When Your Map No Longer Matches the Territory

Have you ever awakened at 3 AM, not because of tomorrow's meetings or that unfinished project, but because of something less definable? A restlessness. A questioning. A disquiet that persists despite all outward markers of success.

I'm noticing a pattern among many of the leaders and others I work with. They've done their work, whether it’s personal development, spiritual practices, or leadership development. They've achieved success by all that our culture declares: material wealth, influence, and recognition. And yet, there it is: that 3 AM feeling that something still isn't quite right.

"I've checked all the boxes," a CEO client recently shared with me. "I've built the business, I've done years of inner work, I've got the lifestyle I thought I wanted. So why do I keep waking up with this feeling that something's missing?"

What if nothing is missing at all? What if this disquiet isn't a problem to solve but a signal to attend to?

The Crossroads of Mastery and Mystery

There's a particular challenge that emerges when we've mastered certain terrains. The very maps and tools that created our success: the frameworks, our best sensemaking skills, our restorative practices, and our growth mindsets, all begin to show their limitations. Not because they were wrong, but because the territory itself is transforming.

Think about it. The approaches that produced breakthrough a decade ago now yield diminishing returns. The ways of seeing that once expanded our perspective now constrain it in subtle ways. The questions that once opened new doors now lead us down familiar corridors.

This isn't unique to our personal journeys. We're witnessing a similar pattern playing out in our wider systems and culture—established structures straining under the weight of complexity they weren't designed to hold. The post-modern breakdown isn't just happening "out there." It's happening within us too, especially among those who've been most committed to growth, making a difference and consciousness.

A founder I work with put it this way: "It feels like I've gotten really good at a game that suddenly changed its rules. And the skills that made me a master are now making it harder to learn the new game."

What if your expertise in one way of seeing is precisely what makes it difficult to see differently?

Signs of the Pivot

How do you know if you're being called to pivot? Beyond that 3 AM disquiet, there are subtle indicators worth attending to.

Have you noticed yourself doubling down on approaches that once worked reliably but now seem to miss the mark? This often looks like trying harder rather than differently. More workshops, more practices, more frameworks—but with a nagging sense that you're accumulating rather than transforming.

Or perhaps you've experienced what feels like regression, those moments where despite all your development, you find yourself caught in old patterns. This can be particularly disorienting for those who've prided themselves on their consciousness.

"I thought I was beyond this," a leader told me recently. "I've done so much work on myself, and yet here I am, feeling like I'm back at square one with these fundamental questions about purpose and direction."

What if these aren't signs of regression but necessary stages of progression? What familiar certainties might you need to hold more lightly to allow something new to emerge?

I'm reminded of a recent conversation with a colleague, Trish Blaine, when she brought up the metamorphosis of a butterfly and how many people don’t understand that it isn’t one day a caterpillar and the next a butterfly. We talked about there is a point where the caterpillar has done all it can do as a caterpillar. It has mastered caterpillar-ing. And then it enters the chrysalis—a place of breaking down before becoming something entirely different. Inside that chrysalis isn't neat, orderly transformation. It's messy dissolution. The caterpillar literally liquefies before reorganizing into something new.

That 3 AM disquiet? It might just be the first signs of your chrysalis.

The Hope Within Disruption

While many look at our current moment, both personally and collectively, and see only breakdown, I find myself increasingly optimistic. Not despite the disruption, but because of it.

When existing maps fail us, we're forced to develop new navigational capacities. When familiar approaches no longer yield results, we're invited to perceive in fundamentally different ways.

I've been accompanying several individuals through this territory, and I'm noticing something fascinating. Those who resist the disquiet, treating it as a problem to solve with familiar tools, often find themselves exhausted and discouraged. But those who approach it with curious attention discover unexpected vitality and possibilities.

A tech executive I work with shared: "For years I tried to solve that restless feeling with more achievement, more practices, more knowledge. Nothing helped. It was only when I started sitting with the disquiet itself—not trying to fix it—that I began to sense what wanted to emerge through me. Now I see it wasn't emptiness I was feeling, but fullness trying to find expression."

What whispers from the future are you beginning to hear when you stop trying to silence the disquiet?

I'm not suggesting this transition is easy or comfortable. It rarely is. But I am suggesting it might be necessary and ultimately life-giving. The very discomfort that wakes you at 3 AM might be the energy of emergence seeking expression through you.

Perhaps the most powerful pivot we can make is not between strategies or approaches, but in how we relate to uncertainty itself. Not as an enemy to be conquered, but as fertile soil from which something new is already sprouting.

That 3 AM feeling? It might just be what the future feels like as it's being born.

What's your experience with this territory? I'd love to hear how you're navigating the space between mastery and mystery. Drop me a note or leave a comment—this is a conversation worth having together.

Do you want to take this further and explore working together?

If you want to schedule a 30-minute, cost-free call, click here.

To read more by me, go here.

The Pivot Podcast, here.