Where you meet yourself more honestly.
Drew is a Therapist. Writer. Thought Leader. Guiding people through transition, identity shifts, purpose, and the work beneath the surface.
ABOUT DREW
Hey everybody. Here’s the stats: M.A., LPC, LMHC (I’m licensed in NJ & NY). But the real work has always been helping people face themselves honestly enough to actually change. For more than two decades, I’ve worked with individuals in seasons of transition—grief, reinvention, ambition, heartbreak, identity shifts, relational complexity, and the strange middle chapters where what once worked no longer does. My work is rooted in the belief that transformation rarely comes from avoiding life’s harder questions, but from learning how to face them directly. And, therapeutically, I tend to be direct, conversational and interactive—with strength and tenderness.
I specialize in helping people confront the internal thresholds that shape us: the deaths of old ways, the pressure of purpose, the cost of growth, and the challenge of building a life that feels honest.
My approach blends psychological depth, existential reflection, humor, art, and practical insight. I care deeply about helping people not just feel better, but become more awake—more honest about who they are, what they want, take risks, and discover what needs to change.
Through therapy, writing, retreats, and group experiences, I create spaces where people can examine what’s no longer serving them and move toward something more meaningful.
Your guide to alignment
Work with Drew
I offer individual therapy and consultation first and foremost. It’s my first love—the work I experience as most intimate, consistent, and deeply human. I also specialize in the Enneagram, and for those wanting to focus more intentionally on that work, I offer typing sessions, coaching, and long-form exploration using the system as a tool for self-awareness, personal growth, and relational understanding.
In addition to therapy, each of my books includes accompanying coursework designed to bring the material into lived experience. These are currently year-long, curated community groups that meet virtually over twelve months. Many participants continue those relationships long after the course ends, gathering in New York City for yearly reunions to deepen the bonds they’ve built together. The work is reflective, connective, and deeply immersive—something I care about enough that I’m building a retreat center in Baja, Mexico to expand these experiences into in-person weeklong retreats and gatherings beginning in 2027.
You can explore more about that vision below. Either way, my work is ultimately about helping people understand themselves more honestly and navigate the deeper questions that tend to emerge during life’s more demanding, transitional, and transformative seasons.
ENNEAGRAM AND DEPTH WORK
A significant part of my work has been devoted to the Enneagram—not simply as a personality system, but as a powerful framework for self-awareness, transformation, relationships, and understanding the deeper motivations that shape our lives.
Drew’s specialties
High functioning men
Career & purpose
Life groups
Enneagram personality typing
Grief, loss & transition
Relationships & boundaries
Midlife transitions, aging & existential themes
Drew’s Books
THE COFFIN CLUB: A Practice. A Reckoning. A Resurrection.
I’m also the creator of The Coffin Club, a book, a course, a body of work, community, and philosophy built around a simple but demanding premise: when we engage mortality, endings, and impermanence more consciously, we often live more fully.
Through sharp writing, dark humor, and Obituary Assignments designed to make you uncomfortable enough to change, this book doesn’t just ask you to think about mortality—it pushes you to train for it. To practice the small deaths and the big ones. To strip away distractions and find out what actually matters before the final cut.
F—IT, MY 40s
…is a sharp, honest, and darkly funny exploration of midlife—not as crisis, but as confrontation. Part memoir, part cultural reflection, and part survival guide for the weighted middle, the book examines what happens when youth’s illusions begin to fade and deeper questions about identity, purpose, relationships, ambition, sex, friendship, grief, and mortality become harder to avoid. Through personal stories, psychological insight, and unflinching self-examination, Drew explores what it means to live inside the “Depth Curve” of life—where happiness may dip, but meaning has the potential to deepen. This isn’t a guide to getting your life together. It’s an invitation to stop pretending, face what’s real, and build a second half of life that actually fits.
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LAUNCHING 2027Mexico Retreat Center: Casa Caracara
CASA CARACARA
A retreat center in Baja California Sur, Mexico
Casa Caracara is a retreat center in the making, rooted in the wild beauty of Baja Sur and designed as a space for reflection, connection, and return. Created by Drew as an extension of his work in transformation, community, and depth, Casa Caracara is more than a destination—it’s an environment built for people seeking perspective in the midst of transition. Blending striking landscape, intentional design, meaningful conversation, and restorative experiences, the center will host retreats centered on purpose, reinvention, friendship, creativity, and the courage to live more fully. Part sanctuary, part gathering ground, Casa Caracara is being built for those who need space not to escape their lives—but to re-enter them with greater clarity, vitality, and truth.
FAQs
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Sessions aren’t overly structured, but they’re not passive either.
We talk. We slow things down. We pay attention to what’s happening underneath what you’re saying—patterns, reactions, places where something doesn’t quite line up.
Sometimes it’s direct. Sometimes more reflective.
At times it can be uncomfortable—but not in a forced way. More in the sense of staying with something long enough that it starts to open.This isn’t about quick fixes or surface-level insight.
It’s about understanding yourself more honestly—and from there, making changes that actually hold.
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Some people sit across from me in the West Village.
Most don’t.I work with people both in person in New York City and virtually across the U.S., Canada, and abroad.
Virtual sessions are straightforward and tend to become just as natural as being in the room. For many people, they allow for more consistency, flexibility, and access—especially during periods of transition, travel or change.
If you’ve found me through my writing or YouTube, this is often how we end up working together.
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Fees
I have a standard fee for sessions, and most of my work is built around that.
That said, I try to leave some room where I can.
If something about this work feels important to you, but the cost feels like a stretch, it’s still worth reaching out. In some cases I’m able to adjust my fee, or find a way to make it workable.
I’m honored by you’re interest in working with me and want to honor you by trying to make this work.
Insurance
I’m an out-of-network provider, which means I don’t bill insurance directly.
That said, many clients still receive partial reimbursement through their plans. If you have out-of-network benefits, insurance will often cover a meaningful portion of the cost—sometimes more than people expect.
The process is straightforward:
you pay for sessions directly
I provide you with a receipt (superbill)
you submit it for reimbursement
Most plans reimburse somewhere in the range of 60–80%, depending on your coverage.
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Call or Text: 908-451-5592
Email: Drew@DrewNewkirk.commy instagram, TikTok and YouTube can be found below by clicking on those icons, give a follow.