Reading Guide

Reading Guide

Trail Blazer Toll

“To be a First and Only in America is a delicate balance of surviving where you come from while acting like you belong where you’re going.” 

1) In the prologue to her book, Alejandra opens with a memory of preparing to speak to first gen students at Harvard and feeling in her gut that the frame of “I did it, so you can too” would be “unfair and incomplete.” This prompts her to ask, “Why are we still sold a one-dimensional narrative of what it takes to achieve the American Dream?” What are some of the common narratives about reaching the American Dream you’ve heard throughout your life? Do you believe that with hard work anyone can attain the American Dream, despite their life circumstances? Why or why not?

2) Alejandra talks about the unique experiences of First and Onlys—“those of us who are the ‘first generation’ or the ‘only’ person in our family, community, or social demographic group to cross a threshold.” Are there any areas of your life where you are a “first” or an “only”? What are some unique thresholds that you have crossed? In what ways have those experiences shaped your perspective? Is either of your parents a “first” or an “only”?

3) Recognizing that the circumstances of being a First and Only vary and evolve over time, Alejandra writes of “a particular set of experiences, challenges, and expectations that come with the territory”—what she describes as the “Trailblazer Toll.” She says that “those who smash through glass ceilings are then left to clean up the shards on their own.” Do you believe there are “emotional costs” associated with social and economic mobility? What might be an example? Alejandra points out that “there is only a 7.5 percent probability that a child born to parents in the bottom fifth of the income distribution will reach the top fifth.” How do these challenges make it more difficult to overcome the odds?

Invisible Inheritances

“Each day, we have the choice to become a better ancestor.” 

1) While in grad school, Alejandra created a genogram to map out the Invisible Inheritances in her family, revealing several patterns that had played out over generations: “Three generations of women in my family had primarily been single mothers. Three generations of women in my family struggled to make ends meet. And then the boldest line…three generations of women in my family had been in emotionally tumultuous relationships with chaotic men.” Using the genogram outline on page 268, how would you describe the recurring themes you have observed in your own family—both emotional and behavioral? Do you believe it’s possible for trauma to be passed down from one generation to the next? What are some positive legacies that have been passed down by your family? What does it feel like to see your family history laid out in this way?

2) Alejandra writes, “We may each have ancestral legacies, yet understanding what they are—and deciding which ones we’d like to continue or disrupt—allows us to then challenge their power more intentionally.” In what ways have you repeated your family’s Invisible Inheritances? In what ways have you disrupted them? Does the idea of being a “cycle breaker” in your family feel like pressure or purpose? Or both?

3) Reflect on Alejandra’s statement: “We heal generational trauma when we choose to evolve versus repeat, creating new inheritances for generations to come.” What does it mean to you to “become a better ancestor”?

The Parentified Child

“In time, I came to understand that erasing my own experience wasn’t virtuous; it was self-abandonment. And abandoning yourself is never an act of love.”  

1) Alejandra recalls “needing a sanctuary in the middle of the constant commotion” of her childhood home—from her grandfather’s drinking to her family’s fluctuating access to resources. She says, “The instability in my environment felt like a problem I had to solve. I saw hemorrhaging around me— from money to food to energy to options—so I made myself the tourniquet.” Describe the dynamics of your childhood home. Did you ever feel responsible for the well-being of your family members as a child? Were you a “good kid” or a “little adult”? How did this influence your thoughts or behavior as a child?

2) As a Parentified Child, Alejandra found herself acting like the “family helper, translator, doctor questioner, form filler, concept explainer, living dictionary, and therapist.” She also “developed a heightened sensitivity and learned to scan people’s moods for survival—noticing subtleties in their body language and showing up however the moment asked for.” Did you ever perform practical tasks on behalf of the adults in your life? What effect do you believe it has on a child to take on the role of the “responsible one” or the “caretaker” in their family? Do you ever find yourself drawn to people-pleasing or caretaking in your adult life?

3) When discussing the lingering aftereffects of household dysfunction, Alejandra points to a groundbreaking Felitti/Anda study in the 1990s that looked at the long-term impact of adverse childhood experiences (ACEs) and found that toxic stress from ACEs is linked to chronic health issues later in life. She quotes Gabor Maté, who says, “If you don’t know how to say no, your body will say it for you.” Does this ring true to you? What do you believe are the consequences of not expressing one’s feelings? Were dysfunctional dynamics in your childhood home ever openly acknowledged or discussed? What was the family stance on therapy and mental health generally?

Bicultural Balancing Act 

“As First and Onlys, we have dual citizenship to worlds that often appear at odds with each other.” 

1) Alejandra describes the summer before high school as a time when “I had unconsciously paired cultural pride as a Latina with gang culture—while being told that studying and getting good grades meant you were ‘acting white.’” She recalls “searching for a sense of belonging, more than anything, but I wanted it from both teachers and troublemakers.” Have there been moments in your life when different parts of your identity felt like “mismatched puzzle pieces”? What is your version of a Bicultural Balancing Act? Describe the different perspectives or sets of experiences that live within you. How do you juggle them all?

2) “Makeup became my war paint that summer—black eyeliner, thick mascara, dark brown lipliner, and light brown lipstick that were discarded by my mom. When I traced my eyes and lips with black and brown lines, it felt like I was putting on a shield to protect myself…baggy pants were my armor.” What types of protective “war paint” have you worn in the past? In what ways did it obscure the truth of who you are? Alejandra recalls that later on in high school, “I started gobbling up accomplishments...the busier I was, the less anxious and more in control I felt.” Has perfectionism or high achieving ever been a part of your armor?

3) On preparing to go to college, Alejandra says that her sense of who she was “remained more polarized than ever.” She writes, “Lean too far one way and I’d be a sellout. Lean too far the other way and I’d be an outsider.” What societal messages can you think of that promote the idea of “selling out”? How does the fear of being labeled a “sellout” create an emotionally exhausting balancing act for first-generation young people in particular? What makes you who you are?

Chutes and Social Ladders

“Social mobility is like the children’s board game Chutes and Ladders. If you’re lucky enough to land on a ‘good deed,’ you climb the proverbial social ladder at a meteoric speed. If you accidentally land on the ‘wrong spot,’ you backslide down a chute so fast your head will spin.” 

1) Discussing her first year in college, Alejandra writes, “USC was my first big social ladder. It was when I had no choice but to coexist within disparate social classes for the very first time, and when those two sets of circumstances were just one blurry summer apart.” When in your life have you experienced the culture shock of being in a new social environment or social class? How did you adjust to your new environment? Were there traps that set you back?

2) Alejandra reflects on various “reality checks” at the sorority and with her new classmates, writing, “When you’re Brown in a predominantly white environment, your otherness tends to be mirrored back to you more often than not.” What does she mean by this? What are some ways that your “otherness” was reflected back to you in college or later on in life? Alejandra found some footing by remembering her mom and grandmother: “Just as my mom’s boldness had persuaded me to grasp at every opportunity, Abi’s fascination with decorum and good manners had taught me how to behave once I’d arrived.” What are some practical lessons, strategies, or tools you picked up from observing your loved ones that have helped you to navigate foreign experiences or environments?

3) Alejandra quotes a statistic that a third of first-generation students drop out of college and 90 percent don’t graduate on time. Why do you think this is the case? She writes, “In part, it’s because we are prepared for the classroom but rarely supported in our new lives outside of it.” Do you agree with her assessment? What are ways that first-generation students can be better prepared for the college experience? How can colleges and universities better support first gen freshman, beyond the classroom?

The Lonely Hustle

“Hustling certainly isn’t unique to First and Onlys, but in our case, the drive behind it is magnified....It’s not only your own survival in the balance; it’s also the welfare of the people you love.” 

1) In “On the Bound,” Alejandra describes graduating from USC with no job or clear career path, which led to a time in her life she calls “the Lonely Hustle,” writing, “When you chase dreams that your family doesn’t understand, your choices can often be questioned repeatedly—at the very moments when hesitation and skepticism can be the most damaging.” Think about a job or a goal you hustled for that your loved ones may not have understood. What were some of the messages you received at the time? Have there been situations where you’ve strategically chosen the harder road and then experienced a lack of support from your family? How important is it to you to feel understood?

2) Alejandra has a turning point in the kitchen of Gladstones Malibu that ultimately leads her to apply to graduate school: “I had two choices at that moment—sink into a pool of hopelessness or kick hard against the bottom and try to reach for the surface.” Think back to a pivotal turning point in your life or career. What were the circumstances that brought it on? What did “reaching for the surface” look like for you?

3) After Robert encourages Alejandra to apply to an Ivy League school, she reflects, “I wasn’t used to anyone encouraging me to be more bold than I already was, and I realized how much I craved being egged on versus discouraged.” How do you judge what you’re capable of? Do you sometimes feel underestimated by the people around you? Is there someone who challenges and motivates you to reach higher? If not, what are ways to bring more emotional support into your life?

Blindfolded Cliff Jumping

“They say if you can’t see it, then you can’t be it. But that concept doesn’t only apply to the successes. It also applies to the calculated perils, pitfalls, and plunges. If we can’t see the nosedives of others, it’s harder to steel ourselves against the terror of our own.” 

1) Because Alejandra had to take out over $150,000 in student loans, she recalls that “going to Harvard would mean betting big on the earning potential of a future version of myself, someone I wasn’t certain I was capable of becoming.” It was a risk she ultimately chose to take. What is your past and current relationship with risk? How do you figure out which risks are worth taking? Share the biggest Blindfolded Cliff Jump you have taken professionally. Thinking back now, what did you learn?

2) When considering dropping out of Kellogg to go back to the Obama campaign, Alejandra says, “Common sense, reason, and security all pointed toward staying put....But there was logic, and then there was my gut. And my gut was screaming at me.” How important is it to tap into our intuition when weighing risk? When was a time you operated “purely on raw instinct”? Do you ever find yourself ignoring your own instincts? How would you advise someone on following their instincts versus listening to others?

3) Abi told Alejandra, “One step at a foot in front of the other,” when she was overwhelmed as a child, words she reminded herself of when she flew one-way to DC with “no plan B.” By concentrating only on the most immediate step ahead, Alejandra was able to “tolerate ambiguity”—an ability she says First and Onlys often develop out of necessity. Why do you think First and Onlys can benefit from tolerating ambiguity? How comfortable are you with it? When there is uncertainty in your life, are you more likely to stay the course or rethink your approach? Share an example of a time when you embraced uncertainty and ambiguity.

Imposter Syndrome Plus

 “Regardless of how confident we may feel, First and Onlys often receive subtle (and not so subtle) external messages that we are different, don’t quite measure up to our peers, or are lacking in experience, exposure, or pedigree.”

1) In “Everlong,” Alejandra writes of starting her job at the White House, “There’s nothing like the FBI digging into every inch of your past to trigger a good old- fashioned case of impostor syndrome.” What is impostor syndrome, to the best of your understanding? Have you ever experienced impostor syndrome? When? How did it affect your actions or reactions in that situation?

2) Alejandra unravels the common understanding of impostor syndrome, saying, “Feelings of inadequacy don’t just appear out of thin air or arise solely from our own insecurity. Self-doubt doesn’t happen in a vacuum.” She asks, “Wouldn’t any person—no matter how self-assured they are—experience legitimate feelings of estrangement in the same situation, when confronted by social systems that disadvantage them and favor the privileged and connected individuals who control them?” Was the initial 1970s assessment of impostor syndrome as an “internal experience of intellectual phoniness” accurate, or do you think there are other dynamics at play? Do you agree with Alejandra’s observation that our “external environments give rise to our feelings of inadequacy”? What are some examples of incoming messages First and Onlys might receive within traditional hierarchical systems?

3) “For First and Onlys, full acceptance into social systems not meant for us often takes championing from someone at the top of the hierarchy,” writes Alejandra, “a signal to the larger group that we belong.” How important do you believe “the encouragement, championing, and protection of those within the power structure” is for First and Onlys? What role have mentors played in your own life and career? Describe a time when a mentor’s guidance or support made a difference for you. What advice would you give to someone seeking to find a mentor?

Breakaway Guilt

 “I was in a common in-between land for First and Onlys. Successful enough to breathe easier and start saving some money, yet not successful enough to bring my entire family along with me.”

1) Alejandra remembers moving back to LA two years after leaving the White House and observing, “My life had moved out of survival mode, and theirs hadn’t.” She recalls that the pride she felt about creating a new life for herself was “laced with financial trauma” and that “simply establishing financial automy and boundaries” felt like she was abandoning her family. Where do you think Breakaway Guilt comes from? Have you ever experienced it? If so, how do you deal with those feelings? What kinds of dynamics emerge when the highest earner in a family is not the parent?

2) Returning home from a disastrous meeting with a potential donor for her congressional campaign, Alejandra says, “something deep inside me broke.” She writes, “In the process of breaking cycles, forging a new path, and trying to belong, I had done to myself the very thing I was most afraid of. Time and time again—I had held back my feelings, my needs, myself. I had abandoned myself.” What does it mean to “abandon yourself”? Reflect on that idea. Are there parts of yourself that you have suppressed or ignored in order to fit in? Looking back now, would you have done anything differently?

3) Throughout First Gen, Alejandra returns to the idea of “belonging.” She says, “My climb as a First and Only was, in many ways, a mad dash toward belonging. What I was willing to sacrifice for it. Trade for it. Abandon for it. How I twisted and silenced myself to fit into the different versions of me that I wore like ill-fitting costumes.” Why do you think belonging was so important to Alejandra? Where do you belong? Humans are wired with a fundamental need to belong. Where do you think this comes from? How can we maintain a strong sense of belonging, independent of whether or not others accept us?

4) “The honor lies in the crossing.” What does this mean to you?

It’s Only Love That Gets You Through

1) In her “Author’s Note,” Alejandra shares resources that have been helpful to her in the past and present, including instructions on how to create your own genogram and information on transcendental meditation and culturally competent therapy. She says, “A vital part of my own journey has been to make wellness and healing a priority.” Did you grow up around the idea that wellness and healing should be a priority? Are they a priority for you now? What kinds of activities or strategies do you engage in to cultivate peace in your life?

2) Finish this sentence: “To me, peace is...”

3) Remembering the fireplace that Abi built out of cardboard, Alejandra says, “I learned something critical that day that has been a lifeline...there is nothing we’ve been searching outside of ourselves for that we can’t just as easily create.” Reflect on and share an insight you’ve gained from examining the eight components of the Trailblazer Toll Alejandra describes in First Gen.