Individualized Coaching

Our 1:1 engagements help you slow down, deepen self-connection, and navigate your transition with intention, clarity and courage.

“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.”

—Josh Forman, Founder & Executive

I offer a highly specialized and integrated approach to coaching that combines elements of executive coaching, career coaching, and life coaching. Rather than focusing solely on just the professional aspects of transition, I take a whole-person approach, recognizing that personal and professional aspects of life are intertwined. This is especially true for those approaching or navigating the midlife passage.

Personalized & Holistic

Everyone and their journeys are unique, which is why I invest the time to understand where you are in your life, career, and transition process. By providing personalized support and guidance that meets you where you are, we co-create a plan to help you move forward with confidence and clarity, no matter what inner and outer obstacles are in your way.

Throughout the engagement, I help you mine your history for insights, assess your current situation, clarify your values, sharpen your vision, and create a comprehensive action plan that takes into account all dimensions of your life, such as family, finances, health and spirituality. I also work with you to overcome any obstacles or challenges that may arise during the transition process. This can include helping you address issues related to self-doubt, fear of change, or any other emotional or mental blocks that may be preventing you from moving forward.

During onboarding, we explore who you are as a multi-dimensional human and identify your goals, both as an individual and professional. Each time we meet, we will focus on your desired outcomes, explore your emotional context, surface what’s most important, uncover any roadblocks, and establish actionable practices and next steps. Everything we discuss is always confidential.

Our focus is not just to help you make a successful transition to your next calling, but to help you create a balanced, fulfilling, and purpose-driven life. This is accomplished through a combination of coaching, teaching, assessments, exercises, and practices. Recognizing that every individual is unique, there is no one-size-fits-all engagement at Downshift. Each one is tailored to align with your specific history, life circumstances, values, personality, and goals.

In addition, I offer specialized services designed to meet the unique challenges and aspirations of high performers during pivotal transitions. These include burnout recovery protocols, think week planning, sabbatical design and digital detoxes.

We’re Partners

I view coaching as a creative partnership. That’s why I consider you a “partner” instead of a “client.”  Together alongside you, I aspire to create a symbiotic relationship where we grow, learn, and thrive together. Every relationship begins with a foundation of mutual trust, respect and creative expression. Like in any relationship, we're going to bump up against our edges and hopefully go beyond them together.

Like any true partnership, I’m available whenever you need me over the phone, by text, or by email. You can think of me as an extension of your inner circle and an integral part of your support team. If you happen to visit or live in New York City, I love meeting up IRL for sessions, meals, and walks.

What I Bring

I bring my full self to the coaching relationship. Yes, I'm a trained and ICF-certified Coach but I'm also an advisor, teacher, meditator, father, former venture capitalist, AA-sponsor, and more. You're getting 40 years of lived experience, 10 years as an operator, 10 years as an investor, and 6 years as a coach. Most of the time, I show up wearing my coaching hat. Occasionally, I'll put on my advisor hat if that's what you want or need. I've helped dozens of CEOs, VCs and leaders both personally and professionally on a range of topics. I’ve also navigated my own complex transitions.

Throughout an engagement, I utilize a range of frameworks and approaches, including: Internal Family Systems, Conscious Leadership, Mindfulness-Based Stress Reduction, Presence-Based Coaching, Acceptance Commitment Therapy, Appreciative Inquiry, Powerful Questioning, Visioning, and the Enneagram. I also believe in the three centers of intelligence – the head, heart, and body – and help you tap into their wisdom to make more aligned decisions. 

By providing a safe and supportive environment, my goal is to empower you to help you cultivate the self-awareness, clarity, and confidence required to navigate the next chapter of your life.

Partner Success Stories

  • “Working with Steve helped me to pursue a new chapter that is truly energizing. He helped me find a way to start, offered frameworks for exploration, and challenged me to deepen my self-awareness. The process resulted in my finding a sense of security and authenticity, and, surprisingly, discovering dimensions in my life that went beyond my career.”

    Jess Hunt

  • “Steve helped me navigate a very tumultuous period where I shut down one company, went through the process of discovery on what I wanted to do next, and got me to an incredible place. Having him as a thought partner on the journey was an incredible unlock, and I highly recommend Steve to anyone going through a period of transition.”

    Neil Parikh

  • “Through a series of deep discussions, Steve helped me shape my vision for my life and career. We then evaluated a wide range of offers together, and he was instrumental in helping me make a transformational decision for myself and my family. As I’ve shared with my closest friends and colleagues, I found it invaluable to have Coach Steve on my side.”

    Dan Parham

  • “Steve has been a catalyst. When we started working together, I was clear on what I wanted but the journey towards it was murky. He asked me all the clarifying questions and probed in ways that made me look at my situation differently. It was obvious that he deeply listened, picked up on things that I didn't, and helped me re-orient.”

    Saira Jesani

  • “Today I feel very secure about my work and my sense of ambition — my quality of life has turned around in a big 180. I feel energized and inspired again, and I am confident that I have a path forward in my career for a long time ahead. Having Steve in my corner was a superpower, and there was no chance that I could have done it without him.”

    Jesse Chand

  • “Instead of looking for outside validation, Steve brought me on a journey deeper into myself - my identity, my assumptions, my fears and desires… to break down the engrained societal constructs, break through the paralysis, and find the agency to explore what defining success looks like for me. And that was just our first session!”

    Quinn Fitzgerald

  • “Steve has been an essential partner in my professional journey over the last year, guiding me to figure out what really matters and create a life that aIigns with those values. I always leave our conversations feeling energized and inspired. I highly recommend Steve to anyone looking to get clarity on their path forward.”

    Dan Pfeiffer

  • “When I met Steve I was at a critical inflection point that I didn't want to muck up. Thankfully, I had someone to challenge the stories I was telling myself and help me reframe them in order to make better quality decisions about my future. I’m finally building the business I’ve dreamed about for years. Steve’s support has been invaluable.”

    Jon Mackey

 FAQs

  • My ideal partner is a high performer who has tasted success in their career and is now seeking to write their next chapter.

    Designed for diverse professionals who’ve tasted success or reached the top, yet long for deeper significance, our Downshifters include:

    • Founders recovering from their last startup

    • Executives searching for fulfillment beyond title

    • Athletes leaving the game behind

    • Creators seeking a new stage

    • Investors pondering what constitutes a truly meaningful life

    I look for partners who are self-aware, deeply curious, patient, and committed to the process. You are ready mentally and emotionally to do the inner and outer work required to navigate a transition. 

  • There are no long-term contracts, obligations, or large upfront payments. All I ask for is a mental and energetic commitment of at least three months. Most partners start to feel the positive effects of our sessions within the first month, but long-term progress largely depends on your commitment and attitude. My hope is this initial commitment blossoms into a successful long-term relationship.

  • I charge a monthly retainer rather than a "per session" fee. My average monthly rate is currently $2,500. That said, I never let money get in the way and offer scholarships if there's a strong fit and desire to work together. The amount I charge is largely dependent upon your ability to pay. I believe it should be enough where you feel like you’re making a significant investment in yourself, but not so much that it causes stress and resentment. 

  • I purposefully keep the practice small for the time being. I usually work with 12-14 coaching partners at once.  That's why I view our initial conversations as a fit process rather than a sales process. And I expect for you to fully commit to the process and relationship.

  • I don't subscribe to a "one-sized fits all" or templatized approach to coaching. Context matters and is critical. While I draw on frameworks, case studies and other resources when necessary, I believe you are inherently wise and resourceful to determine the best path forward. My immediate goal is to help you develop novel perspectives and approaches rather than providing just advice or answers. I tailor the approach based on your situation, challenges, experiences, cultural norms, values and knowledge.

  • I typically meet with each "coaching partner" twice per month. You can also text or email me at your convenience. I also make myself available for "spot coaching" if you need support in between sessions. Remember, this is a partnership. You can think of me as an extension of your personal board of directors. I'm available when you need me, not just when we have time scheduled.

  • Coaching sessions typically last an hour, but sometimes go longer depending on your objectives and how much we're able to achieve in the allotted time.

  • I typically coach Monday through Thursday from 11am ET to 5pm ET. That said, I have flexibility if we need to work around your schedule, move things around or talk in a moments notice.

  • I send an email 48 hours in advance with prompts for you to contemplate and complete. This allows us to hit the ground running and make the most of our time together. Here are the questions I typically send in advance:

    How would you rate last week from 1-10? Why?

    What progress have you made since our last 1-1 session? Any big wins?

    What have you learned?

    What is your top priority right now? Why is it most important?

    What are the 1-3 topics you would like to cover this week?

  • A typical session has four phases. The first phase is a quick check in. This provides each of us an opportunity to share how we're showing up energetically and emotionally. After our check ins, we spend five minutes highlighting any key events, milestones and/or learnings since our last session. We then dive into the main topic(s) which takes the bulk of our time. Finally, we spend the last five minutes summarizing key take aways and next steps.

  • I send an email with detailed notes typically 12-48 hours after a session. These notes are structured in three sections — follow ups, your reflections and my reflections. Follow ups include specific next steps and timing. Your reflections include any notable quotes and questions that you surfaced. My reflections often include general thoughts, reframes, and questions for reflection. I maintain a coaching log in Notion so you can access the notes on demand and track our progress.

  • There are countless ways you can leverage me when we're not together. As I indicated above, you can always text or email me at your convenience. I also share curated books, articles and resources depending on your learning objectives. Additionally, I review reflections, emails, decks or any other materials created along the way. If you're not sure, just ask. I strive to be an expansion of your inner circle and active member of your personal board of directors. I will always aim to have a 24 hour response time. That said, if you have an emergency or a time sensitive deadline, I always encourage you to text me.

  • This varies from person to person. A number of partners have felt and seen the benefits during our very first session. That said, I would expect to see outcomes and results in one or two months. We should always know what success looks like and whether we are moving closer towards whatever that might be.