About me.

👋 Hey there, I'm Steve Schlafman.

Just about everyone calls me Schlaf (pronounced shh-laugh).

As an ICF-certified executive coach, I guide high performers through transitions, share insights as a writer and podcaster, and impart knowledge as an educator. Presently, I lead Downshift, the pioneering decelerator program designed for high performers in flux. I also write "Where the Road Bends," a newsletter that delves into personal evolutions and life's pivotal shifts. When I'm not coaching and creating, I tinker on side projects such as The Ultimate Annual Review.

Outside of work, I love to spend time with my family, meditate, read, ride my bike in the mountains, cook, watch the Patriots, listen to music, build complex Lego sets, and get lost in nature.

I split my time between Manhattan and the Catskills.

⛰️My Transition Journey

“Everyone has his own specific vocation or mission in life; everyone must carry out a concrete assignment that demands fulfillment. Therein he cannot be replaced, nor can his life be repeated. Thus, everyone's task is unique as is his specific opportunity to implement it.”
—Viktor Frankl

In January 2017, at the ripe age of 37 and just a year after I got sober, I made Partner at the multi-billion dollar VC firm I had given my life to. Despite climbing to the top of the mountain, something was still missing deep inside me. Everything I worked so hard to achieve had finally arrived, but I felt no different.

Despite the money, power, and status that VC provided, the job and lifestyle left me burnt out, and unfulfilled. My ego craved these benefits but my soul yearned for more. I realized those alone weren’t enough to bring me happiness and purpose in life. I could no longer run around New York City and pack my schedule with back-to-back-to-back meetings. I was spent physically, emotionally, and spiritually. Deep down inside, I craved a new vocation that was more aligned with what I valued, who I was becoming, and what energized me.

Several months later, I walked into my weekly partner meeting and I resigned without a grand plan. When they asked what my plan was, I told them, “I think I want to become a coach.” That conversation kicked off a five-year transition where I wandered in the wilderness without a compass or a map.

I was initially drawn to coaching because I’ve always loved helping people, and my wife, who founded The Sill, struggled in the early days. I had an unfiltered view into the life and mind of an entrepreneur. I saw her wins, losses, and everything in between. This situation helped me gain a deeper appreciation for entrepreneurs and the inner battles they wage and the sacrifices they make to realize their visions. Through supporting my wife and dozens of founders, I discovered that I could invest in their development as leaders and humans instead of their companies. This energized me and filled me up. I also realized that I crave and value authentic relationships and conversations geared toward helping people evolve.

That’s why I risked everything I had worked so hard for and walked away from investing at the prime of my career. The desire to create a new ambitious life centered around service, balance, and creative expression outweighed the desire for comfort and stability.

Even though coaching was the calling that found me, the process at times was disjoined and disorienting because I held on tightly to what was familiar—including old roles, patterns, beliefs and identities—and didn’t have a clear vision for where I was heading. I took one step forward and two steps back more times than I want to admit. Even though I was coaching full-time and thriving, I didn’t know what direction was north, south, east or west. Despite appearing successful on the outside, I still felt out of alignment and lost.

After sitting still and listening to myself for the better part of 2022, a new vision and mission emerged that was deeply aligned with who I have become—to help high performers in midlife discover and manifest their next calling. In other words, my vocation is to help executives and entrepreneurs navigate work-life transitions so they don’t have to face the wilderness alone like I had to.

I’m now creating the coaching company I wish existed in 2017 when I knew deep down inside investing was no longer for me.

💼 Professional Experience

I’m an ICF-Certified Professional Coach. Since 2010, I have coached, advised, and invested in more than 100 founders and leaders in just about every sector and stage. I’ve received certifications in The 15 Commitments of Conscious Leadership, Coaching for Transformation, Mental Health First Aid, and Tiny Habits. I'm also taken courses on Internal Family Systems (IFS), The Shadow, Nonviolent Communication (NVC), Men's Emotional Leadership (MELT), Neuro-Linguistic Programming (NLP) and the Enneagram.

Prior to becoming a coach, I was a Partner and Principal at top Venture Capital funds in New York City, including Primary Venture Partners, Lerer Hippeau Ventures, and RRE Ventures. Before investing, I held a variety of operating roles at Microsoft, The New England Patriots, Stickybits / Turntable.fm, and Massive Inc. I graduated Summa Cum Laude from Northeastern University with a degree in Business Administration.

📅 My Timeline

Here are the moments, milestones, and accomplishments from my life that have shaped who I have become.