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Chasing Clouds

[Listen to me read this reflection here]

To try to know is like chasing clouds. I cannot actually do it for very long, as everything changes.

I have a desire to know. It feels safe. Even if it is a false sense of safety, the thought that I know, or that someone knows, feels safe to me.

To not know is far more common though, yet so uncomfortable.

I used to associate not knowing as being undesirable. If I know, I am good. If I do not know, I am not so good.

To not know is the most honest, humble and human that I can be.


To live in tune with reality is to understand that not only do I not know, but others do not know either. Parents, teachers, leaders and more may have the best intentions, however will not always know.

I am learning to give myself permission to not know. In doing so, I also create the space for others to not know.

There are countless examples where not knowing is in fact reality.

The pandemic has shown me how much we as a collective do not know. The direction of the pandemic is still not known, despite what we may hear. I know this can feel frustrating, however it is reality. Reality does not discriminate to only offer what is desirable and hide what is undesirable. Reality offers it all.

I would prefer that politicians, public health leaders, medical practitioners and scientists say that they do not know more often, versus to fool themselves, and me, into thinking that they do know. It needs to be okay to not know, for all of us. Clearly it is not.

For example, in job interviews, I would rather a candidate admit they do not know something rather than fool themselves, but not me. It demonstrates humility and honesty, which are admirable qualities, especially in the context of a job interview.

It has taken me the better part of a decade in business to learn that I do not actually need to know everything. I wrongly assumed that my clients, my team, my investors and more all expect me to know everything about my business, all the time. The reality is that I cannot. They do expect me though to solve problems, find opportunities and provide direction, all of which I can do, without expecting myself to know it all, all the time.


Last weekend, I decided to go 100% screenless for 100 hours. No phone, no laptop, no TV. I also cut out the news, was highly selective with what I read and what I ate. This self retreat helped create the space for me to check in with myself and to see what it is that I know.

Rather than evaluate myself, my life and the world, I chose a different reflection prompt for this retreat: “What have I learned about myself, those around me and the world, in the past few months?”.

Speak with an expert and you hear someone who may show conviction, but is closed to hear alternatives and new ideas. Every thought leads back to the same original idea.

For example, I host regular AMA (Ask Me Anything) sessions with the dozens of students working with me, and I recently became aware of how often my answers to their questions end with “and meditate”. Regardless of the topic, I have a fixed and firm belief on something, and as an expert.

Contrast this to keeping a beginner’s mind. It is simply when I approach life as a beginner, not an expert. I become curious to discover something new, open to different perspectives and ready to experience the joy of wonder.

To know is to carry an expert’s mind, and as a result, to be closed to reality.

To not know is to carry a beginner’s mind, and as a result, to be open to what reality can teach me.


The past is not a good predictor of the possibilities for the future. It is an indicator perhaps of one possibility, however the past does not tell me the range of available possibilities for the future.

It may be convenient for me to extrapolate the past into the future, be it for my business, the stock market or even my own habits, however I am only fooling myself. “It was” does not mean that “it will”. For example, ‘it was raining yesterday, so that means it will be raining tomorrow’, does not hold true.

To let go of my desire to know can feel scary. However, after some time, I learn how to be a little more present with this moment, as I truly do not know what the future holds.

When I say, even to myself, that ‘I know’, I am really saying that ‘I think’, that ‘I believe’ or that ‘I feel’. Thinking. Believing. Feeling. These are not only more accurate but more important, and more human.

The word ‘knowing’ brings to mind images of a dictionary. Boring and dusty. The words ‘thinking’, ‘believing’ and ‘feeling’ inspire movement, curiosity and discovery.

Thinking, believing and feeling also create the space for someone else to think, believe or feel something different than me. Even if it is about the exact same thing.

This is how I learn about the value of understanding over agreement. To admit that I do not know opens the door to develop greater empathy and compassion for others.


Most of all, I do not know myself.

I will spend an entire lifetime trying to know myself, however will never truly know, as I keep changing.

To know myself is like chasing clouds.

The best approach is to pick a set that are present for me right now, and give them all of my attention without distraction, knowing that I do not know where they will go, how long they will be visible to me and which ones will come into my awareness next.

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