What happens when you leave your career (and identity) behind

A deep dive into what you may encounter while navigating the void between the first and second halves of life.

What happens when you (or the universe) blow a big hole in the life you once knew?

What experiences do we drift in and out of when we allow our prior identity to fall apart?

What is the experience of being in the void between your old life and the new life that hasn’t yet emerged?

And what are we to do while drifting in uncertainty?

It’s been nearly five years since I quit my career at its peak and left it all behind. My life now is undeniably different than it was while I was still in the hot seat of startup life. With the benefit of time, spaciousness, and divine guidance, I can look back at my departure from my former professional identity and speak to it with greater depth and understanding.

That’s what this essay is about.

The First Mountain: The Path Well-Traveled

The first mountain of life is well-lit, well-mapped, and easily described. It's the one our culture celebrates: excelling academically, securing a practical degree, landing a position in a growth industry, ascending the ladder, accumulating wealth, gathering status symbols, and building influence.

This path offers the comfort of clarity—measurable milestones that signal progress.

Until one day, the metrics lose their meaning. The work feels like performance rather than purpose. The internal void becomes impossible to ignore. You're not just exhausted—you're existentially empty. You're not merely busy—you're fundamentally misaligned with the life and work you’re still living.

You no longer want to be on the first mountain of life. It no longer feels hospitable to you. You must leave this mountain.

What began as a whisper evolves into a persistent doubt that grows louder each month. On paper, everything looks perfect: the impressive title, the comfortable income, the professional recognition. You've scaled what society celebrates as success. But something fundamental has shifted, and you feel a growing discontent with the life you know.

It’s not because you’ve failed. The mountain you've been climbing no longer belongs to you. It’s time for you to step off of it. That inner voice of discomfort is your soul speaking to you, saying, “It’s time to let this go. It’s time we start our next season of life.”

You fight it. You push the beachball beneath the water, but it bounces back up, begging you to attend to it. Slowly, you relent to your soul’s call for something new.

So you make the terrifying, honest, uniquely human choice to walk away—to abandon the career that defined you and gifted you security you might not have had earlier in your life. You step into the unmarked wilderness.

Therapists call this the liminal space—the threshold between two worlds. I like simple metaphors, so I call it the valley between two mountains.

Let’s talk about what happens in the dreaded valley.

The Body Revolts

This transition isn't just psychological for those wired to achieve—it's biochemical. It lives in our bodies. We become conditioned to the intensity of our work, and our nervous system comes to expect its daily dose of thrash and stress.

Mechanistically, it’s no different than the chemical dependence we form with someone we love. Our body has grown to expect its daily hug and the presence of that beautiful woman next to us. But suddenly, she is gone. She leaves you behind, and you are left alone with unsatiated neurotransmitters. The mind is expecting the familiarity and comfort of your lover. But she is nowhere to be found. The chemical manifestation of love is unmet. In it’s absence, the body revolts.

And so it goes with your chemical addiction to achieving.

If work was your addiction—and for many of us, it is—you experience a painful withdrawal. Your nervous system, conditioned to constant adrenaline and dopamine hits, short-circuits without them.

You crash. Pleasure evaporates—the world drains of color.

This is anhedonia—the biological reality of removing a dominant stimulus, whether substances or the high-octane rush of work life. To your nervous system, it doesn’t matter. It wants its daily dose. But in the valley, you don’t get it.

Your mind will seek other sources of satisfaction. Maybe more sex can fill it? Perhaps a newly formed substance dependency? Or, I’ll doom scroll on social media for a quick fix.

This phase can last months—for me, about a year. I was angry, easily irritated, and ambivalent toward most things I once found pleasurable, seeking alternatives to reintroduce some intensity into my life.

I didn’t have work anymore. But I did have marijuana. So, I smoked a bunch of it. Daily in most cases. I paired that with gorging on junk food. And for the first time in my life, I felt sick and lost my athleticism. But that was better than the alternative (my mind told me). Anything to avoid the discomfort of no longer feeling needed for the work I can do and the problems I can solve for others.

I didn’t have work to validate my self-worth anymore, but I could at least numb myself to sleep each night with shit food and a hearty joint. So, I did. That went on for a couple of years until I began to break through the fog of the valley between our two mountains of life.

The Unacknowledged Grief

The hallmark of the valley is its spaciousness. A mountain dominates all space, as our work life did.

The valley is the opposite. Our life is now defined by openness. In that empty space, old pain will find room to reveal itself. Your work obsession made it easy to mask the feelings your mind sought to avoid.

But that’s okay. Your soul’s call for change was also your soul’s recognition that it was time to face the inner shadow that silently shaped your thoughts, attitudes, and behaviors.

In the valley between the two mountains of my life, I healed the younger version of myself that never felt adequate. 10-year old Andy remained stifled inside of me, begging to be attended to. But I buried his cries with work, money, and a relentless search for another professional accolade until I couldn’t do it anymore.

While in the valley, I let the younger version of me grieve and uncork the anger he held for nearly three decades. I let it flow. Shaking, sweating, screaming, sobbing, and rage came pouring out of me. I yelled at God, “Why have you done this to me!?” God answered back, “So that you could heal.”

And that I did.

For many, the first mountain isn't simply career—it's survival. Achievement becomes armor. A shield. A way to outrun childhood wounds.

In my case, work helped me survive childhood grief following a few hard years and the death of my mom when I was ten. Success became safety. Titles became protection. Abandoning that identity felt like emotional suicide.

But in the valley, that armor begins to crack. The buried feelings surface. And this isn't a detour—it's the essential path. You must face what you've been fleeing. The sorrow. The isolation. The uncertainty. The shame.

You must not rush through it.

This is the gateway to healing.

The valley opens up before you so that you can come undone in the spaciousness it provides. It’s a nest for you to mend your wounds and come in contact with the parts of you that want to be recognized, healed, and integrated.

The work to be done here is not on your laptop. The work is with your body, mind, heart, and soul.

The Relationship Reckoning

Then comes the cleansing fire of relationships.

The valley reveals who stands with you—and who was merely attached to your title, status, or utility. It's humbling, sometimes heartbreaking, to recognize how many “connections” were primarily transactional.

People from the first mountain of your life are often keen to relate to you based on what they can gain from you. You don’t want to bring those people into the valley—and you certainly don’t want to lug their asses up the second mountain you’re now climbing.

This is your chance to observe your relationships. Who has been extractive? Cut the ties. Burn the bridge. Let them go.

Who is genuinely rooting for you, no matter what new direction you’re heading in? Embrace them. And to all the rest—those who demonstrate through their actions that they’re connected to you because of what you can do for them—cut them loose.

One day, I went through my phone and purged 60% of the numbers. A few months later, I trimmed down another 20%. I let many old friendships fade away, especially those that showed no interest in where I was going or how I was evolving. Some clung to the old version of me they were familiar with. They tried to get me to play our old games. I wasn’t having it. I was letting that version of me die. It felt lonely—but eventually, those relationships were replaced by new friendships with people who embraced the new version of me.

One such friend used to exclaim, “We’re homies! We look out for each other.” My intuition sensed that was bullshit. With time, it was proven right. The only times I heard from her while in the valley was when she wanted money from me — to have me as an investor in one of the startups she was always trying to pimp out to me.

Gross.

Consider this a necessary purification. Review your connections. Your social circles. The people you maintain contact with out of habit or perceived advantage. If they belonged to your first mountain identity but no longer align with who you’re becoming—release them.

This isn’t rejection. It’s reclamation. And it creates space for new, authentic relationships rooted not in what you do or who you used to be but in who you are.

The Tension With Financial Practicalities

When you leave an established career, your relationship with money is brought to the surface. The steady paycheck—that biweekly affirmation of your market value—suddenly vanishes. With it often goes a cornerstone of your identity: the provider, the achiever, the financially independent self. This shift triggers more than practical concerns; it excavates your deepest beliefs about security, worthiness, and freedom.

Money anxiety during this period can awaken primal fears. Your nervous system floods with stress hormones when it detects a potential threat. You might find yourself obsessively checking accounts, feeling shame about reduced spending power, or making fear-based decisions that contradict your deeper intentions. This isn't mere worry—it's your survival instincts responding to perceived scarcity.

Yet, within this constraint emerges unexpected clarity. You begin distinguishing between genuine needs and habitual wants. The expensive dinners, the status purchases, and the reflexive spending that once felt essential suddenly reveal themselves as choices, not necessities. Many in transition discover they require far less than they imagined to feel content, but only if they are willing to sit in the valley long enough.

I found myself spending 4-6 month stretches in low-cost countries. I showered under a hose, ate boiled eggs with instant noodles, and slept on the notoriously stiff mattresses of Southeast Asia. I had one backpack with enough clothes to last me a week before needing cleaning. I washed them while I showered and hung them up to dry on the balcony. Life was simple, bills were low, and I felt free and happy.

I stripped down my material wealth to a 5x9 storage container, primarily full of camping gear and boxes of books, and a 2023 Honda Civic. Yes, I had money saved up and invested for the long term. I was in great financial shape due to my workaholism and was empowered by the buffer it gave me. Yet I also discovered that I needed very little to get by from there on out. The bank account didn’t need to get bigger. My material footprint needed to get smaller.

So it did and has remained that way since.

I can hear the naysayers already.

“You don’t have kids!”

“You don’t live in Silicon Valley!”

Correct. I don’t.

But you also don’t have to live the lifestyle you have. You’re clinging to your situation and refusing to acknowledge it by directing your attention to mine.

This financial recalibration, though uncomfortable, often catalyzes creativity. Without the cushion of abundance, you become resourceful in ways your former self might have considered beneath you. You discover the satisfaction of making rather than buying, repairing instead of replacing, and finding value in what you already possess. This isn't frugality—it's a fundamental reassessment of what constitutes enough.

The Social Pressure

Our culture harbors a discomfort with uncertainty. This becomes painfully apparent when you leave a defined role behind. "So what's next?" becomes the question you dread most at gatherings. Family members, friends, and former colleagues expect a narrative of a purposeful transition with a clear destination. Their anxiety about your undefined state may exceed your own.

This constant demand for explanation creates a peculiar pressure. You feel compelled to manufacture certainty where none exists, to present a coherent story about your journey while living in the messy middle. You find yourself crafting palatable explanations that sound more directed than your reality, further disconnecting you from your authentic unraveling experience.

You dread when old friends and colleagues ask, “So, what are you up to now?” Conditioned to respond with a list of upcoming achievements and notable goals, you avoid saying the obvious — you’re not doing much, and it probably feels like shit.

So, you make stuff up. Strangers ask about you casually, and you describe yourself as if you were entombed in a professional time capsule, grasping onto the most impressive-sounding title you can conjure up.

I’ll demonstrate with my own egoic nonsense.

After I left Silicon Valley, I spent over a year reading, writing, and journaling at a Christian-themed coffee shop in a small farming community far away from Silicon Valley. Someone would spark up a conversation and ask me, “What do you do?” At first, I clung to the fancy-sounding titles.

“Oh, I’m a Venture Capitalist.”

Inside, I cringed. I thought to myself, “What a fucking douche. They don’t care and probably don’t know what that is. And I hated the job anyhow! Just be honest, you douche.”

It took me several months before I started to answer truthfully. I wasn’t some fancy tech guy anymore—I never really was. I was larping as a fancy tech guy, but that’s never who I truly was. It was a costume that I wore well—nothing more.

Learning to say, "I’m not doing much right now, and I’m honestly a bit confused and trying to figure out what’s next in my life," becomes a quiet act of courage. These words, spoken without apology or elaboration, create space for genuine exploration. They acknowledge the reality of transition: that true transformation requires a period of not-knowing, a fertile void where new possibilities can germinate without premature definition.

This is the nature of the valley. It is blanketed in fog with no apparent trail to follow. It is ambiguous by design. Without a trail carved, you must find your own way through. That’s the whole point! You’re not walking someone else’s trail anymore. You’re bushwhacking your trail.

The most valuable companions during this time are those rare individuals who can sit comfortably with your uncertainty. They ask questions that open rather than close possibilities. They reflect back your emerging insights without rushing to conclusions. They understand that this chapter of your story is written in questions, not answers—and that this ambiguity is not a problem to be solved but a process to be honored.

Circumambulation and Non-Linearity

We instinctively seek narratives of transformation that move in a straight line: from problem to solution, from confusion to clarity, from pain to resolution. The actual transition experience, however, rarely follows such a convenient trajectory. Instead, you travel a spiral path—seemingly returning to the same challenges again and again, but each time with a new vantage point, a slightly deeper understanding, and a little more inner strength.

Carl Jung referred to this pattern as circumambulation—the psychological process of circling around the Self, our deeper center of being. Rather than moving directly toward wholeness, we approach it obliquely. We orbit it. Sometimes, we feel close to it; other times, we feel lost and far away. But the path winds for a reason: transformation isn’t linear, and the soul doesn’t grow by marching forward in a straight line. It deepens through layered revisiting—through the sacred rhythm of approach, retreat, and return.

Progress during this period often follows a “two steps forward, one step back” rhythm. Moments of breathtaking clarity—when the path ahead seems suddenly illuminated—give way to periods of disorientation when you question everything, including the insights that felt so certain days before. This oscillation isn’t failure; it’s the natural movement of integration as new awareness collides with old patterns. It’s how the psyche metabolizes change.

The temptation to return to familiar territory can be overwhelming when you face the discomfort of the unknown. Former colleagues mention job openings that would utilize your established skills. Recruiters dangle roles that promise to restore your professional identity. These moments of wobbling aren't weakness—they’re gravitational reckonings with the inertia of the known.

I had many moments of wobbling faith in the valley between the two mountains of my life. For 8-months, I took on paid consulting gigs with various startups. That helped me keep one foot in my old world while dangling my other foot into the abyss of the unknown.

At one point, I contemplated setting up a solo venture fund where I could invest in mental health and wellness companies. I got halfway through the fundraising process before I paused, asked myself if this was what I truly wanted to do, and was met with an immediate instinctive response, “Fuck no. I don’t want to do this crap anymore.”

So, I shut it down before it ever took flight.

Learning to distinguish between genuine evolution and subtle forms of retreat becomes a necessary act of discernment. Does this opportunity, though seemingly familiar, reflect the deeper values now awakening in you? Or does it seduce you back into a story you’ve outgrown?

The journey through the second half of life isn’t about rigid progress—it’s about learning to recognize when a backward glance is an act of wisdom and when it’s an act of escape.

In Jungian terms, the Self isn’t something you “achieve” once and for all. It reveals itself over time through the spiral of return. Through the looping path of circumambulation, we are drawn again and again to the center—not to arrive once, but to become ready to receive it.

The Challenge of New Routines

When structured work disappears, the unfamiliarity of the void is magnified by the absence of routine.

The rhythms that once shaped your days—morning commutes, scheduled meetings, lunch breaks, end-of-day emails—suddenly vanish. You find yourself in the disorienting position of consciously creating what was once imposed from the outside: the structure of your time.

This unstructured space is both a gift and a challenge. You're free to rediscover your natural rhythms without the pressure of external expectations. Are you truly a morning person, or were you adapting to workplace norms? Does your creativity flourish at conventional hours, or do your best ideas emerge at times your old schedule would have deemed unproductive?

Still, the absence of structure can stir up anxiety. Many find themselves either frantically filling the hours with trivial tasks or frozen by the sheer abundance of choice. Both responses reflect the same underlying discomfort: without someone or something else defining what “productive” means, how do you measure the value of a day? What makes a day “enough”? And more pointedly—how do you assess your worth when there's no checklist to complete?

I flailed during the first year of my professional break. The vacuum left by the disappearance of work-induced busyness was quickly filled with doom scrolling and endless loops of internal chatter. My mind turned inward and spiraled without the distraction that achievement used to provide.

Eventually, I realized I needed to rebuild a structure—but this time, one rooted in different values. Instead of organizing my days around accomplishments, I began to build a rhythm around self-care. Mornings started with hot yoga. Then, a few hours at a local Christian-themed coffee shop—reading, writing, socializing, and simply reflecting. When the weather allowed, I’d go for a long walk in the afternoon, letting the inner work continue in motion.

But it wasn’t all graceful. I felt lost and confused much of the time. Doom scrolling and smoking pot were fallback habits—temporary escapes from the unsettling stillness of the valley. I cycled in and out of structure, repeatedly losing and reclaiming my footing. Over time, the thrashing quieted. A little more consistency. A little more rest. A gentler rhythm began to take hold.

Creating new routines takes patience and experimentation. Productive structure fundamentally differs from the frantic busyness to which we often default. True structure provides containers that support your emerging priorities and honor your natural energy cycles. Busyness, by contrast, mimics the pace of your old life—but without its rewards or recognition. The difference becomes clearer as you learn to tune into your internal signals rather than measuring yourself against external benchmarks.

Finding New Sources of Value

If you've been conditioned as a high achiever, one of the most profound challenges during a major life transition is learning to reconstruct your sense of value and self-worth.

Professional life gives you ready-made answers to the existential question: How do I matter? Your contributions are measured, evaluated, compensated, and—at least occasionally—recognized. Even when the system is flawed, it offers clear feedback. You know where you stand.

If you're anything like me, your entire world—dating back to elementary school—was shaped by external measures of success. First came grades, academic accolades, internships, job offers, promotions, and funding rounds. One milestone after another. Then suddenly… it’s gone. There’s no longer anyone around to tell you how valuable you are. And if you haven’t built a strong internal sense of worth, that silence can be deafening. You might look for comfort in friends, family, or a partner. But not everyone has those support systems in place—or can lean on them.

When those external scorecards disappear, you're left with the deeper, more difficult task: defining your worth on your terms. This isn’t a minor adjustment—it’s an existential unraveling. You begin to see how much of your identity was built around performance. Achievement-based cultures tend to reward what’s visible: outcomes, titles, impact metrics, and social proof. But the most meaningful human contributions—presence, wisdom, care, creativity— defy measurement.

This recalibration can stir up deep discomfort. You begin to notice the subtle ways you’ve internalized capitalism—the belief that your value is directly tied to your productivity. Even if you reject that idea intellectually, you might still feel the urge to produce, achieve, and prove your usefulness through output. Releasing that pattern takes time, practice, and a lot of self-compassion.

This was a significant struggle for me. Much of my career success came from making tangible contributions to the growth of technology companies. When that ended, I found myself wondering: What do I offer now? How do I matter without a scoreboard? My brain tried to turn everything—even this newsletter—into a high-growth business. What started as a way to connect with others on a healing journey became another hustle. I tracked metrics, set deadlines, and stressed over subscriber counts.

How stupid. I thought, “I see what you’re doing, brain. You won’t turn this newsletter into a new stressful startup.”

Eventually, I had to coach myself through it. I stopped writing on a schedule. I let go of goals and metrics. Now, I write when I feel moved to write—no agenda, no financial objective, just honest expression, with the added joy of knowing it might help someone else feel a little less alone.

There was a time when my success was measured in millions of dollars and billions of users. Now, I measure a day by something much quieter: the sense of peace in my body and the heartfelt messages from people who tell me something I wrote helped them during a hard time.

Over time, you begin to discover new sources of meaning. The quality of your presence in relationships. The integrity of your choices. The alignment between your actions and your values. The beauty you create—or even notice—in a single moment—the freedom to express your truth, regardless of who’s watching.

These aren’t metrics you can plot on a chart. But they form a more stable foundation for identity that doesn’t rise and fall with your résumé, bank account, or calendar. And that’s what makes them real.

The Role of Mentors and Witnesses

No significant transition happens in isolation, though it often feels lonely. Those who navigate the valley between the two mountains of life most successfully surround themselves with intentional support—people who can offer different forms of companionship for different aspects of the journey.

Mentors who have traveled similar paths provide invaluable perspective when you're convinced you're losing your way. They remind you that disorientation is not just normal but necessary—that your confusion isn't a sign of failure but of honest commitment to transformation. These guides don't offer maps (for each journey is unique) but rather a confirmation that the unmarked path can lead to flourishing.

Equally important are witnesses—those who may not understand your experience but commit to seeing you through it without judgment or premature solutions. These companions offer the gift of presence, creating space to articulate half-formed insights and messy emotions without shaping them into coherence. Their steadfast belief in your process sustains you when your own faith falters.

These people hold space for you while you dissolve in a self-made cocoon when you shed an old identity. They have no motives other than to simply be there for you.

I found guidance from others undergoing their own flavor of personal transformation. I turned to shamans, healers, coaches, and spiritual teachers at times when I felt most untethered. They would guide me back to shore, where I could continue my journey.

Therapists help process the emotional dimensions, especially when transition activates old wounds. Coaches provide frameworks and accountability as you experiment with new possibilities. Spiritual directors accompany the existential and meaning-making aspects of your journey. Creating a personal "transition team" doesn't indicate weakness; it reflects wisdom about the multidimensional nature of transformation.

Unexpected Gifts: The Hidden Treasures of the Void

Though the valley between mountains initially feels characterized by loss, many who traverse it eventually see it as a period of unexpected abundance. As the noise of constant striving subsides, creative impulses resurface—sometimes reconnecting you with childhood passions long abandoned, other times revealing entirely new modes of expression.

Relationships may deepen and transform during this period. Without the persona of professional identity mediating your connections, you become available for more authentic engagement. Some relationships fall away, but those that remain often evolve into connections of new depth—founded not on what you do or provide but on who you genuinely are.

Many experience a heightened sensitivity to beauty and meaning during transition. Without the deadening effects of chronic stress and overwork, your perceptual field expands. Colors seem more vivid, music more moving, and natural settings more alive with significance. These aren't merely pleasant experiences; they're glimpses of a more embodied, present way of engaging with existence.

Perhaps most significantly, this journey cultivates an expansive sense of possibility that transcends conventional paths. Having stepped away from the script once, you develop the capacity to question other assumed limitations. The boundaries between personal and professional, between purpose and livelihood, between success and meaning—all become more permeable and available for conscious redesign.

This expanded perspective brings about more compassion for yourself and others navigating life's transitions. Knowing the vulnerability of uncertainty, you recognize it in others, even when disguised by confident facades. A new dimension of you comes online — a part of you able to relate to the pain inherent in the human condition. Emotions are felt more strongly. Your relating with yourself and others deepens.

It turns out that the valley isn't merely a space between destinations. It's fertile ground for becoming more fully human—authentic, connected, and alive to the full spectrum of experience.

The Second Mountain: An Unseen Summit

While in the murky valley, some of you will constantly seek the trailhead that marks the second mountain of your life. It craves something other than lostness and will make every attempt to fabricate a new linear path to climb.

However, what makes this transition so wrenching is that when you descend from the first mountain, the second doesn't immediately reveal itself. The two mountains of your life don’t stand toe to toe with each other.

What’s more, there is no visible peak on the second mountain. There is no trail map. There is no worn path to follow. This time, you're not climbing something predefined—you're creating something from raw possibility.

That’s the essential difference between the first mountain of your life and the second mountain. The world you were born into defined the first mountain. That’s why you can see it and find your way up it. Others have told you what it looks like and how to climb it. The world around you doesn’t define the second mountain. The second mountain is uncharted territory that only you can discover and ascend. It’s a solo journey into an unknown land. It is the “wayless way,” as Christian mystic Meister Eckhart described.

You're not just changing careers—you're transforming who you are.

And so you descend into the valley between these two mountains of life.

You don't merely feel uncertain. You become utterly lost.

You don't simply lack motivation. You question your very purpose.

For a time, there's no clarity, no plan, nothing solid to grasp. Only space. And the uncomfortable task of learning how to be when you've spent a lifetime learning how to do.

The second mountain of your life is revealed as you create it and as your complete authenticity unfolds, month by month and year by year, as Robert Frost wrote in “The Road Not Taken.”

“Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth…”

And later in the final stanza, the most essential lines:

“I took the one less traveled by,
And that has made all the difference.”

The Revealing, Not Choosing

The truth is that some transition quickly. They know precisely what calls them next. But for many of us, the second mountain isn't a destination we choose. It's a life that reveals itself as we become ready to inhabit it.

Readiness requires surrender. It demands that you stop pushing and start listening, abandon external measurements, and rebuild your inner compass. Shift from doing to being, from proving to expressing.

Eventually, something transforms. The grip loosens. The grief softens. And you begin to glimpse what's next—not in your calendar or résumé, but in your body, values, relationships, and vitality.

It might not register as success to others. But it will feel like alignment to you.

That is the second mountain. And you'll recognize it when you steadily stumble into it somewhere down the road.