Startup founders are embracing ‘radical self-inquiry’ to keep their emotions from ruining their companies

Many American entrepreneurs contend with hero syndrome.
Many American entrepreneurs contend with hero syndrome.
Image: Mike Blake/Reuters
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Startup founders are notorious for their life hacks—embracing spiritual practices like fasting, experimenting with Stoicism, not to mention the mind-altering effects of ayahuasca—all in the name of building a company. Another to add to the list: radical self-inquiry.

It’s no longer good enough to have an idea and a solid business plan. Being an entrepreneur today means embodying an ethos. One can’t just be self-aware, transparent, or honest; one must be radically so. It’s a double-edged sword: heightened mental clarity and self-awareness are generally a competitive advantage. But the pressure to hit peak self-actualization is dangerous when it leads founders to view their ventures as the end-all-be-all definition of self.

A lot of this stems from how America defines “entrepreneur”—as a heroic, superhuman figure, something out of Greek mythology.

“There’s an archetype especially in the US, and it subsequently translates to Europe and lots of other parts of the world, around the notion of what a leader is,” Brad Feld, a venture capitalist with the Foundry Group, said during a panel about mental health and entrepreneurship at Boulder Startup Week. That archetype incorporates the fallacy that leaders are flawless and that they can’t show vulnerability and weakness.

Feld’s fellow panelist, serial entrepreneur Tom Higley, said that “startup CEOs tell these stories about who they are and it’s kind of a manufactured story, it’s a marketing story, it’s the one that’s supposed to work for them.” Obsession with that ”iconic American entrepreneur” narrative has proven to be too much for some to handle on their own.

A number of entrepreneurs have turned to Jerry Colonna, a well-known executive coach whose clients include leaders at Etsy and Soundcloud, for assistance with handling the nuts and bolts of running a company as well as with the psychological/emotional aspect. Colonna supports founders by bringing them through sessions of “radical self-inquiry.”

Radical self-inquiry is exactly what it sounds like: a deep exploration of self. It’s typically a highly uncomfortable process, the kind that happens between a counselor and a client with the goal of improving one’s self awareness. In the context of Silicon Valley startups, the motivation is more secular; it is a means to an end: embodying the iconic entrepreneur ethos and delivering financial returns.

On a Gimlet Media podcast, Colonna shared that in the high-pressure environment of a startup, its founders inevitably end up revealing what he calls shadow qualities. “If you’re not conscious or aware through what I often refer to as a radical self-inquiry,” he explained, ”the culture that gets created around you is going to reflect pretty much your worst character traits. Your shadowed qualities as a leader. The parts of yourself that you want to push off to the side.”

“One of the most beneficial things we as founders can do for the long-term health of Gimlet [Media] is to deal with our own emotional baggage,” Gimlet Media co-founder Alex Blumberg shared on the episode of its podcast titled, Shadowed Qualities with Colonna. “Haul it out in the light, rummage through it. Take a hard look at what’s inside.”

While Blumberg and others may have the right intentions, Silicon Valley’s incessant quest for self actualization is skewed toward an end goal (success, recognition). Any philosopher will tell you that self inquiry is about the journey, an end in and of itself. In fact, failure—contending with perceived disapproval from peers and the dissolution of the ego—is perhaps the best pathway to self actualization. It requires true reliance on one’s core self. Of course, that’s not the message any founder wants to hear.