Look Before You Leap: Lessons On Calculated Risks

Look Before You Leap: Lessons On Calculated Risks

“Living is a form of not being sure, not knowing what next or how? We guess. We may be wrong, but we take leap after leap in the dark.” — Agnes de Mille

Have you ever seen a flying squirrel? We all know that's impossible, yet I managed to see where the fable comes from, just this week on a walk to the local park...

As I sat on the swinging bench, contemplating all that life is and could be, I saw a furry creature scampering down a precariously thin branch, high up in the foliage of a nearby tree. From the look in his eyes, you could see the twinkle of adventure and jittery excitement of adrenaline-filled anticipation coursing through the animated body. In those beady eyes, there was a longing to leap, a yearning to fly, and just across the open sky lay a desirable branch beckoning the attempt. It was almost too good to be true...

I sat there watching, curiosity piqued and breathe bated, as the tiny squirrel gave it a thought for a long couple of seconds before darting off on an adjacent branch to see if other paths were possible. A quick journey to the edge of that route determined there was no way to transfer trees without the original approach sited on that first viewing. So, the squirrel scampered back around and up onto the original perch to reexamine the gap of sky bridging the space between where he stood and where he longed to be.

As he mustered up the energy through what appeared to be frantic pulsing, the squirrel wasted little time, harnessing the energetic pumps then suddenly taking flight, soaring through the sky and bridging the divide.

This story does have a happy ending as the squirrel, careening through the air, splashed into the welcoming leaves and meager twigs of the neighboring branch. It had indeed been a successful mission.

As I sat there and contemplated this series of events, it occurred to me what I witnessed was bizarre because in life it is an anomaly. In that moment, it occurred to me: most leaps don't go according to plan.

What Goes Into Making A Leap

Most times, when we make what we would consider a "leap," we don't know whether or not that leap will be successful. There is always a measure of doubt at play. Yet, there are parts of the process we can recognize as important check-points for good decision-making in determining which leaps are worth taking.

Calculating the reward

Usually, the first order of business involves calculating whether or not there is anything to be gained from attempting the leap. In the squirrel's eyes, there must have been something quite tantalizing that awaited him over in the nearby tree. This is true for us in the leaps we choose to take, the calculation of whether the reward is worth us doing something challenging, uncertain, and scary.

Evaluating the risk

Along with reward will inevitably come the flip-side of the coin: risk. Risk is what's at stake if the leap doesn't go as envisioned. Risk is what you have to lose in the event of the worst-case scenario. Taking the time to fully evaluate what's at stake is important in choosing which leaps to take, and especially important in choosing when not to. Apparently, for our friend Mr. Squirrel, taking the time to climb all the way down one tree in order to trot over to the other tree was too time-consuming of a task. To him, it was obviously worth the risk of jumping...

Looking for alternative paths

One piece of wisdom we can especially glean from Mr. Squirrel is the practice of examining all your options. Taking the time to see if there are alternative paths to gain the reward help ensure we don't miss out on ways to achieve the desired result without putting as much on the line in doing so. Alternative routes often mitigate risk, and evaluating all possible options is always a wise practice before leaping.

Reassessing our own ability

Once we've gone through the reward, risk, and alternative paths, we must come to terms (as honestly and objectively as possible) with our abilities as well as our limitations. At the end of the day we are all human, and there are limits to what is humanly possible. Having a "come-to-Jesus" moment with ourselves will naturally bubble up when approaching the moment of a possible leap, and that is NOT the time you want a fairy-tale perspective on your personal skills.

Going for the jump

Finally, in any leap there comes that moment when... you just have to send it. When leaping, there is no looking back. There is no doubting the decision. There is only what is in that moment, and what is is the fact that you just leaped. You took the chance and made the jump! Mr. Squirrel didn't think twice about it. Once he had evaluated the risk and reward, looked for alternative paths, and reassessed his own ability, there was nothing left to do other than jump. The worst thing anyone can do is make a half-hearted effort in this climactic moment. We must cast all future concern aside and leap with full confidence, presence, and acceptance of what's to come.

What Results From Leaps

Every leap has an outcome. The results from a leap fall into one of three categories:

  1. You Make It!

  2. You Fail :(

  3. Something Else Occurs

If we're honest with ourselves, #1 rarely (if ever) happens. Part of the nature of "leaps" is that they aren't a guarantee, and, more times than not, they don't have a probable outcome. Even if you are "successful" in the leap, the outcome will almost always be different than expected or anticipated. This is why we can bank on #2 or #3 being the result. Something will inevitably happen from a leap, and what transpires will be different than you imagined. The anomaly will always be #1.

How To Make Leaps Helpful

In light of what will (likely) come from the leap, the question is: how can we make it helpful? How can we grow from leaps? How can we make leaping successful?

Any leap can be successful, regardless of which of the three outcomes ensue. The way we can guarantee success is by making it helpful, and the way we do that is by:

A) Sitting In It

While this is not the advice you often hear, sitting in the pain or joy of whatever results is important. We must not be avoidant of pain, sorrow, disappointment, grief, unmet expectations, and other feelings that show up after leaps. These are all healthy emotions, a part of the human experience, and cannot be completely avoided. They all have something to teach us, so take the time in that space to learn from them.

B) Processing What Transpired

Learning comes through reflecting and processing what has happened and why. We must set aside the time and make space to reflect on all that occurred and what actions or mindsets led to the results that followed. This is the necessary work that allows our experiences to be turned into learnings and makes our investment of energy and effort pay dividends down the road.

C) Realigning Your Identity

Inevitably, our identity will begin to be connected to the leap itself, naturally placing a piece of our worth and value in the results that are produced. Although this is naturally a product of our invested energy, focus, and effort, it is never helpful. A necessary practice is to consciously and intentionally realign our identity with what is true outside of the leap and whatever comes from it.

D) Standing Back Up

With the chances of everything going exactly according to plan being slim, there will come the moment when we need to simply stand back up on our feet. There's something to be said for the powerful act of getting up off the ground, from refusing to stay down after a fall, from accepting an outcome that was different than we had hoped yet not allowing it to keep us off our feet. This is tenacity, resolve, and will-power at its finest.

E) Keep Moving Forward

Leaps are only defining when we let them be definitive. But life is fluid, things are always changing, the future is always being pulled into the present. The leap you just took will never be your last, there is always more to come. After we've sat in the results, processed what transpired, realigned our identity, and stood back up on our feet, there's no other option than to keep moving forward. It's as simple as taking the next step, and as profound as knowing the best is yet to come.

• • •

Leaps are worth it. They challenge us, stretch us, grow us, mold us. They inspire us, frighten us, and cause us to become something beyond our current self. Whether you're a squirrel or a human, I hope these words give you comfort, confidence, and trust that: the leap you're eyeing, the challenge you're considering, it will be worth taking if infused with intentionality along the way.

What awaits on the other side? Only you can know that answer, and it's always waiting to be discovered.

“If you keep standing on the verge of greatness, you’ll eventually get the courage to leap into it.” – Curtis Tyrone Jones

Engage: Understanding Entrenchment, Embeddedness, And How We Grow

Engage: Understanding Entrenchment, Embeddedness, And How We Grow

The Most Important Shot: A Maxim For Golf And Life

The Most Important Shot: A Maxim For Golf And Life