide it was all a huge mistake. From where I’m sitting, both of those choices sound exciting and rewarding. There’s no way you wouldn’t have an adventure and learn a ton about yourself. The important thing is not what you do, it’s whether or not you can keep your neuroticism, perfectionism, and shame out of the picture enough to be productive and enjoy yourself.

That’s not specific to you. That’s the core of artistic risk: Can you manage your emotions, your expectations, and your productivity enough that you feel good along the way? We artists are a  moody species! We have to have a lot of tools to manage ourselves. Take that self-management seriously. Read books about it. The struggles and self-doubt you’re facing are common to the artist’s life. But it’s a great life for those who lean into these challenges instead of stigmatizing themselves for being who they are.

One thing the books sometimes leave out? Art should be fun! It’s not about suffering. You’re choosing a joyful path, so celebrate that! Think of acting and performing. Picture how vulnerable but also how happy it makes you, to access all of that feeling on a stage. My God, what a high-wire act! Why would anyone choose that? But that’s part of what you love about it, isn’t it? You have to leap into a world of feeling without knowing how well it will go. You have to reject the logical hard-work-and-duty parts of your brain, and love the poetry-writing part of your brain instead. Drama and writing are your way of loving yourself.

It’s time to build your new religion and own what you love the most. Yes, it will feel embarrassing. I embarrass myself often. Yes, it will feel like a risk. Taking big leaps often means falling. Commit to the leap. Follow the feeling.


Ask Polly appears here the first three Wednesdays of every month. Additional columns and discussion threads are available on the Ask Polly newsletter, so sign up here. Polly’s evil twin Molly’s newsletter is here. Order Heather Havrilesky’s new book, What If This Were Enough?here

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‘Should I Leave My Good Job to Pursue My Artistic Dreams?’