The realization that I’m more than a decade removed from college is difficult for me to comprehend. Dare I ask: where did the time go? A rhetorical question posed and gone unanswered time and time again. With each year passing by seemingly more quickly than the last, I felt it important to reflect on where I’ve been and how I got here. In many ways, I feel no different than I did ten years ago, despite considerable change in my personal and professional life. As I look back at the many years of experiences and growth, I’m satisfied and can smile when I recognize one simple constant: I’m still really kinda winging it… just… more confidently.

But wait… what does that really mean? To “wing it” is just a stupid English idiom that means to improvise, but where does one draw the line between preparation and improvisation? While I can’t definitively provide the answer, I’m here to say: you can certainly do too much of both. There is no shortage of literature written about various forms of preparation and individual growth techniques, but I can assure you that there is no magic recipe, as there are exceptions to nearly every rule. The fine line between preparation and improvisation lies within the depths of each individual person, and with each opportunity, each lesson learned, we subsequently grow more powerful and confident.

At 23, I operated with a false sense of confidence (some may call it arrogance) that I was well-equipped to do anything I desired, but doubt can quickly set in when reality pays a visit. Winging it then was more or less just a shot in the dark – not from any particular mistake(s) I had made, but simply from the fact that I was young and deprived of living through any practical real-life challenges. In retrospect, I recognize how ill-equipped I really was to tackle anything outside of my comfort zone.

Winging it works best when previous life situations and experiences have prepared you to put your best foot forward. Easy to say now – it sure is funny how clear hindsight can be.

At 33, I believe that confidence develops from always playing the game, being willing to fail (fast), and learning from each experience. While humbling, it helps me to frame it such that no one ever truly fails: you either succeed, or you learn. Over time, this mentality inherently allowed me to nurture my strengths while acknowledging my weaknesses. The perspective is critical, because the world is far too chaotic and random to attempt to prepare for every scenario, and it’s futile to deny such a basic observation.

I challenge anyone reading just as I would challenge myself: find your balance. When you discover the optimal mix of preparation and improvisation, winging it becomes comfortable and natural, and you’re a better teammate and leader as a result. For me, the path to discovery has been a ten-year journey of trial and error, and it’s far from over.

So – what’s the difference between 33 and 23? Well… a lot. I’m a little older and hopefully a little wiser, but truthfully, I’m still really kinda winging it… just… more confidently.