At the Crossroad of Humility and Wisdom

by Simon Goland, October 8, 2024

We finished a hike and then stopped at a sweet little cafe with a sunny patio, where Luna the puppy was welcomed and allowed to hang out with us. The conversation, somehow, ventured into a topic both my friend and I had thoughts and experiences to share. So we did. We explored a seeming duality of owning what we know, without appearing arrogant, yet also being humble at the same time. Don’t remember us reaching any final conclusions, yet the theme insisted on staying in my awareness afterwards.

Hence this reflection…

“Every act of conscious learning requires the willingness to suffer an injury to one’s self-esteem. That is why young children, before they are aware of their own self-importance, learn so easily; and why older persons, especially if vain or important, cannot learn at all.” – Thomas Szasz

There’s a fine line between humility and owning your wisdom, one that most of us trip over from time to time. It’s like walking a tightrope, with false modesty on one side and bloated self-importance on the other. The trick, I suppose, is to avoid swinging so wildly that you fall into either extreme and knock yourself unconscious. Instead, it’s about finding a sweet, precarious middle where you can speak your truths without sounding like a walking know-it-all-already while still keeping the refreshing capacity to admit, “I don’t know.”

For me, this dance began in earnest when I first started teaching and facilitating. It didn’t even cross my mind to get feedback at the end of a course or a facilitation experience, because… why would I? I was already a legend in my own mind. My ego was strong, big, and inflated, and the pedestal I placed myself on was very high. After a period of time, someone asked me whether I am getting course evaluations, and I was genuinely baffled by this concept at first. Then, I thought it might be a good idea, though the thinking behind the scenes was, “Well, I know I am great, so let’s get more confirmation of that from others too.” Still the ego. Still strong.

“Before we can receive the unbiased truth about anything, we have to be ready to ignore what we would like to be true.” – Ann Davies

My journey away from that way of being, of tumbling down the pedestal, was long, convoluted, full of detours, and filled with many wake-up calls. As I look at what I have been learning along the way, I can see that there is something rather sneaky about wisdom—it doesn’t usually announce itself in grand, sweeping gestures like an oracle unveiling the secrets of the universe. It tends to arrive quietly, the way rain sneaks in at dusk, gathering in puddles around your feet before you even realize you’re wet.

I still remember one of my first encounters with the need to navigate this space. It happened during my coaching course, when the lead faculty delivered a very direct feedback to me in front of the whole class. “You are sitting here like this wise and all-knowing professor,” she said, “and I am not even comfortable giving you feedback.” A wake-up call and a painful fall from the pedestal.

Humility is the first frontier of learning. And wisdom is, evidently, not about standing on a pedestal and declaring your greatness; it’s about showing up as you are, with your accumulated knowledge and scars, and offering them to the world, trusting that someone might find them useful. But—and here’s the kicker—also trusting that they might not. Humility and wisdom both involve a strange form of surrender: the humility to admit you don’t have all the answers and the wisdom to know that what you do have is worth sharing, even if it doesn’t land perfectly every time.

The tricky part, of course, is avoiding what I would call the “impostor syndrome with a superiority complex.” This delightful condition is when you secretly doubt yourself but overcompensate by talking as if you’re the expert on all things. I’ve fallen into this trap more times than I care to admit, and a lot of of it stems from my upbringing with a very strict father who demanded top grades in everything, all the time (and missing even one point ended up being physically painful). It usually happens when I’m feeling particularly vulnerable or unsure of my place in a room, so I start grasping at the straws of what I do know, clinging to them for dear life, as if my identity depends on proving something to everyone else. Spoiler alert: It doesn’t. Another spoiler alert: it took me a long time to figure this one out.

“In life our surprises often coincide with our lapses of attention. All learning begins not with what we know but by focusing our attention on what we don’t know. That’s what learning is, after all: not whether we lose the game, but how we lose and how we have changed because of it and what we take away from it that we never had before, to apply to other games. Losing, in a curious way, is winning.” – Richard Bach

But here’s where the beauty of humility comes in. Humility has this wonderful way of giving you permission to be wrong—or, more accurately, to not have to be right all the time. When you accept that it’s OK not to know everything, suddenly you don’t feel the need to inflate yourself with borrowed brilliance. You can simply be. You can share what you know without attaching your entire self-worth to whether someone agrees or finds it impressive. And you can remain open to learning something new, even from unexpected sources.

What I have been learning, again – for a long time – is that wisdom is a tricky thing. It is not about certainty. It’s about a deep, gut-level understanding that life is messy, mysterious, and unpredictable, and the more you dive into it, the more you realize how much you don’t know. The paradox is that this very realization makes you wiser. It’s like holding a handful of sand—the tighter you grip it, the more it slips away. But if you cradle it gently, you’ll keep most of it.

I’ve learned to embrace this in my own life. Finally, I might add. Though, perhaps, a better description will be that I am still in the endless process of embracing. I no longer feel the need to hoard my wisdom as if I’ll run out or as if admitting I don’t know something will diminish what I do know. And the humour in it all—the real cosmic joke—is that the more I own my wisdom, the more I see that I’m still learning, still stumbling, still discovering things that turn my old certainties on their head. It’s humbling, in the best possible way, to know that life is an endless process of becoming, and even the wise are still students at heart.

Wisdom, turns out, is a very dynamic and evolving thing. So is humility. No stopping places to arrive to.

So, where does that leave us, those of us trying to walk this tightrope between humility and wisdom? I’d say it’s a lifelong balancing act, one where you’ll occasionally fall off and have to dust yourself off, ideally with a laugh. The goal isn’t to get it perfect (because spoiler alert: you won’t), but to keep walking, arms outstretched, with grace and humour. Offer what you know, own your experience, and remember that true wisdom doesn’t need a megaphone or a spotlight—it is quietly confident, open to learning, and always tinged with the humility that comes from knowing there is so much more to discover.

“When I look inside and see that I am nothing, that is wisdom. When I look outside and see that I am everything, that is love. And in-between these two, my life turns.” – Sri Nisargadatta Maharaj

And maybe, just maybe, it’s in those moments of misstep that we learn the most.