The Next Major Wave In Coaching

Hey there! I'm writing from Asheville, North Carolina where I arrived yesterday for a solo "Think Week".

If you're not familiar with the concept, a Think Week is a period of time where you disconnect from your daily routine and immerse yourself in deep thinking and reflection. The concept was popularized by Bill Gates, who used to take two one-week breaks every year to leave behind his regular work routine and think deeply about the future of technology and Microsoft.

I'm excited to spend the next four days with a healthy balance of rest and rumination. Topics I’m actively thinking about include AI and coaching, the evolution of my coaching business, and transition frameworks. I’m also devouring two excellent books—Between Two Kingdoms and The Anatomy of Change. I can’t wait to report back on what I learn, discover, and decide.

This is my third Think Week in six years, and I always walk away with so much energy and clarity for the future. I'm especially grateful for my wife since I have two kids and it's more difficult to get away from my family for solo travel and exploration, which is something I love doing. 

If you’ve taken a Think Week in the past or plan to take one soon, I’d love to hear about your experience or what you’re planning. I also love helping people design their own. You can always contact me here.

Without further ado, here’s the essay—it’s a big one for me, so I hope you enjoy. Have a great weekend!

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I remember when we first met, I was in a really tough spot — I felt lost and didn’t know where to go. I felt stuck at my startup, but it didn’t feel easy to leave because I didn’t know where else to go to. Earlier in my life I had felt so energized and inspired by technology and creativity — I had hoped to dedicate my career and life to it. But after a few steps, I burned out and I lost that feeling — I was worried I might never find it again. That feeling — that hunger — was such a foundational part of my life, and the thought of losing it put me in an identity crisis of sorts.

In my moment of transition, it felt like the stakes were so high — it was one of the most challenging moments of my life. There were so many difficult pieces to navigate — gracefully leaving my company, maintaining my friendships and relationships with my co-founders and investors, doing deep introspective work to determine what would make me truly happy, creating a plan to interview and steer myself towards new opportunities, and actualizing my new future. 

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. I speak about the coaching experience from you to my friends and peers often, and I always highly recommend it. Having you in my corner was a superpower, and there was no chance that I could have done it without you. Looking back today, it feels like I’ve stuck the landing on everything.

I unexpectedly received this heartfelt note from a former client last summer. In addition to moving me deeply, this letter perfectly captures the emotional turmoil that high performers often feel when navigating the complexities of transition and change. It also captures the transformative power of Professional Transition Coaching.

In the past five years, I’ve met dozens of high performers in work and life transitions who express myriad emotions and thoughts that reveal their inner struggles and the desire for something new. This includes C-Level executives at public companies, YC founders who are lost and burnt out, VCs who are afraid to leave the profession, and CEOs of unicorns navigating new life situations such as divorce or parenthood. No one in any profession, regardless of status and rank, is immune to the stirring of the soul, especially in midlife.

These people often describe a sense of going through the motions at work, feeling disconnected from their true selves, and questioning whether they've reached their peak. They may grapple with the conflict between their inner and outer lives or feel their values no longer align with how their life looks. For some, the attraction of a side project or the dream of a fresh start beckons, while others acknowledge they want more, crave a new challenge, or yearn to finally listen to their heart. Amidst this turmoil, they may feel burnt out, drained, or even lost. As they contemplate the possibility of a new calling, they might find themselves torn between conflicting desires or struggle to envision a clear path forward. In essence, these high performers are in the throes of transition, seeking guidance to navigate the uncertainty and discover a path forward. 

I've listened to these stories more times than I can count, and I keep hearing from high performers who have nowhere to turn yet they are craving support.

This refrain reminds me of my own transition, which began six years ago when I resigned as a Partner at RRE Ventures. Through my own experience and these discussions with high performers, it's become clear to me that not only is there a gap in the market, but also a deep need in the world.

Why Now?

Many high performers today are navigating these transitions alone and without direction. They might turn to their friends or family, but they might not feel safe sharing what’s really going on inside of them. Even worse, they might be the recipients of projection and receive bad counsel. In other words, the people we’re closest to may not be equipped to help us. 

These professionals might turn to therapy for guidance. But the interplay between life and career and the specific context of the work environment are not specialties of the average therapist; they may be able to ask helpful questions, but are limited in their ability to untangle decades-long work-life knots. So the struggling professional might look outward to their network or the market, to see what people in their position should do—continuing to look for scripts that are handed down and valued by society but may not apply in any way to their inner needs and desires. Or they talk with an executive recruiter who is hired and paid by an employer to fill a specific role in their company—this isn’t what someone in transition needs. 

Transitions are often chaotic periods with emotional ups and downs, and it can be difficult to decipher what one truly values and wants amidst an inner tug of war.  

The need for Professional Transition Coaching goes well beyond the inner and interpersonal dynamics. Several emerging megatrends are going to reshape the world, amplifying the need for support during times of change. Just last week, Bill Gates wrote that AI is “the most important advance in technology since the graphical user interface.” I believe that we’re going to witness more transformation this decade than we have in the past quarter-century, primarily because AI is an exponential technology.  We stand on the cusp of a new era in computing that will unleash a wave of creativity. It will also revolutionize the way tasks are performed and render many skills and jobs obsolete. New jobs and career tracks will emerge. This shift only emphasizes the increasing importance of guidance and support during life and career transitions. 

(No one is exempt, including me, since AI coaches will proliferate and support us across all dimensions of life. In fact, this is a tidal wave in the coaching industry that’s building momentum in the distance)

As the largest generation alive, millennials are now reaching midlife, with over 70 million of them residing in America alone. However, unlike previous generations, they face unique challenges that make midlife a vastly different experience. With COVID, student loan debt, soaring housing costs, and a volatile job market, millennials are dealing with headwinds that previous generations never encountered. Moreover, many of them are juggling the demands of raising children later in life while caring for aging parents. In many ways, the millennial experience of midlife doesn't measure up to the promises made to them by society. Additionally, many of those who pursued careers in tech were told that their jobs would lead to fulfillment and wealth, yet reaching the summit has left them scratching their heads, feeling empty, and asking, “Is this all there is?’” As a result, many of these people are now asking themselves big questions about what they really want and what they truly value.

The tech industry is currently facing the most volatile times since the dot com crash in 1999. According to Layoffs.fyi, there have been more than 315,000 layoffs since the beginning of 2022. We’re only three months into 2023, and the number of layoffs is already close to surpassing last year's number. To add to this, the NASDAQ is down 18% in the past year, and many unicorns that went public over the past three years have seen their stock prices plummet by 60-80%. Given this valuation reset, many private companies that raised money at nosebleed valuations without commensurate traction will struggle to raise subsequent funding. On top of this, a major banking crisis has shaken the trust and stability in the banking system that underlies our innovation economy. Taken together, this has caused fear and panic, with thousands of workers losing their jobs and many more worried that they may be next. People are scrambling to find ways to protect themselves and their future by investing in themselves and their skills.

Leaders of all kinds are quietly suffering, wanting an experienced and impartial sounding board, yet they're struggling to find it. I read it in their emails and hear it in our discussions. I’ve come to appreciate that it's not that the system has failed them; rather, it's as if the time has come—the universe is itself primed and ready for something new.

What is Professional Transition Coaching?

In the wide world of coaching, the tiny niche of transition coaches help people navigate significant life transitions such as moving to a new city, becoming a parent, navigating divorce, or recovering from a death in the family. Transition coaching has been a small category in the coaching industry for years. It’s so small, in fact, that I couldn’t find any data on the segment. It’s a cousin of life coaching but hasn’t risen to prominence, especially among leaders and within startup and creative communities. Moreover, few executive coaches work with leaders looking for their next direction. When they do, it's often not a specialty and doesn't receive the same attention as their other offerings which drive the bulk of their revenue, such as leadership development. 

As I outlined above, this is an enormous gap in the market, between the needs of a growing number of individuals desperate for guidance and the guidance actually being offered. 

Professional Transition Coaching is the bridge, and I’ve been quietly developing my own philosophy and methodology for a while. Professional Transition Coaching is a highly specialized and integrated approach that helps high performers navigate significant work-life transitions with clarity, confidence, and purpose. It draws on elements from executive coaching, career coaching, and life coaching to create a holistic and personalized experience that addresses the unique challenges and opportunities of each professional.

Given transitions and life itself are complex and chaotic, this approach recognizes that personal and professional aspects of life are intertwined, and that successful transitions require a comprehensive understanding of the individual's unique circumstances, knowledge, behavior patterns, values, and goals.

Unlike traditional executive coaching and leadership development, Professional Transition Coaching considers all aspects of the individual's life, including career history, strengths and limitations, network and relationships, and well-being. By providing personalized support and guidance, the coach co-creates a plan to help the individual move forward with confidence and clarity, no matter what inner and outer obstacles are in their way.

The Professional Transition Coach helps the individual mine their history for clues and insights, assess their current situation, clarify their values, sharpen their vision, and create a comprehensive action plan. The coach also works with the individual to overcome any obstacles or challenges that may arise during the transition process, including issues related to self-doubt, fear of change, or any other emotional or mental blocks.

Professional Transition Coaching is not a one-size-fits-all approach. Each engagement is tailored to the individual and their unique circumstances. Through a combination of coaching, teaching, assessments, exercises, and planning, the coach helps the individual create a balanced, fulfilling, and purpose-driven career and life. The focus is not just on making a successful transition to the next calling, but on creating a sustainable and fulfilling life that aligns with the individual's values and goals. 

Said another way, the objective of Professional Transition Coaching isn't to help the client find a job; instead, it's about helping the client discover who they are and how to express that to the world.

Methods and Outcomes

In Professional Transition Coaching, there are nine essential methods I’ve designed to guide clients through the complex process of work-life transitions:

1. Assess: I use a variety of tools and assessments to help clients determine where they are in the transition process. These include self-assessment exercises, goal-setting worksheets, and values assessments, all of which help clients gain a deeper understanding of their unique needs and aspirations.

2. Educate: I provide my clients with a comprehensive education on the transition cycle, drawing upon key theories and concepts in the fields of psychology and adult development. Throughout our coaching relationship, I introduce clients to a range of relevant practices and provide them with the resources they need to make meaningful progress.

3. Reflect: I provide a variety of exercises for my clients to deeply explore their personal and professional history. These exercises help clients gain valuable insights into their core values, unique patterns, capabilities, and resources, and provide a wealth of lessons learned to draw upon in the future.

4. Pause: I empower my clients to cultivate stillness and mindfulness through a range of activities and practices, such as meditation and journaling. These practices are designed to help clients increase their self-awareness and presence, and to develop greater clarity and focus.

5. Envision: I help my clients envision new possibilities and pathways by guiding them through a range of visualization exercises. These exercises are designed to help clients develop a clearer sense of purpose and direction, and to build the confidence and resilience needed to navigate the complexities of work-life transition with greater clarity.

6. Unblock: I work with my clients to unblock limiting beliefs, negative self-talk, and other unconscious and conscious blockers that may be keeping them stuck in old patterns. By helping clients challenge old narratives and gain a deeper understanding of their inner conflicts, I empower them to resolve internal tensions with more clarity and compassion.

7. Design: I collaborate with my clients to design personalized rituals, ceremonies, and practices to help them to demarcate the end of a chapter, honor the past, and connect with their inner source of creativity. By co-creating transformative experiences, I help them gain closure, find deeper meaning, and unlock new sources of inspiration.

8. Plan: I collaborate with my clients to set clear, achievable goals that align with their core values and aspirations. Together, we develop actionable plans and establish ongoing support and accountability, empowering them to achieve their desired outcomes and move forward in the transition process.

9. Experiment: I collaborate with my clients to design and prototype experiments based on their goals and aspirations, such as reading a book, enrolling in a course, or networking with experts. Through this iterative and experimental process, my clients learn what energizes them and begin to build momentum.

As I guide clients through these methods, it is clear that each person's journey is unique but the benefits and outcomes are similar across the board:

1. Greater clarity and focus: By helping clients identify their core values and priorities, I help them stay focused on what matters most and avoid distractions and overwhelm.

2. Enhanced self-awareness: Through reflective exercises, mindfulness practices, and feedback, clients develop a deeper understanding of their strengths, weaknesses, and blind spots, and use this knowledge to make better decisions and build stronger relationships.

3. Improved resilience and adaptability: As clients learn how to navigate change and uncertainty with greater ease, they become more resilient and adaptable to new situations and challenges.

4. Increased confidence and motivation: By helping clients align their goals with their values and strengths, I help them build a sense of confidence and motivation that comes from knowing they are on the right path.

5. Sharpened vision and purpose: I help clients gain clarity on their vision and purpose, and align their transition with their long-term goals and aspirations.

6. Enhanced understanding of change and transition: Through coaching, teaching, and exercises, clients can learn about the process of change and transition, and develop skills and strategies for navigating these challenges effectively. Change is life-long, and these skills are meant to serve clients long after our work together is through.

I Was Born For This

Professional Transition Coaching for high performers aligns perfectly with who I am, what I’m great at, what I value, what I love, and what pays the bills. In other words, it’s my IKIGAI—the thing that gives me purpose and meaning. 

I spent the first decade of my career as an operator and the second decade of my career as an institutional VC at some of the top early-stage funds in NYC. Despite the money, power, and status that VC provided, the job and lifestyle left me burnt out and unfulfilled. My ego loved these benefits but my soul yearned for more. I realized those alone weren’t enough to bring me happiness and purpose in life. Deep down inside, I craved a new vocation that was more aligned with what I valued, who I was becoming, and what energized me. 

After years of inaction and a lot of heartache, I finally knew I wanted a path that would allow me to use my skills and experience to help others achieve their own goals. At the time I didn’t know what it was, but once I found my values, I was ok taking a risk to follow them. Several months later, I walked into my weekly partner meeting and resigned without a grand plan. When they asked what I planned to do, I told them, “I’m not entirely sure. 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 left the profession at the prime of my career—before I made FU money—to follow my calling as a coach, teacher, and creator. Over the past six years, I have spent thousands of hours coaching and training, honing my skills, and developing the tools I need to help high performers navigate the challenges of major life transitions. I’m now creating the coaching firm I wish existed in 2017 when I knew deep down inside investing was no longer for me. 

As someone who has personally navigated significant transitions, including getting sober and becoming a parent, I understand the challenges and uncertainties that come with making these changes. That's why I'm passionate about Professional Transition Coaching and the transformative impact it can have on individuals who are seeking clarity, purpose, and fulfillment. This is the kind of support that I wish I had access to when I quit my job at RRE Ventures in 2017.

Choosing this path and embarking on this journey wasn't driven by a business plan or a calculated market opportunity. It wasn't rooted in "customer development" as a means to identify a profitable niche. I’m tapped into a deeper, more authentic source of inspiration, allowing myself to become a conduit for the universe that is ready to share this idea with the world.

And I didn't come up with this on my own—it unfolded from the complexity and chaos that envelopes a human’s life on earth, and from the vulnerability and uncertainty my clients and friends have shared with me over the years. With the benefit of hindsight, the role I’m now so happy to step into feels like it was inevitable, a calling that was gift-wrapped and handed to me by the universe. 

As the renowned music producer, Rick Rubin writes in The Creative Act: A Way of Being: 

“These rhythms are not set by us. We are all participating in a larger creative act we are not conducting. We are being conducted. The artist is on a cosmic timetable, just like all of nature…

In this great unfolding, ideas and thoughts, themes and songs and other works of art exist in the aether and ripen on schedule, ready to find expression in the physical world. 

As artists, it is our job to draw down this information, transmute it, and share it. We are all translators for messages the universe is broadcasting.”

By tapping into our innate gifts and becoming conduits for the universe's creative act, we can discover what truly lights us up, embrace our authentic selves, and manifest a work-life that aligns with who we really are.

So, as you reflect on your own journey, ask yourself: what will your next calling be?"