Sissy: A Coming of Gender Story; Jacob Tobia

Sissy: A Coming of Gender Story; Jacob Tobia
Genre: Memoir
Published: 2019
Pages: 315
Hogwarts House Recommendation: Ravenclaw

Jacob may have been born a male, but they didn’t stay that way. From an early age, Jacob was far more interested in the feminine; looking up to female characters, dressing up, playing with Barbies. This called to mind a term that would stick with Jacob: Sissy.

As they grew older, however, his parents thought it prudent to hide Jacob’s non-conforming identity for reasons of “safety.” The world did not always agree with Jacob’s gender. In some cases; it seemed out to get it. Throughout childhood and as a teenager, Jacob takes you through their journey of self-discovery, proving that gender is more than just a matter of male and female. Ultimately, between the success and failures, Jacob will discover that self-expression is the key to living an authentic life.

Transphobia has always confused me. Think about it. Imagine your kid coming out to you, and you as a parent being like, “You’re the WRONG gender? Get out of my house! I no longer love you and never will again!” I can’t think your love for your child was very strong to begin with if something as superficial as gender affects your entire opinion of them; if that’s all it takes for you to get rid of them.

These are the same questions Jacob explains in their memoir. Why does so much ride on gender? Why do we insist on placing each other into categories…and get angry at each other when we refuse to be labeled? Why does their mother insist she supports them, when she actually encourages them to be more like a guy? However, these questions really aren’t answered. Instead, Jacob presents a different transgender narrative, making for a different book than I thought I was going to get, one that was just as much about. Jacob themselves isn’t taking measures to physically transform into a female, like taking hormones. Instead, they dress up and express femininity that way, along with using the pronouns them/they. And they really love gowns and high heels, something that will last into adulthood.

There is a lot to be learned here. Jacob essentially takes us through their childhood, from dressing up and liking Barbies to going to college and dealing with the social systems in place there, from first coming out as gay at sixteen to fully accepting their feminine identity. While Jacob was indeed celebrated on campus, it didn’t mean that there weren’t little things ingrained in the system trying to bring them down that cisgender people (read: people who identify as the gender they were assigned) won’t notice. I especially liked their thoughts on what it meant to be professional; how the workforce seems to cater to straight white men, and while overt discrimination isn’t as present as it once was, it can display itself in other ways. A born male wearing a dress, for example, won’t be seen as “professional” and may have cost Jacob some scholarships. One thing that did make the Christian in me very happy was that church was a big part of Jacob’s life. While they did take a break from it, they seemed to be mostly accepted, something I wish all Christians would do, as we are a faith of love. Jacob even presents the idea that discrimination is against the Bible’s teachings, as we are supposed to love and embrace one another. It’s not God making a mistake, Jacob argues, if that’s who they are. Overall, they aren’t hesitant about sharing their struggles, but they celebrate the joys and the funny moments as well. It’s not all doom and gloom. Many people in Jacob’s life were quick to accept them. Others were not.

Obviously as a cis woman, I’m hesitant to “critique” anything, because who am I to say whether Jacob is wrong or right? (Except for when they insulted my Hogwarts house…HOW DARE YOU??!??) However, I am a book blogger, it’s my duty to share opinions, and it would be unfair to give it five stars just because Jacob is transgender (see their chapter on being a college campus token–being celebrated for being diverse comes with its own set of rules). Most of the “issues” here, though, were writing-related and I won’t get into them…organization, footnotes (unnecessary and distracting in nonfiction in my opinion, unless you’re crediting someone) and maybe getting a bit sidetracked. What I mean by that is that Jacob is one of those people who figures that since they’re talking about one social issue, they’ll address them all. Paragraphs about cultural appropriation (why white US citizens shouldn’t dress as Native Americans for Halloween), health care politics, the NFL’s treatment of women, and diversity are all present. Although having interesting things to say, most of them distract from the overall ideas and could have been cut.

I also would have liked to hear more about Jacob’s professional life as a culmination of their initial story. I don’t know what they do in LA, but apparently that are very successful in their job. I would have loved to see where they’re at now since I have not heard of them before this book and was a bit disappointed I couldn’t learn more. I guess the theme here, though, was growing up.

In exploring gender and knocking down stereotypes, Sissy does what it sets out to do, nitpicky writing pet peeves aside. It’s a very eye-opening memoir; if you are cisgender, you will learn something. If you’re looking to inform yourself, pick it up and learn something new. If you struggle to accept trans people, even more reason for you to read it. Just try. Love is easier than hate. This book is not “shoving gayness in your face” or “presenting an agenda.” Jacob is right: gender doesn’t need to be serious. This is a way that people are born, and by reading each other’s perspectives, we can change to become more accepting ourselves.

Book Club Questions

To be used for book clubs/blogs/thinking, and answers in the comments are also welcome if you are inspired!

  1. Jacob says that we all have experienced some sort of gender-based trauma, whether we stay the gender that we are assigned at birth or not. Can you recall a time like this in your childhood? If not, can you recall a time you thought “Man, boys (or girls) are so lucky to be able to do this?”
  2. What is one idea you had about being transgender that was proven incorrect in the book? How so?
  3. Based on Jacob’s experiences, what are some steps that we can take to create a more friendly and suitable world for LGBTQ people? How can you personally start living by these principles today?
  4. Describe a time that you deviated from your gender roles. Did anything come of it?
  5. Jacob mentions several well-known institutions. Did the way these locations, organizations, and how people treated Jacob make you think less of them?


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