An Elder’s Compass: A Guide for Would-Be Coaches

Over the past few years, my inbox has often been jammed with variations of the same question: How do I become a coach?

Sometimes it comes from a product leader, a founder, or an executive who has lived through the turbulence of scaling and wants to turn their scars into service; they’ll have heard me on some podcast or read my book, Reboot, and—having been moved by what they experienced—they feel the call. Sometimes it’s a colleague who has experienced firsthand the power of being coached and feels pulled to do the same for others. And sometimes, like a note I received recently from a man named Josh, it’s simply a heartfelt request:

“I’m transitioning into executive coaching for product and engineering leaders and am looking to connect with experienced coaches like you to learn how you got started and what’s worked best.”

I always read these notes with care. Because behind the question is often a longing: a longing to help, a longing to serve, a longing to be present to another human being in the midst of their becoming.

But here’s the hard truth: coaching has exploded as an industry. The number of certified coaches has skyrocketed. The number of uncertified coaches—well-intentioned, perhaps, but often unprepared—has grown even faster. Add to this the rise of AI coaching and the proliferation of venture-backed platforms promising “scale,” and it can feel as though coaching has become another growth market, another hustle. Which breaks my heart even as it terrifies me.

So what guidance can I offer? What compass might help the would-be coach orient themselves in this noisy, crowded field?

The Call to Coaching

Most people don’t wake up one morning and declare themselves a coach. The call usually arrives more quietly.

It might arrive in the form of a colleague who sits with you and says, “You really helped me through that.” It might come after years of being mentored and realizing you’ve internalized a way of listening that changes others. It might, as it did for me, come out of your own suffering. Suffering and having finally put the pieces together and realizing that I could combine my practical business experience with my deep love of Buddhist dharma and the healing effects of psychotherapy.

Our wounds become the currency of empathy. When we’ve sat with our own pain, we can sit with another’s without flinching. When we’ve learned to navigate our own shadows, we are better equipped to guide others through theirs.

So before embarking on the journey of becoming a coach, ask yourself: Am I willing to use my struggles in service of others? Not to fix them, not to offer easy answers, but to be with them in their not-knowing. To be, as I was commanded years ago when I was on a vision quest (without any substances) in a desert in Utah, to be Holder of Stories of The Heart. This—and only this–is where coaching begins.

The Discipline

This work is not casual. It is not for the faint of heart. It will challenge you as you’ve never been challenged before. (And when that happens, you’ll know you’re doing it right.)

There are dozens of training programs—some independent, some tied to universities or business schools. The International Coaching Federation (ICF) certifies many of them. Each has a different methodology and emphasis. The temptation, in a culture obsessed with shortcuts, is to think you can bypass the discipline. Don’t.

The temptation is to think that your years-long training as a student with a guru, perhaps, will qualify you to deal with the complex issues that can arise in the space you’ll create with your client. Or, because you raised venture capital for your startup (which may or may not have successfully returned capital to your investors), you’re qualified to coach. Or, perhaps, you’ve developed a unique framework when you were a leading executive at a large company and, therefore, you’re now ready to coach others.

You’re not. You’re ready to mentor folks, perhaps. You may even be ready to be a consultant to them. But you are not ready to take up the mantle of being a coach.

Treat training with the seriousness of graduate school. This is not a weekend workshop to add another line to your résumé. It’s an apprenticeship in presence. The process deserves respect. Respect and time; it’s an old joke but, like wine and cheese, the best coaches age gracefully and ripen with the fullness of time.

And beyond training, you’ll need supervision. At Reboot, we created Reboot Supervision for this very reason: even trained, well-trained coaches need a place to bring the complexities of their practice, the countertransference, the doubts, the “stuckness” that arises when you’re holding another person’s life in your hands. Without that container, a coach risks using their client to work out their own unfinished business. It is the ethical responsibility of every person called to coaching to do this work. For the rest of their lives.

The discipline of coaching is, in essence, the discipline of radical self-inquiry.

If you are not willing to confront your own patterns, you will inevitably impose them on those you coach.

The Practice of Presence

Presence cannot be scaled.

This is where the industry’s infatuation with venture capital so often goes wrong.

A few years ago, I watched as companies accepted large rounds of funding with the mandate to “grow at all costs.” The logic was the same as any tech startup: add users, expand rapidly, become the dominant player, generate a return for your investors. Lather, rinse, and repeat.

But coaching is not software. You cannot “optimize” for presence.

I had a conversation not long ago with a founder who had built a coaching company.

They told me, candidly, “You were right. We shouldn’t have pursued growth. I should have pushed back on the feeling that building a coaching business as a ‘lifestyle business’ is a bad thing.”

I understood their regret. Because in the drive for scale, something essential was lost: the stillness that makes coaching transformative. When a coach is rushed, when sessions are commoditized, when the emphasis shifts from relationship to throughput, the work hollows out.

And if AI is substituted for presence, the hollowing becomes complete. AI will no doubt simulate aspects of coaching, but it cannot replace the embodied wisdom that arises when two people sit in the unrepeatable alchemy of a real conversation. It is in the space between client and coach, the space Irving Yalom talks of in his book, The Gift of Therapy, the space the late Doug Silsbee wrote about in The Mindful Coach (which is embodied in the training program the wonderful folks at the training firm, Presence-Based Coaching have built their programs around) the space that Theodor Reik says is created by the healer when they “listen with the third ear”) that the magic of growing into adulthood occurs.

A Lifestyle Worth Living

Let me reclaim a phrase that is often maligned: “lifestyle business.”

I and my co-founders have built a lifestyle business. I work with clients I love. I work alongside colleagues who stretch me and make me laugh. I earn a good living doing work that matters. This is not small. This is not lesser. This is a life worth living.

Not every business needs to become an empire or have an “exit,” not every coach needs to reach tens of thousands. If you can help a few hundred people live with more integrity, presence, and compassion, isn’t that enough?

As I age, as I add grandfather to my long list of titles, as I feel more and more comfortable as an elder in this field, I want to release new coaches from the illusion that bigger is always better. The most redemptive work often happens in the smallest rooms, in the quiet of one person being seen.

An Elder’s Advice

So here is my compass for those who feel called to this work:

1. Begin and continue forever with your own inner work. If you haven’t been coached, if you haven’t sat with your own shadows, start there.
2. Choose training with rigor. Don’t look for shortcuts. Find a program that challenges you, that matches the kind of coach you want to become.
3. Seek supervision. Even the most experienced coaches need others who can mirror them, question them, and keep them honest.
4. Find colleagues. Coaching can be lonely. Surround yourself with peers who will hold you, challenge you, and remind you of your humanity.
5. Remember that your presence is the tool. Techniques matter. Frameworks matter. But in the end, who you are—your capacity to sit with another without judgment—is the essence of the work. The most important tool a coach has is a well-asked, open and honest question. Those questions which arise from your inner being, from the space between coach and client, are the questions that best serve the client.

This is not a quick career move. Coaching isn’t the answer to the question of “What should I do with my life now that my company is no longer operating?’ It is a lifetime’s work. It is a lifetime commitment to being of service.

A Blessing

And so, for those who feel called, I offer this blessing, written with my co-founder Ali Schultz, in the style of John O’Donohue. May it guide you as you step into the vocation of coaching:

May you always coach from the center of your being.

May you never lose touch with your struggles, so that you may use them as the currency of empathy, so that you understand who your client is and how you may be of service.

May you have the wisdom of the wild things—the knowing of the sparrow when it’s time to fly, the nightsight of the owl that discerns what lingers in shadow.

May your being be a safe place. An offering, a pause, a stillness. May your presence be a mirrored container for someone to feel seen.

May your listening be a big ear for others to hear their voice clearly.

May you set out to do the work of a lifetime, surrounded by resources in your work, your heart, and your life.

May you have good colleagues to lean on and learn with. May the earth hold you as it rests in the cosmos.

Coaching is not about techniques alone. It is about becoming the kind of person who can hold another in their becoming. If this is the path you choose, walk it with reverence and grace.