A Book Group Discussion Guide For
Lead Anyway
The Glow-Up Guide to Leadership That's Real, Not Perfect
Welcome to Your Book Group
Lead Anyway isn't a leadership book written from the corner office. Dr. Lauren Young wrote it from what she calls “the beautiful middle” — the messy, unfinished, still-figuring-it-out stretch of a career and a life, where most of us actually live. Across twenty-two chapters she moves from a Wisconsin basement to a Palm Springs desert to a Vermont farmhouse, from middle school locker rooms to statewide championship gyms, telling the stories that shaped how she leads: as a millennial, as a mom by both infertility and adoption, as a woman who spent years learning that taking up space isn't the problem — shrinking is.
Each chapter follows the same rhythm the book is built on: a story, a “Glow-Up” section of practical tools drawn from that story, and a “Lead Anyway” charge that closes the loop. This guide follows that same rhythm — for every chapter you'll find two or three discussion questions grounded in specific scenes from the book, plus a quote worth reading aloud and sitting with.
Use as much or as little of this guide as your group needs — see “How to Use This Guide” below for a few suggested formats.
How to Use This Guide
Option A — One meeting, whole book
Read the entire book ahead of time. Open with the Warm-Up Questions below, then work through the six Part synthesis questions (one per Part, found at the end of each accordion section) rather than every chapter question, and close with the Closing Reflection Questions at the bottom of this guide.
Option B — Three meetings
Cover two Parts per meeting (roughly seven or eight chapters each) — a good middle ground for groups that want depth without a six-month commitment.
Option C — Six meetings, one Part each
The most thorough option. Read one Part between each meeting and work chapter by chapter — you won't run out of things to talk about. Click each Part below to expand it.
However you split it up, you don't need to answer every question. Pick the two or three that hit hardest for your group and let the conversation run.
Key Ideas Before You Begin
Lauren builds a personal vocabulary across the book that's worth knowing going in:
- The Glow-Up / Lead Anyway structure — every chapter pairs a personal story with a practical “Glow-Up” toolkit, then closes with a “Lead Anyway” charge that ties the story back to the reader's own life.
- Third Space — a place outside home and work or school where belonging is chosen, not assigned (a locker room, a gym, her backyard “GRL Cabin,” the pickleball court). The concept anchors her doctoral research and Chapter 21.
- Mental Managers — Lauren's metaphor for the internal “crew” that manages her focus, mood, and capacity, and needs fuel, rest, and limits the same way any team does.
- The Hinge Generation — millennials as the generational bridge between analog-raised Boomers and Gen X and digital-native Gen Z and Gen Alpha.
- Seen, Valued, Appreciated — the three words Lauren says show up, across every generation, when people are asked what they want from a leader.
- O-Lineman — someone who uses their own credibility to clear space for you in a room, the way an offensive lineman blocks for the player carrying the ball.
- Dopamine Menu / Burnout Watch List — Lauren's concrete, personalized tools for restoration and self-monitoring, offered as an alternative to vague “self-care.”
- Tugboat vs. Speedboat — a leadership self-image: steady and load-bearing versus flashy and attention-seeking. Lauren identifies as the former.
A Note on Sensitive Content
Lead Anyway doesn't flinch from hard material. Across the book, Lauren writes candidly about body image and being bullied for her size, infertility and the long road to motherhood, a passing but direct reference to a night she questioned whether she wanted to keep living, parenting a child with ADHD, and a political controversy over transgender student-athletes that brought her hate mail. None of it feels gratuitous on the page, but a book group isn't a therapy session. A few suggestions:
- Preview Chapter 13 (infertility, adoption, and a reference to suicidal thoughts) and Chapter 17 (a transgender-athlete policy debate and hate mail) before your meeting so you can pace the conversation.
- Remind your group at the start of each meeting that sharing personal experience is always optional, never expected.
- If Chapter 17 sparks a debate about the underlying policy, consider steering the conversation back toward Lauren's leadership choice — whether and how to stay inside a system you disagree with — so the discussion stays productive for a group that may hold a range of views.
- If anyone in your group is struggling with thoughts of suicide, the 988 Suicide & Crisis Lifeline (call or text 988 in the U.S.) is available free, 24/7.
Warm-Up Questions for Your First Meeting
- The book's refrain — “lead anyway” — appears at the end of every chapter. Before you started reading, what did that phrase mean to you? Has it changed?
- Lauren writes this book “from the middle of the climb,” refusing to pretend she has arrived. How does that framing change the way you read leadership advice, compared to a book written from someone who feels “finished”?
- Which chapter title made you the most curious, nervous, or excited before you'd even started reading it — and why?
Chapter-by-Chapter Discussion (click a Part to expand)
Part One — Where It Started
Chapters 1–5: childhood, the generations we lead across, girls and sports, belonging, and the jobs that trained us before we had titles.
Chapter 1. Basements, Bubblers, and Breaking the Mold
How Childhood Rules About Gender Shape the Leaders We Become
- Lauren traces her instinct to “shrink” back to specific childhood scenes — the Barbie basement, the bubbler monitor, the kindergarten teacher telling her to put her hand down. Which moment from your own childhood taught you when to take up space and when to shrink? Who was watching, and what did they teach you without meaning to?
- The chapter argues that teaching girls to be “nice” is a safety message, not just a personality one — and that niceness has never actually protected anyone. Do you agree? How did that reframe land with you?
- Lauren's glow-up move is to “find your O-lineman” — someone who uses their own credibility to clear space for you. Who has been an O-lineman for you? Whose lane have you cleared for someone else?
“Girls are groomed to be agreeable... And we discipline them—socially and professionally—when they are not.”
Chapter 2. The Hinge Generation
Leading Across Five Generations Without Losing Yourself
- Lauren describes millennials as “the hinge” — translators between generations who grew up analog and lead digital. Where in your own life or workplace do you feel like a translator between generations?
- The grandfather who wants a paper program at the championship “had nothing to do with technology. It had everything to do with dignity.” Describe a time modernizing something — at work, at home, in your community — collided with someone's need for the old way. How was it handled?
“Compassion isn't softness. Compassion is leverage.”
Chapter 3. The 70 Percent Problem
Why Girls Quit Sports Twice as Often as Boys—and What We Lose When They Do
- Lauren argues that when girls quit sports, “we're losing future captains of boardrooms, classrooms, and communities” — that sports are often the first leadership lab girls get. Did you play sports growing up? If you quit, what happened right before you did?
- The chapter reframes the bench as “the leadership incubator,” not a punishment. Have you ever been sidelined or “on the bench” professionally? How did you — or your leader — treat that season?
“Girls don't quit sports because they lack grit, or drive, or heart. They quit because somewhere along the way, adults stopped seeing them.”
Chapter 4. The Illusion of Belonging
How Knowing Yourself Becomes the Way You Lead Anyway
- Lauren distinguishes fitting in (“a performance contract”) from belonging (“an unconditional lease”). Where in your life right now are you fitting in versus truly belonging — and how can you tell the difference in your own body?
- She describes physical cues — the urge to hide in the bathroom during a networking session, the tight chest before a conference — as her nervous system giving her an honest read on a room. Have you learned to trust signals like that, or do you usually talk yourself out of them?
“You don't have to belong everywhere to belong to yourself.”
Chapter 5. Bagels at Dawn, Paper Cuts at Midnight
Where Everyday Moments Quietly Build Extraordinary Leaders
- Lauren traces her leadership instincts to unglamorous teenage jobs — a paper route, babysitting, a bagel shop, a paper mill. What was your own first “survival job,” and what did it teach you that no seminar ever could?
- “Be the tugboat, not the speedboat” is one of the chapter's central images. Are you more tugboat or speedboat by nature — and is that the role your current environment actually needs from you right now?
“Leadership isn't announced. It's revealed.”
Bringing It Together
Across these five chapters, Lauren keeps returning to rooms — a basement, a gym, a bagel shop — that taught her how power and permission actually work. Which room from your own life comes up most often when you think about how you learned to lead?
Part Two — Taking Up Space
Chapters 6–9: the body, the systems built to reward conformity, the chaos of a first job, and the relationship that taught her to trust herself again.
Chapter 6. Not Here to Be Small
What Growing Up “Too Much” Taught Me About Leadership and Space
- Lauren names her inner crew of “mental managers” who keep her functioning, and describes how she fuels, rests, and sets limits for them. What would your own mental managers need from you this week?
- The middle school “moose” chant — and the silence from adults that followed it — shaped how Lauren reads a room today. Was there a moment as a kid when your body became “public property” for other people's comments? How did the adults around you respond, or not respond?
“There is no prize for being small. There is power in being full size.”
Chapter 7. Teach the Room, Not the Ritual
Why Real Learning—and Real Leadership—Isn't About the Perfect Notebook
- The “perfect notebook” becomes a metaphor for barriers that reward conformity over competence. Where have you seen — or maybe even enforced — a “notebook rule” that measured polish instead of substance?
- Lauren failed her teaching-licensure exam four times before becoming a teacher, then a principal, then a doctor. How has a personal failure ended up shaping your empathy as a leader, parent, or friend?
“Barriers rarely protect the work. They protect the system.”
Chapter 8. No One Prepares You for Naked Bowling
On Courage, Cringe, and the Confidence to Lead Anyway
- This chapter moves between real chaos — a bowling alley beneath the classroom, a mental health crisis, a scissors incident, a prank, all in one wild year — and Lauren's takeaway is that “chaos doesn't build character. It reveals it.” What has an unexpectedly chaotic season revealed about your own character?
- She describes learning to “jump into someone's lifeboat” but not “go down with the ship” after a friend's mental health crisis in college. Where is your own line between compassion and self-preservation, and how did you find it?
“Leadership doesn't arrive in perfect moments. It arrives in the middle of the mess.”
Chapter 9. My Desert Rebirth
Learning to Lead Myself Before I Could Lead Others
- Lauren calls the slow erosion of her confidence in a controlling relationship “the dimming.” Have you experienced — or watched someone you love experience — a version of “the dimming”? What helped reverse it?
- Her principal's response to a frightening incident — “Is this the hill you want to die on?” — becomes a turning point. What are your own nonnegotiable “hills,” and did you choose them ahead of time or discover them in the moment?
“Your body is not overreacting. It is informing.”
Bringing It Together
This section moves from Lauren's body to the systems around her to her own hard-won instincts. Where in your life is the gap widest right now between the “full-size” version of you and the version the room seems to expect?
Part Three — Becoming a Leader in Public
Chapters 10–13: credibility, mentorship, knowing when to move on, and the years of infertility and adoption that reshaped how she leads through pain.
Chapter 10. Growing Up in Public
How Young Leaders Build Credibility When Everyone's Watching
- Lauren describes the “experience penalty” young and millennial leaders face — being read as unpolished rather than simply new. Have you faced this kind of double standard, or watched someone you lead face it?
- “Credibility is a bank account,” she writes — built through small deposits, drained by withdrawals like gossip or broken promises. What's one deposit you could make this week with someone who's watching you closely?
“Credibility isn't about perfection; it's about alignment—what you say matching what you do.”
Chapter 11. The Woman Who Told Me the Truth
How Mentorship Became the Missing Variable in My Confidence, Clarity, and Growth
- Jo taught Lauren through lived moments, not formal lessons — showing up at a hospital bedside, writing thank-you notes to a custodian, adapting her tone person by person. Who has been your Jo? Have you ever told them what their mentorship meant to you?
- Jo's filter for hard decisions was simple: “Is this good for kids? And would you be proud if it hit the newspaper?” What's your own version of that filter question?
“Mentorship at its best is legacy. Every confident leader you admire had someone, somewhere, who poured into them first.”
Chapter 12. The Geography of Becoming
How Knowing When to Move On Becomes the Most Underrated Leadership Skill
- Leaving Los Angeles for Idaho wasn't rock bottom for Lauren — it was outgrowing “fine” in search of something true, which she calls a harder leap than leaving crisis. Have you ever left something good in search of something honest? What made you brave enough, or what's still holding you back?
- Research she cites suggests most professionals need a major pivot every seven to ten years to stay engaged. Where do you sit in that cycle right now?
“Every brave move becomes a breadcrumb for the next version of you.”
Chapter 13. The Long Road to “Momma”
What Infertility and Adoption Taught Me About Leading Through Pain
- Lauren writes candidly about years of infertility, public professional attacks arriving at the same time, and a night when she “questioned why I was even here.” What did it mean to you that she named that moment so directly? What do you think leaders owe each other in terms of honesty about pain?
- Chace's adoption came together in twenty-eight days, on a completely different timeline than the one she'd planned. Lauren frames it as proof that “sometimes the best path forward isn't the one you planned.” Where in your life has a detour turned out to be the destination?
“The path to your dreams rarely looks the way you imagine, but sometimes the most beautiful destinations come from the most unexpected beginnings.”
Bringing It Together
Lauren credits Jo, a series of hard moves, and years of private grief with making her the leader she is now. Which of those three forces — mentorship, geography, or pain — has shaped your own leadership the most?
Part Four — Leading Real Humans
Chapters 14–16: parenting a neurodivergent child, becoming a leader in the pandemic, and refusing to accept exhaustion as the price of being a working woman.
Chapter 14. My Minor in ADHD Studies
Neuroinclusive Leadership: Systems That Unlock Performance
- The “shovel the ramp first” image becomes Lauren's argument that accommodations built for one person often end up helping everyone. Where have you seen a change made for one person, or one kind of brain, end up benefiting the whole group?
- She writes that ADHD “doesn't care if it's a binder or a laptop” — the tool isn't the real problem, the mismatch is. Think of a system at your workplace or in your family that quietly punishes a certain kind of brain. What would “shoveling the ramp” look like there?
“You have never been “too much” or “not enough”; you have been brilliant in environments that were too narrow to hold you.”
Chapter 15. What Are We Gonna F*cking Do?
How Millennials Learned to Lead Through Chaos, Care, and Uncertainty
- Toddler Willie's blunt question — “What are we gonna fucking do?” — becomes family and professional shorthand for collaborative problem-solving. Is there a phrase, from a kid or otherwise, that has quietly become a leadership tool in your own life?
- Lauren argues fairness isn't sameness — that her two sons, and by extension anyone she leads, need fundamentally different things from her. Where do you default to “treating everyone the same,” and is that actually serving the people involved?
“Your people don't need a hero. They need a human with steadiness in their voice and hope in their posture.”
Chapter 16. Sprinting Marathons Without Finish Lines
The Modern Working Woman Is Expected to Do More Than Ever, and We're Calling Bullshit
- Lauren keeps a specific “dopamine menu” instead of vague self-care advice. What would three items on your own dopamine menu be — and does anyone in your life actually know what they are?
- “Not all help helps,” she writes, describing well-meaning support that ends up adding to her plate instead of lightening it. Can you think of a time someone's help made things harder? Could you say so if it happened again?
“Rest is leadership prep, not indulgence.”
Bringing It Together
This section argues that “fair” isn't the same as “the same,” and that rest is infrastructure, not indulgence. What's one system in your own life — at home or at work — still built for a version of “normal” that doesn't actually exist?
Part Five — When It Gets Hard
Chapters 17–19: leading when policy collides with your values, learning to hand the wheel to someone else, and the mental load that never clocks out.
Chapter 17. Leading When It Breaks Your Heart
When Your Values Are Tested, Your Leadership Begins
- Facing a policy she opposed, Lauren chose to stay in her role rather than resign, reasoning that her presence let her “shape how this policy was carried out.” Do you see staying inside a system you disagree with, in order to soften its impact, as a form of courage, a compromise, or both? When would you make the opposite choice?
- She names a clear, personal nonnegotiable: “We don't make people feel less than. Ever.” What is one of your own nonnegotiables — and has holding it ever cost you a relationship or an opportunity?
“Leadership doesn't break your heart because you're doing it wrong. Leadership breaks your heart because you're doing it right.”
Chapter 18. Pickleball and the Art of Not Being in Charge
Practicing the Lost Skill of Putting Your Phone Down and Letting Someone Else Drive
- Lauren catches herself trying to “run the show” even at a casual rec league — and describes the relief of realizing she wasn't needed. Where in your life could you practice being “just another person” instead of the one in charge?
- Her “pause” ritual — walking to the fence and back before reacting to a bad shot — helps her reset before she responds to anything. What's your version of the fence walk?
“Momentum doesn't respond to pressure; it responds to patience.”
Chapter 19. Chicken Nuggets and the Millennial Juggle
Where Leadership Meets Lunch Boxes and the Mental Load Never Clocks Out
- Lauren writes about the exhausting blur of “running statewide championships in the morning and slinging chicken nuggets by 5:00 p.m.” Where does your own leadership and home life blur together, and does that blur feel sustainable right now?
- She frames boundary-setting — even a quiet, unspoken one — as legitimate, not something that requires a big announcement. What's a boundary you've been meaning to set but haven't said out loud yet?
“Your rest is rebellion. Your boundaries are a revolution.”
Bringing It Together
These three chapters are about different kinds of pressure — political, competitive, domestic — and the same tool keeps showing up underneath all of them: the pause. Where in your life could a deliberate pause change the next decision you make?
Part Six — The Beautiful Middle
Chapters 20–22 and the Epilogue: starting before you feel ready, building a third space, and carrying the weight of leadership as proof rather than burden.
Chapter 20. You Just Have to Start
Because They'll Talk Anyway, Give Them Something Worth Talking About
- Lauren applied to a doctoral program, joined a hundred-mile relay with two days' notice, and started teaching, all without feeling ready. Where in your own life are you waiting for a permission or readiness that may never come?
- She distinguishes “stillness that's sacred” from “stillness that's scared.” How do you tell the difference in your own life right now?
“Confidence is the result, not the requirement.”
Chapter 21. The Third Space: Where Belonging Lives
Where We Remember Who We Are When the World Tells Us Otherwise
- Lauren defines a third space as somewhere outside home and work where belonging is chosen, not assigned. What is your third space right now — and if you don't have one, what could it become?
- The night she signed her book contract, she texted her sisterhood, “I'm freaking out,” and they held her up. Who's in your version of that group text, and when did you last let them see you scared?
“Belonging isn't earned. It's created. Together.”
Chapter 22. The Beautiful Weight of Leadership (with Epilogue)
Where Courage Meets Care—and Calls It Leadership
- The chapter's central claim is that “leadership breaks your heart because you're doing it right.” Has there been a moment in your life — as a leader, parent, or friend — that hurt precisely because you were doing it well?
- In the epilogue, Lauren rejects a tidy ending in favor of “the messy middle” and writes, “Heavy be the crown. But it sits on me full size.” What would it look like for you to stop waiting to arrive and start leading — or living — from your own messy middle?
“The weight isn't the burden. The weight is the proof. The weight is the privilege.”
Bringing It Together
Lauren ends the book insisting there's no tidy arrival — only “the messy middle,” lived in full size. As your group closes this book, what does your own messy middle look like right now, and what's one thing “leading anyway” could mean for you this month?
Closing Reflection Questions
- If you had to describe Lead Anyway's core message in one sentence to a friend who hasn't read it, what would you say?
- Which “Glow-Up” practice from the whole book are you most likely to actually try this month — the O-lineman, the dopamine menu, the burnout watch list, the fence walk, naming your nonnegotiables, or something else?
- Who in your life needs to hear “lead anyway” from you right now?
Bonus: Pairings for Your Meeting
A few of Lauren's own touchstones from the book, if your group wants to set the mood:
On the playlist
- Zedd, “The Middle” — Lauren's midlife anthem (Ch. 6)
- Taylor Swift, The Tortured Poets Department, especially “thanK you aIMee” (Ch. 6, 14)
- Noah Kahan — “comfort hoodie” music (Ch. 6)
- A nineties country playlist and the Eagles' greatest hits (Ch. 6, 10)
On the table
- Bagels and coffee (Ch. 5's 3:30 a.m. shift)
- String cheese and seltzer — Lauren's “emotional first aid” (Ch. 6)
- Chips, salsa, and a margarita, or a red wine with a little chocolate — her “dopamine menu” (Ch. 16)
- A sleeve of Thin Mints (you'll understand by Chapter 22)
Bonus: Try This Between Meetings
A few of the book's Glow-Up practices work especially well as a group challenge — try one and report back at your next meeting:
- Name your mental managers. Spend five minutes writing down what your version of Lauren's “internal crew” needs this week — fuel, rest, or a limit — and do one thing about it before your next meeting.
- Build a dopamine menu. Write down three specific, non-generic things that actually restore you, and tell one person in your life what they are.
- Find or build a third space. Identify one place in your life, outside home and work, where you belong rather than perform. If you don't have one, take one step toward creating it.
- Write your nonnegotiables. In one sentence each, name two or three hills you'd stand on before you're ever asked to.
Connect
Learn more about Dr. Lauren Young's work at LeadAnywayLeadership.com and theGRLinitiative.com.
Thanks for reading Lead Anyway with your book group — and for leading anyway.