The Journey Through Lostness: From Disorientation to Discovery

A Guide to Embracing and Navigating the Wilderness in Life

The winter of 2018 was one of the darkest seasons in my life.

Just months before, I left my role as Partner at RRE Ventures, where I burnt myself out and felt like I didn’t belong. This was the first time since my early teens that I didn’t have a job, a reality it turned out I wasn’t prepared to navigate. In the weeks and months after I quit, the monotonous days and nights melded into an endless loop. Untethered in the wilderness of uncertainty, I was unable to find any bearing.

Most days, I stayed in bed until my wife ripped the sheets off me. The silent force of my own inertia held me down like gravity, while the living city bounced outside my door. I couldn’t see any possibilities—the world beyond my room felt distant and disconnected.

On the days I mustered the energy to venture out, I’d aimlessly wander the streets of the West Village. This city, once a symbol of clear direction and ambition, now felt like an elaborate maze without an exit. Sometimes, I’d find refuge in Washington Square Park, sitting in solitude amidst the lively backdrop of jazz and the buzz of college students. There, a single, gnawing question haunted me: "What the hell am I doing with my life?" These moments of introspection often spiraled into self-beratement for choosing to leave an incredible job—a decision that felt like abandoning a sure path to wealth and success.

Because I didn’t want to show any vulnerability or weakness, I found myself compelled to tell my colleagues and friends that I wasn’t confused and floundering and in pain, I was embarking on an exciting new venture! I pitched them the concept of Genuine VC, a unique fusion of capital and coaching, as my next big endeavor. Despite the enthusiastic front I presented, this ambition felt hollow deep inside me, especially when contrasted with the reality of my day-to-day life. I spent countless hours at my desk engaged in a dance of distraction, mindlessly adjusting pixels in a PowerPoint without any real purpose or progress. My life was the epitome of being busy yet profoundly unproductive. Where I had been trapped under the weight of inertia, I was now trapped in a cycle of futile motion.

The narratives I constructed in my mind became my own barriers. "No one will hire, partner, or invest in me," became a mantra of defeat, reinforcing the walls of my self-imposed labyrinth. My wife, always my anchor, saw the storm within me and urged me to seek professional help, to find a job, or to simply do something to break the vicious cycle. However, pride—stubborn and blinding—led me to ignore her pleas and refuse her advice. 

I had convinced myself that sheer willpower could be my way out, that I could bulldoze my way through the fog of uncertainty. Willpower and tenacity had always been my go-to strategies, the backbone of my previous evolutions and achievements. Pushing forward with all my might was all I knew. Faced with depression and a profound sense of lostness, my naivety and blindness prevented me from seeing that these old methods, while successful before, weren’t the right tools for navigating this new transition and stage in life.

I was utterly lost. Navigating this new terrain baffled me. The map that once guided my career had become obsolete and I was clueless about how to draw a new one. I had been conditioned to view any halt in progress and momentum as a direct path to obscurity. I worried that even a brief pause would derail my high-flying venture career. I worried that my deal flow would dry up, my market value would erode, my relationships would wither, and I'd lose touch with the latest trends and companies. 

Despite all this, something deep within me insisted I needed to stop. Not to forge ahead with the same old map. To accept my lostness, recalibrate, and move slowly in a new direction.

Six years later, my inbox is regularly flooded with heartfelt emails and DMs from prospective clients, stating:

"I'm in uncharted territory."

“I’ve lost my fire.”

“I'm not where I thought I’d be.”

“I don’t know how to proceed.”

“I’ve been going non-stop for 20 years.”

"I feel so lost."

These people are not alone. 

To be lost is to be human

Feeling lost is a fundamental part of the human experience, a feeling that traces back to the dawn of history. It's a theme deeply embedded in our earliest stories, including "The Odyssey" and numerous other epic tales.

Just like our ancestors who ventured into the wilderness for millennia, equipped with little more than their senses, determination, and a hope for discovery, we too navigate the unknown in our lives. The edge of the known, filled with uncertainties and challenges, serves as our crucible for learning and evolution. Here, our changing desires and expectations meet a world that's always in flux. When our sense of self doesn't match our reality, we're called to step into the unknown—intellectually, emotionally, spiritually, and physically. While this journey may be disorienting and unsettling, it’s this very path that guides us to new discoveries within ourselves and our lives.

Lostness affects even those who appear successful and seem to have everything figured out. Scores of professionals, especially those perceived as successful and at the peak of their careers, wrestle with deep feelings of being lost and intense insecurities about their place in the world. Substack and LinkedIn are now teeming with these stories! This experience is becoming increasingly common as Gen X and millennials find themselves thrust into midlife and as the pace of the world accelerates, challenging our sense of stability and direction.

Lostness, in essence, occurs when our path is clouded with uncertainties about who we are, where we're going, and why we make the choices we do. This often leads to feeling disconnected from our paths, our purposes, and sometimes, from ourselves. Because loss itself is a part of life, feeling like we are the ones who have become lost is inevitable.

Everyone's encounter with lostness is profoundly personal and distinct. Being lost is a powerful metaphor that means something different to each of us, influenced by our unique experiences, life context, and histories.

It could be the unsettling feeling of losing direction, watching dreams slip away, relationships fading, or finding our creativity and drive waning. Lostness can emerge from aspects of life that once filled us with joy, fulfillment, or excitement, but no longer feel right and we’re not sure why. When we experience loss, of a person, a place, an ability or passion we used to have, this challenges our sense of belonging, identity, and purpose, too–we can become lost after losing something important to us.

Change is constant, and it’s change that triggers feelings of lostness. These feelings are not indicators of failure but are, instead, markers of our participation in an ever changing reality and a timeless human narrative. They remind us that, like those who journeyed before us, we too are explorers at heart, destined to seek, to struggle, and ultimately, to discover and evolve. 

The question is: what do you do when you feel lost?

Stop to locate yourself

Wilderness guides advise the lost wanderer to simply stop. Stop talking, moving, thinking, and stand still. This pause isn't just about gathering our thoughts; it's a crucial strategy for avoiding deeper confusion. In our hurry to solve our predicament, we often exacerbate it, spiraling further into disarray. Sound familiar?

If you shared with me that you felt lost, I wouldn't simply offer directions or advice on your next steps. Such guidance would not benefit your growth and development. Instead, inspired by David Wagoner's timeless wisdom in "Lost," I'd encourage you to "stand still." I'd ask you to notice your breathing, feel your feet on the ground, take in your surroundings, observe the objects in the room, and reflect on your inner state. Through this exploration, you would see that you're not physically lost but experiencing a feeling of lostness. Together, we would then explore what this sense of being lost signifies for you.

Only with this understanding can you begin to effectively navigate your feelings of lostness and discern your way forward.

This moment of stillness does more than help us collect ourselves; it makes it easier for others to find us and assists us in finding ourselves. The inclination to keep moving, ingrained by our constant push for progress, actually hinders our ability to navigate out of lostness. By choosing to stop, sit, and breathe, we counteract our body's stress response. The activation of the parasympathetic nervous system in these moments does not just calm us physically but also clears our minds, lowering our heart rate and facilitating a mental clarity essential for discerning the next steps.

Such deliberate stillness and presence, though it may feel counterintuitive, is the bedrock of sound decision-making when we're lost or in transition. It disconnects us from the panic-driven cycle fueled by our sympathetic nervous system and reconnects us to our higher reasoning faculties. Ultimately, it equips us with the mental clarity needed for effective problem-solving and pathfinding, underscoring the profound strength found in calmness and patience. Slowing down not only reduces our stress response but also quiets our mind, helping us see the bigger picture and notice intuitions or insights that were obscured by stress.

Following the wisdom of a wilderness guide: after pausing to catch your breath, the next step is to explore your surroundings. By being fully present, you proceed, keenly observing your environment and trusting your senses to guide you. This exploration can take you to a vantage point, offering a wider perspective. Perhaps you'll spot smoke in the distance, beckoning you onward, or the sound of a rushing river might lead you to follow its path.

As you follow the river's path or are drawn toward the distant smoke, you're led not just through the physical wilderness but toward a moment of introspection. It's here, in this space of reflection, that understanding and articulating your lostness becomes the next crucial step.

Understand and articulate your lostness 

Once we manage to slow down and embrace stillness, the next step is to admit that where we find ourselves isn’t where we want to be, that we could indeed be lost. This acknowledgment can be difficult, as our ego often fights to keep its sense of control and competence. Acknowledging our lostness not only avoids additional distress and confusion but also lays the groundwork for change. Staying in denial just prolongs our disorientation, trapping us in a cycle of stagnation. However, by facing our lostness directly, we pave the way for discovering how it manifests along with its root causes.

In confronting our lostness, it's crucial to pinpoint the areas of life where this feeling predominates. Is it in our careers, within the dynamics of family or partnerships, or perhaps in our sense of place and belonging? Identifying the specific realms where lostness takes hold can illuminate parts of our lives that remain unaffected and may still offer a sense of direction and stability. This differentiation not only helps target our efforts to find clarity but also reminds us of the aspects of our lives that remain secure and grounded amidst the uncertainty.

Once we pause and acknowledge we're feeling lost, it's time to go deeper. This involves asking ourselves probing questions that help uncover the underlying meanings and behavioral patterns associated with our sense of lostness. This step is about more than quick answers or fixes. It's an opportunity to grasp the wider context behind our lostness and identify the patterns that brought us to this point.

These questions are designed to illuminate the deeper meanings and patterns underlying your sense of being lost:

• How are you lost? What are you looking for? 

• What’s your experience of being lost—cognitively, emotionally, and somatically? 

• How long have you felt this way? What changed? 

• Is it all the time, or are there specific triggers? What are they? 

• Have you ever felt this way before? When? What happened? 

• What do you believe about yourself when you’re lost? 

• What are your behavior patterns when you feel this way? 

• When you’ve been lost in the past, what was missing? 

• How did you find your way forward? What happened? 

Through this exploration, we can uncover what's beneath the metaphor we've constructed: we aren't actually "lost"—it's likely not the first time we've felt this way. We're using this metaphor to symbolize something missing, something we badly want to find or recapture.

Are you searching for a purpose, or looking to rekindle or cultivate a skill? Perhaps you expected to feel like a master after a decade in your career but find that's not the case. It's possible you're no longer motivated by what used to drive you, or you thought you’d feel differently after reaching your definition of success. Maybe you're longing for a new calling in life, or craving love, connection, or belonging. How do you react when you realize that something is missing?

Whatever it may be, understanding what's missing and observing our reactions to its absence helps us know ourselves, our expectations, our behaviors, and our deepest desires. 

Navigating the fluid nature of reality poses its own set of questions. How do we make sense of constant change and recurring lostness? What can we learn from its ever-evolving nature? Finding peace within this flow, leaning into and embracing the uncertainty, becomes our opportunity. Most crucially, how do we accept and find comfort in being lost, making it a place we can call home?

Find your through-lines

In the midst of lostness, when our wits and senses are all we have, the task is to rediscover a path that bridges our past experiences with our future destinations. Amidst such disorientation, this task can seem daunting, even for the most experienced and capable. These paths we seek are our through-lines.

Through-lines are the enduring elements that link your past, present, and future–think values, meaningful relationships, and passions. When orienting in lostness, these elements constitute your bearings, so it’s essential we take time to get to know them.

Though many through lines exist, here are the ones that I relied on when traversing my own wilderness:

• Values: The core principles guiding your actions over time, shaping your behaviors, identity and interactions.

• Relationships: The deep bonds with family, friends, mentors, or partners that offer support, love, and belonging.

• Passions and Interests: Joy-sparking activities or subjects that have been consistent sources of engagement.

• Rituals: Established practices or routines that provide consistency and structure.

During my transition, it was these through-lines that kept me anchored and moving forward. Each morning, I'd engage in morning pages to spark creativity and end the day with gratitude journaling. Prioritizing physical activity, I'd go for long bike rides along the West Side Highway and the Hudson River, embracing movement and nature. Throughout, the unwavering support from my wife, family, and close friends was indispensable. These through-lines, among others, proved to be powerful beacons during my times of lostness, helping me regain my footing in the world. They offered me a framework upon which to rebuild my sense of self and direction, serving as reminders of what truly matters even when the path ahead seemed obscured.

Drawing on these through-lines during my times of lostness was like finding the golden threads in a vast tapestry, each one guiding me back to a sense of stability and direction. These threads—my values, relationships, passions, and rituals—wove together the disparate pieces of my experience, creating a pattern that made sense of the chaos. They anchored me, not just to the world around me but to my core self, illuminating the path through the wilderness of uncertainty.

By embracing and holding onto these through-lines, we not only find our footing in moments of lostness but also weave a richer, more enduring narrative of our lives. Each through-line contributes a distinctive thread to the fabric of our existence, laying a foundation that steadies us through change. As we navigate our path, these enduring elements remind us that, even in the face of uncertainty, we remain tethered and guided home by what fosters meaning in our lives.

Lostness is a cycle that brings us home

Remember, feeling lost is a universal aspect of being human. Our expectations—our maps—are constantly challenged. Recognizing that lostness is, in some degree, an enduring trait rather than a transient state informs how we move through it. Stepping back, we observe a landscape in constant flux, changing with the seasons and over time. 

In this ever-changing sea of life, embracing the present over our expectations and tapping into our inner wisdom is crucial for navigating successfully. When reality doesn’t match our expectations and desires, we encounter pain, fear and disorientation. That’s precisely why we must slow down, ground ourselves, understand our lostness, and identify the through-lines that enable us to move forward, allowing us to revise our old maps and chart new ones.

Time and again, we find that we no longer have to cling to what we think is safe and comfortable, in the form of old beliefs, stories, roles, identities, and relationships. Each step along the unfolding path, though uncertain, leads us to new discoveries about ourselves and our lives. That path we discover is woven within us—lit by essential qualities such as wisdom, patience, compassion, courage, creativity, and surrender. 

In embracing the continuous nature of lostness, we recognize its transformative potential—not as a force of upheaval but as a tide of renewal, gently reshaping the shores of our lives. Just as rivers carve canyons, our experiences of feeling lost carve deeper channels of insight and wisdom in us, revealing new landscapes of possibility.

Everything changes. In this ever-turning wheel, each moment of lostness is a step towards finding ourselves anew, reminding us of the endless dance between being lost and being found, losing and finding, and the beauty that lies in the exchange. Wherever you are, you are where you need to be. 

Just take a pause. Breathe. Look up. Look around.