Outgrowing who you’ve been?
You don’t have to navigate the journey alone.
If you’re being honest with yourself—if you really get quiet and listen—there’s a part of you that says, this isn’t me anymore.
You’re changing. The places you once found a sense of self and meaning—your career, relationship, community—no longer feel like home.
Instead, there’s a gnawing dissatisfaction. A restlessness. A tension in your heart between the life you’ve been living, and the person you’re becoming.
Part of you says it’s time for a new chapter—but another part of worries that the path forward isn’t clear. Part of you craves change—but another part is afraid of what that change could cost.
Outgrowing who you’ve been can feel like a disruption to your path. But across psychology, philosophy, and myth, these moments are seen as powerful initiations: rites of passage that strip away inauthenticity to make space for a more honest and vital chapter of life.
I’m Hailey, and this is the type of change I’ve had the privilege of helping people navigate for nearly a decade.
Private coaching may be for you if:
You feel like your inner world and your outer life no longer align, and you can no longer ignore the tension and dissatisfaction you feel.
The external compass points you used to follow—success-chasing, approval-seeking, meeting others’ expectations—no longer feel meaningful, and you want your own values to start guiding your path.
Your old sources of meaning and and purpose have stopped working, but the new ones haven’t formed yet—and you’re tired of feeling stuck in the “in-between” phase of change.
Part of you wants change, but part of you fears it. You want to take steps to listen to your heart without pushing too hard or too fast.
Navigating this period of change feels overwhelming, and you crave a structure that supports, grounds, and guides you as you embrace the person you’re becoming.
Coaching offers a grounding structure through the process of transition, helping you find steadiness, clarity, and direction through this season of change.
“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
MY APPROACH
When we’re outgrowing who we’ve been, we crave clarity. 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? What do I believe in? 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 move through this transition with clarity and self-trust.
Grounding & Orientation
We begin by taking a clear look at why you’re outgrowing this chapter of your story. 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. This helps the difficult moment make sense.
Clarity & Direction
From there, we help you uncover not just what you’re outgrowing, but what you’re being called towards: new sources of meaning, ways of living, and values that align with your heart. We create a coaching plan that helps you continue finding and following these desires at your own pace.
Self-Trust & Action
The in-between phase of transition often takes longer than you expect, which can feel frustrating when you’re used to figuring things out quickly. Together, we focus on strengthening your ability to trust yourself—to move forward in aligned ways, even when you don’t have it all figured out yet. Our sessions combine clarity with courage-building and gentle accountability so that you make consistent progress toward the life you want.
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.
“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
How does the coaching process work?
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.
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TWO WAYS TO WORK WITH ME:
6-Month
Container
My 6-month coaching container is for those who know they’re outgrowing who they’ve been and are ready to begin reshaping their life in response. You may not have total clarity about what’s next, but you trust that something important is changing. You want support not just understanding this shift, but living into your next chapter.
Over six months, we move from insight into action. Together, we help you build self-trust; clarify what’s no longer aligned and what’s calling to you; and take thoughtful, real-world steps as you begin stepping into a new chapter of your life.
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My 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.
3-Month
Container
My 3-month coaching container is for those who suspect they’re outgrowing who they’ve been, and want a dedicated place to explore and make sense of the misalignment they’re experiencing. It’s a good fit if you’re not yet ready to make big changes, but want to understand what’s shifting internally.
These three months are about gaining clarity, not about pressure to change. We help you reconnect with your values, clarify what no longer fits, and explore what you may want more (and less) of—so that you can move forward with a deeper sense of understanding and direction when you’re ready.
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My 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 3 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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Coaching is a thought-provoking and creative process that inspires you to create the future you want. It focuses on visioning, imagination, skill-building, enhancing confidence, and moving toward your desired future. Coaching is action-oriented, and every session concludes with clear, tangible steps that you can take in-between sessions to get closer to your goals.
Therapy, on the other hand, often emphasizes psychopathology and healing from the past. It focuses heavily on developing skills for managing difficult emotions, coping with hardships, and healing past traumas.
Overall, therapy is a better fit for those hoping to treat mental illness; process acute trauma; or diagnose mental health concerns. Coaching may be a better fit for those who want help leaning into desire, taking concrete action, and designing a life that inspires them.
Many of my clients participate in coaching while also participating in therapy. Both are supportive in different ways, and tend to complement each other well.
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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.