Navigating Transitions with Steve Schlafman

Jason Jacobs (0:00)

On today's episode of The Next Next, I'm pleased to bring on Steve Schlafman. Steve is the founder of Downshift, a professional transition coach who's based in New York and guides executives and founders through intentional transitions and recovery from burnout. Steve also writes Where the Road Bends, which is a newsletter exploring personal evolutions and life transitions. Now, I've known Steve a long time, back even before the days that he was a venture capitalist. He went on to be a VC at several top firms in New York, and then he went on a journey of his own, where he learned how to be an executive coach. He thought about combining coaching and investing in raising a fund that offered coaching as a key differentiator. And now he's focused on Downshift, where he's specifically working with founders and other high performers who have been running hard for a long time, who are in the process of transitioning out. And rather than just blindly running hard straight into the next thing, they're longing to take a step back to take stock, to ask themselves what are the key criteria that's going to make me happiest personally and professionally in this next chapter, because we don't have that many chapters in life, and especially as you get older, you want to make them count. We have a great discussion in this episode about Steve's journey to doing the work that he does, about what types of clients tend to get the most value from his services. We also talk about what types of transitions that are going through, what some of their challenges are, and what some tips are for people that are going through these kinds of transitions to do so effectively. We have a great discussion in this episode and a timely one for me, and I hope you enjoy it. But before we get started, I'm Jason Jacobs, and this is The Next Next. It's not really a show, it's more of a learning journey to explore how founders can build ambitious companies while being present for family and not compromising flexibility and control. And also how emerging AI tools can assist with that. Each week, we bring on guests who are at the tip of the spear on redefining how ambitious companies get built. And selfishly, the goal is for this to help me better understand how to do that myself while bringing all of you along for the ride. Not sure where this is going to go, but it's going to be fun.

Okay, Steve Schlafman, welcome to the show.

Steve Schlafman (2:29)

Thanks, Jason. So stoked to be on.

Jason Jacobs (2:33)

Yeah, it's kind of interesting because I think, well, one, I've known you a long time. Two, we're, you know, of a similar age and demographic, midlife, you know, entrepreneurs, flash investors. And so some commonality there. Three, I think some of the work you're doing now with Downshift in terms of helping ambitious people, you know, unwind from intense periods and figure out what's left and where to go and how to proceed. And I don't want to put words in your mouth, but that's certainly relevant to some of the stuff I'm sorting through. And then I think the last piece is just that I was actually a client of yours from a coaching standpoint when I was kind of unwinding from how I've been spending my time operationally over the last six years. And so you've kind of had a front row seat, took some of the transition that I've been going through as well. So just psych to have you on and to catch up in public, I guess.

Steve Schlafman (3:27)

Yeah, it's a real honor. It's rare for me to want to jump on to a podcast and get going. But this one, The Next Next, I really feel the energy and the spirit coming through you. And yeah, I'm just I'm thrilled to see what unfolds in this next journey for you.

Jason Jacobs (3:43)

Well, to kick things off, Steve, maybe for those that don't know you as well as I do, talk about the work you're doing now and what led you to the work that you're doing now.

Steve Schlafman (3:53)

Yeah. And I want to put a pin on that for a second. And if you had asked me that question a decade ago, I would have said, I'm a VC and this is what I do and this is who I am in that context. And 10 years later, I think it's really important to note that I see myself as much more than just a professional. Certainly, I'm the founder of a company called Downshift. Yes, I'm a coach and a guide that helps ambitious professionals navigate transition with a lot of intentionality. And at the same time, I'm appreciating that I am so much more than that.