Why (and how) do you have a coach?

Turns out you don’t have to figure it all out alone

Every now and then, in the middle of a conversation, I’ll casually mention something I talked about with my coach. And almost without fail, I get the look. A tilted head. A curious pause. Sometimes a skeptical squint. “Wait… you have a coach?”

I’ve gotten used to it.

I don’t play a sport. I’m not training for a marathon or gearing up for the Olympics. So the word “coach” tends to throw people off. Is he a life coach? A career coach? A therapist in disguise? For a while, I tried to explain. I’d caveat and clarify, give him a more specific label. But eventually I stopped. “Coach” is actually the most accurate word I’ve found. The rest can stay mysterious. And yes, the sports analogy is a fair one (we’ll come back to that later).

It’s been surprisingly difficult to put into words what my experience with a coach has meant to me. Maybe that’s why it feels important to try. What started as a quiet experiment has turned into something valuable beyond words. So if you’ve ever wondered why someone might choose to work with a coach, or if the idea has never even crossed your mind, this is my attempt to share one perspective.

Who is this piece for?

This article is for anyone who’s ever considered working with a coach, or wondered if it might be useful, but weren’t quite sure where to start. It’s also for those who may have tried working with a coach before, but didn’t find the right fit.

In the sections that follow, I’ll explore what coaching means to me, what led me to my coach, why I keep coming back to the practice, how our sessions work, and what I’ve learned so far. I’ll also share a few ideas on how to begin if you’re curious.

To be fully transparent, this is also a wholehearted endorsement of my coach, who I believe is one of the most gifted people I’ve ever had the privilege to work with. That said, coaching is deeply personal. What resonates for one person might not land for another. So rather than suggest a single path, I’ll also share a few thoughts on how to think about coaching in a way that aligns with your needs, intentions, style, and goals.

What does coaching mean to me?

Even though I haven’t played an organized sport since childhood, I still love the sports analogy when it comes to coaching. I think I first came across it in the book Trillion Dollar Coach, about Bill Campbell, the legendary mentor to some of Silicon Valley’s most influential leaders.

The best sports coaches aren’t micromanagers. They’re not constantly interrupting with fixes. They offer targeted insights, help shape vision and confidence, and then step back. They give space to try, to fail, to grow. The most effective ones aren’t there to play the game for you – they’re there to help you play it better.

That’s the kind of coaching relationship I find meaningful. One that blends challenge and care. One that listens before jumping in with a solution. One that sees you not as a problem to solve but as a person to witness and support.

My favorite description of the coach role comes from

David Emerald Womeldorff

, author of The Power of TED (The Empowerment Dynamic):

“A Coach sees the Creator essence in those they support and holds them as ultimately resourceful and resilient. Unlike the Rescuer who reinforces the powerlessness of a person in the Victim role, a Coach uses the art of inquiry, curiosity, and deep listening to support others in discovering what is best for themselves.”

That last part really stuck with me. A good coach doesn’t offer rescue. And they’re not trying to fix you – because they know that you are not broken.

Instead, a coach stands beside you. They help you see what you might not have noticed. They ask thoughtful questions. They reflect things back that you didn’t realize were even in play. And they do it in a way that’s generous and grounding, less prescriptive or forceful.

In his book, Emerald also describes the coach’s companion role: the Challenger. Someone who calls you forward. Not to criticize or impose, but to inspire. They hold the vision for what’s possible, even when you can’t quite see it yourself.

“Challengers are catalysts for learning and are willing to stand for the vision, even when others do not. Rather than criticizing or blaming, a Challenger inspires others to reach for the highest good of all involved.”

This combination, when you have a coach that knows how to be a challenger when needed, is quite powerful. It’s not about performance optimization in the way the business world often frames it. It’s about truth, perspective, and intentional growth.

Michael Bungay Stanier, in his book The Coaching Habit, sums up this mindset with one of my favorite little gems, as a coaching haiku:

Tell less and ask more.
Your advice is not as good
As you think it is.

That one makes me smile every time. And it also holds true. The last thing I want in a coach is someone eager to give advice or tell me what they would do in my shoes. That’s not the practice. That’s not the path.

Instead, what I value most is presence. Someone who engages deeply. Who listens fully. Who holds space long enough to really see what’s there. And then, when the moment is right, offers a perspective or reflection that helps me see things from a very different vantage point. One that reveals something profound, without ever making it feel like they’re drawing the map.

Coaching, at its best, is about walking alongside. It’s about honoring the complexity of another person’s path, not simplifying it. Every journey is different. And every journey is valid. The best coaches help us remember that. Not by showing us their answer, but by helping us rediscover our own.

What led me to having a coach?

I stumbled into working with a coach. I wasn’t out searching for one. I wasn’t even sure I believed in the idea.

What I did know was that I was entering a complex and somewhat disorienting phase of life. I felt the weight of transition. However, as I had in the past, I was trying to move through it quickly. If the job wasn’t working, the career path wasn’t fulfilling, or the next step wasn’t clear, my default approach was to outline a plan. Next steps. Get into action. Solve it. Figure it out.

So I began networking. Lots of conversations. Informational interviews. Coffee chats and reconnections. During one of those meetings, a friend of a friend mentioned that someone she knew had recently found his calling as a coach. She spoke highly of him. “You might really get something out of it,” she said. I smiled, nodded, thanked her, and promptly filed it away in the mental drawer labeled Interesting, but unlikely.

Later, I looked at his website. It looked good. Polished. Thoughtful. Still, I was skeptical. I’ve always valued self-reliance. I wasn’t sure what a coach could offer that I couldn’t figure out on my own. And the idea that one person could provide the right combination of insight, support, challenge, and presence, without really knowing me, felt more than unlikely. It felt fantastical. Too good to be true.

And yet, I’ve spent much of my life being moved by the words of great writers. Authors who seemed to speak directly to my inner life. Books that challenged and changed me. So I asked myself, what makes this any different? If a voice on a page can open something up in me, why not a voice in conversation? So I said yes to a free 30-minute session. Just a trial. No expectations. I figured, what’s the harm?

That first session changed something. There was no grand moment, no dramatic breakthrough. Just presence. Questions that made me pause. Reflections that weren’t intrusive, but somehow reached right into the heart of what I hadn’t said out loud. Something inside me recognized the resonance. I didn’t know what this was, but I knew it was something worth following up on more.

Looking back, I didn’t find a coach so much as I had the courage to try, to see what it might be like. And in that simple act of trying, I stumbled into a gift. I discovered that I didn’t have to figure everything out alone. Maybe I could slow down. That I might benefit from walking with someone for a little while, instead of always trying to sprint ahead on my own.

Why I started, and why I keep returning

So, what does it take to find the right coach? Luck? Magic? Maybe a little of both.

Over the years, I’ve met with friends, and friends of friends, who have gone into coaching. All wonderful people. All well-intentioned. Many with thoughtful programs and structured frameworks. But finding the one right coach for you is a lot like dating. There’s no universal metric. When you know, you know.

Okay, maybe that’s a little too gushy. And to be clear, I don’t mean “the one.” Coaching, like any relationship, works best with clear boundaries. There’s a fine line between connection and dependency. A reminder that, yes, may have been reinforced by Bill Murray’s character in What About Bob, who famously clung a little too tightly to his therapist. Helpful insight is valuable. Reliance isn’t. Coaching is not about dependency. It’s about perspective. It’s about finding solid ground. Not in someone else, but in yourself.

That’s one of the things I appreciate most about how my coach structures his work. Sessions are typically conducted weekly, and offered in three-, six-, or nine-month packages. Each engagement has a clear beginning and end. There’s a focus. An intention. A transformation to work toward. And when that work is done, the idea is not to continue indefinitely. It’s to carry the tools forward on your own.

And in many ways, that’s exactly what happened. My coach helped me complete one major phase of a transition. That phase needed closure, and I found it. Now, I’m entering the next chapter. Like many meaningful transitions, I’ve come to recognize that this one has three parts: an ending, a liminal space, and a new beginning. What started with letting go is now something else entirely. I keep returning not to be guided through every moment, but because the space continues to support my growth through these distinct phases.

How I work with my coach

When I started, I thought my expectations were straightforward. I assumed we’d put together a six-month plan to transition out of my current job, figure out what I wanted to do next, and move into it. The usual toolkit: visioning exercises, personality assessments, pro/con lists. You know, the typical stuff. Don’t get me wrong, those tools can be very helpful. But here’s the thing: I had already done all of that. Strategizing was my profession. My career had been built on clarity and planning. I didn’t need more structure.

What I needed was harder to name. And somehow, my coach could see that.

Over time, I realized something was repeating. In every job, the same cycle: initial excitement, deep engagement, challenges overcome, and then slowly, disappointment, disengagement, disillusion. It might have been the mission, the results, the people. There was always something that felt “off.”

Eventually, I had to face the harder truth. The common denominator in all those roles?

It was me.

Not in a self-critical way, but in an honest one. The beliefs I held. The expectations I carried. The reactions I couldn’t quite see. I hadn’t outgrown them. I had just gotten better at working around them.

That was where the real work began.

After pouring my heart out in that first 90-minute coaching session, trying to capture all the pieces of who I was and what I thought I needed, session two surprised me. There was no ten-step plan. No quick wins or templates.

Instead, my coach asked questions. He listened. He probed gently and deeply. What started as a career conversation quickly shifted into something more personal. Not therapy, exactly, but certainly therapeutic. Not because we set out to go there, but because that’s where the work lived.

Unspoken fears. Old stories. Childhood moments I hadn’t fully acknowledged. Fear of failure. Worry about being a disappointment to those I love. These weren’t just emotional echoes. They were active ingredients in how I had been showing up: at work, at home, in my own mind.

Here’s the surprising thing though: my coach didn’t try to fix them. Instead, he created space for me to see them.

Sometimes, he’d ask a question I didn’t understand right away. I’d sit with it, and later, it would unlock something. Other times, he offered reading suggestions: books that quickly earned a place on my personal top shelf. As a lifelong lectiophile, I devoured them. They didn’t just support the work we were doing, they expanded it.

There were exercises, too. Never busywork. Always stretching. He encouraged me to deepen my meditation practice. To write more creatively. To explore moments of play and discomfort. Karaoke made it onto the list. I haven’t done that one yet (part fear, part logistical challenge as a father of three) but I’ll get there.

Eventually, the six-month coaching package came to an end. The transformation wasn’t dramatic, but it was real. Subtle in some ways, profound in others. I was different, and to be fair, still evolving. A chapter had closed. One that I had resisted closing for a long time. I stepped away from not just a job, but a career. Not to chase the next thing, but to pause. To listen. And in that listening, something new is taking shape. I still don’t know what it is yet, but the space to breathe has been a critical ingredient in that search.

We still meet now, but at a slower cadence. Every other week. Sometimes I bring ideas. Sometimes I bring uncertainty. Either way, the process continues. But it’s not to guide every step, rather to help me meet whatever arises with curiosity instead of dread.

And that, I’ve found, is the quiet power of this kind of coaching. Not to give you the answers, but to help you “live the questions long enough” for something to emerge.

What I’ve learned (so far)

It’s hard to summarize what I’ve learned through coaching. The truth is, I’m still learning. Still unfolding. Still working through the patterns and questions that shape me. But along the way, a few insights have stood out. Less like conclusions and more like mile markers.

This is a short collection of what has stayed with me, thus far:

I’ve learned that the inner critic never goes away, but I can shift how I relate to it. Giving it a silly voice or imagining it wearing a funny hat turns its monologue into background noise rather than doctrine. It’s still there, but it doesn’t get the mic. That small shift in perception lets me meet self-judgment with a bit more humor, and a lot more distance.

I’ve learned that creativity isn't a gift we're handed, but a practice we build. Like a musical instrument, the more we engage with it, the more it reveals what’s inside us. It’s less about what we make and more about how we relate to the act of making. Only by creating do we remember we were born to create.

I’ve learned that freedom isn't just the absence of constraints. It’s the presence of possibility, choice, and alignment with something more meaningful than external success. I used to think freedom would come from escaping pressure. But now I see it more as the ability to stay rooted and intentional, especially when things feel uncertain.

I’ve learned that control is an illusion when it's used to avoid pain. Real freedom comes not from controlling outcomes, but from choosing how I relate to uncertainty. The more I’ve tried to predict or preempt disappointment, the more stuck I’ve become. Letting go of that impulse has created space for something more honest to emerge.

I’ve learned that choice is not about picking the right outcome. It’s about choosing how I show up to the moment, especially when the outcome is beyond my control. Even the illusion of choice carries weight. But real choice, I’ve found, lives in how I perceive and respond, not in what I can guarantee.

I’ve learned that asking for help is not a weakness. It’s a way of building connection, and allowing others to show up for me. That act, as simple as it seems, also teaches my kids how to receive support without shame. And it teaches me that I don’t have to do everything alone to be strong.

I’ve learned that endings are hard for me. I’ve often rushed through them, skipped them, or tried to outmaneuver their discomfort. But when I allow things to end, rather than racing toward the next thing, I create space for something deeper to emerge. Closure isn’t always clean, but it’s necessary.

I’ve learned that the pursuit of knowing can become its own form of avoidance. I spent a long time worshiping clarity, fearing confusion. But confusion itself is not the enemy. It’s the entry point. When I stop needing to resolve the unknown and instead get curious about it, something softens. The more I can live with questions, the more I learn to trust what unfolds.

I’ve learned that play is not indulgent – it’s essential. There’s a part of me that’s been long buried under responsibility, under productivity and checklists. I’ve started to meet that buried part again through writing, through laughter, even through the uncompleted challenge of karaoke. Play reconnects me to joy. And joy, it turns out, is a compass worth listening to.

For all that I’ve written here, there’s so much more I’ve learned and still learning. Things that live not in words but in quiet shifts, small pauses, and moments of recognition. These reflections are just a glimpse; the few I can remember well enough to name. I’m deeply grateful for the space that allowed them to emerge, and for the guidance that helped me hear them when I was ready.

Where to begin if you’re curious

If any of this has resonated, and you’re curious to know who my coach is, his name is

Jean Theron

, and you can learn more about him at jeantheron.com. He is one of the most compassionate, well-read, intelligent, and empathic people I’ve ever met, and I obviously recommend him highly.

That said, I still believe that finding the right coach is a deeply personal journey. It’s less about credentials and more about chemistry, resonance, and timing. Before seeking a coach, I’d suggest starting with a few questions for yourself. What do you want in this life? What’s working for you? What isn’t?

One helpful tool I used before beginning coaching was a book: Designing Your Life by Bill Burnett (along with the accompanying workbook). I can’t say it gave me any definitive answers, but it helped me slow down and ask some interesting questions. It opened up space to consider what I wanted to explore, and what I was ready to let go of.

That became the starting point. Not a roadmap, but a willingness to begin.

I’m still a work in progress. But the difference now is that I have more confidence to explore. And more trust that the work itself is the path.

Resources for deeper exploration

If you’re curious to explore more, here are a few books and resources that have supported or shaped different parts of this journey:

• Jean Theron – Coach
  The coach I’ve worked with and recommend highly. Thoughtful, compassionate, deeply intuitive. Learn more about him and his approach here.

• Designing Your Life by Bill Burnett and Dave Evans
  A helpful primer for rethinking how to approach your life and career, especially when you feel stuck or ready for change.

• Designing Your Life Workbook
  A practical companion to the book, filled with exercises that help you get curious, reflect, and experiment with new directions.

• Trillion Dollar Coach by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle
  A tribute to Bill Campbell, who quietly coached some of the most influential leaders in Silicon Valley. A reminder that great coaching is often more about presence than expertise.

• The Coaching Habit by Michael Bungay Stanier
  Simple, direct, and refreshingly honest about the value of listening over telling. Especially helpful if you want to bring a coaching mindset into your own relationships.

• The Power of TED (The Empowerment Dynamic) by David Emerald
  A compelling reframing of victim-consciousness, and an introduction to the roles of Coach, Challenger, and Creator in any meaningful transformation.

• How to Do the Work by Dr. Nicole LePera
  A guide to recognizing and healing emotional patterns with a blend of psychology and holistic self-awareness.

• Transitions: Making Sense of Life's Changes by William Bridges
  A timeless reflection on the phases of transition: endings, the in-between, and new beginnings. Insightful and deeply human.

Of course, there are many other thoughtful coaches, books, and tools out there. If you’ve come across something that’s helped you along the way, I’d love to hear about it in the comments.

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