Actualized Leadership: Fear of Failure: The Dark Side of Achievement

Actualized Leadership: Fear of Failure: The Dark Side of Achievement

I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.

Michael Jordan

It seems to me that the best one can do is not to fear mistakes, but to plunge into them.

Abraham Maslow

In our last series “The Shadow Trilogy,” we examined Jung’s concept of the Shadow and how to identify and integrate it into our total being.  Our focus in that series was at a broader level of meeting and managing our Shadow – our reflexive, irrational side that emerges under stress.  The purpose of the next three blogs is to focus on the 3 Leadership Shadows related to the three leadership styles, and on understanding how natural strengths can become “career-limiting” derailers when not effectively managed.

The 3 Leadership Shadows, Fear of Failure, Fear of Rejection, and Fear of Betrayal, all contain the same three elements: Irrational thoughts, unfounded feelings, and self-defeating behaviors.  These three elements occur in a sequential and self-repeating cycle: Irrational thoughts trigger unfounded feelings, which in turn activate self-defeating behaviors.  If your Leadership Shadow remains denied or ignored, this vicious cycle repeats itself until we tragically experience “paradoxical intent,” first identified by Viktor Frankl: The self-fulfilling prophecy of encountering that which we fear the most.  Today, our focus is on the leadership style of Achievers, and how to manage the Fear of Failure Leadership Shadow.

Achievers, those driven primarily out of a strong need for Achievement, are the backbone of our organizations.  Achievers are excellent accountants, planners, organizers and salespeople.  Many strike out for entrepreneurial success on their own, and they are not adverse to rolling up their sleeves and doing everything, from making the million dollar sale to brewing the coffee.  Achievers focus on winning, success, and improvement, and are organized, detailed-oriented and technical experts.  It’s easy to see how this approach leads to career advancement, or six NBA championship rings.

However, when the Fear of Failure Leadership Shadow is activated, the strengths identified above become inherent limitations.  Under stress an Achiever will transform in unproductive ways: organized becomes rigid, detail-oriented devolves to being obsessive, and expertise leads to micromanagement.  Much like Dr. Jekyll’s transformation into Mr. Hyde, experiencing stress in the form of ambiguity or “losing” triggers the Fear of Failure Leadership Shadow, and the ugly transformation.  The existential and ironic tragedy is that when this happens Achievers are actually more likely to fail.

As stated above, the Leadership Shadow Cycle starts with irrational thoughts, which create unfounded fears and negative feelings, which in turn lead to counterproductive and self-defeating behaviors, as illustrated in the following table:


Fear of Failure Leadership Shadow Cycle




I have to always be perfect. Inadequate Becoming obsessive and nitpicky.
No one can else can do this as well as I can. Frustration Being overly critical and micromanaging.
I am not enough without my accomplishments. Shame Taking on too many projects, or staying over-scheduled.


You might be asking yourself how, exactly, could this be?  Wouldn’t fearing failure actually help prevent it?  To a certain degree a “healthy” fear of failure can lead to new levels of achievement, such as getting up earlier, working later, or striving to exceed your goals.  However, if left unabated and unmanaged, this cycle will eventually lead Achievers to the one place they fear the most: failure.

So what about situations where you give it your very best effort and still fail?  Although unpleasant, disappointing, and uncomfortable, this is where profound insight and learning can occur if we’re open to it.  Failing can also motivate and propel us to new adventures and eventual success.  For example, MJ was cut from his high school basketball team.  The impact that this “failure” had on him is obvious.  If you’ve recently encountered a setback, defeat or failure, do not let it discourage you.  I challenge you to reframe it as being “cut” from your high school team.  What can you learn from it, and how can it motivate you to excel and achieve at new heights in your next endeavor?  You may not fly like “His Airness,” but you will still be in the game.

Image courtesy of Sigurd Decroos


  1. Dominic J. Monetta

    Will, the F/F initially bothered me in my career. Joe, got me out of it by saying (of course this was back in 1967) “Two out of seven women will say yes, just keep asking”. The point is only practice will help. A world class leader will encourage himself to keep trying and watch his stats closely. Joe used to say that management is like a chemistry set, if the experiment fails, wash out the glassware and try another experiment. ……….Dom

  2. Dr Will Sparks

    Dom, thank you, and I couldn’t agree more. Management, and life for that matter, is an experiment (lot of data to collect) that is trial and error. As Roosevelt said in his “Man in the Arena” quote, we will get dusty, bloodied and knocked down, but even when our experiment fails, we will fail while “daring greatly.”

    • Dominic J. Monetta

      Joe would say just be careful not to blow yourself up, otherwise keep exploring.


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