About two years ago, I started a journalling ritual. Wake up, morning exercise, shower, grab my Loop earbuds and journal, and then head to one of my local cafés. I order my Chai (yes, Chai!) and that’s where I write.
Lately, my writing has been circling my work as an executive coach, the real conversations, not the polished stories. The conversations I have with leaders keep bringing me back to a familiar story. One I’ve read countless times to my beautifully neurodiverse son: Oh, the Places You’ll Go!
What started back then as a new parent’s selfish attempt at achieving down-regulation, even if briefly, gradually became something else. A source of quiet guidance about navigating uncertainty, change, and momentum, for both of us.
That story has settled so deeply that it now lives permanently on my right arm in tattoo form.
“You have brains in your head. You have feet in your shoes. You can steer yourself any direction you choose.”
What continues to strike me is how closely a children’s book mirrors the lived experience of leadership in real organisations. The playful, sing-song rhymes carry themes I see leaders wrestling with every week in coaching, often without the language to name what’s happening.
Possibility and agency
The book opens with optimism. You’re reminded that you have tools, movement, and choice.
Over time, many leaders lose touch with this sense of choice. Not because they lack capability, but because structures harden, expectations multiply, and self-doubt quietly fills the gaps. Coaching conversations often start by slowing things down enough for leaders to notice where they’ve narrowed their own options.
When people experience autonomy, that is, real, felt autonomy, something changes. Decision-making becomes less reactive. Energy steadies. Purpose feels less borrowed and more owned. Leaders begin orienting themselves by values again, rather than pressure.
The challenge of choice
Choice brings responsibility.
Leaders face forks in the road constantly: career moves, people calls, strategic bets made without full information. Rarely do these decisions arrive neatly packaged. More often, they arrive tangled in uncertainty, politics, and competing priorities.
In coaching, the work is rarely about identifying a perfect answer. It’s about helping leaders listen more closely to their judgement, test assumptions, and move forward without waiting for conditions to feel safe or complete. Progress comes through engagement with uncertainty, not its removal.
The Waiting Place
Dr Seuss introduces “The Waiting Place”, a space where people linger, waiting for something to happen.
I meet many professionals and leaders in this place. Capable, conscientious, and quietly frustrated. They’re busy and productive, yet feel strangely static. Outward success coexists with an inner sense of delay.
When people start to feel that outcomes sit beyond their influence, action narrows. Over time, passivity can begin to feel protective. The Waiting Place captures this experience with unsettling accuracy.
Coaching offers a pause and an interruption. Often through small, deliberate actions that reintroduce movement. One decision. One conversation. One experiment that reminds someone they still have influence.
Success, setbacks, and resilience
The story celebrates achievement, while also acknowledging how quickly success passes.
Leaders are familiar with highs. They’re also familiar with the weight that follows setbacks, the responsibility, the self-scrutiny, the quiet isolation. When time, energy, reputation, or relationships feel under threat, stress can accumulate fast.
Coaching creates space to make sense of these moments. It helps leaders clarify what they want to protect, what they can let go of, and how to replenish what’s been depleted. Resilience becomes something cultivated over time, rather than demanded in the moment.
Courage and individuality
Every journey unfolds differently.
Leadership often involves moving without a clear map, especially when others’ expectations pull in competing directions. Choosing a path that aligns internally can feel uncomfortable, particularly when it diverges from familiar patterns or external approval.
Coaching supports leaders to spend time with that discomfort, rather than rushing past it. Through reflection and honest conversation, many reconnect with a quieter internal compass that guides decisions with consistency and integrity.
The coach’s view: what leaders bring into the room
There’s a part of this story that doesn’t appear in the book, but it shows up regularly in my coaching room.
Leaders rarely arrive saying they’ve lost their sense of agency. Instead, they say things like:
- “I should be further along by now.”
- “I know what I want to do, but I keep hesitating.”
- “I’m tired of holding all of this alone.”
- “People expect me to have answers I’m not sure about.”
Beneath the competence and titles, there’s often a quiet grief. Not dramatic. Just a sense that something once felt more aligned and spacious, than it does now.
At this point, the story shifts from metaphor to mirror.
Leadership, as it shows up here, has less to do with climbing and more to do with noticing what has quietly shifted. Noticing when momentum has slowed. Noticing whose expectations are being carried. Noticing where choice has been deferred rather than exercised.
A practical reset you can use today
If you recognise some of this in yourself, a simple reflection can help reintroduce movement, without drama.
- Where do I feel most stuck right now, and what explanation (or excuse) do I keep returning to?
- What small decision have I been postponing because it feels uncomfortable or exposing?
- If I allowed myself a little more trust, what would I try next?
No long-term planning required.
Just one step that reconnects intention with action.
Why coaching helps
Coaching creates a structured, human space where leaders can speak honestly, without being managed, judged, or corrected.
Over time, patterns become visible. People’s assumptions can be tested. Responsibility returns to where it belongs. Movement resumes, not through force, but through clarity.
Leaders stop waiting for certainty and start engaging with what’s in front of them.
The call forward
Dr Seuss closes with: “Your mountain is waiting. So… get on your way!”
Change rarely begins with certainty or confidence. More often, it begins with vulnerability and a decision to move.
You already have brains in your head. You already have feet in your shoes.
Your mountain doesn’t require perfection.
People, including you, are more capable than they believe.
So get on your way.
