The Trouble with Maps
(They are not the territory)
We love maps. OK - I know I do.
Neat, clear, and predictable - maps promise certainty. They lay out the route, charting a straight path from where we are to where we want to be. They make the world feel manageable. Understandable.
And so, we collect them.
We read the books. Take the courses. Listen to the experts. Absorb their strategies, their frameworks, their step-by-step plans.
Known Knowns
We sketch out our own beautifully detailed maps—convinced that clarity is the missing piece, that if we can just get the plan right, everything else will fall into place.
And yet, when we finally step into the real world, the ground feels nothing like the maps we’ve studied.
Because maps are not the territory.
The Messy Reality of the Unknown
The moment we leave the safety of planning and enter the landscape of real change, everything shifts.
The road that looked clear on paper is suddenly covered in fog.
The neat sequence of steps is now riddled with obstacles we never saw coming.
The confidence we felt while planning is nowhere to be found.
Because real change is not a set of neatly ordered steps. It’s a landscape of uncertainty—messy, unpredictable, and full of resistance.
The moment discomfort shows up, we default to old habits.
When a decision feels risky, we hesitate.
When we feel lost, we retreat to what’s familiar.
And just like that, the old scripts take over. Back to square one.
Our ego, protective but suffocating, urges us back onto paths we’ve already walked. They simply feel safer, even when they lead nowhere new.
We tell ourselves we need a better plan. A clearer strategy. More research. But the truth is, we don’t need better maps. We need to become better navigators.
We fixate on tactics. The "what" and "how" of change.
What system should I use?
What’s the best morning routine?
What’s the most productive way to get this done?
And yet, the biggest gap isn’t in our plans, but our capacity to execute them, aka handling the discomfort, staying in the stretch zone and not running away.
Because the real challenge isn’t knowing what to do. It’s doing it when things get hard and following through when motivation fades, when fear creeps in, when self-doubt whispers into our ears.
That’s the skill we need most—the ability to move forward through uncertainty, discomfort, and resistance. Ouch.
Navigating the Gap
Any ambitious task worth doing will stretch you. We’re not talking about creating things we’ve done before, but rather our personal Quest.
It will demand patience when you crave immediate results, test your resilience when things don’t go as planned and require courage to make decisions without guarantees.
This is where most of us get stuck —not because we lack intelligence or ambition, but because we underestimate what real change requires.
We prepare for a journey of strategy and before we know it, we find ourselves in a journey of self-transformation. Because the real magic isn’t in the plan. It’s in who we need to become in the process of navigating it. Still - easier said than done.
This is the part of the story we often miss in the world of everything “self-” : it’s damn hard to do this alone.
No matter how many books we read, no matter how much advice we gather, when we hit the inevitable wall of uncertainty, our nervous system will panic.
We’ll start to doubt ourselves, convince ourselves we’re not ready.
We’ll retreat to old comforts, telling ourselves we’ll try again later.
This is why we need co-regulation—someone who can help us stay grounded when fear takes over. Someone who can catch us when we stumble, remind us that resistance is normal, and keep us moving forward when we’re ready to turn back. A spare pre-frontal cortex to get us back on track when we spiral out.
Because knowing the way is one thing. Walking it is another.
And when the territory feels impossible, the fastest way through is not another map—it’s someone who has been there before.
Unknown Unknowns
The real work of change isn’t about finding the perfect strategy, but strengthening the part of us that can handle uncertainty.
Because the territory will always be unpredictable.
There will always be detours, obstacles, and moments of doubt.
But our ability to navigate that?
To move forward without guarantees, without certainty, but with courage?
That is the skill that changes everything
I’m currently running my own experiment. I’m looking for 2-3 people who want to venture off the map and into the territory. If you have a meaningful project or transition you’d love to explore—with company and support—I’d love to hear from you!