Private Coaching
A compass you can trust
My Pathfinder Process gives you clarity and direction through the process of transition.
Who you’ve been no longer fits who you’re becoming.
The tension between your inner truth and outer world has become impossible to ignore.
Inside, you’re thinking:
“This isn’t me anymore.”
“From the outside, everything looks great. But inside, I feel hollow.”
“I got everything I thought I wanted, but it didn’t fulfill me.”
“I don’t know what’s next—but I know it isn’t this.”
“I feel like I’m performing.”
“There has to be more to life than this.”
“Something deeper is calling me — but I don’t know what it is.”"
My Pathfinder Process gives you the clarity to know how you got here, what you want next, and where you’re headed—
and the courage to trust your gut, take the leap, and build the life you’re craving.
PERHAPS YOU’RE:
Questioning your profession.
You’ve hit every milestone, but still feel empty—or maybe you’re craving a career that feels less like a performance and more like you.
Ending a meaningful relationship.
After ages of agonizing over this relationship, you’ve made the brave choice to end it—and you’re ready to find yourself again.
Leaving behind a belief system.
Your old faith or ideology no longer rings true—and you’re craving solid ground as you reconstruct your sense of meaning.
Making a major lifestyle change.
Chasing a long-held dream. Choosing a non-traditional path. Breaking an old habit. You’re finally making the change, and you want support.
“I’d given up on having a career that felt like my calling. But then I saw one of your posts about living disconnected from meaning, and I thought, That’s me! I don’t want to live like this! I was raised with a lot of family pressure to get a lucrative job and our coaching helped me untangle their expectations from MY values. I am so unbelievably grateful to you for encouraging me follow my heart. I start grad school this spring to become a family therapist. At age 42. Let’s go!” — Dylan
I’m Hailey. Like so many of my clients, I woke up one day in a life that no longer fit.
I was raised in a culture that insisted that fulfillment came from success. Growing up bullied, achievement was one thing that always made me feel seen—so I never questioned the story.
Success became my North Star. I built my life around it: thriving coaching business, six-figure book deal, hundreds of thousands of followers.
People said I was living the dream. And I was—on paper. But behind the scenes, chasing achievement left me burnt out, hollow, and disconnected from a real sense of meaning.
I pushed on this way for years, waiting for a satisfaction that never came. Then, at the peak of my career, a devastating series of emergencies opened my eyes to the painful truth:
I’d been sold a lie of fulfillment—and in chasing it, I’d lost connection with myself, my loved ones, and my community. I had tied my identity to a pursuit I no longer believed in.
I could keep living a life I’d outgrown, or I could stop chasing what the world told me to want and reorient my life around something deeper. Something more alive.
Through the wilds of transition—through fear, identity crisis, and self-doubt—this is the story of how I left a life that looked good on paper to build a life that actually felt good.
MY PATHFINDER PHILOSOPHY
Guiding you through the terrain of transition
Transitions are external and internal journeys. On the outside, your job, relationship, community, or lifestyle is changing—but on the inside, something deeper is shifting: your identity, beliefs, values, and sense of meaning.
This in-between space can feel like an identity crisis (trust me, I know)—but in truth, it’s the chrysalis stage of transformation. Every transition is different, but they follow recognizable phases and patterns—and I help you navigate the journey with structure and support.
Unlike other forms of coaching that focus on setting a fixed destination and mapping the fastest route, my work centers the journey itself—because that’s where the clarity and transformation unfolds.
As an ICF‑credentialed coach who has worked with over 500 private clients, I know that the real alchemy of transition lives in the moment-to-moment unfolding of your evolving self: the moments of intuition, flashes of clarity, and feelings and desires you can no longer ignore.
Knowing how to read the terrain of that inner unfolding—helping you make sense of it and let it guide you—is the heart of my work as a coach. And when the next chapter becomes clear, I help you walk toward it strategically. Think of me like a seasoned trail guide who knows the landscape, offering you tools and frameworks that let your inner wisdom lead.
MY PATHFINDER PROCESS: HOW IT WORKS
The Pathfinder Process is my 5-pillar coaching experience that brings your outer world into alignment with your inner truth on the journey of transition.
1. Transition Mapping for Grounding and Orientation
First, we give you a map through the unfamiliar terrain of transitions. Though transitions can feel disorienting, they are predictable processes—and every phase of the journey carries wisdom and opportunities for transformation. We’ll bring clarity to where you are in the transition cycle and offer the best practices to ground you, support you, and spark insight through each stage.
2. Meaning Work for Vision and Direction
Together, we help you explore your meaning—your True North—your “why.” Your meaning gives your journey an overarching direction, even when the final destination and specifics are unclear. Research shows that a meaningful life is built on four pillars—Belonging, Purpose, Transcendence, and Storytelling—and together, we’ll unlock your unique Meaning Blueprint: the personal balance of these four elements that brings you the greatest fulfillment.
3. Values Work for Clarity and Decision-Making
Your values are the core principles that shape your sense of what's important in life. Together, we create your Core Values Compass so you can navigate toward what matters most moment-to-moment—especially when the next step feels uncertain. Your compass gives you the clarity you need you make aligned decisions; determine priorities; set empowered boundaries; and move forward with integrity.
4. Parts Work for Self-Compassion and Courage
Transitions can stir up limiting beliefs and fear. By recognizing, honoring, and soothing the parts of you that are stuck, afraid, or conflicted, we create space for your values—not your fears—to lead the way. External pressures may still show up, but they no longer have to dictate your path.
5. Solution-Focused Coaching for Motivation and Real-World Change
Once your destination comes into view, we’ll make sure you have the tools, motivation, and plan to get there. Together, we’ll pair your big-picture vision with concrete, doable steps so you can start living your values every day. We’ll also get practical—exploring things like finances, logistics, and how to navigate relationships with people who may not understand your new path. This phase gives you the structure and accountability to turn your insights into lasting change.
“Leaving my marriage felt like free-falling. I had no idea where I was going... I just knew I couldn’t live like that anymore. Coaching with you was a godsend because it gave me solid ground when everything else was changing. You made all of my complicated emotions make sense. You helped me rediscover who I was after losing myself in my ex. Now, I love my apartment. My art projects. The friends I’ve made! I feel like me again after decades of feeling like a ghost. Thank you so much!” — Ellen
On the other side of the Pathfinder Process, my clients experience:
RENEWED VITALITY
You feel more alive than you have in ages. By aligning your life with your values and desires, you’ve reclaimed your energy and joy.
AUTHENTICITY
The tension of living a life you’ve outgrown has been replaced with the ease and flow of walking a path that’s truly yours.
DEEPER MEANING
You’re confident you’re living your most meaningful life, because you’ve oriented it around the big questions: Who am I becoming? What do I believe in? What matters to me?
SELF-TRUST
By going against the grain and following your heart, you’ve build confidence, resilience, and trust that you’ll act in alignment with what you need—even when it’s hard.
HAPPIER RELATIONSHIPS
Now that you’re showing up to your relationships from your true self—not a performance—you connect with more presence, openness, and honesty.
JOY and CREATIVITY
Self-suppression stifles your life force. Now that you’re taken the leap to live authentically, your playful and creative energy has returned in droves.
“I remember clearly how lost I felt before our first call. The series of thought-provoking questions you asked throughout the coaching process helped me transform faster than I ever thought possible. I'm literally shocked and amazed at how in alignment my life feels now. Thank you Hailey. You are an expert at what you do!” — Ed
THREE WAYS TO WORK WITH ME:
Pathfinder
1) Pathfinder
A 6-Month Guided Passage Through Transition
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Pathfinder is for those who are ready to take the next, brave step and commit to the process of transition: who are done standing on the edge of change, and ready to take the leap with support.
In this 6-month intensive coaching experience, I’ll walk beside you through the process of change. We’ll bring clarity to where you are in the transition cycle, offer practices to support you through each stage, and explore how external shifts are mirroring profound internal changes to your identity, values, and beliefs.
Together, we’ll explore the big questions—Who am I becoming? What do I deeply value?—and equip you with the clarity to define the path forward on your own terms. When you’re ready, we’ll help you take brave action to shape your life around what matters most.
This package includes:
12, high-impact Zoom coaching sessions: Energizing and collaborative 50-minute experiences designed to spark clarity, build inspiration, and move you forward with intention.
Strategic action steps after every session: You’ll walk away from each coaching session with tailored, doable action steps that translate your insights into meaningful, real-life change.
Email support in-between sessions: You don’t have to wait for your next session to get support. Ask questions or share wins in real-time via email.
The Core Values Compass Assessment: A powerful assessment tool that gets you crystal clear on the values that will guide your journey, inform your decisions, and set your priorities.
The Pathfinder Journaling Workbook: A journaling practice is encouraged throughout transition, and these 30+ prompts will help you quiet the noise and reconnect with your gut and heart.
The Pathfinder Resource Library: A hand-picked collection of books and podcast episodes that educate, inspire, and help build camaraderie with other meaning-seekers in transition.
Your Investment: $479/month for a minimum of 6 months, with payments due on the first of each month.
Strategic Planning for Joy
A 3-Month Guided Passage for Those Transitioning from Achievement to Enjoyment
2) Strategic Planning for Joy
Strategic Planning for Joy is perfect for passionate doers who are done pouring all of their planning energy into work: who want to start bringing their fire and delight to their soul’s favorite side projects.
This 3-month guided experience helps you discover what becomes possible when you brought the same level of vision, intentionality, and big-picture thinking that you bring to work to the non-work pursuits that you love—like your friend group. Your folk band. Your book club. Your travel goals.
Together, we’ll get clear on a project, pursuit, or community that brings you alive—map out an intentional plan to nurture it—and build in regular structure so that your joy is a priority, not an afterthought.
This package includes:
6, high-impact Zoom coaching sessions: Energizing and collaborative 50-minute experiences designed to spark clarity, build inspiration, and move you forward with intention.
Strategic action steps after every session: You’ll walk away from each coaching session with tailored, doable action steps that translate your insights into meaningful, real-life change.
The Pathfinder Journaling Workbook: A journaling practice is encouraged throughout transition, and these 30+ prompts will help you quiet the noise and connect with your gut and heart.
The Pathfinder Resource Library: A hand-picked collection of books and podcast episodes that educate, inspire, and help build camaraderie with other folks in transition.
Your Investment: $447/month for a minimum of 3 months, with payments due on the first of each month.
Create Your Core Values Compass
3) Create Your Core Values Compass
A 2-Hour Consultation for Clarity and Direction
This consultation is perfect for those who are just beginning to suspect that they’re outgrowing their old lives: who are seeking a powerful starting point for change, without necessarily taking the leap just yet.
When you know what truly matters to you deep down, the path forward becomes clearer—and it gets easier to let go of what no longer aligns. That’s why identifying your core values is a pivotal step in pathfinding through the process of transition.
In this in-depth, 2-hour consultation, we’ll use a blend of assessment tools, powerful questions, and deep reflection to get crystal clear on the values that drive you.
You’ll leave our session with your personalized Core Values Compass; an actionable roadmap for living in alignment with your values starting today; and post-session reflection prompts that help you continue your discovery and take aligned action forward.
This package includes:
One, high-impact 120-minute consultation: A thought-provoking and in-depth session with powerful questions, tools, and reflections to clarify and define your core values.
Strategic action steps after your session: You’ll walk away from our consultation with tailored, doable action steps that translate your insights into practical change.
Pre- and post-session reflections: Depth-centered reflection prompts help you prepare for our session and integrate all you’ve discovered afterwards.
The Pathfinder Resource Library: A hand-picked collection of books and podcast episodes that educate, inspire, and build camaraderie with other folks in transition.
Your Investment: One-time payment of $479 due at time of scheduling.
You don’t have to wander through the wilds of transition alone. Apply here to walk beside someone who knows the terrain.
COACHING WITH ME IS:
#0: Not therapy.
Therapy traditionally centers understanding the past, fixing problems, and addressing emotional distress and mental health concerns. Coaching is a desire-driven, future-focused, and actionable process—an uplifting space where you can slow down and get inspired about designing a life that aligns with your values.
#1: Possibility-driven, not problem-driven.
Our sessions focus on what excites you, rather than what’s “wrong” or needs fixing. By shifting the lens from limitations to opportunities, we help you see new paths and build a life that honors your deepest values.
#2: Actionable, not abstract.
We transform your lightbulb moments into concrete action steps so that you’re walking the walk, not just talking the talk.
#3: Provocative, not passive.
I meet you where you are—but I won’t let you stay there. With warmth and candor, I invite you to think more expansively and challenge your limiting beliefs. I know you are capable of depth, courage, and transformation.
#4: Self-honoring, not self-improving.
You don’t need to improve yourself. You need permission to listen to the self that’s dying to break free. We help you strip away external pressures and get inspired to live in a way that’s aligned with who you are.
My Credential & Training
I hold a Professional Certified Coach credential from the International Coaching Federation (ICF). ICF-credentialed coaches meet stringent requirements for education, coaching experience, and adherence to the ICF Code of Ethics.
I was trained as a coach at Erickson Coaching International, Winner of the 2024 ICF Impact Award for Distinguished Global Coaching Education Provider.
Frequently Asked Questions
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I host private coaching sessions on Tuesdays, Wednesdays, and Thursdays from 11am—3pm 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.