Say yes to new adventures … Leadership insights from skydiving!

It’s curiousity that inspires us to conquer our fears, reach for new dreams, and explore new horizons!

You can smell the newness and energy in the air …. it’s “back to school season”.  For most, it’s that dreaded last long-weekend of the summer; for others, it marks the start of new adventures and challenges!  My favourite Labour Day memory is from 2009.  Together with a few friends, I decided to “take the plunge”, so to speak, and signed up for a skydiving experience of a lifetime!

You’re probably thinking “why would I ever take any advice (much less advice on leadership) from some risk-seeker who accepts a challenge and jumps out of a plane?!”  Well, the best lessons in life come from our experiences – both successes and failures – and that’s no different for lessons on leadership and coaching!

To quote the legendary Babe Ruth (who many consider as one of the greatest sports heros in American culture): “Every strike brings me closer to the next home run.  Don’t let the fear of striking out hold you back”.  

As you can see from the photos of my skydiving adventure, the view of the earth from above is absolutely breathtaking …. and experiencing this was beyond anything I could have ever imagined!  We sometimes confine ourselves (and limit our goals/dreams) to what’s in our peripheral vision. Skydiving helped open my eyes to the unlimited possibilities and opportunities that were achievable by conquering fears, embracing challenges and being open to new ideas and experiences!

Without risk, there is no reward!  Success requires the bravery to both conquer our fears and turn our dreams into reality!  As a leader or coach, this means ensuring your team is encouraged to grow and evolve – or better said, do not feel discouraged from trying new things and making mistakes.

This is especially true today, in this digital age of “disruption”, where customers/technology/markets are constantly evolving, and businesses are being disintermediated by the next great “app”!

Change leadership is no longer a nice-to-have, it’s essential.  Be a distruptor (i.e.: be open to change) or face disruption!  On paper, this seems like a no-brainer.  However, in practice, we know that change is not at all easy.

The two most powerful motivators for momentum in any change initiative are fear and inspiration.


Most are probably reading this and saying, “nope, that’s not me”!  Well, truth be told, fear is most often the starting point for most change.  Fear is a powerful motivator …. it’s a catalyst for action!  Today, “threat of disruption and disintermediation” have become new rallying cries and momentum builders for change initiatives across many organizations.

The irony is that fear disrupts true creativity!  With fear, we are motivated to take action and find a solution (which is definitely a good thing) …. The caveat though, is that often the solution we are seeking is one that takes us back to our “comfort zone”.

Using a sports analogy, it’s like running on a track …. Fear is that starting pistol that gets us off the ground and moving forward.  In actuality, we’re not moving forward per se, but running (or racing) away from the initial starting block and then we take a circular pattern and run towards the finish line, which ironically happens to be the same point that we initially started from!

Going back to my skydiving adventure …. I absolutely loved skydiving, it truly is an experience that I will always remember vividly.  But, as much as I conquered a challenge (fear), the truth is, I’ve never been motivated (inspired) to try it again!  For me, skydiving was about conquering a fear, not inspiration to achieving a goal!


Inspiration breeds curiousity … curiousity leads you to new paths and goals.  It’s akin to running a marathon rather than running on a track.  It’s a slower start, and we are no longer racing away from a starting block but instead are moving forward and running toward a new path.  And as in all marathons, there are pitfalls and stops along the way … we stop for nourishment (which serves as encouragement for our bodies and minds) and we occasionally even stumble or stop/slow down for a breather.

Going back to skydiving ….  My greatest insight that I’ve taken away from the experience didn’t come from the jump itself, but on the preparation prior to the jump.  Those of you who have skydived would understand.  It’s all about the preparation before the jump …. the physical, mental and emotional prep, and ensuring you have the right equipment and tools for the jump itself!   I remember vividly sitting on the plane before my jump (I was the first jumper in our flight/cohort).  It took physical strength and endurance to sit steady and positioned at the ledge of the plane fighting the wind, and waiting for the go-ahead.  It also took mental stamina to withstand the butterflies in my stomach and million thoughts (anxiousness, fear, excitement) running through my head.  [Note: “Included in the gallery are a few photos of my skydiving preparation]

How does this relate to inspiration and change ….?

We need to be more than just leaders, we need to be coaches!  We need to focus on skill-building to ensure our teams have the relevant skills required to position themselves for success both today and more importantly, for tomorrow ….. and, we need to BUILD MENTAL READINESS by inspiring and motivating our teams to constantly strive to grow and improve!  Mental readiness and curiousity does not evolve from fear, but inspiration!

To truly inspire, we need to make it safe for our teams to take on new challenges and goals … and yes, to fail!  Our goal, as leaders, should be to inspire and develop “curiosity” in our teams.  It’s not just about creating a culture of innovation “for the sake of innovation”, but for a broader purpose and vision.

For me, creating this safety zone included leading by example, which included being open and transparent about my own experiences (successes, failures, and learnings).  As an authentic leader, I didn’t try and create any illusions about the end state – after all, with any change, there’s no guarantee what the change is going to result in. Instead of focusing on the outcome (the what), I focused on the journey … and sought to create a sense of excitement about the journey and experience ahead!

One of my absolute favourite quotes is from William Arthur Ward:  “The mediocre teacher tells. The good teacher explains. The superior teacher demonstrates. The great teacher inspires.”  Speeches, videos, books and courses are good …. they serve as a kick-starter, but real change is not a “once and done” event, but a journey.  And journeys involve traveling and experiencing together …. not simply “showing” (photos) and “telling” (events/stories).  A picture may be worth a 1000 words, but an experience is the real thing!

To close, true change leadership comes from inspiring and rewarding curiousity, and not simply motivating through fear …..  After all, it’s curiousity that inspires us to conquer our fears, reach for new dreams and explore new horizons!  At the end of the day curiousity and inspiration trump fear!