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Becoming Comfortable With Uncertainty

Every summer, my wife and kids (and dog), travel back to Vancouver from Calgary to spend time with the grandparents – both my wife’s parents and mine still live in the city we grew up in. We do this for a few reasons, namely so that the boys can spend quality time with the grandparents, and we can visit family and friends. The last two summers my wife and I have used part of that month in Vancouver to have a little vacation time overseas all to our own, no kids… selfish perhaps, but valuable for our relationship. We have great parents who are always happy to take care of the boys for extended periods, and we live busy lives so that one on one time is cherished, something I never truly understood the value of until we had kids. Last year we traveled to Ireland, and this year Croatia – both countries I highly recommend visiting for very different reasons… 

I’m no relationship counsellor, but I think it’s absolutely paramount parents find time to spend with each other, without the rugrats. But I digress… 

This year, my wife had the ballsy idea of instead of flying to Vancouver with the kids, we would make it a family road trip from Calgary. It’s an incredibly scenic drive as you pass through the Rockies, but for those not aware, it’s also a 1,000-kilometre trek (600 miles). And doing that drive with 3 and 5-year-old sons, in a vehicle stuffed with luggage and a big dog, didn’t appeal to me. But, as usual, the boss won, and I’m happy she did. The road trip provided memorable bonding time for our family, with stops for visiting an enchanted forest, ice cream, and all that good stuff. And the conversations drummed up by the boys were fascinating – amazing what they’ll say when you’re stuck in a car together for hours on end. It took us twelve hours to do what usually should be a nine-hour drive, but that’s okay. We had a blast.

Along the way from Calgary to Vancouver, we stopped in a scenic town, the gateway to the Canadian Rockies if you’re coming from the West, known as Revelstoke. It’s a charming place with epic skiing close by, along with mountain views – love it! It also happens to have one of my favorite taco restaurants, hence the reason for the stop… 


Finding New Perspective as an Entrepreneur

While in Revelstoke, I wandered into a bookstore, one of those small-town, independently ran bookstores which always seem to have obscure reads. This was your quintessential ‘granola’ bookstore, with most of its titles relating to the environment, socialist-type political books, Buddhism, reiki and other stuff way out of my realm. But sometimes one needs to venture outside their usual business, biography type reads…

I needed a good book for my Croatia trip, so I picked up Pema Chodron’s ‘Comfortable With Uncertainty – 108 teachings on cultivating fearlessness and compassion.’ I had no idea who the author was, nor that she was an expert in meditation, but the title piqued my interest. Mindset matters in life and especially as an entrepreneur; and I’m always looking for a new edge in that department. Who, as a Type A personality, doesn’t want to learn to be a little more comfortable with not knowing what lies ahead, right? We live in uncertain times, and enjoying the moment is something we probably all struggle with from time to time. When I walked out of the granola bookstore, my wife looked at the book in my hand and said: “that sounds like a good book for you…” Indeed it was. 


Being Comfortable with Uncertainty

While my wife and I were on the island of Hvar, Croatia for a few days, I started and finished this thoughtful and spiritual (although not spiritual by my definition) read. It served as a reminder to ‘smell the roses’ as it were, but it wasn’t fluffy hippy stuff I couldn’t connect with. Chodron provided actionable ways to train oneself to enjoy the present moment, embrace chaos and uncertainty and to practice gratitude for your moments of downfall (the sweet just ain’t as sweet without the bitter). And the educational parables in the book really stuck with me.

From an entrepreneur’s perspective, I found Chodron’s philosophies very inspiring, and comforting… after all, part of the battle of entrepreneurship is about embracing risk and being comfortable in situations most would not be. Having a ‘zen-like’ demeanor and mindset through volatility is a huge X-factor if achieved. In her book ‘Comfortable With Uncertainty’ Chodron attempts to show the reader how to get there, and she does a damn good job. I finished the book a little more relaxed and wanting to be more patient than when I started reading it. And I have some mental tools, thanks to her teachings, to maintain this mindfulness.

Of the 108 teachings in Chodron’s book, three really stuck out for me and I want to share them in this blog. It’s worth reminding everyone that although success is not guaranteed in business, struggle almost certainly is. If you learn to embrace the battle while gleaning the lessons from every speed bump, your odds and appreciation for success are heightened. That’s something Chodron promotes in this book.


3 Teachings from Pema Chodron on Learning to be Comfortable with Uncertainty

The source of anxiety: Everyone experiences some degree of anxiety throughout life. However, some people are almost in constant anxiety, which can lead to nervous breakdowns, heart attacks, and other health issues. I get anxious when big projects don’t go as planned. When I have a lot riding on a deal, and it appears to take a detour (which almost always happens), I experience anxiety.

Triggers for anxiety will be there as an entrepreneur, but you have to learn to deal with them healthily. Interestingly, Pema Chodron explains that the core source of anxiety comes from our mind always seeking safety zones, and the fear of losing our illusion of security. The mind goes to extremes, routinely fearing a loss of something when in stressful situations, which triggers anxiety. Anxiety impacts behavior and performance and is the root of mental suffering.


Don’t resist impermanence: We cling on to certain things in our lives – often for the worse. It can be relationships, material things, routines, whatever. What Chodron explains is that clinging to these things can create unhappiness because nothing in life is static – the same is valid for business. Learn to appreciate impermanence and embrace it. This will open your mind to change, innovation and help you appreciate volatility because you know nothing is forever. Change is a guarantee.


The practice of refraining: Love this one because it is so applicable in this day and age of smartphones and instant gratification. Chodron describes refraining as the quality of not grabbing for entertainment the minute we feel a slight edge of boredom coming on. Think about how many times you reach for your smartphone so you can scroll aimlessly while waiting in line…

Chodron explains that refraining is the “practice of not immediately filling up space just because there’s a gap.”

She continues, “Refraining — not habitually acting out impulsively — has something to do with giving up the entertainment mentality. Through refraining, we see that there’s something between the arising of the craving  — or the aggression or the loneliness or whatever it might be — and whatever action we take as a result. There’s something there in us that we don’t want to experience, and we never do experience, because we’re so quick to act. The practice of mindfulness and refraining is a way to get in touch with basic groundlessness – by noticing how we try to avoid it.”


Comfortable With Uncertainty  by Pema Chodron is definitely not my typical read and partly because of that, I think I benefited a lot from it. It’s an easy but insightful read that any entrepreneur will find value in, whether you’re in touch with your inner-hippy or not 🙂 Mindset matters in business and this book indeed explains how to improve your mindfulness, particularly in those moments of uncertainty. 

Stay hungry,





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