On Deserving

Or, what you do, what you don't

Next month, I will be 29. I’m incredibly proud of everything I have accomplished in my twenties, and I’ve never been shy about my age. I like people to know how old I am. I’ve spent my entire life being told that my personality was unusually (read: uncomfortably) confident and authoritative for a teenager, for a twentysomething. I am hopeful that in my 30s, people will stop calling me intimidating and aggressive—or maybe I just hope that it’ll stop bothering me so much.

But getting older also means grappling with all the things I haven’t done. There’s a lot left on my professional bucket list, and for every achievement I rack up, there’s another one in the distance, already secured by someone younger than I am. Sometimes that genuinely doesn’t bother me—sometimes I am the greatest cheerleader and champion for people who might have otherwise inspired immense envy in me. In fact, I feel that way most of the time. I have long believed that it’s a great strength of the entertainment industry that we aren’t all competing for a finite number of spots. We’re all inventing our professional ladders as we go, climbing up and up and up, then back down, then to the side for a while, then up again. Since music school, when I was surrounded by people whose experience and talented dwarfed my own, I’ve realized that there really is no competition, because we’re all so different. We all serve a different purpose, even within the relatively narrow realm of music-making and songwriting. There was nothing to be jealous of.

But recently, I have been struggling. I’m attributing it mostly to my Saturn return. I have found myself looking sideways at other people and feeling frustrated at the perceived advantages that they have over me. I have found myself looking inward and feeling intense self-loathing—for not posting online enough, for not writing more powerful and technically competent music, for not being bubbly and extroverted enough to form a vast social and professional network, for not inventing sufficient marketing schemes to convince all of you to listen to me, me, me. It’s profoundly selfish. It’s navel-gazing to a degree that astounds even me, a professional navel-gazer. And I want it to stop. The only way I know how to do that is to figure out why.

As I was writing this I got a call from my mother. I told her what I was writing about, and she said: “You’ve always had an interesting relationship to the concept of deserving.” I decided a long time ago that no one deserves anything. It’s too sticky, too messy of a paradigm. I think it started when the first Truly Bad Thing I’ve ever experienced crossed my desk. I didn’t deserve that, I thought, from all the doctor’s office waiting rooms and Zooms with my therapist where I searched for a cure to the multi-system failure that had been wrought by this trauma. When faced with some professional high point, my friends and family would say: you deserve this. And I would bristle. Because surely if you deserve what happens to you, that means the bad things, too. I preferred the alternative: no one deserves anything. You can do things that stack the odds in one direction or another—if you are kind, people will probably be kind in return; if you are a jackass, eventually you might get slapped—but the science is in and I’ve seen enough to call it. There are a lot of unspeakably evil people facing zero consequences for their evil. And on a smaller scale, there are lot of unremarkable people who put in minimal effort who have been able to jump the line to fame and fortune. They don’t deserve that. Maybe you think I do. But who gets to decide that? What do any of us really deserve?

Tangling with this question is finally giving me some peace. I have to acknowledge, with some shame, my own entitlement. You do not owe me this. The platform I have built is, yes, a testament to my hard work and perseverance and talent and intelligence. But it was never guaranteed. None of it was. And the rest of the things I want, none of those are guaranteed by hard work or perseverance or talent or intelligence, either. The reason I have the audience that I have is because I have made the case, one video and one song and one essay at a time, that you will benefit from giving me your attention. I have convinced hundreds of thousands of people across these various platforms that buying stock in Jensen McRae Inc. will give you some kind of return—music that moves you, a worldview that pushes you, a joke that makes you laugh on a day when you really needed it. And if I want more than this—and I really do—my job is not to sit around stewing about all the people who have it easier than I do. My job is to continue to make the case. The way I do that is by making art I truly believe in.

I have been working on my third album for a while (no surprises there). For a while I was absolutely paralyzed with anxiety and doubt. I was writing music that sounded nothing like me. I was making wildly ambitious plans I had no way of enacting effectively. I was grasping at straws because what I wanted, more than I wanted to make a great album, was to prove that I could break into the mainstream. Every attempt left me further and further from my center. And then, one day, I had a session that felt special. It felt familiar, precisely because I had never written anything like it before. It felt like something I’d wanted to write for years, but hadn’t been able to—the same feeling I got when I wrote “White Boy” and “Wolves.” Then I had another session like that, and then another. I don’t know when my third album will be out—it’ll be a year, at least—but I finally know what I’m making. I know what I want to say, and every day I get a little closer to figuring out what it should sound like. I realized that the point of my first two albums was to wrestle the monsters in my closet; on my first, it was the fear of starting my 20s and having to become myself without the safety net of childhood, and on my second, it was the fear of going it alone after disappearing into two different but equally transformative romantic relationships. You’ll know more about what I’m wrestling on the third record when it comes out, but it’s something else entirely.

I sincerely hope that when my next album does finally come out, you will listen to it, and it will matter to you, and you will share it with your loved ones. I hope it soundtracks your happy days and dark nights. I hope it gives you the language to describe what was previously indescribable. I hope it makes you feel seen; writing it is enabling me to finally see myself more clearly than I have in years. But I know that the choice is ultimately yours. You have so much competing for your attention online, and there are so many invisible thumbs on so many invisible scales pushing certain things harder to you than others. If I want to come out ahead of all that noise, I’m going to have to make something truly excellent. Something rare. Something profound.

I’m going to have to make one hell of a case.