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.