The Hustle to Heart Bookclub
A community and refuge for high achievers outgrowing conventional success.
When you live in a world that celebrates the hustle, it takes courage to step off the hamster wheel and build a life rooted in real fulfillment—not just achievement.
Hustle to Heart is a monthly bookclub of high achievers daring to redefine success. Through thought-provoking reads and rich conversation, we support one another as we trade burnout and achievement-chasing for presence, meaning, and vitality.
HUSTLE TO HEART IS FOR:
The successful leaders
who have hit every milestone and earned every title—but still feel like something’s missing. You want to stop prioritizing your career at the expense of your life, and start a new chapter that feels more meaningful.
The driven entrepreneurs
who have built the dream business—but while the recognition, flexible schedule, and financial wins might look great on paper, they leave you overworked and under-fulfilled. You want to reconnect with yourself beyond your business.
The gold star collectors
who have built their identity around achievement—and are finally asking: “What do I want?” External validation hasn’t given you internal fulfillment, and you’re ready to rediscover what lights you up beyond the striving.
The respected influencers
with tons of followers, but a dwindling sense of self. Being a brand, turning life into content, and being addicted to the apps has drained your vitality. You’re ready to stop prioritizing appearances and start prioritizing your quality of life.
I’m Hailey. I built the life I thought I wanted: booming coaching business, six-figure book deal, hundreds of thousands of followers.
On paper, I was living the dream. But after years of striving, the success I’d worked so hard for began to feel hollow—and my heart longed for something deeper.
I grew up believing that success was the key to fulfillment. As a bullied kid, achievement was the one thing that had always made me feel seen—so I never questioned the story.
I built a booming coaching business with hundreds of thousands of followers, a six-figure book deal, and speaking gigs around the world. On paper, I was living the dream.
But behind the scenes, I was burnt out, depressed, and meaning-starved. I kept on this way for years—waiting for a satisfaction that never came—until, at the peak of my career, a series of devastating losses changed everything for me.
This is the story of how hitting rock bottom became the key that set me free from the cage of conventional success—and gave me the courage to build a life abundant with connection, purpose, and heart on the other side.
GOOD BOOKS 📚
GOOD PEOPLE ✨
GOOD BOOKS 📚 GOOD PEOPLE ✨
How It Works
Hustle to Heart is an intimate, 20-member bookclub. Enrollment for the Winter 2026 cohort is now open, with our first meeting on January 21, 2026. We have two groups: a morning group at 11am PT, and an evening group at 5pm PT. You can pick the group that best suits your schedule.
Every month, H2H enjoys a non-fiction book or podcast episode that explores the topic of outgrowing conventional success. Every book has an audiobook version for those who prefer to listen.
Beginning on January 21, H2H meets on the 3rd Wednesday of each month. Our meetings are gently facilitated, with thought-provoking questions that help you reflect on the book and generate rich discussion.
Our monthly coaching worksheets distill each book’s insights into key frameworks and guided prompts—helping you craft a personalized plan to live from heart, not hustle, at a pace that feels right for you.
Between meetings, you can participate in a members-only H2H Discord chat, where you can share thoughts, celebrations, resources, and stay in touch in-between meetings.
ON OUR SHELF 📚
Hustle to Heart is the community you’ve been searching for if:
Community with like-minded high achievers outgrowing conventional success
Reassurance that your longing for a life beyond hustle is valid and shared
Motivation to take concrete, real-world steps that trade hustle for heart-centered living
Thought-provoking conversations that spark fresh insights and expand your view of what fulfillment can look like
Friendship and camaraderie with fellow achievers choosing this unconventional path
Continuous learning and growth in an intimate community that grows with you
You’re seeking:
Values of curiosity, learning, and personal growth
The bandwidth to engage with one book or podcast episode a month
The desire to share and to listen in balanced, open-hearted conversation
Respect for differing perspectives and the ability to disagree thoughtfully
The ability to participate in a video-on Zoom environment to foster community and connection
A commitment to creating a safe and confidential environment for sharing.
You’re bringing:
The Backstory
For over two years, I’ve hosted a non-fiction bookclub in Seattle—and it’s quickly become one of the greatest community experiences of my life.
Over time, what began as twelve strangers discussing ideas over a potluck dinner became much more: a space for rich vulnerability and deep friendship that spans far beyond our monthly meetings.
Firsthand, I’ve seen how powerfully an intimate bookclub can foster personal transformation, create community, and inspire lifelong connection. My goal is to create this same transformative experience in Hustle to Heart—and I hope you will join us!
Join us
📚
Join us 📚
When you join the Hustle to Heart Bookclub, you get:
📚 6 Curated 2-Hour Sessions
Our deep-dive discussions ignite powerful insights, foster camaraderie, and not only normalize, but encourage, stepping off the success hamster wheel for real fulfillment.
📚 Access to the Private Online H2H Community (Discord)
Between meetings, our Discord gives you a space to keep the conversation going, share inspiring resources, and receive ongoing accountability and support.
📚 Monthly Coaching Worksheets
Coaching worksheets distill each book’s insights into memorable frameworks and guided prompts—helping you craft a concrete, personalized plan to trade hustle for heart.
📚 Authentic Connection and Conversation with Other High Achievers
This is a unique community where you can finally get real, say no to the gospel of hustle, and walk alongside others choosing this brave, unconventional path.
📚 Our Schedule:
January 21: The Power of Meaning: Finding Fulfillment in a World Obsessed with Happiness by Emily Esfahani Smith
February 18: The Good Enough Job: Reclaiming Life from Work by Simone Stolzoff
March 18: Rest is Resistance: A Manifesto by Tricia Hersey
April 15: Ambition Monster: A Memoir by Jennifer Romolini
May 20: Life is in the Transitions: Mastering Change at Any Age by Bruce Feiler
June 17: Together: The Healing Power of Human Connection in a Sometimes Lonely World by Vivek Murthy
.
Accessibility is important to me, so when you join, you can select the enrollment rate that best suits your financial situation:
NOW ENROLLING THE WINTER ‘26 COHORT
With only 20 spots in each cohort, The Hustle to Heart Bookclub is an intimate community designed for depth, curiosity, and rich conversation. To keep the experience meaningful, we use an application process to bring together the group that would most benefit.
Questions?
-
The Winter ‘26 cohort meets on the third Wednesday of every month. The morning group will meet from 11am-1pm PT, and the evening group will meet from 5-7pm PT. Future cohorts may take place at different times; check this page for details.
-
Yes. In order to ensure a vibrant, connected community environment, we ask that all members keep their videos on.
-
Life happens—we totally get it! It’s okay to miss a meeting. If you miss three meetings, your space will be given to someone on the waitlist who can be a regular attendee, and your enrollment fee won’t be refunded.
-
Discord is a messaging platform where we can stay in touch in-between meetings. You’re not required to use it, but it’s a great way to post reflections, share celebrations, and get to know each other better.
-
No, members are responsible for getting their own books. Most of the books we read are available for rent at the library, and all are available via audiobook for those who prefer to listen.