The first time I spoke with Steve Schlafman about Downshift, I knew I was on the brink of something big.
In my 10 years as CEO and my 4 years as a coach, I’ve witnessed the escalating amounts of anxiety, depression, and loneliness that grip modern society. I’ve seen it in other founders to levels that make people sick. I got sick after selling my company, I believe in part due to deeply accumulated stress. I’m witnessing the “Anxiety Generation” be gobbled up by technology and fail to connect with the earth right under their toes. I saw myself use work like alcohol, to numb the pain and desire to feel worthy.
I can’t help but see unadulterated speed as a partner-in-crime to declining mental health. We use the “cult of busy” to paper over deep, unaddressed pain. Slowing down isn’t just a practice; it’s a revolutionary act in a world obsessed with speed. And I’m seeing others across various industries start to question complexity and busyness and seek out presence practices like yoga and meditation to slow down. There’s a culture shift beginning, but there’s a gaping hole in slower lifestyles that the Western person can easily adopt. Navigating entrepreneurial transitions often involves not just scaling businesses but also understanding when to decelerate for mental and emotional health.
So when my friend and fellow coach Derek Haswell offered to introduce me to Steve about his search for a co-facilitator for Downshift, I was intrigued. I had heard about Steve through our overlapping circles, and I’d read about the beta launch of the first Downshift cohort. Downshift is a “decelerator” program that helps high achievers slow down, reflect, and transition to what’s next in a community of peers.
It reminded me of my own lonely, scary path of transition after I sold Chewse in 2020. I processed it alone on a beach in Hawai’i. The angst, the regret, the self-doubt, the guilt—it all swirled in me as I tried to release it in the ocean. Nature was a beautiful partner, but I also longed for others who understood what I was going through. Navigating entrepreneurial transitions during that time was like feeling my way through the dark. I ended up leaving several founder communities because I didn’t feel they were in the same phase as me. They were building, I was demolishing. The Downshift community sounded like what I would’ve wanted during that uncertain, dark time.
So I took the intro, and as I drafted up an email with an overview of my background, it hit me: I might be an incredible fit for this. I’ve spent the last 7 years studying philosophies, techniques, and modalities that utilize a core state of being to unlock change: slowness. I even moved to Hawai’i to immerse myself in a slower, grounded culture. I got more excited, and that email basically wrote itself as I detailed my journey with deceleration.
I was eager about our first call. The founder ego in me chafed at this—since when did I apply to a job?! But I gently set that aside to hear more about Steve’s vision for Downshift. Steve had been through his own journey with hustle culture, having been a Partner at a multi-billion-dollar VC firm, only to realize he wasn’t happy. The fast-paced lifestyle left him physically and emotionally drained, and he realized he needed a change. So he left and became a coach. I feel a kinship with his story, though from the founder’s side of the table. Our conversation centered around navigating entrepreneurial transitions and how Downshift could be a beacon for those facing similar crossroads.
He made it clear that he was looking for a co-creator in this process, not a supporter of him as the cult personality. My founder ego reared its head with interest. I had the chance to build and operate again, in a space that deeply aligned with my emerging interests in human transformation. I was doomed from the first call 🙂
Steve is a huge reason why I’m joining. I’m eager to work alongside a team again. Being a coach is tremendously rewarding, but I don’t get to collaborate with other coaches at the level that I get to collaborate as an operator. But just filling that hole with anyone wouldn’t draw me to a new project. Steve, in particular, is that draw. He’s thoughtful, earnest, and despite being a former VC, he’s action-biased (sorry VCs!). We share a similar coaching language, but we have the hearts of operators. And I’m already learning so much from his coaching experience.
Shout-out to my new colleagues, David Spinks and Matt Yao, who I’m eager to work alongside. As fate has it, I was assigned to David as a 500 Startups mentor for his food startup 10+ years ago. I love how these early threads are weaving a tapestry of our parallel paths from operator to coach and back again.
Am I Enough?
The decision to join Downshift required me to confront my own fears about not being enough. I guess that fear doesn’t go away easily! I’ve only coached for 4 years, and I have so much to hone in on with my craft. I decided to take the leap of vulnerability and tell him, “I’m not as experienced a coach as you. Am I the right person for this vision?”
I’m not discounting my skills as a coach. I have an innate curiosity, intuition, and an emerging set of skills that I use to help many clients transform. But that insidious question reared up: was I enough to co-lead a coaching container?
And that’s when he got real and said that he was looking for operator DNA because he hadn’t operated before. The melody of our song harmonized for me in that moment: the mutual exchange of skills, ideas, and inspiration came to life. I started to see the blend of operator and coach, how we could reach across the aisle and uplift each other—while allowing our zones of genius to be the core of what we offer to our Downshifters. Navigating entrepreneurial transitions with someone who complements your strengths and challenges your weaknesses is a game-changer.
My Own Transition to Operator-Coach
Joining a program dedicated to transition requires me to acknowledge my own transition. I wrote a few weeks ago about starting a new business—which, ironically, I was going to incorporate this week. It’s a product dedicated to helping high achievers in fast-paced life slow down with a daily morning ritual. Oddly, it has the same mission as Downshift, but in a caffeinated format.
I was at a fork in the road: CPG or Human Transformation? I worried I was choosing coaching over operating and that I would be letting go of my founder skillset. But I’ve come to realize that by joining the Downshift team, I’m still engaging as an operator but in a space that is more directly aimed at slowing people down. It’s not OR, it’s AND.
I’m pressing the pause button on my CPG brand. To stay in alignment with my own philosophy of simplicity as a path to freedom. It’s not easy to pause something I’m excited about, but this is part of my personal curriculum in slowing down and enjoying my life and work. Navigating entrepreneurial transitions is often about making tough choices, and this is one of those moments for me.
I guess I’m a free agent for the Universe, and it’s calling me to help people slow down, go inwards, and align with their most authentic selves. Looking back, Chewse challenged the cultural zeitgeist of Silicon Valley by mirroring my authentic style of vulnerability and love. My coaching practice (which will continue alongside Downshift) challenges founders to lean into their authentic leadership style and externalize it as their culture. And now I join Downshift to challenge the idea of constant acceleration by supporting leaders in slowing down to find true alignment in their lives.
As I enter my mid-30s, I have enough dots to draw a fresh line of what my calling is in this lifetime. It’s a strange, jagged path to get here. And Steve and I are clear that this collaboration is an experiment to see how we work together. Like so much of my new approach to life, I’m embracing the emergent path instead of gripping to a certain plan. It gives us more space to play, make mistakes, and dream together. I can’t wait to share what emerges with you all!
Join Our October Cohort ❤️
Applications are open for our October cohort and we’re hosting a Q&A on Friday, 9/6 with the sign-up here.
We kick off in beautiful Upstate New York for our 3-day in-person retreat to kick off the experience. We then continue the journey virtually with online workshops geared towards a curriculum and experiences to help navigate the uncertainty of transition. Navigating entrepreneurial transitions is at the heart of what we do, and this cohort is designed to support you through it.
Please don’t hesitate to reach out if you have any questions. I feel lucky to share this experience with you!
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