One of the first questions I ask Jackson is how he feels about trans characters played by cisgender actors. “I hate it. I’ll be really real with you,” he says. “There are a lot of trans people who are offended by it. I don’t want to ever say that an actor can’t portray someone outside of their experience. That’s obviously what actors do. But I do think that we’re in a time and place where social issues are becoming more and more important to audiences and they want to see those social issues played out in the entertainment and theater industry.” So, for example, Eddie Redmayne plays Lili Elbe in The Danish Girl — as a trans woman. “He’s probably going to do a lovely job,” Jackson says. “But I don’t know if he’s going to know all the details of the inner life of a trans woman. That’s a really hard thing to imagine unless you’ve been there, because it’s a lifelong, continuous struggle in a world that is arranged very, very differently than the one that he lives in.” Later, I realize Jeffrey Tambor won an Emmy for portraying this exact experience Jackson is talking about, so I email him to ask him what he thinks of Tambor. "I have no comment on Jeffrey Tambor," he writes. "But I hope that stories about trans people can someday be told by openly trans people. We so rarely get to own our own stories at that level and have them told the way we'd like them told. To me, it often feels like cis people telling each other about us." He adds that Transparent does have trans people on staff, which gives him hope. The question looming over our conversation — and the entertainment industry in general — is, if there are trans roles, why aren’t trans actors playing them? There are a lot of ways to answer it, but Jackson points to a lack of resources in general for trans people, including spreading awareness and getting trans actors the training they need. Getting trans actors into trans roles isn’t as simple as casting directors selecting them from a crowd. Jackson talks at length about how trans actors don’t have access to adequate training. “So a trans person may walk in and they may be perfect for the role, but they may not be trained as well as Eddie Redmayne or as experienced [as him],” Jackson explains. Still, he doesn’t think it’s an excuse not to cast a trans actor, if the production is concerned with authenticity. “A really good director and a really good company and production will say, ‘Right, we’re gonna get you a coach...we’re gonna invest a little bit of extra time and money into getting you, like, up to speed with the rest of the production so that you can have this opportunity because it’s important. I don’t think anyone’s doing that work.” Consider Jackson's own experience. When he decided to transition, he began with a very low dose of testosterone so he would experience hormonal changes at a slower rate than most. “I did that because there’s this thing that happens with the vocal chords with trans men where if you transition the medically recommended way, [the chords] thicken very quickly. You get this deep voice that you haven’t figured out how to use yet, necessarily.” So, as an example, a female actor who was transitioning to a man would need to invest further resources into retraining himself with his new voice. Not only is it a barrier for trans actors, but Jackson thought that his decision to transition would effectively end his career. “I decided to go on testosterone and I was like, that’s it. I’m done with acting. I will never get another role as long as I live because I’m making this choice.” But just two months after he began transitioning, the universe delivered a sign that he had made the right decision. Jackson was cast as a trans character in a play in Chicago . “I remember seeing my name on the program and being like, wow, now it’s in writing,” he says. “It was a very big moment.” And Jackson knows how fortunate he is. He calls himself “privileged.” Over breakfast, he admits, “It’s so silly to be talking about me auditioning for plays and things when walking home at night is literally deadly any day of the week for trans women.” He’s talking about the brutality trans women suffer. “They consistently get swept under the rug because of these intersections of race and misogyny and patriarchy and poverty and transgender issues that come together and compound on these people who are just trying to fucking be happy and live their lives like everybody is.” The challenge weighs on him. “Everybody’s traumatized and it’s really hard to hold each other up.” Jackson has managed to land five trans roles since 2011, but he still struggles with how he may have set up additional hurdles for himself by transitioning in the first place. After breakfast, I join Jackson in a class he occasionally attends that’s popular with LGBTQ actors. Brad Calcaterra, the teacher, doubles as a life coach, identifying vulnerabilities in his students and exposing those feelings to make them better actors. One by one, each student goes up to the front of the room. Calcaterra asks them probing questions: "What’s one hurdle you wish you could remove from your life? In what ways are you sabotaging yourself?" When it was Jackson's turn to face the class, Calcaterra asks him similarly pointed questions about how he may be holding himself back in his career, or what doubts he has about himself. Jackson admits that sometimes he thinks about wanting to “hit the reset button” and go back to “pretending” to be cisgender. “Why am I trans if I want to be an actor?” Calcaterra, in the tone of voice that’s perhaps responsible for why he’s become such a popular teacher, gives Jackson the mix of tough love and assurance he needed. “I don’t think the part is ever going to fit you the way you want it to,” he tells Jackson, addressing his fears that maybe transitioning has made him too niche and available for too few roles he actually wants. But Calcaterra reminds Jackson of the importance of what he’s doing by working as a trans actor. “You have a lot of voice. We need that in the world,” he added. Victoria, a trans woman in the class couldn’t help but tell Jackson, “You always say things that are exactly what I’m thinking.” As I watch Jackson rehearse before his audition, I'm struck by how talented he is. He's singing a song called “A Little More O’ Me.” It's a moment of triumph for his character, Sam, a man in mid-transition who realizes he has his first facial hair. “Somebody might just give it half o’ glance,” he sings of his whisker, “and it’s somethin’ simply knowin’ they could have the chance, the chance to see a little bit more o’ me.” I feel myself welling up. Maybe Calcaterra's theory isn't quite right. This seems to be the perfect role for Jackson. The lyrics, the character, the entire story seem tailor-made for his experience. Now he just needs the director to give him the chance to prove it.