Calculating Risks in 2026 as a Travel Advisor

Why embracing calculated risk—not avoiding it—is the key to building teams that accelerate toward better.

 

Contributed By: Chad Burt, C0-Owner – OutsideAgents.com

 

Like so many things today, risk is seen as a binary question with a yes or no answer.  It is not.  It is a non-binary value we estimate, calculate and calibrate.  This is especially true when it comes to employees as their risk assessment is most often performed with “making the boss happy” as their winner’s circle.  As an employer, this scares the crap out of me.  “Happy” is a destination at which the journey ends upon our arrival.  It’s a mindset that must be changed.  So, recently, we invested a week of our time in Las Vegas.  At a Learning Development conference, I had the privilege of helping some of my favorite crew members rediscover, redefine, and embrace risk.

 

 

Behind the wheels of Ferraris, Lamborghinis, Corvettes, Austin Martins, and Porches Amber, Jean, Tim, Luke, Alex, and I rediscovered risk as fluid ranges rather than self-imposed barriers holding us back like speed limit signs in the desert.  At over 130 miles per hour, we were ultra-aware and hyper-focused as time slowed, and opportunities emerged at every turn. Instinctively, we gaged risks, estimated rewards, and tested our theories in real-time.  We watched the video in awe as, lap by lap, we evolved.  Second by second, we improved.  Mile by mile, we found new answers to the question of “How can…?” as we left “Can I…?” far behind.

 

 

By the second lap, we were sipping the Kool-Aide like we were having afternoon tea.  We were making progress as “Can I should I cut this corner” became “How can I cut this corner better?”  “Can I go faster and not die?” became “How can I go faster and still live life without a limp?”  

 

By the fourth lap, we were downing the Kool-Aide like we had walked rather than drove through the desert to the track.  As our lap times decreased, our understanding of risk increased.  We rediscovered risk as a value to be calibrated relative to its reward.  “No,” they were coming to understand as I already did, is simply the bottom of the success scale.  

 

 

By the 7th and final lap, we were guzzling the Kool-Aide and chugging success.   The video showed the spark of discovery dancing in our eyes as success became clear on the horizon.  Something had changed in each of us.  High on a combination of adrenaline and Kool-Aide, we each had new perspectives on Learning Development, risk, success, and everything else in the world.  I was ecstatic, and they were too.  Collectively, though, we had evolved to become greater than the sum of our parts.

 

 

Now, getting “it right” doesn’t happen at the finish line.  Instead, we chase the checkered flag of perfection by improving lap by lap.  We know that change over time (acceleration), is far more important than getting to the checkered line quickly (velocity) as acceleration measures improvement where velocity measures performance.  Obstacles, like turns and bumps in the road, are unavoidable and outside of our control.  How we overcome them, though, measures who we are, and who we’ll be.  As my grandpa always told me, “it’s not how we fall, but how we rise.”

 

 

Today, they see the finish line as a mile marker on the road to better instead of the end of the track.  They want to do their best by doing better.  They embrace every mistake as a step forward they didn’t know about yet.   Most importantly, they no longer need to make me happy, they want to make me happier.  They want this because “happy” is the end of the race where we’ve done the best we could do given the limitations of time.  It’s just a snapshot.  “Happier,” on the other hand, is just the beginning of “better,” which is ultimately and always better than best.  It’s a 4k video which doesn’t end.  It’s fluid and in motion, just like life.

 

 

Standing in the winner’s circle, we know it’s the beginning, not the end, of something we are yet to discover.  We’re excited to see the unknown, not afraid.  We understand risk, we can do the math, and our calculations will lead to where we need to be.  We want the chance to improve incrementally, with each lap and every attempt.   

 

Hopefully, you noticed that at no point did I suggest to my crew they hop in a super car, shout “Yeeeehaw,” boil their tires, and hope to live.  Rather, I was urging them to account for risks, plan to overcome them, and improve over time not to live, but to thrive.  That’s how you win, in business and in life.

 

Hopefully, you will also notice the pictures in this article.  Each of them shows the effect of drinking the Kool-Aide: they start off tense and scared, find their groove, and discover the elation of overcoming risk to win their own personal race.  

 

P.S.  I learned another valuable lesson, too.  You can write off racing exotic sport cars on your taxes, if you do it right: Assess your risks, keep your receipts, and be careful of bumps in the road. I’ll let you guess which picture is mine.