The Path to Becoming a Coach

From Passion to Profession: A Comprehensive Guide for Aspiring Coaches

Interest in the coaching profession is at an all-time high. It seems like scores of recovering founders and executives are pursuing careers in coaching, and I'm all for it. I believe that everyone can benefit from having a coach to help them evolve their consciousness and reach their full potential. Becoming a coach and building a thriving practice is possible, and one of the most rewarding things I’ve done in my life.

I receive emails on a weekly basis from friends, acquaintances, and readers who are curious about my path to becoming a coach and what the process looked like for me. While I would love to respond to each one individually, the demands of being a parent and a solopreneur make that challenging. That said, I remember how many people were generous with their time and insights when I was just starting out, and I want to pay that forward by sharing advice, wisdom and experience. 

But before I dive into that, I want to tell you a quick story. Back in 2016, shortly after I got sober, I started exploring Buddhism as a way to enhance my spiritual life. I took a course on Coursera by Robert Wright, a professor at Princeton, called Buddhism and Modern Psychology. The course left me wanting more, but I was overwhelmed by the different concepts and the sheer volume of resources available. I wasn't sure where to start or how to sift through all the information. So, I reached out to my mentor, Jerry Colonna, the Founder and CEO of Reboot, who is also a devout Buddhist. I asked him for guidance on how to learn more about Buddhist philosophy and how to apply its teachings in a modern context.

Jerry's response was unexpected and truly insightful:

“The Buddha taught that there were 84,000 doorways to the dharma (I kid you not…that’s the number) and the point is to just pick one and walk through. Don’t worry about picking the “right one.” The point is to Start Where You Are.

The wish to know the path wholly and clearly before taking a step is, in fact, a reaction to fear. The brave heart takes a step.”

I share this story in the context of coaching because there are countless doorways into the profession: mentors, courses, workshops, certifications, retreats, podcasts, books, mastermind groups, and more. There's no one-size-fits-all approach, as each pathway is unique and depends on your values, experiences, interest, and life context.

What I'm about to share with you is my personal journey and perspective on getting into the profession. It's not the only path to becoming a coach or serving others, but I hope that by sharing my experiences, you'll be inspired to find your own path that calls to you.

The First Door

Back in 2011, my wife started The Sill in our Lower East Side apartment, and that gave me a front-row seat to the life of an entrepreneur. I saw firsthand the highs, the lows, and everything in between. It provided me with a newfound appreciation for the daily struggles and sacrifices that entrepreneurs make to bring their visions to life.

I witnessed it all: breaking up with a co-founder, running payroll late at night, taking calls and sending emails around the clock (even while on vacation), balancing the books, dealing with suppliers and partners who treated her differently because she's a woman, waking up at the crack of dawn to receive a shipment, creating and sending proposals to clients, working weekends at the store or office, handling employee matters like hiring and firing, losing key clients, worrying about cash flow, and sometimes feeling completely overwhelmed and alone.

When I came home from my VC job at the end of each day, I found myself unintentionally slipping into the role of a coach–helping my wife navigated a variety of inner and external challenges. Around the same time, other founders and operators in the NYC tech community began reaching out to me as a neutral sounding-board and friendly counsel. I loved playing this role and always left these conversations feeling energized and inspired, regardless of the topic. I felt I was providing more value in this context than I was as a VC.

The Second Door

In the summer of 2013, while on a road trip, I stumbled upon an episode of This Week In Startups featuring Jerry. I had never heard of him and I wasn’t familiar with executive coaching, but his message to founders and his way of being deeply resonated with me. I was captivated by his story and the notion of helping founders develop as leaders and humans. So, on a whim, I sent him a cold email and received a reply within hours. Several weeks later, we met at his Flatiron office to explore a potential coaching relationship.

Within just one hour of talking with Jerry, I knew that I needed a coach for myself. I also had an innate sense that I wanted to become a coach once my investing career came to a close.

After our time together, I began to see that the founders in my portfolio weren't getting the kind of support they truly needed to thrive. Sure, every VC firm offered help with hiring, strategy, and financing, but they often neglected their founders' development as leaders and humans. It occurred to me that we focused solely on the outer game of entrepreneurship, overlooking the inner game. But based on my experiences with my wife and friends, I knew that the inner game was just as crucial—if not more so—than the outer game. And it was then that I realized there was an opportunity to bridge the worlds of VC and coaching.

The Third Door

In April 2016, I attended a Reboot retreat for VCs, and it was a truly transformative experience. When I got back from the trip, I told my wife, “I think want to become a coach. So many founders could benefit from this and there’s a huge void in the startup ecosystem.” She skeptically responded, “Steve, you’ll make an amazing coach one day but you can do that later in life when you retire.” Still, there was a voice inside my head whispering that coaching could be my true calling.

A year after that retreat, I made Partner at RRE Ventures—a big deal, for sure—but something felt off and gnawed at me. As my friend Seth Goldstein once told me, being a General Partner at a large VC firm is like getting tenure at a university. And while I could easily envision a comfortable, successful life as an institutional investor, I couldn't shake the feeling that there was more out there for me. I didn't have the passion or fire for that role and style of investing, so I made the tough decision to step away from RRE.

In the following months, I thought a lot about what I wanted to do next. While I kept coming back to coaching, I also knew that I had a lot to learn about the profession. I didn’t even know what I didn’t know. So, I reached out to friends and acquaintances who had transitioned from operating to coaching, including Jim Rosen, Sharon Dougherty, Jonathan Basker, Ravi Raman, Dan Putt, Albert Lee, and Tarikh Korula. They were all incredibly generous with their time and advice, and with their help, I began to gain a basic understanding of the coaching profession and how to get started.

Many of them suggested that I consider participating in a coaching certification course, and the one that stood out the most was Coaching for Transformation (CFT). Not only was it popular among my friends, but it was also conveniently located at The Open Center—just twenty blocks from my apartment in the West Village.

After some careful consideration and a few conversations with my wife, I made the $10,000 investment and enrolled in CFT. Even though I wasn't sure if coaching would be a long-term career for me, I decided to dive in head first and fully commit to the process. I figured that at the very least, CFT would give me a solid foundation of skills and knowledge to share with founders I invested in. 

As soon as the course began, I knew that I had found my calling—that quiet voice inside my head was now shouting it from the rooftops. Nine months later I was certified by the International Coaching Federation (ICF) and working with a handful of awesome clients. I haven’t looked back since. 

The Unfolding Path

Nearly six years have passed since I embarked on my coaching journey. In that time, I’ve supported dozens of clients, logged thousands of coaching and training hours, and built a thriving practice of which I’m incredibly proud.

Since completing my initial certification, I have pursued nearly a dozen additional courses and certifications, ranging from Tiny Habits and Conscious Leadership to Internal Family Systems (IFS) and the Enneagram. This pursuit of knowledge and desire to hone my expertise has led me to consume countless books, podcasts, and videos on topics such as psychology and consciousness. Beyond my education as a coach, I have facilitated workshops, team off-sites, and Mastermind groups, and published dozens of essays and exercises, including the popular Ultimate Annual Review.

I now operate a thriving coaching practice where I support 12-15 high-performers, helping them navigate significant work and life transitions. With freedom, flexibility, and autonomy, coaching has become a central part of my life's work, and I’m incredibly grateful for the opportunity to do this work every day. I’m also able to support my family and desired lifestyle, which was one of my major concerns when I was starting.

Through my training and practice, I've come to realize just how vast and deep the field of coaching really is—it encompasses psychology, philosophy, spirituality, adult development, and much more. I’ve also come to appreciate that your path depends on your subspecialty—be it executive, life, career, wellness, financial, or something else—and will be influenced by who you aim to serve and what energizes you. In my case, I primarily work with high performers in transition, so I also invest my time learning about change management, the shadow, vision, purpose, life design, among many other topics.

The path to becoming a coach and honing your craft is a never-ending and ever-unfolding journey. I could spend the rest of my life participating in training programs, listening to podcasts, watching videos, and reading books, and there would still be more to learn. Many coaches I know feel the same way.

Below is a comprehensive FAQ that answers the many of questions I’ve received from friends and acquaintances over the years. This covers topics from "What is coaching?" to "How do you structure your coaching engagements?" and includes valuable resources such as certification programs, books, online courses, and podcasts. While not exhaustive, I hope it offers a solid foundation if you’re curious about coaching or beginning your own journey into the profession.

I intend to update this guide over time, so don't hesitate to reach out with any feedback or additional questions. I’d be delighted to incorporate your input or plug any gaps of understanding.

Remember, coaching is an ongoing journey of learning and growth, and the key is to take that first step, open that first door, and then trust your intuition. I wish you all the best on your coaching journey and hope that you find fulfillment and success in helping others bring their visions to life.

Good luck and happy trails.

---

☀️ Coaching Basics

What is coaching? 

According to the Online Etymology Dictionary, the term "coach" originated in 1550s Germany as a reference to a "large kind of four-wheeled, covered carriage" used to transport people from one place to another. The word "coaching" literally meant to help people get from where they were to where they wanted to be.

Fast forward nearly three centuries to 1830, and "coach" was adopted as slang at Oxford University to describe a tutor who "carries" a student through an exam. Then, in 1861, the term was used in the context of sports for the first time, to describe a person who trained athletes for competition.

Throughout my journey as a coach, I've come across many different definitions of the practice. Some of the words that often come up include "potential," "growth," "learning," and "performance." Here are a couple of my personal favorites:

“Coaching is a  thought-provoking and creative process that inspires leaders to maximize their personal and professional potential.”

–The International Coaching Federation (ICF)

"Coaching is unlocking a person's potential to maximize their own performance. It is helping them to learn rather than teaching them." 

–Timothy Gallwey, The Inner Game of Tennis

At its core, coaching is about helping someone achieve their full potential and maximize their performance by using techniques like asking powerful questions, providing frameworks, and offering accountability. The goal is to support them in reaching a new destination, whether that's in their personal or professional life.

If you're interested in exploring coaching further, I invite you to check out An Entrepreneur’s Guide to Finding a Coach, a Slideshare I published in March 2020. I may be biased and it’s a bit outdated, but I believe it's an excellent primer on coaching that will help you get a sense of what a coach does.

What makes a great coach? 

In my experience, there are several key characteristics that set exceptional coaches apart from the rest.

• Active listening: A great coach truly listens to their clients, hearing not only the words spoken but also the emotions, thoughts, and desires that lie beneath the surface. This allows them to connect with clients on a deeper level and offer more effective guidance.

• Emotional intelligence: Exceptional coaches possess a high degree of emotional intelligence, enabling them to recognize and manage their own emotions as well as those of their clients. This skill is crucial for building rapport and fostering trust.

• Adaptability: Coaching clients often present a wide range of challenges and situations. A great coach is adaptable and can shift their approach as needed to address the unique needs of each client.

• Empathy: The ability to empathize with clients, understanding their feelings and perspectives, is essential for a successful coaching relationship. An empathetic coach can better support clients through difficult times and help them feel heard and understood.

• Accountability: A fantastic coach holds clients accountable for their actions and commitments, supporting them in staying on track toward their goals. This accountability helps clients make meaningful progress and maintain their motivation.

• Humility: Great coaches recognize that they don't have all the answers and are willing to learn from their clients, peers, and mentors. They embrace a growth mindset and are open to feedback, allowing them to continuously improve as a coach.

• Strong communication skills: Effective coaches are skilled communicators, able to convey their thoughts, ideas, and insights clearly and persuasively. They can also ask powerful, thought-provoking questions that encourage clients to reflect and explore their own thoughts and beliefs.

• Curiosity: Great coaches love to learn, grow and develop. They are well-versed in multiple methods and perspectives, drawing from a broad range of knowledge to adapt to each client's unique needs. They are lifelong students of the profession, constantly learning and evolving to expand their pallet of skills.

• Presence and awareness: Great coaches cultivate deep presence and awareness during sessions by fully immersing themselves in the moment, focusing on their inner experience and clients without distraction. This level of presence allows them to genuinely connect with their clients, tune into what’s present and absent, and avoid projecting thoughts and emotions onto the client. 

• Expertise: Great coaches are not only well-versed in a broad set of coaching skills, but they are also keenly aware of the domain or niche they are coaching in. By understanding the unique environment and context of their clients, they can provide tailored guidance and support that is both relevant and impactful, leading to more effective coaching outcomes.

How do you become a great coach?

Embarking on the journey to become a great coach requires dedication, self-reflection, and continuous growth. At the core, one must commit to their personal development as both a human being and a coach, striking a balance between ego and identity development with competency and skill-based learning. This growth can be achieved through various avenues such as courses, therapy, coaching, books, peer groups, retreats, and more.

It should go without saying—actually coaching clients is a fundamental part of the process of becoming great. Practicing techniques and approaches with discipline and frequency is essential for refining one's skills, learning from each interaction, and evolving one's coaching approach, especially if you build reflection into your process. Regularly seeking feedback from clients as well not only helps a coach improve but also demonstrates their commitment to providing the best possible support.

Participating in a coaching supervision or mastermind group can be invaluable for learning from other experienced coaches and gaining fresh insights. These groups offer a platform for coaches to share their experiences, discuss challenges, and collaborate on creative solutions. Personally, I've been part of several mastermind and supervision groups, and they've been tremendously helpful.

To truly excel as a coach, it's important to study a variety of coaching methods and philosophies. A diverse knowledge base enables coaches to adapt their approach to suit the unique needs of each client, and develop their own style. A sign of a truly dedicated and growth-oriented coach is the willingness to step outside of their comfort zone and try new techniques with clients.

There are no shortcuts to becoming a great coach—it takes time, patience, and practice. In my own journey, I felt like a fish out of water for nearly five years. It wasn't until I completed my intensive training with Conscious Leadership Group and Alelthia that things really began to slow down and click. To achieve greatness, you must remain committed over a long period of time. As George Leonard wrote in Mastery: The Keys to Success and Long-Term Fulfillment, “At the heart of it, mastery is practice. Mastery is staying on the path.”

What distinguishes coaching from therapy, advising, and mentorship? 

Rather than attempting to summarize what has already been written on this topic, here are four articles that offer useful insights into the differences and nuances between these different approaches.

These resources should help you gain a better understanding of what sets coaching apart.

• What’s the Difference Between a Mentor, an Advisor and a Coach?, Zak Slayback

• Life Coach vs. Therapist, Tony Robbins.com

• The Difference Between Coaching and Therapy, Co-Active Training Institute

• 5 Differences Between Coaching and Psychotherapy, Everywell Mind

It's important to note that coaching is not therapy, but it can indeed be therapeutic. As clients work with coaches to gain clarity, develop self-awareness, understand deeply engrained patterns, and cultivate new behaviors or perspectives, they may experience a profound sense of self-compassion and well-being. This healing aspect of coaching is an essential byproduct of the self-unfoldment journey, emphasizing that although coaching is not therapy, it can certainly offer valuable therapeutic benefits.

One final note that I want to stress—there’s a gray area between coaching and therapy, and the distinction between the two is not exactly clear-cut. However, there are certain areas that generally fall outside the scope of coaching. These include diagnosing and treating mental illness and helping clients navigate serious traumas, which are more appropriately addressed by a licensed therapist or mental health professional.

🏋️‍♀️ Training & Development

When do you recommend pursuing formal coaching education?

If you're considering pursuing formal coaching education, it's worth thinking about your personal goals and circumstances. Some coaches choose to pursue training early in their journey because they’re convinced this is the right path, while others may wait until they have more experience under their belt. In fact, I’m mentoring a few coaches who are actively working with clients but haven’t pursued formal education. 

Personally, I pursued coaching training early in my journey. While I informally coached and advised founders for six months, I quickly realized that I could better serve my clients with an expanded toolkit of coaching frameworks, techniques, and vocabulary. I'm glad that I committed myself to learning and development early on, as it has allowed me to become a more effective coach and gain confidence.

One of the benefits of pursuing coaching education is that it provides a structured and rigorous learning environment that can help you develop your coaching skills and knowledge more effectively. In addition to gaining new tools and frameworks, I also appreciated the sense of community and collaboration that came with participating in a coaching program. It provided me with valuable opportunities to learn from and connect with other coaches, which has been instrumental in my continued growth and development as a coach.

Another benefit of formal coaching education is that it can provide you with a clear set of standards and competencies to strive for. This can help you to develop your coaching skills and improve your ability to serve your clients. Additionally, many programs are designed to help you learn not only about coaching but also about yourself, providing valuable opportunities for self-discovery and personal growth.

Keep in mind that coaching education programs can be a significant investment in terms of time and money, with many programs costing between $8,000 - $15,000. However, I believe that investing in yourself and your education is one of the best things you can do for your coaching practice and your clients.

If you're unable to afford formal coaching education, there are still many ways you can develop your coaching skills and knowledge. Consider attending workshops or webinars, reading books and articles on coaching, or seeking mentorship from a more experienced coach. The most important thing is to remain committed to your own learning and development, as this will ultimately benefit both you and your clients.

What training programs do you recommend?

It's worth highlighting that there are thousands of coaching certification programs available worldwide, but not all of them are accredited by the International Coaching Federation (ICF). Given this, the coaching industry can sometimes resemble the Wild West, making it challenging to spot truly valuable programs from all the noise.

While many programs adhere to the ICF's core competencies and ethical standards, they can differ in other ways. For instance, the program I completed, Coaching For Transformation (CFT), had a strong emphasis on social justice, while New Ventures West is heavily influenced by Ken Wilber and his integral theory.

These are some of the ICF-accredited programs that I’ve heard good things about from coaches I trust and respect.

• Co-Active Training Institute (CTI)

• New Ventures West

• The Hudson Institute

• Newfield Network

• iPEC

• Columbia University Coaching Program

• Georgetown University

• Presence-Based Coaching 

Unfortunately, the certification program that I completed, CFT, is no longer available in the US. However, there are many excellent options available that can provide you with the skills and knowledge you need to become a successful coach.

As I indicated, there are countless non-accredited ICF programs, but this doesn’t mean they’re not worth exploring at some point in your journey. The key is finding out from experienced coaches which ones are worthwhile. Some of the most impactful courses I’ve taken aren’t accredited by the ICF, including Conscious Leadership Group, Aletheia, Coaches Rising, and Evryman. I’ve also heard rave reviews from coaches who have trained with NLP Marin and The Strozzi Institute of Coaching. 

I have some friends who recommend CTI due to its increased flexibility. CTI's program is divided into five modules, allowing participants to invest their time and money incrementally. This structure enables individuals to enroll in the first module, "Fundamentals," and then decide whether to continue based on their experience. This approach may be particularly appealing for those who are intrigued by coaching but not yet ready to commit fully to the profession.

If you're considering a coaching certification program, it's essential to do your research and speak with program faculty and alumni to gain a better understanding of what the program entails. This can help you determine whether the program aligns with your goals and expectations and whether it will provide you with the skills you’re looking for.

Many programs offer informational sessions, webinars, or open houses that can help you get started in this process. Attending these events can give you a chance to meet with teachers and learn more about the curriculum, the program's approach to coaching, and the types of students the program attracts.

When speaking with faculty and alumni, it's helpful to ask specific questions that can help you understand their experience with the program. For example:

• What inspired you to pursue coaching, and why did you choose this program?

• What was your experience with the program like, and what were some of the most valuable lessons or takeaways for you?

• How has the program helped you in your coaching practice, and what specific skills or techniques have you been able to apply to your work?

• What sets this program apart from others, and what type of student is best suited to the program's approach?

Asking these types of questions can help you gain a better sense of whether the program is right for you, and whether it can provide you with the knowledge, skills, and support you need to become a successful coach.

What’s the process to become certified by the ICF? 

To become an ICF-certified coach you must enroll in a program that has been accredited by the ICF. They often include five or six highly interactive and inspiring weekend-long workshops, and they are often supplemented by weekly teleclasses to learn and practice core coaching concepts. In addition, these programs provide plenty of opportunities throughout the nine months for peer-to-peer coaching and mentoring.

Here are the specific requirements if you want to become a certified coach by the ICF.

• Coach-specific training: You must complete a minimum of 60 hours of coach-specific training that meets ICF standards. The training can be obtained from an Accredited Coach Training Program (ACTP), Approved Coach Specific Training Hours (ACSTH), or Continuing Coach Education (CCE) providers.

• Coaching experience: You must have at least 100 hours of coaching experience with at least eight clients after completing your coach-specific training.

• Mentor coaching: You must complete at least 10 hours of mentor coaching with an ICF-credentialed coach to receive feedback on your coaching skills and competencies.

• Coach knowledge assessment: You must pass a Coach Knowledge Assessment (CKA), which is an online multiple-choice test that measures your understanding of the ICF Core Competencies and Code of Ethics.

• Code of Ethics: You must pledge to adhere to the ICF Code of Ethics, which outlines ethical and professional standards for coaches.

• Membership: You must become a member of the ICF and agree to comply with its policies and procedures.

After you've met all the necessary requirements, you can apply for certification from the ICF at the Associate Certified Coach (ACC) level. As you progress further in your coaching journey, you can pursue the next two distinctions, which are Professional Certified Coach (PCC) and then Master Certified Coach (MCC).

I'm proud to share that I recently completed all of the requirements for PCC, and I'm currently on the path to becoming an MCC. Pursuing ICF certification has been a significant part of my journey as a coach, and I believe it has helped me to become a better coach by providing me with a clear set of standards and competencies to strive for.

Is getting “certified” by the ICF necessary?

The short answer is no. Certification isn’t necessary to practice coaching, and I know some powerful coaches have built successful practices without it. Life experience and other forms of training can be just as valuable in developing coaching skills. However, like in any industry, there are also inexperienced practitioners and charlatans. Certification can be an important tool for clients and potential employers to assess a coach's credibility and dedication to the profession.

Personally, I believe that getting certified is a worthwhile investment in your coaching career. In addition to demonstrating your commitment to learning and the coaching profession, certification programs can provide a wealth of knowledge and personal growth opportunities. I want to reiterate—these programs offer a structured and supportive environment to learn and practice coaching skills, while also providing a framework for understanding coaching competencies and ethical standards.

Through my own certification journey, I not only learned a great deal about the art of coaching, but also about myself. The process of training and certification can be transformative, allowing you to delve into your own values, beliefs, and assumptions. Additionally, certification can help you to become more effective and confident in your coaching practice, enabling you to take clients to deeper levels of growth and change.

While certification may not be necessary to practice coaching, it’s an effective tool for professional development and personal growth. 

What courses do you recommend if I’m not ready to commit to full certification? 

Aside from Co-Active Fundamentals, there are various cost-effective and outstanding options worth considering. I frequently suggest WBECS and Coaches Rising, which are two companies known for delivering immersive online courses at reasonable prices. 

While these providers don't offer "certifications," their online courses serve as excellent starting points, as they expose both the aspiring and experienced coach to world-class instructors and a community of coaches for collaborative practice. These classes are typically priced around $750, offering considerable value for the investment. 

Personally, I've taken three courses with Coaches Rising—The Neuroscience of Change, The Power of Presence, and Inside Coaching—and consistently felt that I was receiving excellent value for both my time and money.

What books do you recommend?

Since my coaching journey began six years ago, I've consumed dozens of books on coaching and personal transformation. Here are some of my all-time favorites for new coaches: 

• Coaching for Performance, Sir John Witmore

• The Coaching Habit, Michael Bungay Stanier

• The Prosperous Coach, Steve Chandler & Rich Litvin

• The Mindful Coach, Doug Silsbee

• Presence-Based Coaching, Doug Silsbee

• The 15 Commitments of Conscious Leadership, Jim Dethmer et al. 

• Coaching to the Human Soul, Alan Sieler

• Changing On The Job, Jennifer Garvey Berger

• NLP: The New Technology of Achievement, Steve Andreas

• Co-Active Coaching, Henry Kimsey-House et al.

• Atomic Habits, James Clear

• No Bad Parts, Dr. Richard Schwartz

If you're interested in exploring a more extensive list, feel free to take a peek at my bookshelf.

What podcasts do you recommend? 

I frequently recommend the following podcasts that focus on coaching, personal growth, and self-improvement:

• Coaches Rising

• Reboot

• The Tim Ferriss Show 

• The Knowledge Project

• The Huberman Lab

• The Art of Accomplishment

Each of these podcasts brings a unique perspective to the world of coaching and personal growth, offering valuable lessons and insights for listeners at any stage of their development journey.

Do you coach and mentor up-and-coming coaches?

Absolutely, coaching and mentoring aspiring coaches is something I'm genuinely passionate about. Right now, I'm formally coaching two solopreneurs who are embarking on their own coaching journeys, while also providing informal mentorship to several others. Many of these mentees are founders or executives contemplating their next career steps and looking to explore the world of coaching.

These connections have developed organically, and I find it incredibly energizing and fulfilling to assist those at the beginning of their coaching journeys. This enthusiasm is a key reason why I've put together resources such as this guide and consistently share my experiences, insights, and knowledge with others. Supporting the growth and development of the next generation of coaches is a responsibility I take seriously and find deeply rewarding.

Additionally, I've had the privilege of establishing a Coach In Residence role in my own practice, where I actively mentor and support a promising, up-and-coming coach, like Micah Baldwin. This generally involves providing guidance, lending infrastructure, sharing insights, and offering feedback to help the aspiring coach develop their skills and confidence, while simultaneously launching their own practice.

I'm committed to continuing this mentoring work because it’s so impactful and meaningful. While my schedule may become more demanding, I'll always strive to make time to give back to the coaching community and help aspiring coaches find their footing.

Do you work with a coach? 

Always! At any given moment, I'm collaborating with one or two coaches to delve deeper into myself, explore new directions, and cultivate new skills. Over the past ten years, I've worked with more than a dozen coaches, each bringing their unique skill set, background, and approach to help me evolve. 

For instance, I'm currently working with Rachel Jepsen, a phenomenal writer, editor, and coach, as well as participating in a mastermind group for coaches focusing on startup leaders. I’m also working with Dr. Josh Klapow, a former clinical psychologist and startup founder who now specializes in coaching executives and athletes.   

In addition to personal growth, coaching is also an excellent way to observe how other practitioners hone their craft and structure their engagements. I've gained invaluable insights about myself and the art of coaching from every professional who has supported me.

If you're going to coach others, working with a coach yourself is crucial. How can you promote and advocate for coaching if you haven't fully embraced it? If you've never worked with a coach before, I highly recommend taking this step early in your journey to determine if coaching is the right path for you. 

As Jerry Colonna once said to me, you need to work on yourself so your shit doesn’t spill into your sessions.

📈Getting Clients

Who’s your ideal client? 

I believe it's crucial to ultimately identify the clients you want to serve and coach, but arriving at that decision takes time, exploration, and self-reflection. It's entirely okay if you're unsure at first! 

Focusing on a niche as a coach has numerous benefits. By targeting a specific audience, you can tailor your services to address the unique challenges and needs of that group, making your coaching more effective and relevant. Additionally, niching down enables you to become an expert in your chosen area, which in turn establishes your credibility and builds trust among your clients. Finally, by concentrating on a niche market, your marketing becomes more targeted and effective, allowing you to better connect with potential clients and stand out from the competition. In other words, embracing a niche helps you create a sustainable, thriving coaching practice.

As you’re getting started, if you don’t already know your niche I suggest coaching a diverse range of potential clients to identify those who energize and fulfill you. You may initially envision coaching growth-stage entrepreneurs, only to later find that you prefer working with HR professionals. The best way to uncover your niche is by actively coaching, following your energy, and taking inventory of your skills and resources. In other words, embrace coaching wholeheartedly, pay attention to the types of clients and topics that truly energize you.

That being said, most experienced coaches I know generally work with two or three distinct client profiles. Early in my journey, I coached three types of clients: early-stage entrepreneurs with no more than 150 employees, General Partners at VC firms, and executives navigating career transitions. These clients naturally aligned with my background, expertise, and passions. 

Recently, I shifted my practice to focus exclusively on “high performers in transition.” It took me more than five years to pinpoint my ideal client niche, but my passion and unique qualifications make me perfectly suited to serve these clients. Now everything I do is in the service of helping high performers navigate work-life transitions and manifest their next calling.

What do you look for in a new client? 

My ideal clientele primarily consists of senior leaders seeking a new calling in work or life, founders who have either sold or shut down their companies, entrepreneurs feeling lost and unmotivated, aspiring solopreneurs and creators, and retired professional athletes.

When it comes to selecting clients, coachability is crucial. My ideal client can articulate why they want a coach, their goals, and the person they aspire to become. They have a history of working with coaches, mentors, or teachers and possess an insatiable curiosity about themselves and the world. These individuals cultivate self-awareness through practices like journaling or meditation, are committed to the coaching process, and are willing to put in the time and effort required. They take responsibility and ownership for outcomes, including onboarding, session preparation, and follow-ups, and are open to experimentation and making adjustments.

There are certain non-negotiables I consider when choosing a coaching partner. It's essential that I genuinely like them, care about their success, and find them to be good, ethical people. I should be able to spend at least a day with them without getting bored, respect their previous accomplishments, and feel excited to help them even without payment. Additionally, I must have a deep interest in and belief in their current pursuit. My clients seek a coach on their own terms and have a strong desire to contribute to something larger than themselves, driven by a powerful internal motivation.

The coaching relationship is a vital aspect of my practice. Clients should have the desire and ability to work together for at least six months, if not longer. Ideally, our relationship will evolve to the point where I can become part of their inner circle or personal board of directors. My primary role is that of a coach, but I can also serve as an advisor when needed. I remain invested in their development and success even after our formal coaching relationship ends. Ultimately, our relationship should be symbiotic, allowing both of us to teach, learn, grow, and thrive together.

How do you know whether you and a potential client are a good fit? 

Determining whether a potential client and I are a good fit is a crucial aspect of my coaching practice. My first step is to understand who the client is and why they are looking for a coach. This is often done over email. Once I determine if there’s a potential fit, I’ll engage with prospective clients in a 30-minute "chemistry call," during which we get to know each other and discuss their coaching needs. If I feel there might be a strong fit, I offer a complimentary session to further assess our compatibility.

These calls not only allow me to evaluate whether someone meets my coaching criteria but also help both of us determine if our personalities and styles align. If I sense a strong connection after the first or second call, I'm open and honest about my desire to work together. However, it's essential to remember that mutual fit is crucial for a successful coaching relationship. If we aren't a good match, that's perfectly fine—my priority is to ensure that every prospect finds the right coach for their needs.

In fact, I often tell prospective clients that I view these initial calls as a "fit process" rather than a sales pitch. This perspective emphasizes the importance of compatibility for both parties, ensuring that the foundation of our coaching relationship is built on trust, understanding, and a genuine desire to collaborate.

How do you determine if a client isn’t a good fit? 

Often, a less-than-ideal fit emerges when the client primarily seeks advice, resists cultivating self-awareness, or appears uncommitted to the coaching process.

While it can be challenging to gauge this during the enrollment phase, the first few months provide valuable insights. To better understand the client's mindset and readiness for coaching, I ask a range of questions during the enrollment process and carefully listen to the depth and thoughtfulness of their responses. 

These inquiries include:

• Why are you seeking coaching, and why is now the right time?

• What opportunities and challenges are you currently facing?

• What significant questions are you asking yourself?

• What are your goals for the next 3-6 months?

• What type of coach are you looking for?

By evaluating their responses, I can gauge their commitment and openness to coaching, which helps me determine if we're a good fit. However, it's essential to remember that the assessment of compatibility is an ongoing process that might evolve as our coaching relationship progresses.

How did you get your first clients? 

When I started my coaching journey, I reached out to friends and former colleagues to let them know I was training to become a coach and seeking clients to help me sharpen my skills. I also took advantage of social media, announcing that I was open for business. These efforts paid off, and I secured four initial clients who played a crucial role in my early development as a coach.

In those beginning stages, my primary goal was to gain practice and experience, so I was open to coaching any executive or entrepreneur who was interested. I wasn't focused on optimizing for a specific type of client or niche; instead, I welcomed the opportunity to work with a diverse range of individuals, knowing that each would contribute to my development as a coach. This approach helped me build a solid foundation and refine my coaching techniques, ultimately preparing me for a more targeted practice down the road.

How do clients find you? 

When I opened my practice, a lot of my early clients came through references, word of mouth, and Twitter. Occasionally, I’d publish an essay on my site or run a free webinar, and Ultimate Annual Review was also an effective way to generate leads.

Over the years, things have evolved a bit. I now have a newsletter and podcast called Where the Road Bends, and these, along with an occasional tweet, are the primary ways I drive traffic to my site. I typically publish two essays and two podcasts per month—I don't see these activities as “work” because I genuinely enjoy doing them and they come naturally to me.

My clients now come from four primary sources: referrals from my network, my website, Twitter, and LinkedIn. I've found that the key to success in marketing yourself as a coach is to take a long-term view, identify a niche, and focus on building an authentic brand. There are many ways to generate demand, including blogging, social media, referrals from other coaches and clients, word of mouth, speaking engagements, presentations, and coaching platforms like BetterUp.

Of course, everyone's path is different, and what works for one person may not work for another. It's important to experiment and find the methods that resonate with you and your style. It's also important to remember that building a following and attracting clients takes time and effort. People sometimes ask me how I scaled to 70K Twitter followers, and I have to remind them that it took me 15 years to build that audience!

Ultimately, I believe that the best marketing you can do is to be excellent at what you do and provide a valuable service to your clients. When you do that, word will spread, and your reputation will grow organically.

Do you work with coaching platforms like BetterUp or companies like Reboot?

While I haven't personally utilized coaching platforms like BetterUp or worked with companies like Reboot, I recognize the potential value they offer to some coaches. While I've been fortunate enough to maintain a steady stream of clients, command my desired rates, and enjoy a high level of autonomy in my practice, these platforms can be an excellent option for those just starting out or looking to expand their reach.

Coaching platforms can offer a range of benefits, including outsourced lead generation, association with a reputable brand, and a community of coaches to connect with. They can also provide opportunities to refine coaching skills, outsource administrative tasks, and expand your network of like-minded professionals. Ultimately, whether or not to work with these platforms is a personal decision based on individual goals and needs.

Do you refer clients to other coaches? 

All the time. I’ve cultivated and nurtured a referral list comprising several dozen practitioners over the past five years. The list is comprised of trusted professionals with whom I have collaborated, trained with, or fostered deep relationships. I take great care in recommending or referring a coach, ensuring that they are not only an ideal match for the client but also demonstrate excellence in their work and unwavering dedication to the art of coaching.

When referring clients to fellow coaches, I do not expect any form of compensation in return. While some coaches offer "referral fees" that may amount to as much as 20% of the contract value or the first month of the engagement, I personally do not endorse such practices. I choose not to accept referral fees to maintain unbiased recommendations, always prioritizing the client's best interests and needs in finding the perfect coach.

What’s your enrollment process? 

To kick off the client enrollment process, I typically receive an introduction to or email from a potential client. I then assess whether they could be a good fit for my coaching style and approach. If it looks promising, we schedule a “chemistry call,” which is an opportunity for both of us to assess whether we have a mutual energetic fit.

After the call, I send a follow-up email that summarizes what I heard and any action items we discussed. If it seems like we have a good chance of working well together, we schedule a complementary coaching session. This session is a chance for us to work together in a low-pressure setting and see how we each work.

Finally, after the complementary coaching session, we determine whether we're a good fit and decide whether to work together. I believe it's important for both the client and me to feel confident that we can work together effectively and achieve their goals before moving forward.

💰Monetization

How do you charge for your engagements? 

My pricing and business model have evolved over the years. When I first started coaching, I took a slightly unconventional approach to pricing by offering a “pay what you can” pricing model. 

Rather than setting a fixed price per session or monthly retainer, I allowed my first clients to pay me a per-session fee they were comfortable with. I gave them only two guidelines: it shouldn't be so much that they would resent me, but it should be enough that they saw it as an investment in themselves and were fully committed to the process. I was able to do this because coaching was a side hustle and not my primary source of income.

This approach allowed me to gain valuable experience as a coach while also building trust and rapport with my clients. It also helped to remove some of the financial barriers that can prevent people from seeking coaching.

Once I committed to coaching as my primary form of income, I had enough market data and client testimonials to suggest that I could charge far more than the per-session fee my initial clients were paying me. I eventually settled on a monthly retainer rather than a "per session" fee. This dramatically simplified the administrative aspects of my practice, removing the need to sell and track packages.

My *average* monthly retainer is $2,500. I have some clients who pay me $1,250 per month and some that pay me $5,000 per month. Pricing is determined by the client’s ability to pay. I never let money get in the way if there's a strong fit and desire to work together. I’m told by my peers that I can charge more based on my training and experience, but I’m not trying to optimize for every last dollar. 

Ultimately, pricing is just one aspect of coaching, and it's important not to let it overshadow the value of the work that we do and its many rewards. Whether you're charging $50 or $1,500 per session, the most important thing is to approach each coaching engagement with an open mind, a willingness to learn and grow, and a commitment to helping your clients achieve their goals.

What are typical rates for coaches? 

There’s a huge range in the industry. I’ve seen $150 / hour on the low end and $3,000 / hour on the high end. According to old data from the ICF, the average rate for coaches making $100K is $365 / hour. Because coaching is becoming commoditized on the low-to-mid end of the market I’d imagine this rate might get squeezed over time. At the higher end, I think the rates will hold at least for the time being.

Do you take equity in a client’s company or projects?

This is an understandable question, especially in the startup world where equity can be a major component of compensation and incentives. But, I never explicitly ask for equity from a client. There are a few reasons for this. It can potentially create a conflict of interest or impact the dynamic of the coaching relationship. Additionally, I'm no longer an investor, and I’d rather not have to assess whether the company is a worthy investment. My focus is solely on helping my clients achieve their goals and reach their full potential.

It's worth noting that there are many coaches who do ask for equity as part of their compensation, as they see it as a way to align their interests with those of their clients and potentially reap the benefits of a successful company or project. However, I know many respected coaches and mentors who do not take equity, and personally, I fall into the latter camp.

Ultimately, my goal as a coach is to provide the best possible service to my clients, and I believe that requires maintaining clear boundaries and avoiding any potential conflicts of interest.

How do you talk about the return on investment (ROI) of coaching? 

The most insightful perspective on the value of coaching can be found in The Prosperous Coach by Steve Chandler and Rich Litvin. They articulate the essence of what coaching truly offers:

“You aren’t billing for time elapsed. You are billing for the very real possibility of a goal being achieved that would not have been achieved without fearless coaching. Your client has a default future that will occur on its own if his life does not change. When he pays you he is paying for his life to change.”

As a result, the ROI in coaching is the value clients ascribe to their transformation. While it may encompass quantitative measures such as revenue growth and an increased valuation, it is not confined to these metrics alone. It is crucial to acknowledge that the true value of coaching transcends tangible outcomes, as it also embraces the discovery of novel ways of being, which are inherently difficult to measure. Nevertheless, you’re selling the transformation and the change rather than your time. 

👩‍🏫 The Coaching Engagement 

How do you structure your engagements? 

When it comes to my coaching engagements, I believe that it's important to tailor the approach based on each individual's unique needs, experiences, and context. I don't believe in a "one-size-fits-all" approach, and I strive to help my clients develop novel perspectives and approaches that are specific to their situation. While I do draw on frameworks, exercises, and other resources when necessary, I believe that my clients are inherently wise and resourceful and can determine the best path forward with the right support and guidance.

To start, I typically ask for an energetic commitment for 3-6 months, but the duration is mutually determined. I don't believe that any coaching relationship should last forever, but I'm always open to the possibility of building a long-term relationship with my clients. Historically, the average engagement has been nine months.

During our coaching engagements, I meet with each client at least twice per month, either over Zoom or the phone. I make myself available for "spot coaching" if a client needs support in between sessions, and they’re encouraged to reach out to me through text or email at your convenience. It's important to me that my clients feel supported and know that they can count on me to be there for them.

In terms of the medium of our coaching sessions, I don't have a preference between Zoom or phone. Both have their own unique strengths and limitations, and I leave it up to my clients to choose the one that works best for them. If they happen to based in or visiting NYC, I also love meeting in person at my office in Tribeca.

Ultimately, my coaching engagements are about co-creating a partnership where we work together to help my clients make meaningful progress in their life and careers.

How many clients do you work with? 

At the moment, I'm working with 15 clients, although my ideal range is between 12-14. I find that maintaining this client load allows me to strike the right balance between coaching sessions and other crucial activities such as writing, research, and ongoing learning. By managing a reasonable number of clients, I can provide each individual with the attention and focus they deserve, while also nurturing my own professional development and growth.

That being said, the number of clients a coach works with can vary significantly. I know coaches who work with as few as 10 clients at a time, and others who handle upwards of 40 clients. The optimal number of clients really depends on one's personal bandwidth, business model, and coaching style. Some coaches prefer to offer more intensive, immersive experiences with a smaller number of clients, while others may opt for a larger client base and shorter, more focused sessions.

Ultimately, it's essential for each coach to find the sweet spot that allows them to maximize the value they deliver to their clients while also preserving their own well-being and ensuring sustainable success in their coaching practice.

How do you onboard a new client? 

To onboard a new client, I have a well-defined process in place that allows us to get started on the right foot. I start by having the new client sign the coaching agreement, which outlines the terms and conditions of our coaching relationship. Once that's done, the first invoice is sent, which can be paid easily and securely through Bonsai, my online payment system.

Next, I introduce them to the coaching home base, a centralized resource in Notion that houses all the tools and materials they'll need for the coaching experience. This helps them become acquainted with the resources that will be available to them throughout our engagement.

Our kickoff session is a 60-minute call where we get to know each other better, discuss their goals and intentions for our coaching engagement, and set the tone for the rest of our time together. After that, the client completes the Snapshot of Me, a powerful self-discovery tool that helps them gain clarity on their life story, values, strengths, challenges, and vision for the future.

The following week, we have our first coaching session, where we use the insights gained from the Snapshot of Me to dive deeper into their coaching goals and develop a plan of action for achieving them. Two weeks later, we have our second coaching session, where we continue building on the momentum and insights gained from our previous session. From there we settle into a bi-weekly cadence.

This process is designed to set clients up for success from day one. It helps us get on the same page and create a solid foundation for our coaching engagement.

How much time do you spend on each client per month? 

I believe that dedicating enough time to each client is essential to providing quality coaching. I generally meet with each client for a minimum of two hours per month. However, I also recognize that every client is unique and has different needs, which is why I structure my engagements to be flexible and open-ended.

In addition to the two hours per month that I spend with each client, I also dedicate time to preparing for each session and reviewing notes afterwards. Typically, I spend at least 30 minutes preparing for each session to ensure that I am fully present and engaged during our time together. After each session, I take time to review the notes and type up a summary, which takes another 30 minutes on average. So at a minimum, I spend a total of four hours per client.

That said, some of my clients are in transition and often request extra sessions and additional support. In those cases, I’m happy to adjust my schedule and make myself available to meet them as needed. Ultimately, my goal is to provide each client with the time and support they need to achieve their goals and make meaningful progress in their journey.

How long is a typical engagement? 

When it comes to coaching engagements, my approach is open-ended and flexible. I ask for a minimum energetic commitment of three months, but I'm not looking to lock clients into long-term packages or engagements. I believe that coaching relationships should be mutually determined and founded on the potential for a long-term partnership.

That being said, I don't believe that coaching relationships should last forever. I think it's important to set goals and intentions for our time together and to work towards achieving them within a reasonable timeframe. On average, my coaching engagements last around nine months, but I have worked with some clients for over a year.

Ultimately, the length of a coaching engagement depends on the needs and goals of the individual client. Some clients may benefit from shorter, more intensive engagements, while others may prefer a longer, more gradual approach. Whatever the case may be, I strive to be flexible and responsive to the unique needs of each client.

How do you measure your impact with each client? 

When kicking off a coaching engagement, I always begin by identifying my clients' goals and establishing clear metrics to measure success. Every three to six months, depending on our progress, we revisit these goals to evaluate whether they still align with the client's current needs and desires. This helps us stay focused and ensures that we're making meaningful progress toward their desired outcomes.

Throughout the engagement, I provide opportunities for clients to share feedback, both verbal and written. This allows us to improve our coaching relationship and make any necessary adjustments to ensure that we're working effectively together.

I also have regular check-ins with my clients to evaluate their progress and satisfaction with the coaching engagement. I ask questions like "How are things going? Are you getting what you wanted out of this? Are you seeing and feeling progress?" These conversations allow us to address any issues or concerns in real-time and make any necessary adjustments.

Finally, I look at my monthly renewal rate to track client satisfaction and ensure that I'm consistently delivering value. If clients are churning, it's a clear sign that something needs to change, and I use this feedback to improve my coaching practice and better serve my clients.

When does it make sense to wind down a relationship?

Every three months, I schedule a dedicated time to have an open and honest conversation with my clients about the coaching relationship. During these check-ins, we discuss what's working well, what's not working, and where they might be feeling stuck. We also talk about any changes they'd like to see moving forward, and whether they feel like they'd like to continue for another three-month sprint.  We also explore whether the coaching relaetionship is still a mutual fit.

I don’t believe any coaching relationship should last forever, and there are natural stopping points along the way. For example, we may reach a point where several milestones have been reached, and it's a good time to reassess and determine whether to continue working together or not. Alternatively, if a client isn't fully committed to the process, or if their needs have shifted and require a different type of coaching or support, it may be time to wind things down.

Ultimately, the decision to continue or wind down a coaching engagement is usually a collaborative one, and it's important to have open and honest communication throughout the process to ensure that both parties are on the same page.

How do you prepare for a session? 

To ensure that I provide the best coaching experience for my clients, I have a standard routine that I follow to prepare for each session. First, I review the client's goals that we set during the onboarding process. This helps me to stay aligned with their objectives and ensure that we're making progress towards them.

Next, I review the notes and homework from our last session. This helps me to track the client's progress and recall important details from our previous conversations. I also review the prep email reflections that I receive from the client in advance of the session. This provides me with additional insight into their intentions, thoughts, and experiences since we last met.

Before the session starts, I take 10 minutes to get present and centered. I believe that it's important for me to show up focused and fully present for my clients, so I take a few moments to clear my mind and get into a positive, centered headspace.

Finally, I get on Zoom five minutes before the session starts to ensure that my camera and microphone are working properly. This way, I can begin the session on time and without any technical difficulties.

Overall, this prep routine takes around 20 minutes and allows me to provide high-quality coaching sessions for my clients.

Do you give your clients homework? 

Absolutely! At the end of each session, I always take time to have a "meta conversation" with my client, where we discuss key takeaways, next steps, and homework. This conversation is essential because it helps ensure that my clients are making progress between sessions.

The homework assignments that I give to my clients are tailored to their individual needs and goals. They may take many different forms, such as reading a book, journaling every day, or practicing a new habit or skill. These assignments are designed to help my clients integrate the insights and ideas that we explore during our coaching sessions into their daily lives.

In addition to homework, we may also discuss micro-exercises. These are small actions that my clients can take every day to build momentum and reinforce the new patterns of thinking and behavior that we're working on in our coaching engagement. Micro-exercises can include things like noticing a pattern in your thoughts or actions, reciting a daily intention, or taking a few minutes each day to reflect on their progress.

It's important to remember that coaching sessions are like planting seeds of growth and transformation. Homework and micro-exercises are like sunlight and water that help these seeds grow and thrive in the real world. By committing to homework and micro-exercises, my clients will be well on their way to making meaningful progress in their journey.

What do you do after a session? 

Following every coaching session, I review my notes to ensure I captured all the essential insights, action items, and progress made. This helps me keep a record of our unfolding relationship and ensures the client and I are on the same page.

After the session is over, I send the client a summary of the notes via email. The summary includes a list of any agreed-upon action items, detailed notes on what was discussed, and any materials referenced during the session. Additionally, these notes are uploaded to the client's coaching home base in Notion, which they can access at any time.

These notes are not only helpful for the client to reference, but they also play a vital role in my preparation for upcoming sessions. By reviewing these notes beforehand, I can ensure that we stay on track with our goals and build upon the insights gained in previous sessions. Additionally, these notes help me to measure the client's progress, adjust our coaching approach if necessary, and ensure that we are always aligned in our expectations and goals. Overall, the notes serve as a valuable tool for both the client and myself, and are an integral part of the coaching process. 

How do you schedule sessions? 

Scheduling sessions is an important part of the coaching process, and I make sure to remain flexible to meet the needs and preferences of each client. Some clients prefer to book their sessions themselves, and for them, I’ve found Calendly to be a great option. I’ve set up workflows that automatically send scheduling links after a session, which makes it easy and convenient for them to find a time that works best.

For those who want a more structured approach, the majority of my clients have recurring meetings on my calendar. This has several benefits, including ease of administration and ensuring that we stay on track with our goals. Finally, there are clients who prefer to book time for our next appointment at the end of a session. This can work well too, as it allows us to quickly find a time that works for both of us.

Recently, I’ve started working with a virtual assistant who handles all of my scheduling. This has been a game-changer, as it frees up more of my time to focus on coaching and writing. Having someone to lean on for administrative tasks like scheduling has helped me to be more present and engaged during coaching sessions, which has been a win for both me and my clients.

How much time do you spend advising versus coaching? 

As a coach, my primary goal is to help my clients develop new skills and capabilities and discover the answers for themselves rather than simply providing advice or sharing my own experience. Therefore, I tend to spend about 65% of my time coaching and the remaining 35% advising. That being said, every session is different, and sometimes the advising component may take up more or less of our time depending on the client's needs and goals.

I believe that it's important to strike a balance between coaching and advising. While coaching helps clients develop their own insights and solutions, advising can provide them with additional perspective and expertise. However, the deeper I go into the coaching profession, the less I want to rely on advising, even if my clients may sometimes want me to step into that role more frequently. Ultimately, I believe that coaching empowers clients to learn more deeply about themselves and take ownership of their own growth and development, which leads to more meaningful and lasting change.

How much of your coaching is focused on work versus life? 

In my experience, especially as a professional transition coach, life and work are inseparable. That's why the coaching topics I focus on depend on each client. Some of my clients prefer to concentrate solely on work-related challenges, while others welcome exploration of their personal lives as well. But in many cases, the two are closely connected and can't be separated.

Overall, I approach coaching from a holistic perspective. That means we look at the client from multiple dimensions, including career, health, relationships, finances, and more. As a professional transition coach, I specialize in supporting high performers navigating work-life transitions. So naturally, my coaching approach is integrated and addresses both work and life.

In other words, my coaching approach is a hybrid between life, career, and executive coaching, and all domains are fair game for exploration. My goal is to tailor my approach to the needs and desires of each individual client. Whether we focus primarily on work or explore a broader range of topics, my ultimate aim is to help each client thrive in their personal and professional lives.

That said, when I coached executives and investors, the majority of the conversations focused on the work context and setting. In other words, the type of coaching and the client ultimately determines the balance between work and life.

What other services do you offer? 

Beyond my one-on-one coaching, I offer an array of services designed to facilitate growth and development for both individuals and teams. Some of these offerings are one-time or occasional engagements, allowing me to cater to diverse client needs.

These services include but are not limited to:

• 360 reviews, providing comprehensive feedback for individuals from various perspectives

• Team offsites, fostering team-building and collaboration

• Mission, vision, and values workshops, helping organizations and individuals refine their purpose and direction

• Post-mortems and retrospectives, facilitating learning and improvement from past projects, events or chapters

• Energy and calendar audits, optimizing time management and productivity

• Zone of Genius assessments, identifying individual strengths and areas of expertise

• Co-founder alignment processes, ensuring strong partnership foundations

• "Think Week" retreats in The Catskills, offering an immersive experience for deep reflection and strategic thinking

While one-on-one coaching remains my primary focus and accounts for over 90% of my revenue, I recognize the potential for growth in these additional service offerings. As my practice evolves, I may explore ways to expand, optimize and market these services more effectively.

💼 The Business

Is your business incorporated? 

Yes, I incorporated my business as a single-member LLC as soon as I left institutional investing and became a full-time coach. This structure allows me to separate my personal and business finances and protects my personal assets from any legal liabilities that may arise in the course of my coaching practice.

In addition to the legal protection, incorporating has other benefits. For example, it provides more flexibility in terms of tax planning, as well as potential cost savings in certain areas such as healthcare and retirement plans. It also helps me project a more professional image to clients, which is important in a competitive market.

Incorporating my coaching practice was a relatively straightforward process. I consulted with a lawyer to ensure that I completed all the necessary paperwork correctly and filed the required documents with the appropriate state agencies. It cost less than $1,000 to set up. If you don’t have a lawyer in mind, ask friends for recommendations or there are a variety of online options such as Legal Zoom. 

Do you have business insurance? 

As a professional coach, I believe it’s important to have business insurance to protect my practice and assets. I have a comprehensive policy that covers property damage, liability claims, and professional negligence. My property coverage ensures that any property I own, lease or rent is protected from theft or damage. My business liability coverage protects me from claims that may arise from damage caused to someone else's property or bodily injury.

However, the most important insurance I have is professional liability coverage. This insurance helps to protect and defend me in case of a lawsuit claiming that my professional negligence has caused financial harm to my clients. This coverage gives me peace of mind knowing that I can focus on serving my clients without worrying about legal repercussions.

The annual premium for my $1M policy is around $1,500 per year, which is a reasonable investment to protect my business and my clients. Overall, having comprehensive business insurance is an essential part of running a coaching practice and ensures that both my clients and I are protected. 

All that said, I didn’t make this investment until a year after I went full-time. At that point, I had a full roster of clients and enough evidence to suggest that coaching would be my profession for the foreseeable future.

What do you use for an agreement?

Once I went full-time, I invested $1,000 to have an experienced lawyer create a custom coaching agreement based on the specific nature of my coaching practice. Having a solid, customized agreement in place has been invaluable in ensuring that both my clients and I are clear about expectations, boundaries, and responsibilities from the outset. Most importantly, my legal risk as a business owner is minimized.

That said, I recognize that not everyone has the resources to work directly with a lawyer. Fortunately, there are a number of excellent templates available online, such as this one offered by Practice. These templates can provide a solid starting point for those looking to create their own coaching agreements. Just remember that it's important to review and adapt any template to suit your unique coaching style and practice, making sure that it covers all relevant aspects of your client engagements.

What technology and tools do you use to power your practice? 

I leverage a variety of technology and tools to power my coaching practice. I believe that investing in the right tools can make a significant difference in productivity, efficiency, and the overall client experience. These tools cost me a few thousand dollars per year, but they're worth every penny because they save me time and headaches.

The tech I leverage includes:

• Bonsai for automated and recurring invoicing

• Calendly for scheduling and scheduling workflows

• Notion for client notes, CRM, and templates

• Airtable for forms

• Zoom for video conferencing

• Otter.ai for meeting notes 

• Superhuman for email (snippets save me a ton of time)

• Miro for collaborative brainstorming

• Squarespace for my website

• Substack for my newsletter

• Brex for banking and expense management

• Loom for feedback

• Raindrop for my resource library  

• Pitch for presentations 

• Zapier for automation

• Chat-GPT for data synthesis and summarization

I’m an angel investor in and huge fan of tools like Practice and Superset. I would absolutely use one of these software platforms if I was starting out because it combines many of these tools into one. I don’t currently use them because I have a few quirks in my business, but once they implement the features I need, I intend to migrate to one of those platforms. 

How do you scale your time? 

To streamline my coaching practice and make my life easier, I have incorporated a variety of processes to help me stay organized, save time, and maintain a high level of professionalism.

Some tools and processes I leverage include

• Automated Invoicing: Using a platform like Bonsai to automate invoices helps me save time and ensure timely payments from clients.

• Exercise Templates: Creating exercise templates using Chat-GPT and storing them in Notion enables quick access and customization for each client's unique needs.

• Session Note-Taking: Utilizing a service like Otter.ai can help me capture session notes efficiently, providing an accurate record for future reference.

• Snippets: Using tools like Superhuman to store snippets of frequently used text or instructions helps me respond to client inquiries more quickly and consistently.

• Calendly Automations: Implementing workflows in Calendly can simplify appointment booking and create a tighter customer experience.

• Session Tracking: Integrating Google Sheets with Zapier allows for seamless tracking of client sessions, goals, and progress, making it easy to monitor and analyze your coaching practice's performance.

By incorporating these practical processes and tools into your coaching practice, you can focus more on the actual coaching and client relationships, ultimately enhancing the quality and impact of your services. 

✨General Advice

What are your days like? 

As a coach, my days are busy, structured, and balanced. Maintaining a healthy work-life balance is essential for my personal well-being and the success of my coaching practice. My typical day begins at 5:30am with an hour of exercise and meditation to get my blood flowing and energize me for the day ahead. After that, I spend quality time with my family until 8:30 when I take my daughter to school.

Once I get to the office, I dedicate my mornings to reading, writing, and research, which helps me stay up-to-date with the latest coaching trends and techniques. I also “work on” the business if there are any immediate projects or tasks that need my attention. My mornings are strictly reserved for non-urgent and important work.

From 12:00 pm to 6:00 pm, I have client sessions, chemistry calls, and network with friends, acquaintances, or other coaches. It's during these hours that I get to “work in” the business, supporting existing and prospective clients. 

After my work day, I make sure to take time for my family, enjoying dinner and quality time with them. From 8:30pm to 9:00, I respond to any urgent emails or messages. Finally, I end my day with an hour of reading to unwind and relax.

This routine allows me to prioritize my health, family, and work while maintaining balance and structure. It also enables me to stay focused and productive, making the most of my time to support my clients and grow my coaching practice.

When did you know you were ready to go full-time?

A couple of years into my odyssey, I was immersed in Great by Choice, by the renowned author and researcher Jim Collins. There, I stumbled upon a powerful metaphor he referred to as "fire bullets, then cannonballs.” 

“Picture yourself at sea, a hostile ship bearing down on you. You have a limited amount of gunpowder. You take all your gunpowder and use it to fire a big cannonball. The cannonball flies out over the ocean…and misses the target, off by 40 degrees. You turn to your stockpile and discover that you’re out of gunpowder. You die. But suppose instead that when you see the ship bearing down, you take a little bit of gunpowder and fire a bullet. It misses by 40 degrees. You make another bullet and fire. It misses by 30 degrees. You make a third bullet and fire, missing by only 10 degrees. The next bullet hits—ping!—the hull of the oncoming ship. Now, you take all the remaining gunpowder and fire a big cannonball along the same line of sight, which sinks the enemy ship. You live. 

This concept swiftly became a guiding principle as I navigated my own transition, conducting experiments, dipping my toes into uncharted waters and seeing what I learned about myself.

In other words, it was a gradual realization that came after conducting a series of experiments over three years. Through these experiments, I sought to answer several key questions that would determine whether coaching was the right path for me:

• Do I genuinely enjoy the process of coaching?

• Am I truly passionate about coaching and helping others?

• Does coaching offer a broad enough scope to satisfy my curiosity and thirst for knowledge?

• Am I able to attract high-value clients who resonate with my coaching style and philosophy?

• Do clients find significant value in the coaching engagement?

• Can I generate enough income through coaching to support my family and desired lifestyle?

• Does it provide a lifestyle that aligns with my values? 

Once these questions were answered affirmatively, I knew I was ready to transition into coaching full-time, confident that it was the right career path for me.

What do you wish you knew before starting?

Before starting my coaching journey, I wish I had known that everything was going to work out in the end. Not only would I build a highly successful practice that could support my family and my desired lifestyle, but I’d also genuinely love the work and deeply connect with my clients. If I could tell my past self anything, it would be to trust the process and have fun. Everything will unfold exactly as it's meant to, and the key is to stay the course, remain patient, and embrace the journey with open arms.

What advice do you have for new coaches? 

For new coaches, the journey can be both exciting and challenging, especially as you’re building new skills and launching a practice. 

Here’s some advice to help you navigate the early days of your coaching career:

• Meet the client where they are: Recognize that each client is unique and tailor your approach to their specific experiences, needs, and goals.

• Take it slow: Be patient with your own growth and the transformation of your clients. Coaching is a process that requires time and perseverance.

• Practice, practice, practice: Continually hone your coaching skills through consistent and deliberate practice. The more you coach, the more you learn about yourself, your clients, and the craft itself.

• Play the long game: Focus on cultivating your skills and building a sustainable coaching practice rather than chasing short-term gains. This means investing in your own growth, cultivating relationships, and refining your methods over many years.

• Experiment with different clients: Work with a diverse range of clients in your early years to determine what client needs, goals, background, experience, questions, or circumstances energize you, so you can hone your niche.

• Find a mentor or a coach: Seek guidance from experienced coaches who can offer insights, support, and encouragement as you navigate your coaching journey. 

• Don't stop learning: The best coaches are lifelong learners, always eager to expand their knowledge and skills. Stay curious, embrace new ideas, and continually seek opportunities for professional growth.

• Go beyond your comfort zone: Growth only happens outside of our comfort zones, and as a coach, it's important to embrace challenges and new experiences. Pushing your own boundaries behaviorally, cognitively and emotionally will help you grow as a coach and better support your clients.