On Disillusionment

Breaking down a rite of passage

I'm currently working with a client who's experiencing profound disillusionment. This isn't unusual—most people go through this phase at some point, and it often coincides with the entrepreneurial journey. I want to explore this topic because understanding disillusionment before it hits might help you navigate it more skillfully when it arrives.

Over my 15 years in Silicon Valley, I've noticed that disillusionment comes in two forms. First: when you achieve the very things you were taught to pursue—press coverage, funding, exits, wealth, marriage—only to discover they don't deliver the feelings you expected. Second: when strategies and approaches that once reliably worked suddenly stop producing results, forcing you to question everything you thought you knew.

Both forms of disillusionment represent the same core experience: the collapse of beliefs that have structured your understanding of how to achieve fulfillment.

These moments are inevitable. And while deeply painful, they also represent important opportunities for profound growth.

The Root of Disillusionment

At its core, disillusionment stems from beliefs we develop early in life. These beliefs form our operating system—the unconscious programming that drives our decisions and behaviors.

Recently, I worked with a client whose childhood in a religious community instilled the belief that self-sacrifice was the ultimate virtue. Self-denial wasn't just good—it was the path to goodness, worthiness and acceptance.

As an adult, this defined their leadership and relationship style, which emphasized providing at their own expense. More troublingly, it led to consistent self-sabotage disguised as sacrifice—repeatedly turning down lucrative opportunities because, on some level, they believed accumulating any success or wealth was evidence that they hadn’t sacrificed enough.

These patterns never led to the recognition or admiration they unconsciously sought. Instead, it left them depleted across all areas of life. Recently, they came to the painful realization that not only were they taught a belief system that was false, but that the life they had built based on these beliefs isn’t the one they want at all. They realized it’s time for an intervention.

Their story highlights something I've seen repeatedly: our professional struggles often reflect deeper psychological patterns established long before we entered the workplace. The entrepreneur who can never delegate is replaying the childhood message that they can't trust others. The founder who can't celebrate achievements is running on the programming that nothing they do is ever enough. And so on.

When Playbooks Stop Working

Disillusionment doesn't only arrive in moments of peak success. It can also appear when strategies that once worked suddenly fail.

We're experiencing this collectively right now. The economic environment, technological landscape, and cultural context are shifting rapidly. Playbooks or personality traits that reliably produced results for years or even decades are suddenly not working like they used to.

This creates a particular kind of disillusionment—the realization that what you thought was skill or wisdom was partially the result of favorable conditions. The beliefs and approaches you trusted weren't as solid or timeless as you imagined.

This is especially painful because it often feels like a personal failure rather than a contextual shift. You followed the formula you were taught, did everything "right," and the expected outcomes didn't materialize. The disorientation is profound—not just "my goals didn't satisfy me" but "my entire approach no longer works."

Entrepreneurial Vulnerability to Disillusionment

Entrepreneurs seem particularly susceptible to both forms of disillusionment. The startup journey is fueled by future visions—not just of what your company might become, but the ways it will bring you success and fulfillment. You anticipate the satisfaction, impact, freedom, status, and meaning that the journey will bring—this often forms the core of many entrepreneurs’ motivations.

When these expectations collide with reality, the gap can be jarring:

• You land a feature in a major magazine, only to find the momentary satisfaction quickly fades, and business metrics barely move

• You close a funding round after grueling months of pitching, but instead of relief, you feel the weight of new investor expectations and the pressure to raise again

• You achieve an exit that looks impressive from the outside but leaves you questioning your identity and purpose once the adrenaline subsides

• You finally earn enough to buy the house, car, or lifestyle you wanted, only to discover these acquisitions still leave you wanting more

• The strategy that built your company suddenly stops working, forcing you to question everything you thought you knew about your business and market

I've sat with countless founders, whether friends or clients, in these moments of realization. What makes them so disorienting is that they challenge not just particular goals or strategies, but the entire paradigm under which you've been operating.

Why Disillusionment Is So Painful

The pain of disillusionment goes beyond simple disappointment for several reasons:

First: it disrupts your identity. When the beliefs that have organized your understanding of yourself and the world collapse, foundational questions emerge: Who am I if not my company? What matters if not these achievements? What's the point if this doesn't bring fulfillment?

Second: it triggers time anxiety. There's often a sickening moment of recognizing years or decades spent pursuing goals that now seem hollow, or engaging in behaviors that were actually self-sabotage. This can create fear that it's "too late" to course-correct.

Third: it creates social disconnection. When you're questioning values that others still embrace, conversations with peers, investors, or even family can suddenly feel performative or empty. This isolation intensifies the disorientation.

Finally, disillusionment removes the old map without immediately providing a new one. The principles and metrics that guided your decisions no longer feel reliable, but their replacements aren't yet clear.

The Opportunity Within Disillusionment

Despite its difficulty, disillusionment contains the seeds of genuine transformation. It's the necessary dismantling of illusions that precedes more authentic reconstruction.

This process isn't new. It's been documented across traditions and disciplines for millennia—what depth psychology calls "the individuation process," what Joseph Campbell termed "the hero's journey," what religious traditions often describe as spiritual awakening, and what contemporary writers like David Brooks explore in "The Second Mountain."

Brooks' framework offers a particularly accessible modern parallel. He describes how people often begin by climbing what they think is the only mountain that matters—career advancement, wealth accumulation, status attainment—only to discover at the summit (or after falling down the mountain) that there's a second, more meaningful mountain involving contribution, relationship, and purpose. The journey between mountains necessarily involves the "valley of shadow"—a period of disillusionment where old values are questioned and new ones have yet to fully emerge.

Richard Rohr, in "Falling Upward," similarly describes how the second half of life often begins with the collapse of the identity and achievement structures built in the first half. This collapse isn't failure but prerequisite—the necessary dissolution that precedes a more integrated way of being.

What all these frameworks share is the recognition that disillusionment isn't an unfortunate detour but an essential passage. The entrepreneur who loses faith in conventional metrics, the leader who questions achievement-based worth, the innovator whose trusted approaches stop working—these aren't stories of failure but of inevitable evolution.

The transformation involves a shift from externally-validated definitions of success to internally-aligned ones. The formula changes from "achieve X to be worthy" to "express my authentic values through my work," or from "this strategy always works" to "this approach may need adjustment based on the current environment."

Notably, this isn't about abandoning ambition or impact. Many who navigate this transition create more significant value than before. But they do so from different foundations.

Navigating Disillusionment

If you're currently experiencing disillusionment, or sense it approaching, here are some principles for moving through it productively: