Private Coaching
Chasing success makes life feel hollow. This is a space to rediscover real meaning, purpose, and vitality.
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 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 or longings 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
If this feels familiar, private coaching offers a space to examine the role success has played in your sense of meaning—and begin building a life that feels more fulfilling and alive.
This work isn’t 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.
MY APPROACH
My coaching lives at the intersection of meaning, identity, and life transitions. We help you rebuild a more fulfilling and vibrant life after success has taken up too much space.
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.
From there, we create a customized coaching plan around your goals, and the relationship with success—and with work—you’d actually like to have. We care more about how it feels than how it looks.
My coaching approach is warm, active, and provocative. Sessions blend the depth of existential inquiry—"What makes life meaningful?"— with the practicality of solution-focused coaching: "What can I do about it today?"
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.
“For years I didn’t understand why I felt so empty. Coaching with Hailey helped me realize that even though I was successful, I was completely disconnected from my values of creativity and freedom. It’s no wonder I didn’t feel like myself. Coaching gave me the conviction to stop climbing the corporate ladder. I was able to step back, slow down, and pour my time into the things that fill up my soul. Now, I feel at peace. Thank you, Hailey.”
— Marie
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 or a one-off conversation. Our work unfolds gradually, with space for insight, reflection, and real-world application.
Typically, we meet bi-weekly for 50-minute sessions. Coaching relationships tend to span between 3 and 6 months: long enough for us to explore deeper questions of meaning and identity, while also supporting real shifts in how you live and work.
Coaching is active and collaborative. Sessions are customized based on your coaching plan, draw from a broad well of frameworks and tools, and often end with invitations for what to pay attention to—or experiment with—in the week ahead.
We begin with a conversation to explore whether this work feels like the right fit for you and your needs.
“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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THREE WAYS TO WORK WITH ME:
I offer a few options for working together depending on the level of support you’re seeking:
Private Coaching: 6-Month
Container
My 6-month coaching container is for those who feel that success has taken over more space than they want it to—and trust that something needs to change, even if they’re not sure what. It’s well-suited for moments when your old sense of meaning, identity, and life direction are loosening, but new ones haven’t fully formed yet.
Six months offers enough time to slow down, get clarity about what’s no longer aligned, and experiment thoughtfully with new ways of living and working.
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This 6-month Private Coaching container includes:
12 bi-weekly, 50-minute private coaching sessions (held via Zoom)
Email support between sessions for check-ins or clarifying questions
A coaching workbook offering an optional educational supplement to our sessions (containing journaling prompts, coaching frameworks, and reflection exercises)
Optional action steps and/or experiments between sessions
Optional book, article, and podcast recommendations to support your process
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The standard investment is $479/month for 6 months. This program is currently available at $359/month for 6 months through January 7.
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 wanta 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 via Zoom)
Email support between sessions for check-ins or clarifying questions
A coaching workbook offering an optional educational supplement to our sessions (containing journaling prompts, coaching frameworks, and reflection exercises)
Optional action steps and/or experiments between sessions
Optional book, article, and podcast recommendations to support your process
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The standard investment is $479/month for 6 months. This program is currently available at $359/month for 6 months through January 7.
Private Coaching: 2-Hour
Consultation
My 2-hour consultation is a single, extended session for people who are seeking greater clarity as they stand at a success crossroads: a decision, transition, or internal conflict.
This focused conversation helps you slow down; explore your options through the lens of your meaning, values, and desires; and leave with greater clarity about which path feels most aligned.
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This 2-hour consultation includes:
One 2-hour private coaching consultation (held via Zoom)
Pre- and post-session reflection prompts help you prepare for, and integrate, our session
Optional book, article, and podcast recommendations to support your process
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A one-time payment of $479.
If my work resonates with you, the next step is a conversation.
We begin with a brief call to explore what’s bringing you here, what you’re hoping to gain from coaching, and whether working with me feels like the right support at this moment.
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.
To get the process started, you can submit an interest form here.
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.