Last weekend, after landing the airplane following an ideal flight on a clear, cool, cloudless March day, I performed the last element of my typical post-flight ritual – entering the flight into my logbook – and realized that I had crossed a personal milestone. I have flown various small airplanes for a little more than 100 hours since my first day of training. I thought it would be an opportune time to document some reflections after those 100 hours, more than 350 successful (but not always pretty!) landings, and approximately six years of learning and experience.

Thinking back to those 100 hours spent in the air and the stretches spent in-between flights triggers a complex array of emotions for me. Flying is simultaneously the most terrifying and rewarding thing that I do. I’ve learned a lot about things I expected to learn about, but the more profound lessons were those I never expected.

When I started flying, I was somewhere on the spectrum between passionate and obsessed. During my initial training, when I wasn’t in the air I was reading about flying, thinking about flying, and listening to podcasts about flying. I didn’t read books unless they were flying books. The joy of flight was my constant companion. I love learning, and learning to fly pushed all my buttons – from the development of stick-and-rudder motor skills, to learning about engines, to forecasting weather, to aerodynamic principles – all of which challenge very different parts of my brain in very satisfying ways.

And this is to say nothing of the joy of flying itself. I am such a bad golfer that I don’t know what it feels like to hit a perfect golf shot. But I think it must be akin to what it feels like when the airplane’s wheels chirp to confirm a perfect landing, or you navigate to a new airport with nothing but a map and a watch, and it finally reveals itself amid the fields and trees below. There is something so ultimately satisfying about knowing that your success is 100% determined by your own planning, skill, and judgment. For me, flying for an hour buys a whole day of emotional “high.” Nothing else can replace it. It’s truly the best you can feel with all your clothes on.

But after being a pilot for a couple of years, life intervened, and I stopped flying. My wife and I were expecting our first child, and I had just quit my job to found a new company. I wasn’t broke, but money was tighter than it ever had been for me. Around this same time, a local tragic accident killed a teen-aged student pilot and his experienced instructor. As if that weren’t enough, the airplane in which they perished was N18677, which during my training had been my favorite of the Cessna 150 rental fleet at the local FBO. I had logged more hours in N18677 than in any other airplane. I had flown my first solo flight in it. I had trusted that airplane, and it had not only kept me safe but had in many ways inspired the passion that kept me coming back to the skies. When it crashed, a lot of my assumptions about the safety of personal flying crashed with it.

For all these reasons, my risk tolerance was dramatically lower than it used to be. Something about expecting a baby, and then meeting and knowing that tiny, precious, fragile person who depends so much on me, coupled with N18677’s crash, made me not want to fly. It seemed too selfish a risk to be exposing my family to. The periods of time between flights, which used to be consumed with a love of learning about flying, became periods of anxiety and fear about it. I didn’t fly at all for about 18 months. It didn’t help that I had found a new educational passion, learning how to be a father, and that I had to buy life insurance for the first time and realized that it’s pretty expensive for private pilots. But really, the money had little to do with it. I rationalized that it was about the expense. It wasn’t. It was all about fear.

Gradually, these forces that kept me away from the skies receded, and after taking to the skies again – initially, mostly with an instructor to give me more comfort – the passion that had lay dormant within me was rekindled. But while every flight was enjoyable, I can’t say that I looked forward to flying in between flights. The emotional “high” of taking a flight lasted a few days, but then the fear would creep back in and crowd it out. I flew periodically because I knew I needed to in order to preserve my investment in the craft, but I was in a vicious cycle of being afraid to fly, so I wouldn’t fly, which made the last flight farther back in time so my skills were rustier, which made me more afraid to fly. I found that when I did go flying, it was “practice flying” – retracing old routes and practicing things I already knew how to do, with the simple goal of not letting my skills atrophy. I was practicing and preparing for something valuable, but never doing the valuable thing. In retrospect, this flying-for-maintenance’s-sake seemed useful, but it just wasn’t rewarding enough to keep me in the airplane as frequently as I needed to be.

Somewhere along the way, Steve Jobs died. In reading about his life, I stumbled upon his 2005 commencement address to the graduating class of Stanford University. In that address, he said, “Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose.”  I let that sink in. Maybe the timing was coincidental, but it was around this same time that I began to fly again. I hypothesized, if I were given a terminal cancer diagnosis, would I be afraid to tackle Seattle’s complex airspace? Would I stop myself from flying over 10 minutes of terrain to get to Sunriver? Would I avoid shorter airstrips than my home airport’s, even though I always land in half its runway distance anyway? Probably not. The solution to doing these things, and claiming all the psychic rewards that come with them, I realized, is just to do them. This is not to say that caution should be abandoned – I remain a very risk-averse pilot – but instead a realization that I could turn the vicious cycle of fear into a virtuous cycle of learning, doing, confidence building, and improving.

I learned that a healthy level of fear is appropriate when climbing into something that goes 150 miles per hour and can kill you quickly, but that too much fear is counterproductive and actually introduced risk to my flying by preventing me from getting experience. There is a fine line between healthy fear and counterproductive fear. I never anticipated that locating it would be so critical to my practice of flying airplanes. I’ll continue to search for it. I’m sure it will be a moving target, but I’m just as sure that only experience will bring me closer to it.

I’m so grateful to have the rare privilege of being able to fly an airplane, but I’m even more thankful for the things this experience has taught me that never appeared in the textbook or instructor’s lessons. It took me 60 hours to learn to fly an airplane, and 100 hours to learn that fear is a tool that is both useful and optional.