Learning to Love the Don’t Know by observing yourself

How to have fun in the playground of uncertainty.


September’s light and colour flags the changing seasons, and it’s the time of year when people talk about where they’ve been on holiday. I chose to devote mine to my personal development at a meditation retreat. Holidays are precious opportunities to invest in myself and understand what I need to do, to be a better leader. I believe all leaders owe it to themselves and the people around them to self-reflect and invest in regular “all about me” moments.

Of course, it was the worst possible moment to take time out of the business because there’s so much happening. Heading off on a meditation trip may have appeared selfish but it took courage. My leadership team are more than capable of holding the fort (which they did beautifully). Indeed my job as CEO is to ensure the business thrives without me, as I’m not indispensable, so this was the ideal opportunity to leave my phone at home and test my contingency plan. (Question — do you have a contingency plan?)

The retreat was a seminar to learn “Vipassana”, an ancient Indian meditation technique that translates as “to see reality as it is” and I chose it for two reasons. Firstly, everything I’d heard suggested the emotional learning journey was similar to our Leadership in Management course so I wanted to experience it first-hand. Secondly, I was interested in where it would take me.

“Vipassana is the process of self-purification by self-observation. One begins by observing the natural breath to concentrate the mind. With a sharpened awareness one proceeds to observe the changing nature of body and mind and experiences the universal truths of impermanence, suffering and egolessness.”


It may sound a bit extreme for some but believe me it’s one of the most personally rewarding experiences I’ve ever had. And I’ve picked out two powerful reminders, for leaders like me.

Embracing impermanence

First accept uncertainty and impermanence. This is the beauty of a universal law of nature which brings eastern and western philosophies together: when “surrender to impermanence” meets VUCA. Indeed, while it feels natural to want to build a business to last forever, we must recognise that businesses are vehicles designed to meet needs. They have a natural lifespan that’s getting shorter as markets evolve and Moore’s law accelerates innovation.

In 2012 Professor Richard Foster from Yale published a study that proved the lifespan of a company listed in the S&P 500 index of leading US companies has decreased by more than 50 years in the last century to 15 years. That timespan was revised to 10 years in 2015 by scientists at the Santa Fe Institute.

So, as soon as we accept that our business idea has around a decade to succeed before it’s acquired, merged or discarded we can progress with purpose and energy. Impermanence is the norm.

Continual observation

As CEO of a leadership development business, I couldn’t possibly invite leaders to join our CEO peer-group and appreciate how they want to develop their people if I don’t develop myself and my team.

There’s a simple truth here that leaders need to experience the development they believe their teams need. Not simply to know what to expect, but to stretch themselves.

I’ve always invested my own time and money in my development to get better at what I do. As leaders gather more insight and wisdom they need to understand how to use this effectively and shift their approach. I have a coach, and over the years the different methods I’ve experienced have helped me write my own user guide. Some of my traits I will never be able to change, but as long as I’m aware of them, I can organise myself accordingly, plan around them, and make decisions which will not put me on the back foot.

I take care of my own personal development because I believe that many of the world’s challenges can be boiled down to personal, individual issues. And on a business level, now I’m in a role where I can have a significant effect on the lives of those around me, it’s crucial I’m not a toxic boss because I can’t handle my insecurities. Only I can sort me out.

So, what did my ten days of silence remind me? By accepting impermanence and understanding oneself better, we can all enjoy the fact that we will never get “there”, the place we know that’s safe. We can stop worrying about whether what we’re doing is accurate, relevant and up to date.

So good thing we love constantly reviewing ourselves and the world: uncertainty is our playground.


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