How to Navigate Bewilderment in Work (The Wonder Dispatch 03.30.25)

Trail Markers on the quest for meaningful work

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Each morning these days, a male cardinal dominates the Hudson Valley soundscape. A pair of Canadian geese arrived on our pond last week, right on schedule—prepping, as they do each March, to hatch a season of possibility. A pack of friends and I met at an outdoor spot a few nights ago to hang out, catch up, and hatch ideas.

Spring sings with possibility.

And yet.

And yet when it comes to possibility in your work and business these days, that exhilaration can be edged with a quiet unease.

Nature these days doesn’t always follow predictable rhythms, and neither do our work and business lives.

More than likely, when at the crossroads of possibility, you or your team might feel something often not discussed in the psychology of human flourishing and business: Bewilderment.

Bewilderment, wonder's Deep Woods facet, is that unsettling mix of excitement and uncertainty. It is a response to simultaneous positive and negative input that could spark fear, confusion, and creative possibility.

So, let's get perspective on how to recognize bewilderment and how we might readjust our mindset and set of actions to move our ideas and work forward without bypassing the hard stuff.

This month, we’re diving into tools, insights, and strategies for Reimagining Work and Business Models. I trust you’ll find something valuable—or a wee bit wondrous. As always, I welcome your thoughts.

In this week’s Wonder Dispatch:

• 4 trail markers to help you navigate the Deep Woods of bewilderment and still advance the work that matters

• curious resources on my radar

• an opportunity to work together

• more readings on this topic

A few years ago, I keynoted at the Think Better, Live Better Conference hosted by NYT best-selling authors and coaches Marc and Angel Chernoff.

It turns out that Marc and Angel have their own story of bewilderment.

When Marc and Angel realized that their side gig self-improvement blog was gaining thousands upon thousands of subscribers, they wondered if they could leave their full-time positions and devote their finite energy to work of their own making. Their parents and siblings said, "Stay where you are!" But something inside them kept countering those familiar voices.

It felt like a crossroads in the woods.

In moments of bewilderment, you’re both exhilarated by what’s possible and daunted by what’s unknown. Not knowing—who you are becoming, what to do next, or what will happen—is uncomfortable. But if you navigate the discomfort and track bewilderment, you could reach creative and personal breakthroughs. I see it happen over and over again among venture capitalists, writers, lawyers, coaches.

Thankfully, Marc and Angel didn’t leap out of their jobs instantly into a fantasy of creative entrepreneurship. They persisted, honed their coaching skills, delivered, engaged, gathered data, experimented, eventually making a viable path.

They’ve since written NYT bestsellers and hold annual coaching conferences while raising their sweet son.

What made the difference? In part their long-game perspective and their ability to navigate bewilderment almost like a quest.

Building a fulfilling path in life and work is a quest.

What does that mean?

I’ve worked with many hard-working professionals, founders, creatives, and leaders—people who’ve honed their skills, earned their reputations, and invested years in their business or craft. Yet, at some point, they ask themselves, “I want to pay more attention to my ideas” or “I want to stop hiding and finally claim my place.”

This quest looks different for everyone:

• Some want to show up as a different kind of leader—politician, entrepreneur, or artist—by sharing their point of view while also elevating others.

• Others want to level up their business or visibility but feel daunted by the changes that entails.

• Some are ready to move beyond academia and make a bigger impact in the world.

• A few want to completely reinvent their career, aligning it with a new sense of purpose and service.

• Many are driven to foreground their unique perspective—whether through a business, a brand, a book, or another endeavor—but are determined not to fall into the grind or hustle culture.

The common thread? Some of them might need to muster the courage to stand out while they’re also navigating the discomfort of bewilderment—uncertainty in the pursuit of something more meaningful. And through this journey, I’ve witnessed how this unsettling phase can lead to breakthrough moments.

Trail Markers for Navigating Bewilderment

If you find yourself deep in the woods of professional and/or personal transition, here are four Trail Markers to guide your way:

Trail Marker #1: A road map helps, even when it changes.

Even though business plans always change, a big-picture plan still alleviates a little anxiety. You can craft that map and perhaps find a trusted guide to hold it with you.

Trail Marker #2: A compass is even better.

Inevitably, you must know who you are. What are your genius character strengths that only you possess? Who are you at your best without regard for external validation? You discover answers not just by reflecting but also by acting and learning from your actions.

A compass keeps you oriented, even when trails shift. It builds cognitive flexibility, helping you adapt and create your way forward with integrity.

Trail Marker #3: Every bold idea begets a series of challenges.

To write a book, start up a venture, up-level a business, scale a business, launch and monetize a podcast, create a suite of offers, untangle your work for more freedom - these are all big ideas. Each everyday creative genius I’ve worked with has learned to expect challenges. They weren’t born with this mindset; they cultivated it.

The key? Fertilize rather than pathologize confusion. Fertile confusion—when tended well—leads to fresh perspectives, creative breakthroughs, and even a redefinition of who we are.

Trail Marker #4: How you work with those challenges determines in part whether you flounder or flourish

Your nervous system plays a huge role in this. Chronic stress signals fight-or-flight responses, which can exhaust you. But moments of wonder—like tracking bewilderment—help reset your system. They cultivate cognitive, social, and creative resources so you’re less depleted and more fortified.

Psychologist Barbara Fredrickson’s Broaden-and-Build Theory supports this: states of awe and wonder expand our mental, emotional, and social capacity, helping us see and seize new possibilities.

The Quest Requires Spacious Pacing

When I mention this phrase “Spacious pacing” to some clients and Inner Circle members, something shifts. Sometimes it’s a revelation. Sometimes, it’s a countercultural signal going off. Do I deserve to have spacious pacing?

Reaching a clearing in the woods - one of fulfillment, impact, and return - isn’t some idyllic fantasy. It’s that you have a reset on how you respond a little less reactively and a little more creatively to challenges as opportunities. More often than not, you experience more openness, curiosity, connection, expansiveness, impact, and fulfillment.

In short: You up The Wonder Ratio.

You're in this for the long game not for false hopes of hockey-stick growth (that typically leads to more burnout).

That means discerning true urgencies from false urgencies. An urgent task from an important one. And giving due attention and focus to the important, impactful ones even when they don't have an urgent timeline.

So much is possible.

Your Window of Possibility

As you navigate moments of bewilderment, consider these invitations:

• Track Your Trail Markers: This week, notice a moment when you feel uncertain or lost. Which of the four trail markers could guide you forward?

• Reframe the Unknown: What if bewilderment isn’t a dead-end but a doorway? Journal for five minutes about a past moment of uncertainty that led to an unexpected breakthrough.

• Expand Your Map: Seek out a perspective beyond your usual view—a book, a conversation, or an experience that challenges the way you see your current path.

Your Turn to Wonder

• Where is bewilderment showing up in your work right now?

• And how might you track it toward more possibility today and this week?

Hit Reply and let me know or, better, share your thoughts in the Comments with others in The Wonder HUB.

Well, it’s an honor to engage you here. I appreciate your showing up for the work at hand and this one beautiful life.

Would you do me a favor? If something here resonates with you, share this post with others and spread the wonder.

I’ll see you soon here at The Wonder HUB - and next Sunday for The Wonder Dispatch.

Thanks for running with me,

Jeffrey

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Curiosities on Jeffrey’s Wonder Radar

»> Political Empathy Lab (PEL) at U Penn - an inspiring model that gives students stills, tools, and experiences to “exercise” during “dialogue across difference.” More of this, please. H/t to Evelyn Asher

»> Radical Listening: The Art of True Connection by Christian Van Nieuwerburgh and Robert Biswas-Diener - I haven’t started it yet but it dives into a topic instrumental in life, work, Inner Circles I lead, and the retreats I lead. I have a lifetime to learn and teach here.

»> How do you balance creative life with family? Nick Cave | Red Hand Files - I almost wrote about this topic this week - but maybe next week.

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