Soundtrack of Success: How to Take Risks with Kenny Rogers

I’m feeling a little bit country today, y’all!  Let’s take a moment and reminisce on the cool storytelling style of Kenny Rogers in “The Gambler.”  For you young bucks that don’t know this song, back in the day this was a cross-over BEAST! Every pop station was playing it.

Here’s Kenny Rogers performing it on the Tonight Show.  Be sure to take a moment to appreciate the super-sexy large collar and chest hair!  (Keep scrolling down for my reflections on the song.)


The chorus of this song “You’ve got know when to hold ‘em..” should be your playbook for taking risks in your career.  There is no question that success in any field requires some level of risk.  However, there’s a big difference between taking a giant leap forward and stumbling blindly off of a cliff.  When considering that risky new position, business venture, or other life change, ask yourself the following questions:

1.  Do I really want this prize?

I know this sounds like a silly question, but you’d be absolutely shocked at how many of us waste time and energy pursuing things that, upon deeper reflection, we don’t even want.  It’s so easy to go on autopilot and push for the next promotion without asking ourselves, “Am I even on the right career path?” I’ve encountered lots of ambitious people who talk about entrepreneurship but haven’t honestly assessed if they would do well working for themselves or dealing with the frustrations of unpredictable income.  If the reward isn’t worth it, then there is no level of risk that you should be willing to tolerate.

2.  Could I live with the consequences of a failure?

We walk into every risky situation confident in our abilities and hopeful for a positive outcome, but let’s get real, shit happens.  Failure is a possibility, even if it isn’t your fault.  If the unthinkable occurs, can you live with the consequences?  I’m not talking about the natural moments of self-pity and doubt that come after disappointment.  Those are bitter pills to swallow, but you’ll get over it.  Instead, we need to avoid debilitating situations – the ones that strain your mental well-being and resilience. For example, if you were to lose a big chunk of money in a venture, how would you deal with it?  Some people would feel frustrated yet resolved as they broke into their retirement funds to stabilize their financial situation (good risk).  Others might go into near depression just thinking about taking the kids out of expensive private schools (bad risk).  There is no right or wrong answer – just the honest one.

3.  Do I have the political clout to be successful?

Ahh yes, politics rears its ugly head.  Your political clout is all about the quality of your network of fans, mentors, and sponsors.  Will they be there to cushion you if you make a misstep? Do you have “Big Guns” that you can call when you need to borrow influence to push the envelope?   If it all falls apart, do you have life preservers that can help ease you into your next opportunity, reputation intact?

If you answered YES to all 3 questions, then feel free to jump into the deep end.  However, if any NOs popped up, you may want to consider the immortal words of The Gambler, “Know when to run.”


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