Entry One From The Coach’s Log

learnings from the past three months of coaching and self-study

It's been almost three months since I officially announced my coaching practice on LinkedIn and Twitter. The journey has been more intense and immersive than expected, but I’ve made more progress than anticipated. I’ve found myself noticing new curiosities and exploring emergent paths. At times, it’s felt unsettling, but I’ve come to realize it may actually be the underbelly of ambition. The more I immerse in coaching, the more I realize I don’t know, which moves in tandem with growing confidence that I'm on the right path.

Leading up to the announcement in mid-July, I experienced heavy resistance to making my practice public. For weeks, my finished website that was already linked to social accounts sat untouched. I sat at the bottom of a hill, unable to muster the activation energy to take the first step. It took creating space and getting support from peers to get over the hump.

After weeks of feeling stuck, the resistance melted away once I embraced the significance of the moment. Rather than brushing off the importance or postponing the timeline, I accepted that announcing my coaching practice was actually a BFD to me. Through a five day creative challenge¹, and a phone call with Jake, I set a date and leaned in. I made a list of over 150 friends, colleagues, and supporters and sent messages asking for support. On the day of announcing, I had already done “the work” in getting past the resistance, so I wasn’t nervous or anxious. I simply woke up, did the thing, and then went to workout.

In the spirit of a ship's captain documenting their voyage, I'm starting the "Coach's Log" - with this being the inaugural entry. What follows is a collection of observations, learnings, and hunches gleaned from my coaching practice. While these insights emanate primarily from my practice, many of them transcend coaching and could resonate with anyone charting their own course in life or business. I'd love to hear your reactions! Feel free to comment, DM, or email me.

The Business of Coaching 💸

1) Making Your Own Rules

Having my own practice allows me to make my own rules. For example, I offered to mentor someone for free who initially reached out for coaching. I turned inwards, and sensed that in this busy season, I felt comfortable with meeting him once a month, but anything more frequent than that felt like it could encroach on other responsibilities. While I may not be as generous as Mother Teresa, I feel good helping someone without it feeling like an obligation.

My approach to pricing is entirely based on intuition rather than market data. While I don’t recommend this approach which completely overlooks practical aspects, it's been illuminating to feel into the value I provide as a coach. Now, when I share my rates, I have no hesitations or doubts because I've already done all the internal processing ahead of time.

2) Intentionality Behind the Structure and Cadence

Finding the right structure for my coaching practice has been a journey of trial and error. Initially, I compressed all my coaching sessions into Wednesdays and Thursdays. However, as my client base grew, combined with rescheduling and intro sessions, I realized this two-day structure was actually undermining my original goal of creating space. I've since expanded to coaching three days a week.

Between sessions, I schedulel 30 minute breaks to center myself and restore my quality of presence. These breaks are crucial for maintaining energy and stability of attention throughout sessions.

For intro sessions, I've structured them to be 60 minutes long, mirroring actual coaching sessions. This gives potential clients a taste of working with me, eliminating the need for a hard sell.

One area I'm still refining is creating a sense of connection beyond our bi-monthly sessions. I currently offer unlimited async communication through voice memos or email, and follow-up with curated resources based on each session's key theme. These resources are personalized to each client's learning style and bandwidth, and help extend the conversation into the time in-between sessions. Still, I know there’s opportunity to support my clients in a greater capacity particularly during our non-session weeks.

The Practice of Coaching 🧑‍🎨

3) Embracing Versatility Over Niching Down

Contrary to popular advice, I've found value in not narrowing down to a specific niche. There's a bunch of social media gurus telling people to find their niche because it’s good for business. That has been a very tempting message, because when you're new to something, there’s uncertainty in every regard. Being in the depths of not-knowing can be uncomfortable, but I've always resisted the siren call to niche down.

My coaching has spanned health (sleep, mindfulness, daily practices), career transitions (sabbaticals, experiments, self-discovery), emotional fluidity & intuition, and purpose & spirituality. Instead of worrying about what I'm “best” at, and trying on different labels like "career coach", "life coach", or "executive coach", I think the differentiator is my ability to dynamically switch modes as a coach.

In a recent session, we had been working on cultivating a sense of ease, balance, and creativity into my client’s demanding in-office work life. We started off by diving into foundational practices, but then we transitioned into relationships and the power of vulnerability to create a sense of connection. By not limiting myself with a label or niche, I've retained the flexibility to dynamically dance between whatever is most important to the client.

4) The Core of Coaching

For a while now, I've been studying coaching and therapeutic methodologies like Conscious Leadership, Presence-Based Coaching, Coaching for Performance, Coaching for Transformation, and the Hakomi Method. In overlaying these different schools of thought, I've arrived at two crucial competencies in my coaching practice:

• Presence: A state of full engagement in the current moment, without agenda or attachment to outcomes. Open, non-judgmental attention to the client's experience, allowing insights to emerge naturally without forcing direction or expectations.

• Curiosity: Maintaining a genuine interest in the client's experiences and perspectives. As a result, the elements of support and empathy are naturally embedded into questions, inquiries, and challenges.

While I've had to consciously cultivate presence via meditation, journaling, reading, and spending a ton of time alone in nature, curiosity has felt like it's always been with me since I was a kid. The underlying desire to understand the human experience led me down my own path of self-discovery, and it's also what intuitively guides a coaching session.

5) Digital Wellness & In-person Coaching

Helping clients with digital hygiene has emerged as a recurring theme in my coaching practice. We're all grappling with technology addiction's subtle impacts, suffering from an attention deficit hijacked by constant digital stimuli. This limits our emotional awareness and also dulls our intuition and curiosity, leaving many of us sleepwalking through life. We start with frantic morning texts, switch to all-day Zoom calls and finally end with an exhausted face in bed, illuminated by the bright white light of TikTok.

I’ve been helping my clients resist the constant neural connection of modern life through digital boundaries. As Byung-Chul Han notes in The Burnout Society, we suffer from an “excess of positivity” and therefore must cultivate negative potency, the power to not do something. This shows up in coaching sessions by creating an initial bubble of presencing where we take a few moments to simply breathe and gather ourselves. I’ve also extended beyond the session, addressing minute details like phone placement at night, notification settings, app blockers, and end-of-workday rituals. However, while digital hygiene is becoming a more frequent topic, I see it as just one facet of our complex modern achievement society, and therefore just one component of my coaching.

Recently, I've been offering in-person sessions for local clients in NYC, noticing these are not only more enjoyable but also more effective. While virtual coaching is convenient, face-to-face sessions offer unique benefits: fewer distractions, full presence, and richer body language cues. On video, I get the neck-up view, but in-person, I can observe how they're sitting, their energy level, and subtle physical cues.

As people spend more time behind screens, the opportunity to engage in a fully present, device-free coaching session becomes increasingly valuable. It's a pragmatic balance - in-person has its advantages, but virtual remains more accessible. This balance of digital wellness and in-person connection will be a continuous thread in my practice, offering a respite from our increasingly digital lives.

Self-Study 🧘‍♂️

6) The Self-Work of Coaching

“If you think you’re enlightened, go spend a week with your family.”
- Ram Dass

The ever-evolving journey of becoming a coach inevitably involves self-work.

I always find there's more to learn about myself. In the past few months, I've recognized areas for improvement, like handling negative feedback and to balance continual improvement with setting boundaries and acknowledging "enough-ness". My greatest challenge is overwhelm. I know there's always more I can do, and yet, I aim to arrive at a sense of completion each day.

This journey has led to greater acceptance of life's uncertainties. I've noticed I'm less attached to specific outcomes in my career, location, or income. There's a duality I'm sitting with. Although I have specific aspirations, I’m also open to what possibilities might emerge. Instead of gripping onto rigid outcomes, I'm more comfortable with the unfolding nature of reality. This balance of effort and acceptance is perhaps the most valuable lesson I'm learning on this path of becoming a coach.

7) Overcoming Imposter Syndrome

Initially, the thought of coaching people older than me triggered imposter syndrome. As I’ve started to actually coach people older than me, I’ve realized age difference matters far less compared to shared life stages and experiences. The more I coach, the more I realize it's all the same human experience filled with shared emotions, fears, challenges, and ambitions. We're all seeking some amalgamation of happiness, purpose, and belonging.

8) How I Know I’m on the Right Path

Diving deeper into coaching reveals an endless ocean of wisdom. I'm at peace with not knowing everything, which is oddly comforting. My confidence in this path grows as I simultaneously uncover new depths, find joy in the journey, and witness my own evolution. The convergence of continuous learning, genuine enjoyment, and tangible progress signals I'm heading in the right direction.

I have no idea what the future holds, and I’m learning to be okay with that. If I’ve learned anything by now, it’s that life always delivers the right experience at the right time.

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Thanks for reading! If you’re interested in learning more about coaching, check out my website here.

Bonus! - Some Random Musings

• I’ve been exploring sustainable ambition: How to be/live/do in a way that orients towards the long-term while maintaining a streak of good days, without the fear of burnout looming.

• I’m curious about the role of physical fitness in healing and mindfulness. The health & fitness and healing/consciousness communities are siloed but may see a greater convergence in the future.

• I’ve been considering creating content beyond blogs, like short-form videos, but I’m conflicted because I don’t believe TikTok is a net positive. On the other hand, these mediums now reach a majority of the population.

• In reading blog posts² by leaders of the leading AI companies, I’ve noticed a subtle confidence that the more human forms of labor, creativity, and expression are here to stay. Things like surgeons, artists, artisans, teachers, therapists, dancers, chefs, etc… Given the name of this blog, I’m a proponent of this humanist framing.

• I’ve been wondering what happens to human agency as AI, social media, remote work, and the loneliness epidemic converge. AI may free us to pursue our creative passions and indulge in leisurely activities, but the availability doesn’t guarantee that it actually happens. I think there’ll be a transitionary period where people freed from the shackles of work won’t know what to do with it.

• AI coaches/therapists may address different needs than human coaches/therapists. The mental health crisis, loneliness epidemic, and digital addictions affect the masses - issues AI coaches may address at scale. In contrast, human coaches tackle complex individual challenges like burnout, untamed ambition, and quarterlife/mid-life crises. Even if an AI were as effective as a human, I think connection and relatability will be essential. While there is certainly overlap and nuance here, my main point is that it’s not going to be an apples:apples comparison.

1. Shoutout to Kelly for organizing this! It was super fun and perhaps the thing that tipped me from resisting to doing.

2. I’m referring to The Intelligence Age by Sam Altman and Machines of Loving Grace by Dario Amodei