Finding Genuine Confidence

The main psychological challenge that I struggled with during my transition from US Army Blackhawk Pilot to Investment Banking Associate in 1998 was a significant loss of personal confidence. It started on the new job, but bled over to every aspect of my life at that time. Many of you may understand this terrible feeling, when it is difficult to simply look someone in the eyes and have a conversation about the weather, because of how you feel about yourself. 

 Well-intentioned colleagues, family or friends, who sense the problem, may advise that “you need to be more confident in yourself”, as if you can just flip the switch “on”…

As a pilot, I felt in total command of all skills, knowledge and physical capacity needed to plan and execute complex missions, like a flight under night vision goggles, in a foreign territory, arriving at a designated landing zone within 5 seconds of the agreed upon time. I was doing something I loved, and believed I was part of something larger than myself…so meaningful that I was willing to give the ultimate sacrifice doing it. This combination of factors resulted in a surge of supreme personal confidence in every aspect of my life.  

Yet a few years later, I sat in a office bullpen cube as a new banker, and felt minimal confidence in even selecting which PowerPoint font to apply, or how to un-REF a broken financial model. On my daily morning drive to the Charlotte office, I would begin to sweat with anxiety as I saw the building in the distance…honestly. How does that happen? 

After all, aren’t confident people just naturally confident…always? I remember reading about General George Washington in the book “1776” by David McCullough, and I was surprised to learn that this supremely confident leader, who is lionized in the image of his self-assured pose on a boat crossing the Delaware River…actually experienced a lot of self-doubt….what?!

To start, if you are transitioning into a new role…please give yourself some grace as you put in the work to gain competence, and then mastery. It’ll take some time. It’s good pain…it’s good lack of confidence, because you may not be ready to “take the controls”, and so your humility and reluctance is a natural safety mechanism.  

Rarely will you be genuinely confident in any endeavor, without competence. Remember the GOAT, Michael Jordan, after winning six NBA championships? Remember his swagger when he walked on the court, in post-game interviews, and his demand to always take the game winning shot? Well, do you also remember his transition to baseball, and his hesitancy and struggle to hit a curve ball in the minor leagues? Different dude….What happened to MJ?  

Genuine confidence usually emerges when you believe you are competent, usually after putting in the necessary reps (think Malcolm Gladwell’s “Outliers”).  

But even then, your endeavor must be aligned with your dominant attributes and genuine interests to achieve real confidence. Even if you put in 10,000 hours, you still won’t experience confidence if you are misaligned…not true to oneself. This requires honest introspection, so that you can continue to choose the best path (for you) at forks in the road…making “course corrections” on a journey to where your dominant attributes are sought after, and highly valued.

And even then, to achieve supreme confidence, you need to be engaged in endeavors that are consistent with your core values and long term vision of your life purpose. I would guess that few things mattered more to Michael Jordan than to win championships…he was just wired that way. After all, this grown man, with all the trappings of wealth and success, did actually kiss and hug the NBA Championship trophy!

So regardless of where you are on your life journey…transitioning veteran, recent college graduate, re-entering the workplace after raising a family…if you don’t feel confident right now, it may provide clarity to ask yourself these questions:

  1. Have I put in my best effort, and a reasonable amount of time (~2 years) necessary to develop competence?  
  2. If so, does this path truly value, and prioritize, my dominant attributes?  
  3. Does this job really interest me, or am I doing it for all the “other” reasons?
  4. Am I engaged in a pursuit that is meaningful to me, and consistent with my core values? 

Finally, it does help to read the stories of history’s greatest contributors, and learn about their personal struggles and how they overcame them. After all, General George Washington did prevail…and so will you.

You’ve got this…

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