Reflections of Our CEO: On Certainty and Self-Doubt

My nerdiest t-shirt riffs on Plato—specifically on the Allegory of the Cave, one of western philosophy’s most important arguments for reflective understanding. ‘Plato’s Cave Search & Rescue Team,’ says the shirt. My kids shake their heads every time I wear it, but it always reminds me of how rarely any of us sees the whole picture.

The Cave Allegory explains the difference between seeing a thing and understanding the broader concept of the thing. Take for example a chair—perhaps the one you’re sitting on right now. That ‘instance of a chair’ is experienced differently from your understanding of the concept of a chair. So what is a chair?!? It could simply be anything that we might sit upon—an upturned box, perhaps, or a milk crate, or the famously sob-inducing stump on the final pages of Shel Silverstein’s The Giving Tree.

Like so many allegories in philosophy, this can seem like a fruitless extrapolation away from reality, but here’s the thing: our perceptions shape our opinions, and our opinions shape how we navigate the world. So if our perceptions are incomplete, we act from incomplete data. And we make mistakes.

Erroneous certainty drives all our problems.

Three times in as many weeks, various conversations have reminded me of the importance of trying to understand the bigger picture—or the deeper truth—before making a decision, expressing an opinion, or even deciding an idea is fully formed. Here are three things I’ve learned to consider as I navigate my own thinking, understanding, and judgments….

Question your own thinking: Last month, I was invited to facilitate a meeting of two powerful groups that were coming together for the first time. I was more nervous than I’ve been in a long, long time. I felt like an imposter; surely there were others more qualified than me available to run the meeting?! Noticing this response in myself, I asked a simple question of the person who had invited me to facilitate: ‘Why me?’ Their answer was equally simple: “You have relationships with people in both groups, they trust you, and they appreciate how you work.” There may well be more qualified people out there, but these two groups wanted me. So I made the decision to say ‘yes.’

“Increase the aperture of your awareness.”

Question your understanding: A couple of weeks ago, I spent two days in a training on equity and the social dynamics of power. Inclusion and equity have been focuses of my learning for years, now, and I’ve learned enough to know I still have an awful lot to learn. One of the frameworks offered during the course presented a string of characteristics of organizations in which power is held closely and guarded, versus those where power is shared. Of the 15 or so polarities, four or five were familiar. Immediately, my understanding expanded. As one person said during the workshop, it “increased the aperture of my awareness.”

Question your judgments: News of an opportunity to work with a long-respected partner on a new enterprise’s strategy was a lovely way to start my week. Yet the client operates in a sector infamous for its unsustainability. On its face, it was an easy project to decline… but the people involved are smart, committed to sustainability, and just as discerning as we try to be at Junxion. Was there a bigger picture to see here? Could this client have found a real breakthrough in a sector mired in controversy? Was this a moment to lean in to our preference to err on the side of engagement? Turns out the partner was asking the same questions. We’ll continue to explore the question, before either of us judges whether this is a good fit or not.

The problem with all this questioning….

Here’s the irony: by rejecting certainty, we must embrace uncertainty. That’s uncomfortable, to say the least! Get used to it. This is what it means to live and lead in the 21st century, if we’re interested at all in working to resolve important and complex issues.

The world today is perhaps more volatile, uncertain, complex, and ambiguous than it has ever been. In this ever-shifting context, certainty is at best exceedingly rare. More likely, it’s illusory. So how are we to make decisions? To take action? Is failure inevitable?! Yes. Yes, it is….

“There is no innovation and creativity without failure. Period.” So said researcher, author, and celebrated speaker, Brené Brown. In short, failure is inevitable. That’s not the problem. The real problems are our failure to learn when things don’t go as planned, and the erosion of personal and organizational resilience when failures come too frequently.

Is ‘failure’ synonymous with ‘problem’ in your organization?

Learning from failure requires a context in which everyone can speak up without fear of reprisal. Amy Edmondson has written wonderfully about The Fearless Organization. If ‘failure’ is still synonymous with ‘problem’ in your organization, you’d do well to read her work.

Organizational resilience requires a context in which plans and activities can be refined in response to ongoing learning. This is the very essence of agility, a characteristic that’s being celebrated more and more frequently in successful 21st century organizations—and that sits at the heart of Junxion’s Turning Point planning methodology.

Which brings us to personal resilience…. It’s easy to slip from self-awareness and self-reflection to self-criticism and self-doubt. If you find yourself sliding down this slippery slope, it may be time for a rest…. Or it may simply be that the work is complex or chaotic—too much for any one person to handle. Look for the support of friends, colleagues, wise advisors, and experienced mentors.

Most of all, look after yourself. We need your mind, your heart, and your ideas.

Be well,

Be love,


Mike Rowlands is President & CEO at Junxion. He’s working hard to replace judgments with questions, to practice ‘unlearning,’ and to think out loud on issues of importance. You can reach him via [email protected].

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