A Transformation Guide. Interview with Devin Martin

Insights from an elite coach in an essential field.

Oct 22, 2023

[38 minute read]

I believe that the next few years will see explosive growth in demand for genuine personal transformation.

But it’s a treacherous and confusing space, so I decided to consult an expert.

My guest for this interview is Devin Martin. I got to know Devin in late 2017. He works as a “life coach” in Manhattan. I absolutely despise the term life coach. It reminds me of the charlatan-filled mess I encountered when I first tried to navigate this unregulated industry. Back in 2018, I spent a year getting my own coaching certification, from the Functional Medicine Coaching Academy. I adamantly believe there is a central role for someone in your life helping you move forward through periods of stuckness, evolution and transition. But sometimes I suspect that the bulk of the money in coaching is in selling coaching certifications.

In the six years I’ve known him, I’ve come to believe that Devin is different. Firstly, he seems to live his own principles. Secondly, he’s sustained a thriving practice in one of the most competitive cities in the world for fifteen years. Thirdly, and most importantly, he’s had a harsh “initiation process” into his own path.

Tom: So with that introduction, Devin please tell us a little about yourself?

Devin: I have been called a Holistic Health Coach, a Career Coach, a Relationship Coach, a Death Coach, an Executive Coach, and a Psychedelic Integration Coach. When asked, I tend to call myself an Executive Life Coach. All the titles feel both accurate and a bit misleading. I strongly prefer existing outside of a regulated industry, as my methods can be more fluid, but this does make the barriers to entry almost zero. So, it is very much a buyer-beware situation.

For a handful of years, I was the #1 rated coach in NYC on Yelp and Google. At this point, my clients come almost exclusively via referral from other clients. People come to me when they want to shift their perspective and their actions. All of my clients can be considered successful by any traditional measure. Most are also realizing that success ≠ fulfillment. The journey ahead becomes one of self-discovery, personal transformation, and in the deepest way possible, self-indulgence. One of my core beliefs is that if you are radically self-indulgent then what you feel called to do is actually of service to the world. This flies in the face of the type of discipline and self-denial that got most people to the success they have today.

One of my core beliefs is that if you are radically self-indulgent then what you feel called to do is actually of service to the world.

Humans are exquisitely sensitive beings. What is your desire but a manifestation of all that has made you? Being in sync with our surroundings is immensely pleasurable. Going against the flow of life feels terrible. We are the fruiting of our environment. Do we really want to extract wealth? Or do we feel our best when we engage in mutual exchange? Win/win interactions make the earth you are planted in more fertile. Win/lose interactions place you in the middle of a hostile environment. If you are truly, deeply selfish, if you play infinite games, then I believe that what will emerge is exactly what those around you need.

It is only the delusion that you are separate from everything else that leads you to believe that being ‘selfish’ is at odds with being generous. My only caveat is that you must not be shallow. Getting drunk and having sex with strangers every night is a shallow, selfish act. If you were more deeply selfish you would indulge your own yearning to see and be seen. In my experience being deeply self-indulgent causes your cup to overflow. When full we feel compelled to contribute in a way that is all about our unique place in the universe. There are few joys as great as contributing to the wellbeing of others.

Tom: Please tell us your own story, especially your own difficult transition process.

Devin: I had a tough time finding my place in the universe. Two experiences come to mind, one when I was 18 and another just after 30.

I have amazing parents and a LOT went right in my childhood. As a highly sensitive kid prone to extended periods of self-reflection I found ways to suffer regardless. Being raised as a 4th generation Jewish Atheist (Russians), to whom math came extremely easy, made me overly rational. I questioned everything, but I also believed that reality would yield to the intellect. I needed things to make sense in a linear, logical way. I had faith in math and science, but didn’t realize how much I had made it my religion. I didn’t appreciate just how limited a dataset the conscious mind has to work with.

I also had a deep spiritual impulse, a tendency to seek ultimate truth, but few and anemic tools to engage. School became increasingly boring after 5th grade. I craved mentorship and friendship I could not find. I started spiraling into deep depressions towards the end of high school. I looked out at the adult world and saw miserable people. I was acutely attuned to the lack of a vision for how to thrive and enjoy life. It became clear to me that life = suffering.

Around 18 I tried LSD. It shattered my rational mind and nearly lead to me taking my own life. Looking back, I can say that I had a profound realization of what the Buddhists call ‘emptiness’ (shunyata). This is the realization that everything, from thoughts to objects to events, has no absolute essence, or meaning. All meaning is relative based on the perspective we happen to be taking at the moment.

I fell into what I would now call a Spiritual Emergency. Obviously, this is a big part of why we connected.

Words lost meaning. When I realized that a significant portion of my mind was pre-verbal I spent 1.5 years trying to think without words. I slipped into nihilism that manifested as almost three years of suicidal depression. I thought about killing myself every single day. I had a plan. Studying existential philosophy (Nietzsche!) and post-modernism in college made everything worse. Some nights I woke from a recurring nightmare drenched in sweat having a panic attack. The dream was abstract. It had no characters or solid content. It felt like the history of the universe was two math processes that were meant to sum and my experience was the moment of them coming together…and not summing. It made no &*$%ing sense, but it destroyed me.

Today I see it as the death rattle of my rational mind, a Dark Night of the Soul, and a beautiful process. At the time I had no larger context to surrender to. Watching my worldview crumble was simply falling into an abyss.

Dropping out of college was a step towards self-trust. I knew I would probably kill myself if I had to sit at a desk any longer so I got a blue-collar job and allowed my mind to indulge every curiosity. I took control of the information that entered my mind and the values I assign to it. I became an obsessive autodidact. After going through 4 majors in 4 semesters, I picked up the thread in all of them. This meant building my own home recording studio to produce music, leading philosophy discussion groups, studying the mind, practicing spirituality, and writing.

A new, far more complex and nuanced worldview took shape. I became a bit of a mystic. I look back at this experience with a lot of gratitude. It’s a resource I pull from to this day.

My second big initiation was professional. I spent 13 years in the wrong career. I was living a double life. By day, I designed security systems for clients like the Federal Reserve Bank and Fortune 500 corporations. By night, I was a musician, meditator, philosopher, psychonaut and yogi who had started health coaching part time. I had a 6-figure salary, an office on 5th Avenue, and spent most days working from home in Brooklyn or flying around to visit clients. All my friends told me I had it made, but I knew I was out of integrity.

A decade of intense daily practice primed my system for a breakthrough. Again, psychedelics played a catalyzing role. This time it was a week of ayahuasca ceremonies in Brazil that turned up the volume on my intuitive mind. An inexplicable psychic event led to a Kundalini Rising experience that continued for months after I returned to NYC. Then I met the love of my life and got my heart-broken for the first time. One of the reasons it hurt so much was because I knew I wasn’t living my best life. I wasn’t taking the risks I wanted to take with my life. I had a worldview, but I wasn’t living it. I wasn’t making my living with it. I hadn’t found my voice in the world. Not being able to see a path I wanted to take, I decided to say no to all of the things that I knew were not it.

I decided to leave my job, my beautiful Williamsburg apartment, and the city itself. I craved trees. I found a log cabin on top of a mountain in North Carolina on Craigslist. I called the owner and sent him a check for the entire year’s rent. I shaved my head into a mohawk, went to Burning Man for the first time (of course), then put everything I owned in a trailer and drove to the mountain.

I spent a year in isolation. No phone, no internet, no TV. If you emailed me you got an auto-response with my address. I hand wrote letters and sealed them with a wax stamp. I spent my time engaged in transformative practices. I sat in meditation for a few hours every day, did breathing exercises (pranayama), strength training, yoga (asana), chanted, wrote songs, did woodworking, walked in the woods, journaled, dream journaled, read about science, spirituality, intuition, and great literature. Every moment was one of radical self-indulgence coupled with an attempt to resonate with my highest self and to feel one with all things.

In that time a vision emerged of the life I have been living for the past 11 years. I saw my path as a coach.

Hana (who dumped me) and I spent the year sending love letters in the mail. She visited the mountain a few times. I decided to move back to the city to be with her and start my business. We got pregnant two weeks later. After two years, pregnant with #2, we moved towards nature. I owe the success I have today to the work I did that year (and the 13 leading up to it) and the perspectives that emerged through all of the struggle that permeated it.

Tom: Where do you start clients?

Devin: When is the last time you rewrote the narrative of your life?

My consultations start with hearing a bit of your life story. I want to understand how your mind works, how you make meaning, how you make decisions, and not only where you are and what you want today, but how you got there and some of what shaped your worldview. I’m looking for transitional moments. I am obsessed with decision-making. Much of what I do is about helping people calibrate and trust their own inner wisdom. I believe that we are all capable of making great decisions (ones we won’t regret), but most of us over-index on our emotions or our intellect and very few of us have a clear understanding of the difference between our gut and intuition.

If we decide to work together I have clients fill out a goals form. It is up to them to tell me what this work will be about, at least in the beginning. Then the fun begins. I love wrangling complexity into simplicity with people. My favorite conversations are the ones that jump from strategic business decisions to exploring interpersonal friction, move through formative childhood memories, touch daily self-care, sex, mind-altering chemicals, and incorporate a bit of philosophy and psychology to tie it all together. I find that patterns emerge when we can explore many seemingly disparate areas of life.

Many people tell me that the best part of my coaching is the notes I send between sessions. Here my goal is to help people see themselves from another perspective. I lay out key themes I am noticing, insights I may have into them, resources I want a client to look at, and action we have agreed they will be taking. I am often quoting things my clients have said back to them in the notes. I find that in great conversations people slip into an altered state and have brilliant and revelatory insights, but don’t always remember what emerged after. My goal is to give them a touchpoint, something concrete they can refer back to as they upgrade the stories they are telling themselves about themselves. When clients tell me that they have all of our notes printed out and stored in a folder they can reference, I know we are doing good work.

Tom: One of your most enduring legacies on my life and learning was introducing me to the work of Ken Wilber. Could you explain what drew you to him?

Devin: When I left college, my head was a mess. I was disillusioned with the status quo, still anti-religion, but beginning to explore eastern philosophy and practice. I was obsessively curious and constantly learning, but I was also adrift in a sea of disintegrated complexity. Reading Ken Wilber has been psychoactive.

Two things in particular changed, if not saved, my life.

First was coming to understand what I’ll call mysticism or the Perennial Philosophy. This is the idea that there is a core insight at the heart of every religion, a deep knowing or experiential insight about the fundamental nature of reality. In my experience, Buddhism speaks the most eloquently about this when it talks about the shift from self to Self, from feeling as if we are a separate ego to understanding that we are all part of one energy or consciousness. Words fail here, but concepts like nondual and Oneness point in the right direction.

After atheism, I still don’t believe in the god that my parents believe in. The myths, when taken literally, still irritate me. I am no more religious than I was before, but I am deeply spiritual and can respect the core insights that founded every religion and still exist in their mystical sects. The mystical branches of each religion sound remarkably similar. I find it fascinating that Buddha, Christ, Rumi, and Emerson seem to share some core beliefs about the fundamental nature of reality. I find immense value in the parts of the wisdom traditions that speak about direct experiences of transcendence and give you the tools to get there. Ken Wilber’s work laid all of this out for me in a way that didn’t require me to ignore or deny any of my more mathematical or scientific understandings of how the universe works, which brings me to my second point.

Learning Wilber’s Integral Theory, or AQAL, as it is sometimes known, organized my mind. He often refers to himself as a mapmaker. With his frameworks East and West play nice. Science and Spirituality become complimentary, as do meditation and shadow work. I developed a view of human beings that was rooted in developmental frameworks that honor every step of the journey. My thinking about any topic became more rigorous and holistic. I learned tools for seeing what any perspective prioritizes, but also what it tends to leave out. After more than a decade spent reading all of his books and discussing them twice a month with a community of brilliant seekers in Manhattan I developed the capacity to witness my own mind’s working in an elevated way. His work is not for everyone, but for those that resonate with it the process of understanding it is simultaneously a rewiring of the firmware that runs the software that is our conscious thinking. His work has been an invaluable tool for recognizing the ways that my clients make meaning of the world and also for helping them to see where they are stuck and what the next stage of their development is likely to include.

Tom: One of the things I like about you is that you’re incredibly open-minded about different coaching tools and healing practices. Whether it’s energy healing, meditation or psychedelics, I’ve seen a lot of people get locked into a single answer to what are typically much more complex questions. What do you think is most effective in terms of alternative healing modalities?

Devin: Everyone should cook. The fact that this came to my mind when you mentioned ‘alternative’ is obviously ridiculous, but that doesn’t mean it’s inaccurate. I suspect that we will look back and see metabolic dysfunction as the scourge of our era. Chris Palmer has done fantastic work showing that a lack of metabolic flexibility is not only highly correlated with cancer, diabetes, heart disease, and Alzheimers, but also with anxiety, depression, ADHD, OCD and a general lack of emotional regulation. Put simply, packaged foods are killing us while making us miserable. I also get a ton of pleasure out of cooking for/with friends.

Everyone should cook. The fact that this came to my mind when you mentioned ‘alternative’ is obviously ridiculous, but that doesn’t mean it’s inaccurate.

I’m a huge fan of yoga. It has been a part of my life for over 20 years.

Meditation has been an invaluable tool.

I find hobbies, especially those that include creativity to be deeply healing. In the world of workaholics and hyper-achievers that my clients compete in, hobbies can be quite ‘alternative.’

Forced to pick one thing that I think everyone can benefit from, I would pick breathing exercises. I advise most people not to start with sitting meditation, but with breathing instead. The Art of Living breathing exercises taught in the SKY Breathing Course changed my life as much, if not more than everything else I have done. Few things impacted my journey out of darkness and towards the light as much as realizing that I could control my autonomic nervous system simply by changing the way I breathe and that the tone of my thinking is often a reflection of the state of my body emotionally. It is hard to feel anxious without holding your breath in. I find that depression is linked to the opposite, to holding your breath out. Every state of deep contemplation I access in meditation seems to have a corollary breathing pattern.

Forced to pick one thing that I think everyone can benefit from, I would pick breathing exercises.

Controlling your mind with your mind is a nebulous endeavor. Learning to breathe differently and then using specific rhythms and techniques is simple and reliably produces the altered states of consciousness we are after. For the first 10+ years of being a meditator I rarely sat without doing breathing exercises for the first 5-15 minutes.

Tom: What kind of outcomes do you see from people who make dramatic jumps?

Devin: There are two types of changes that I see coaching people.

Type one is circumstantial. I see people leaving a career they don’t believe in and finding work that feels aligned with their sense of purpose in the world. I see people becoming a better partner/spouse. I see people overhauling their lifestyle to be healthier.

Type two is more subjective. What really excites me are the shifts in consciousness that underpin shifts in circumstances. At the most extreme end I see what I can only describe as personality-level shifts. As you know, I work with a lot of powerful people in finance. If you want to make money, there is often a degree of sacrifice involved. People who love art might go into advertising. People who love history might go into law. People who love math might become an accountant or CFO. Each of these people sacrificed a bit of their idealism to find financial stability and/or freedom, but they also maintained a core connection to something innate. Finance is the path of pure sacrifice. If you are able to forget about all of your interests and just pursue money then you may be able to make it through an investment banking internship.

Starting in grade school the best students are the ones who can check the boxes that other people draw, they can sublimate their desire and delay gratification to get into a better school, get a better job, get a promotion, earn a bonus etc. This is a massive strength, but like all strengths, if not tempered it can become a liability. Our schools are producing excellent sheep.

You recently wrote, “Wisdom is the ability to pursue what you love and ignore what you don’t. Wealth provides that freedom.”

I often meet my clients when they have achieved enough success/wealth that they don’t have to work so hard anymore.. but they are. Many have become workaholics. They have developed an inability to stop working. This leads to an atrophying of hobbies, introspection, spirituality, physical health, personality, social connections and love. Essentially, one gives up on their life outside of work to focus on making money or gaining respect. Once they have the freedom they have been chasing they have no idea what to do with it. They have minimized their preferences so much that they can no longer imagine what to do with their time if they are not working.

Seeing someone’s inner life thaw and blossom is why I coach. I remember seeing an investment banker of 20+ years realize that his identity in high school was ‘a singer’. He was almost in tears realizing that he had never once sung to his kids. He had completely forgotten that he liked singing, or even that he ever did it.

I had another client who fantasized, for years, about allowing himself to watch movies in the middle of the afternoon. He also craved time with friends who loved him when he was younger, less wealthy, and more ‘fun’ to be around. Giving himself permission to be playful has made him a significantly happier human being and no less productive.

Tom: Can you share some stories? One of my concerns is that we simply don’t have enough role models or examples of successful people on the other side of their own hero’s journeys.

Devin: You introduced me to Jason Karp. He is now speaking more publicly about his journey (and has mentioned working with me) so I feel comfortable sharing a bit about our work together.

I met Jason when he was considering shutting down Tourbillon Capital Partners. He heard that I was ‘the closer’ who helped people like him finally make the big decisions around a career shift out of finance.

Writing a letter to his LP’s letting them know that he was shutting down what had been a $4B fund meant a lot to him. He was obsessed with doing right by the people who invested with him. He was also going through a major health crisis, in a major transitional moment at Hu, and looking to do business in a new way. Shutting down Tourbillon led to selling Hu and starting HumanCo, a fund which I am incredibly proud to be an investor in. His path out of suffering included a lot of courageous psychological work, but really started when he realized that his diet was killing him.

Today, he is a leading advocate for making healthy food more broadly accessible and is putting his money where his heart is starting amazing brands like Snow Days. His pain became his gift. Hurt people hurt people and the more we heal the more we can support others in doing the same.

Another success story I feel comfortable talking about is Hilah Stahl. Hilah came to me when she was working in product management at Bonobos. Like many employees, she had a sense that she had more to give and was playing with a vision of becoming an entrepreneur. She has a real passion for interior design. Finding the intersection of her skills and her passions generated a vision for a company, and a lifestyle that excited her. She took a massive leap of faith.

Today I am an advisor to her company Spoak. It is a platform for interior design that scales with you, from being a homeowner, to a hobbyist, all the way up to a professional. She has built an amazing product, an enthusiastic, engaged community, and a stellar team of people behind it all. None of this would have been possible if Hilah had not been dedicated to looking deep within her psyche, confronting her demons, and committing to constantly updating her mind and her actions. The leap out of being employed into starting your own company becomes the catalyst for an ongoing experience of self-discovery.

Tom: What are the worst mistakes you see?

Devin: A life without Emotional Diversification is a serious liability and not a ton of fun. Most people understand that they need to diversify their investment portfolios. It has become common knowledge that committing too large a percentage of your resources to one investment exposes you to great risk. It makes you fragile and overly vulnerable to volatility. Only cavalier cowboys invest in just a few stocks. When they do they inevitably end up obsessing over minor fluctuations in their performance. They fixate on the market all day. They create a high anxiety situation.

Consider on the other hand your average index fund holder. She is free to ignore the vast majority of the ups and downs that an average day offers. She feels secure in long term trends and unbothered by day to day fluctuations because her capital is spread out over hundreds of investments. If one investment performs poorly it isn’t like her whole outlook becomes bleak.

Everyone gets this in finance. Few seem to see the correlation to their emotional life. When we get obsessed we become weak. If all one cares about is a single relationship or a single job they become incredibly fragile and incapable of weathering minor fluctuations, setbacks or criticisms. Your wellbeing becomes too wrapped up in how that job goes, in how that relationship goes. To be healthy and resilient we must spread our emotional capital out.

You need some things that you do just for the intrinsic value they provide and many things that are capable of consuming you completely in the moment. This is about hobbies, relationships, projects, learning, creating, travel, jobs, spirituality etc.

Tom: What have you come to believe about the world in the years you’ve been working?

Devin: I left NYC to go live on a mountain for a year right as Occupy Wall Street was happening. Because I was leading the Integral Philosophy Meetup at the time a few people suggested that I go down and give a talk.

Before I could even consider what to talk about I wanted to know who was there, what they believed, and what they were hoping to achieve. The one commonality I could find was a belief that they, the 99%, were wise, but disempowered, while the 1% were both ignorant and powerful. Their response was to raise their middle finger and say f&*K you to the 1%. It broke my heart. I believe that there are no evil babies.

We are all doing the best with the resources that we have. The drive to be a hyper-achiever is often a response to unresolved trauma. If someone is struggling to feel safe in the world then attacking them almost never helps. If you think that people who aren’t satisfied with a 9 or 10 figure income feel safe, then you probably haven’t gotten to know too many of them deeply. To me, fighting against something is never enough. We need to hold a vision of a better way and invest in that. We need to trust in the fundamental decency of every person, attempt to get past our own fear, and approach other people from a place of empathic concern for our shared reality.

The drive to be a hyper-achiever is often a response to unresolved trauma. If someone is struggling to feel safe in the world then attacking them almost never helps. If you think that people who aren’t satisfied with a 9 or 10 figure income feel safe then you probably haven’t gotten to know too many of them deeply.

I realized that I wanted to build bridges. My purpose became bringing wisdom to power. If given the choice between demonizing someone and trying to understand them, engage them, and attempt to enlighten them I will always try to choose the latter. Now that I work with people who are incredibly powerful I also see how much many of them are suffering. This system isn’t working for anyone. Yes, I would much rather have wealth than not, but no part of me believes that amassing a fortune makes you immoral or that attacking the wealthiest is leading towards a solution. I want these people to experience a radical shift in consciousness, open their hearts, and learn to lead in a way that is better for the planet, humanity, and for them personally. In my experience, they want the exact same thing.

Tom: If you’re reading this and have never seen a coach, what would you say they should look for?

Devin: Resonance. It’s a bit like dating. Don’t assume that you should work with the first person you speak with. Date a bit. If you don’t feel deeply understood then you haven’t found the right person. I would also look for someone who asks questions you either haven’t considered or don’t get the opportunity to discuss often.

Tom: Anything else to add?

Devin: Blaise Pascal said, “All of humanity’s problems stem from man’s inability to sit quietly in a room alone.”

Happiness and self-love are inextricably linked. No amount of external validation is ever going to be enough. Chasing achievements, titles, and wealth as a means to feel good enough is chasing the horizon.

If you can’t enjoy the felt sense of being alone in your own body without stimulation then perhaps this is something you should be compassionately curious about.

Tom: Thank you Devin, this was absolutely perfect.

Devin Martin is an executive life coach in Manhattan, his website is www.lifestyleintegrity.com