Steve Schlafman

I was leaving the startup I’d founded after 13 years and needed help navigating two things: how to leave well, and how to figure out what came next. Working with Steve helped me recast how I thought about both. He helped me visualize what success could look like and move forward with confidence, even into the ambiguity. My transition out ended up feeling like the best case scenario. I’m now letting the next chapter emerge without needing to know exactly what it will be. Steve helped me be intentional through one of the most significant passages of my life. I’m deeply grateful.

Working with Steve helped me pursue a new chapter I didn’t know how to begin. He gave me permission to explore, pushed me to look honestly at myself, and stayed with me through the uncertainty. What surprised me most was that the work went far beyond my career. I came out the other side with a sense of security and authenticity I hadn’t expected to find.

I worked with Steve for several years, and he was a profound support for me through a period of transition. Our work together was deeply meaningful to me as I navigated my own relationship to work and ambition. Steve brings an incredible amount of perspective, integrity, and genuine care for me as a human which shows in every interaction and the presence he brought to our work together. Our work focused largely on slowing down and tuning in to what I actually care about, and over the years he helped me make numerous decisions that made space for what I cared about and also felt aligned with how I want to care for myself and the people around me. I trust Steve’s guidance with the things that matter across work and life and would highly recommend working with him.

Steve has helped me through two critical career junctions. Both times he helped me identify the key decisions I needed to make, clarified what was essential, simplified what felt overwhelming, and guided me to a great outcome. He brings a rare combination of coaching skill, domain expertise, and real life experience. There aren’t many people I’d trust with that twice.

For me, Steve was a catalyst. When we started working together, I was clear on what I wanted, but the path toward it was murky. He asked sharp, clarifying questions that made me see my situation differently. None of it felt cookie-cutter. It was clear he was deeply listening, picking up on things I hadn’t noticed, and reflecting them back in a way that helped me find my footing. That’s exactly what I needed. And then, when I no longer needed a catalyst, he suggested we end our work together. What more could you ask for? Hire him.

Steve has helped me through one of the hardest stretches of my life and career. I had just stepped away from Equals, the company I co-founded, and found myself in a deep transition, professionally and personally. Steve helped me build new ground beneath me, rooted in who I actually am and what I want this next chapter to be. Part of that has been unexpected: giving myself permission to explore my creative and artistic side in ways I’d long set aside. One of my favorite parts of working together is the detailed follow-ups after every session. That beautiful writing you see on Steve’s site? You get it in your inbox, personalized for you. It helps me integrate the work and stay connected between sessions.

I came to Steve burned out. I was transitioning from researcher to leading a large organization, and the patterns and beliefs that had made me successful were suddenly hindering me. I sensed I needed to change how I worked and led, but I couldn’t see it clearly at the time. Steve helped me slow down and look honestly at the old patterns and stories I was telling myself. What emerged was a new way of working and leading, rooted in clarity and self-understanding rather than pure effort. I continue to work with Steve because the journey towards clarity and growth is a lifelong process.

Working with Steve during a pivotal moment in my career was one of the greatest gifts I’ve received. I was navigating the emotional and strategic complexities of transitioning out of a hypergrowth startup, and Steve created a space where I could reflect, reset, and reimagine what was next. He gave me tools I didn’t even know I needed. Practical, grounding, aligned with who I actually am. That work laid the foundation for what came next. I’ve since built a new company that feels alive and true to myself. Something I couldn’t have envisioned back then.

Steve is a rare combination: someone who deeply understands the startup game and is a genuinely skilled, empathetic coach. That pairing is hard to find. One moment stands out. I was running Happier and facing a major pivot. Keep going as we were, or press go on a total reset. Steve cut through all my hedging with one reflection: ’Do you want a zombie company?’ That question, delivered at exactly the right moment with deep care, is what makes Steve exceptional.

Steve has been an essential partner during one of the more uncertain periods of my career. When I was sitting with big questions about direction, purpose, and where to focus my energy, he helped me get clear on what actually matters. I always leave our conversations feeling grounded and ready to act. I highly recommend Steve to anyone facing a real crossroads.

I was lucky to connect with Steve at a pivotal moment in my career. I had just left a job I’d had for seven years and found myself in the abyss, that weird but rich liminal space before the new thing emerges. Steve and his community at Downshift provided generous, fertile ground and the right tools to lean into that uncertainty. I will always think of him when I hit moments of transition. I’m lucky to have him in my corner.

Steve helped me navigate a tumultuous period where I shut down one company, went through a real process of discovery about what I wanted next, and landed in a genuinely good place. Having him as a thought partner on that journey made all the difference. I highly recommend Steve to anyone going through a period of transition.

I was navigating a major career transition during one of the most challenging personal periods of my life, and working with Steve was invaluable. He helped me clarify my vision and values, explore a wide range of paths, and ultimately make a decision that changed things for me and my family. I’ve told my closest friends and colleagues: having him focused on success during a pivotal moment made all the difference.

Steve brought me on a journey deeper into myself. My identity, my assumptions, my fears and desires. He helped me break through paralysis and find the agency to define what success actually looks like for me. And that was just our first session. Now Steve is my continued partner on this journey. I feel clear-minded, open, and at peace. I’ve started my own coaching practice and feel more in harmony with my work than ever before.

When I came to Steve, we had just sunset our first product after two years of sweat & tears. We had raised a large seed round and set out to build something ambitious, but it wasn’t working, and it took a toll on me and the team. I didn’t know how to lead through the uncertainty. Steve helped me learn to sit inside the ambiguity rather than fight it. Step by step, something shifted. I became more creative, more grounded, and more able to access my intuition. We found our footing and we’re now off to the races. I’m still working with Steve because the journey of building a company and showing up as a great leader for my team doesn’t end. There’s no one I’d trust more for that kind of work.

When I first met Steve, I was in a really tough spot. I felt lost and didn’t know where to turn. I was stuck at my startup but didn’t know what else to do, so I stayed. After a few years of grinding, I burned out and lost the wonder and hunger that once fueled me. I was worried I might never find it again. Today, I feel secure in my work and grounded in my ambition. I’m energized and inspired in a way I didn’t think was possible anymore. Having Steve in my corner made all the difference.

After eighteen years at Goldman, I co-founded Pinegrove, something entirely new building a team and business plan from the ground up. Steve helped me step into that uncertainty with clarity and conviction. He sharpened how I thought about the transition, helped me access what I already knew, and supported me in growing into the founder, investor, and leader this new chapter required. I’m still working with Steve today. Creating and scaling a business keeps demanding new versions of yourself. He’s been an essential partner in that process.

Steve is truly an N of 1. I haven’t met another coach who combines an acute business sense with a holistic worldview. He came into my life while I was in the middle of a big business build and an equally big shift in my own identity. And over 18 months of working together, I improved both my business performance and my ability to balance home life. If you’re an ambitious person navigating business + life changes, Steve’s the kind of guide you’d be lucky to have as your co pilot.

I built The Big Quiet into a global movement, led mass meditations for thousands, and went on tour with Oprah, and then I had to figure out what came next in the wake of COVID. That kind of transition, stepping away from something you built and opening to what wants to emerge, is harder than it looks from the outside. Steve helped me complete that chapter with intention and care. He created space to grieve what was ending and get honest about what I actually wanted. What emerged was a deeper commitment to speaking and coaching, work that feels deeply aligned and alive with where I am in my life. He’s the person I send the people closest to me when they’re navigating a major transition.

Steve had a meaningful impact on me during an important chapter of my life. Working with him helped me slow down, become more self-aware, and start noticing the patterns that were shaping how I showed up as a founder, partner, and person. He has a way of asking simple questions that quietly open up deeper reflection. Our conversations often stayed with me long after the session ended. I’m grateful for the space he created for honest exploration and growth.

When I came to Steve, I was burnt out and needing to adapt how I led my company. He helped me slow down long enough to find what actually mattered and make refinements to my role. Through our work together I found deeper alignment with my work and a renewed sense of purpose I hadn’t felt in years. What made him uniquely suited to help me was his own journey. The inner work he’s done, his time as a VC, his life as a father. He understood where I was because he’d been in similar terrain himself.

My coaching work with Steve has been one of the most meaningful investments I’ve made in myself. It helped me see the stories I was carrying: that good leadership meant having the answers, moving fast, and fixing what was broken. Over time, that shifted. I’m more present now, more willing to trust the people around me and the process we’re in together. And I’m sustaining it, because I can name unhelpful stories when they show up and come back to what’s actually true. Steve helped me discover a more grounded version of myself.

Working with Steve is one of the greatest decisions I have made in my career. In a season that was filled with a lot of complexity, burnout, and questions, Steve helped me find clarity and rediscover the passion behind my work. Connecting practical advice with deep inner work allowed me to slow down to a speed that helped me find a new level of confidence and conviction in my path. The result of working together was a true level up.

What struck me most was Steve’s ability to hold space for contradiction. He helped me see that slowing down was the pathway to more intentional action. His guidance helped me move from a pattern of constant becoming to moments of simply being, which paradoxically made me more effective in everything I do.

I’ve worked with many coaches and guides over the course of my career. Steve stands out. Through both Downshift and our 1:1 work together, he helped me gain clarity on big life questions I’d been struggling with for years. He also helped me get out of my head and into my body, accessing a deeper intelligence I didn’t know was there. He combines deep business experience with genuine wisdom in a way I haven’t found elsewhere. I’m grateful to have him in my life.

I worked with Steve during a difficult and sensitive professional transition. He helped me get clear on what I actually wanted, define a path forward, and navigate it in a way that honored everyone involved. I’m now on the other side, in a place where there’s far more harmony between my work and my life. I’m grateful to Steve for helping me get there.

A few years ago I reached a point in my career where I lost my bearings and the path upward suddenly became less clear. Steve was my sherpa through that difficult time of transition, helping me focus not on moving upward, but on moving forward in a more sustainable and authentic way. His guidance wasn’t what I initially expected, but it was exactly what I needed.

When I started working with Steve, I was holding on to a situation that had stopped working for me. I couldn’t see it clearly at the time. Steve has a rare ability to help you understand your own blind spots without ever making you feel called out. Through our work together, I found the clarity to step away from my last company and pursue something rooted in impact. It wasn’t an easy decision. But it was the right one. I left with a sense of direction I hadn’t felt in years.

I was at a critical moment and didn’t want to muck it up. Steve challenged the stories I was telling myself, helped me reframe them, and pushed me toward clearer, better decisions. Through that process I found the clarity to leave and launch my own advisory business. It’s what I’d always wanted to pursue. And it was also nice to have someone who saw the good in me and brought it to the surface, even when I wasn’t always ready to accept it.

When I started working with Steve, I was burnt out and unsure if I was still on the right path. What made him different was his lived experience and grounded empathy. He created space to slow down and listen for what had been buried. What I was feeling wasn’t falling apart. It was a signal I wasn’t living the life I actually wanted. Steve helped me see that, sit with it, and act on it, without rushing or abandoning what I’d built. Today, I’m moving forward with greater joy, agency, and calm. He helped me come home to myself.

Steve brings a rare mix of lived experience, intellectual depth, and emotional presence that creates space for meaningful change. He understands both the drive for success and the inner unrest that often comes with it, which made me feel truly seen. What makes him special is that he’s deep in the work himself, which keeps his support grounded and sincere. His commitment to this path feels more like a calling than a profession. Watching him step into a new chapter without needing it all mapped out has helped me rethink how I approach my own ’second mountain.’ He’s someone who’s walking the path with you.