Recently, I had a coaching session with a client who’d been running his own business for years. What once filled him with joy and purpose had started to feel like a slog. He’d already scaled back the amount of day-to-day work he was doing, hoping that would reignite the spark, but something still wasn’t right.
He felt stuck. Unsure about what needed to shift.
As we talked, I could sense that he was stuck in his head, trying to logic his way out of a problem that logic couldn’t solve. So I asked him to close his eyes. I guided him through a meditation to help shift his focus from his mind to his intuition. With eyes closed, we explored the layers of his inner knowing, as I asked different questions that rose into my awareness, one after another.
Then came the question that changed everything.
He paused, and then, out of nowhere, he burst into laughter. It wasn’t just any laugh—it was the kind of laugh that comes from deep within. The kind that signals a profound release. In that moment, he knew. He knew it was time to retire, to let go of the grind, and embrace the next chapter of his life with peace and clarity.
In that moment he knew he’d known this for a while.
In that moment, he knew the past year of scaling back his work was in preparation. To get himself comfortable with letting go and ready to shift into this next chapter of retirement.
This is the magic of coaching. It’s not about having all the answers—it’s about asking the right questions.
For most of my life, I prided myself on being the person who over-prepared, over-studied, and relied on sheer intellect to succeed. Whether it was learning Arabic in record time during my Peace Corps training or landing a job at Microsoft I didn’t have the resume for…. I was always the one who out-disciplined everyone else. I pushed harder and it worked.
Until it didn’t.
Coaching isn’t about out-disciplining anyone. It’s about intuition. It’s about feeling through a conversation rather than thinking through it. Every time I step into a coaching session, I have to let go of the desire to control and the need to plan. Instead, I have to trust in something deeper—something that doesn’t come from textbooks or training manuals.
When you’ve spent your life relying on discipline, this way of operating can feel like a trust fall off a cliff.
Before every call, I get a little nervous. I know I’m stepping into the unknown. There’s no script, no way to prepare for what the client will bring to the table. All I can do is get grounded, center myself, and be fully present. The questions will come, seemingly from nowhere, but always with a sense of rightness. They repeat in my mind until I have no choice but to ask them.
And those questions—they’re the key. They unlock doors the other person didn’t even know were there. They help them see what they’ve been too busy, too scared, or too stuck to notice. They lead to moments of clarity, moments of truth, moments of knowing.
Helping someone reconnect with their inner truth, watching them light up as they finally see themselves clearly—it’s an incredible honor. It’s why I do what I do.
One hour. One conversation. It can change everything.
What are you waiting for? Book a call here.
