FAQs

In my experience, one person benefits greatly from strong coaching: someone attempting a significant upward movement. Personally or professionally, the Talent (i.e. a client) that benefits from coaching is attempting to move from their current position to a qualitatively different destination.  

If you experience strong coaching, after the first session you should be able to see why so many top performers hire coaches. The reason: it is a competitive advantage for achieving larger goals.

Coaching is not a mystical journey, led by a guru with esoteric knowledge. The reasons why it works are not mystery, and not magic. Coaching works because having a second intellect that you respect, in this kind of relationship, helps you think and act more effectively. The “relationship” here means that the coach is outside of your life—the conversation is not performative, not quid pro quo, and not “two-way.” It is dedicated entirely to you (not your boss, company, or family) and your vision. It is a confidential space with a second high-horsepower intellect that challenges you, says things and asks questions other people won’t, sees outside your blind spots and assumptions, and brings additional strategic acumen to your major decisions. It is a kind of conversation, on your life’s biggest questions, you can’t really have anywhere else.

The person who has that will, all things equal, think and build more effectively than the person who doesn’t. In time, they will dream bigger. In my experience, the inner clarity and strength drive both higher levels of external performance, and more internal ability to enjoy them, in a mutually-supporting cycle.

Ten minutes of real coaching is better than writing you a lengthy description here. If you’re curious what real coaching is, book a free discovery session.  There’s zero pressure or sales pitch—I’m not a salesman, and the only people I work with are those who are a great fit.

Calm, but direct. I’m friendly, but not your friend. While the space is safe, my job is to challenge you. If it doesn’t do that—if it feels like other conversations in your life—then I am not doing my job. Coaching should offer conversations that are qualitatively different—in their focus, depth, and candor—than you can have elsewhere. You can have interesting conversations at any café. This is different.

All great coaching is bespoke. I don’t come with answers.  I come with wisdom and experience, an ability to listen deeply, and a lot of questions. Hard questions. You, “the Talent,” have the only answers that will be authentically yours. The answers are not some secret that I already hold. Rather, they are a mystery that both of us are trying to solve, shoulder to shoulder. 

If it’s helpful, my intellectual foundations are a blend. The special operations community was foundational intellectually. While my academic work is in strategic studies, I’m a rather fanatical reader.  The major intellectual pillars of my approach are in classical Greece and Rome, particularly Stoicism; Zen and 30+ years of meditation practice; and Existentialism, particularly Camus. Creatively, I’m a follower of Rick Rubin. These have formed, for me, a model of living that has kept me in a consistent upward spiral.

That said, my own intellectual interests are of secondary importance.  They matter only to the extent they allow me to ask you interesting questions. What matters is your answers, how authentically they reflect you, and how well you can live them in the moments that matter.

This depends almost entirely on the person you currently are, the audacity of your goals, and how well we work together.

That said, you should be having “aha moments” by the end of the second session. If not, we’re not a strong fit—and that’s fine.  Like you, I’m only looking for strong fits. Happy to point you towards other people, resources, and modalities that would better serve you.

On average, six to twelve months, depending on the boldness of your goals. 

That said, some relationships last longer, depending on one question—are you still getting an ROI beyond the value of the investment?   The only reason to continue is a resounding “yes.”  

When we’ve reached a point of completion, we’ll debrief, reflecting on the distance run and the way ahead. If a future day comes when you’re wanting to dream wildly and build strategically again, we can square the guns for a new goal.

While Type A was defined by cardiologists in the 1950s to describe mindsets correlated with coronary risk, I define it here more simply: “Achievement Obsession.” This captures both its strengths and limitations.

The "Type A" profile describes high-energy individuals, on a spectrum that is defined by intense goal orientation, competitiveness, and a chronic sense of urgency. For these leaders, identity is often fused with professional performance, leading to a relentless pursuit of results that often values speed and action over contemplation and clarity. While these traits can catalyze early career success and rapid execution, these natural strengths eventually reach a point of diminishing returns as complexity and scale increase. 

That drive can build companies — or burn them down — depending on how it’s managed. In the relational sport of leadership, constant Type A driving can erode mutual trust, resulting in teams that execute but do not fully engage, are creatively stifled, and eventually have high turnover. Personally, the "grind" often leads to burnout and a sense of fading adventure, where individuals find they know how to compete for success but not how to enjoy it.

We build each session, and our relationship as a whole, from scratch. That said, here are some broad models I’ve pursued successfully in the past.

• Performance Coaching. We dive deep on your professional or personal dream: questioning and defining the desired end state; conducting strategic and operational planning; identifying obstacles, threats, and risks; mapping out human networks; defining contingency plans and adaptations. We set concrete long-term goals, break these into short/mid milestones, and get after it. I hold you accountable to your vision. Relatedly, we work on optimizing your performance and sustaining at that level. Like elite athletes, this includes how to replace anxious energy with calm clarity, thinking about burn rate and recovery, and optimizing over the long arc for output, creativity, and energy.

• The Internal World. Internal clarity breeds external success. People focus a great deal on external goals.  What are your goals internally?  How do you want to feel?  Don’t give the easy answer—when, and more importantly why, are you most authentically thriving?  External goals are just means to ends. What are the actual ends, the drivers of meaning, that animate your goals?  This is an investment in how well you know yourself, and the deep architecture of what makes you sustainably thrive. Winning and creating consistently at the elite level is, counterintuitively, not the product of an unblinking focus on victory. They are a byproduct of authentically thriving, which brings energy and creativity beyond what externally-facing ambition could ever sustainably generate. Internal clarity and strength will increase your external triumphs, sustain them, and simultaneously make them more enjoyable.  

• Leadership. Much of modern leadership is about deep emotional intelligence, allowing you to unlock the potential of your team and, in essence, craft meaning and culture. This kind of emotional intelligence can’t be faked ad infinitum. It implies deep inner clarity (see above), and the ability to lead with authenticity-i.e. mixing vulnerability and ferocious dedication to your people with traditional forms of strength and strategic clarity. You want to build teams that are fiercely committed to you personally, as you are to them. The leader who has this will outperform the leader who does not—enjoying both higher morale and higher performance.

• The Second Front of Family. Just as Type A fuel is incomplete for leading a team, it is incomplete for leading a family. The major muscle movements of domestic life—finding a partner, starting a family, being a brilliant spouse and parent—require of you new skills and ask you new first-order questions. Further, many Type A performers must answer these domestic questions in a way that aligns with huge external ambitions. One of the biggest threats to your external ambitions, and more importantly, the internal happiness of you and those for whom you are most responsible, is the frequency of divorce or enduring suboptimal partnership. Eighteen happy years and two thriving kids into a high-performance relationship, I can help you build a second front that nests authentically with the first. 

• Shadow Work. Where are you weak? Are you brave enough to go there? When are you at your worst—and how do we help that version of you, so that they don’t slow you down? This type of internal work helps high performers enhance and sustain elite performance. An ambitious life almost guarantees repeated Edison-like failures—with no guarantees of Edison-like tenacity. How do you deal with failure and shame?  Do you approach them with a hammer, or with a flashlight? How can you judo loss into strength?  Most Type A people avoid this kind of work, trying to convince themselves (and the world) that there are no shadows. That doesn’t work. In my experience, not only is that no fun (and it isn’t), but that kind of internal mud eventually erodes external performance. It also leads to people who win but can’t enjoy winning. In total confidentiality and mutual candor, I can help here.

• Manhood, Duty, and Hedonism. I’ve read and thought deeply about modern manhood, and the relationships between duty, meaning, freedom, and authenticity. Like all good coaching, my own answers to these questions are irrelevant. But I’ve thought deeply about them, from Sartre and Onfray to Brooks and Rohr and back again. In many ways, from the Ranger Regiment to today, my life has been the pursuit of an authentic modern manhood. I would be excited to invest with you on defining yours, on your terms.

• Meditation. I started meditating at sixteen, not because I wanted to commune on some astral plane, but because I wanted something to help me face the physical suffering of Ranger Regiment selection. I had seen the Rage Against the Machine cover with the burning monk, and thought, “If he can do that, they must be on to something.” From that start, I’ve spent three decades on the cushion, to decrease the noise level in my brain, increase my performance and stamina, and train myself to react powerfully to sudden change and emotion.  I can help build you here.

• On Your Mind. What major questions are you wrestling with right now?  What are the major questions you must answer to have the future you envision?  What are the greatest threats to that future, and how do we overcome or minimize them? Who must you become?  You tell me what questions you’re pursuing, and we’ll see if we’re the right fit.

Possibly. Let’s discuss. Group facilitation is bespoke, tailored to your exact needs. I would need to hear exactly where your team is, and what kind of movement defines success. Once we’re clear on this, if I’m not the right guy for that work, I have a network of strong facilitators—perhaps one of them would be a powerful match.

At a minimum, a facilitation is $1K for a one-hour session, inclusive of vision meeting, prep, session, reflection, and post-session support.