Your life looks good on paper,
but it doesn’t feel right.
One of our culture’s most persistent myths is that success alone leads to fulfillment and happiness.
From a young age, we’re taught to chase achievement, status, and lives that look good on paper—often at the expense of how they actually feel. Over time, striving crowds out the things that make life feel meaningful: connection, presence, community, awe.
Work itself isn’t the problem. The problem is that we expect success to be our source of meaning—so we’re surprised when chasing it leaves us feeling hollow. When we think to ourselves, There’s got to be more to life than this.
This is the type of change I’ve helped people navigate for nearly a decade. I’m Hailey, and I help people outgrowing identities built on approval, achievement, and others’ expectations step into a more vital and self-trusting life.
This coaching may be for you if:
You achieved things you once longed for, and felt surprised by how little fulfillment they brought
Success has become the place you look for worth, stability, or reassurance about who you are
Your life “works” on paper, but deep down, you feel an emptiness or hollowness you can’t quite explain
You feel a growing tension between the life you’ve built and the values that matter most to you
When work is going well, you feel okay—and when it’s not, everything feels shaky
Chasing success has taken precedent over meaningful contribution or making a difference—and you yearn for work that feels purposeful and true
You worry that if nothing changes, you’ll look back on your life and wish you lived it more meaningfully
In private coaching, we examine the role success has played in your sense of meaning, and begin building a life that feels more vital and fulfilling.
It’s not about blowing up your life, becoming anti-work, or rejecting success altogether. It’s about reconnecting with the parts of life—and the parts of you—that got crowded out along the way.
After years of striving, the success I’d worked for began to feel hollow, and my heart longed for something more meaningful.
I built a booming coaching business with hundreds of thousands of followers, a six-figure book deal, and features in The New York Times. 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 fulfillment that never came—until, at the peak of my career, a series of unexpected losses shook me awake.
I suddenly saw how narrow my world had become, and how many parts of myself—and my life—I’d neglected. Success, I realized, was never meant to be my meaning. This realization helped me slowly release the pressures of achievement, and embrace connection, creativity, and a vital new chapter—one where work mattered without being my whole world.
MY APPROACH
When we’re outgrowing our old relationship with success, we crave clarity and direction. Not just the surface-level clarity of “What do I do next?” but the deeper clarity of “Who am I becoming? What really matters to me? And what’s the most authentic path forward?”
These questions are difficult to answer alone, because we’re so deep in it: the uncertainty, the change, the growing pains. My approach helps you untangle these threads, reconnect with your inner guidance, and rebuild a more fulfilling and vibrant life after success has taken up too much space.
Grounding & Orientation
We begin by looking honestly at the role success has played in your life: what it’s given you, what it’s cost you, and how it can no longer carry the weight of your meaning. We examine how your identity, values, and desires are shifting in response to the events of your life, and give you clarity about where you are in the transition process.
Clarity & Direction
From there, we help you uncover not just the relationship with success you’re outgrowing, but what you’re being called towards: new sources of meaning, ways of working, and values that align with your heart. We create a customized coaching plan that helps you continue finding and following these directions at your own pace.
Self-Trust & Action
Together, we help you move forward purposefully: to take aligned action steps toward the life you’re seeking, even if you don’t have it all figured out just yet. Our sessions combine clarity with courage-building and gentle accountability so that you make consistent progress toward more meaning, purpose, and vitality.
WHAT CHANGES?
On the inside, loosening success’ grip on your meaning and purpose brings more ease, vitality, and freedom. On the outside, this looks different for every client:
Some reclaim their energy from work and invest it in the things that striving crowded out:
connection, community, creativity, spirituality, service, presence, nature, play, awe.
Some make a shift into more meaningful careers or sectors,
choosing work that feels genuinely aligned over ladder-climbing and achievement-chasing.
Some renegotiate their work boundaries,
finding ways to keep doing work they love without letting it consume their lives and identities.
The paths are different, but the through-line is the same: rebuilding a life around real meaning, not success.
“Working with Hailey changed my life. Every week I walked away with real tools I could put into practice to reach my personal goals and live a more fulfilled and authentic life. After completing sessions I feel more confident, capable, and in control than I ever have.”
— Eileen
Private coaching includes:
📩 Email support in-between sessions.
Life happens outside of sessions—and I’m here to support you via email. Share what’s moving through your heart, send along a question, or update me about a win or victory.
📓 The Permission to Become journaling workbook.
Over 50 journaling prompts, coaching frameworks, and reflection exercises to offer structure and help you connect with your inner voice through the process of transition.
🖥️ My self-paced, 22-course Self-Advocacy School.
My masterclass teaches you how to connect with your own needs, desires, and values; set empowered boundaries; and leave behind the aspects of your life that no longer align with who you’re becoming.
🎧 40+ curated podcast, book, and article recommendations.
My Resource Library is a wealth of curated podcast and book recommendations, offering structured guidance, wisdom, and real-life stories from fellow travelers in the midst of life transition.
How Private Coaching Works
Private coaching is a one-on-one relationship designed to support meaningful change over time. It’s not a quick fix—though sessions can, and often do, spark immediate new ways of seeing things.
When you become a client, you’ll fill out an intake form about why you’re seeking coaching at this moment in your story, and what you hope to get out of the process. After our first session together, I’ll create a customized, flexible coaching plan around your goals.
We meet bi-weekly for 50-minute sessions, and keep in touch in-between via email. My approach is warm, active, and provocative. Our sessions draw from a deep well of frameworks and tools, and each closes with action steps: invitations for what to pay attention to—or experiment with—in the week ahead.
“With Hailey’s support and guidance, I know what it feels like to tap into my instincts and values. Increasingly, I use those inner signals—rather than the cues I take from others—to guide my decisions. Thanks to Hailey, I’m a better and freer me. I recommend her every chance I get.”
—Hilary
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TWO WAYS TO WORK WITH ME:
Private Coaching: 6-Month
Container
My 6-month coaching container is for those who feel that striving for success has taken over more space than they want it to—and they’re ready to begin making changes. It’s a good fit when your old sense of meaning, identity, and life direction are loosening, and you’re ready to experiment with new ways of living from more meaning, purpose, and vitality.
Over six months, we move from insight into action and integration. We examine the role success has played in your sense of meaning; reconnect with the parts of life—and the parts of you—that got crowded out along the way; and begin building a life that feels more vital and fulfilling.
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This 6-month Private Coaching container includes:
12 bi-weekly, 50-minute private coaching sessions held on Zoom
Monday-Friday email support in-between sessions
Customized action steps at the end of every session
The Permission to Become journaling workbook, with over 50 journaling prompts, coaching frameworks, and reflection exercises
One-year enrollment in The Self-Advocacy School
A resource library of over 40 curated book, article, and podcast recommendations
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The investment for this program is $474/month for 6 months.
Private Coaching: 3-Month
Container
My 3-month coaching container is for people who are questioning their relationship with success and want a dedicated window to explore the misalignment they feel. It’s well-suited for those who want a deeper understanding of what feels dissatisfying, but aren’t necessarily ready to make any big changes.
Three months provides structure and momentum as we help you reconnect with your values, name what you want more (and less) of, and begin considering which adjustments would best serve your life.
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This 3-month Private Coaching container includes:
6 bi-weekly, 50-minute private coaching sessions held on Zoom
Monday-Friday email support in-between sessions
Customized action steps at the end of every session
The Permission to Become journaling workbook, with over 50 journaling prompts, coaching frameworks, and reflection exercises
One-year enrollment in The Self-Advocacy School
A resource library of over 40 curated book, article, and podcast recommendations
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The investment for this program is $474/month for 6 months.
If this work resonates with you, the next step is a conversation.
We begin with a brief call to explore what’s bringing you here and what you’re hoping to gain from coaching. To be clear, this isn’t a sales call; there’s no expectation that you’ll decide on the spot! If working together feels like a fit, we’ll talk through next steps and timing.
My Credential & Training
Holding a credential from the International Coaching Federation (ICF) and certified by Erickson Coaching International, I bring over a decade of experience supporting individuals, groups, and organizations through periods of meaningful change.
I’m the author of Stop People Pleasing and Find Your Power (2024, Simon & Schuster) and my work has been featured in The New York Times, The Gottman Institute, and Vox. My work spans private coaching, group programs, and corporate partnerships, and I’ve facilitated workshops in conjunction with WeWork, Mindvalley, Women in Music, and more
Frequently Asked Questions
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I host private coaching sessions on Tuesdays, Wednesdays, and Thursdays from 11am—3pm Pacific Time, and Mondays from 11am—1pm Pacific Time.
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You get to decide whether you’d like to have your sessions on a weekly or every-other-week basis. Most of my clients prefer to have sessions every other week so they have time in-between for journaling, reflection, and completing their action steps.
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Yup! I’ll send you all of the information you need to log-in and get set up prior to our first session.
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Payment plans are available for private coaching. Financial aid is not available for private coaching.