No matter how tame your flying career may seem, it will always feature milestones; points that are firsts for you. There will be things you’ve never done before, moments that are more memorable than others. These moments are some of those precious little gems we find in the sky.

The first milestone is very often a first flight, perhaps in an airliner, a friend’s plane, or at the controls of your first trainer. My earliest memory of airplanes, which I still hold as a milestone, was when I held my father’s hand as we walked downtown Calgary on a clear summer morning. I was maybe four years old. I pointed up in the sky at a jet going over and proudly proclaimed it to be a DC-8.

My first actual flight in a plane came when I was 11. It was from Springbank Airport west of Calgary. I was in the back seat of a Cherokee Six with a bunch of other youngsters during an event similar to COPA for Kids. I recall a few things about that flight, namely that I was miffed I didn’t get the right seat, and also that I hardly saw anything because I’m pretty sure we were flying in IFR conditions.

I did take one thing away from that day, though. I knew then that low-wing airplanes were the best and sleekest looking things in the sky, because they looked most similar to fighter planes. And I knew someday my own plane was going to be like that.

Aviation books have featured heavily in my aviation career. They’ve fueled my dreams and crammed my head with fantasies of dodging blazing white clouds while shooting enemy planes into searing fireballs; or of landing a bush plane on the edge of danger in the back of nowhere and saving the day for those poor mortals on the ground. Discovering the aviation section of my elementary school’s library was definitely a milestone in my flying life.

My first flying lesson, like anyone’s, will stay with me forever. I was in a two-seat open-cockpit Beaver ultralight on a sunny mid-February afternoon. To this day I’m uncertain who was more desperate – me or my instructor – to have flown in that cold. I wanted the flying time, he needed the money.

Naturally, the first solo was an enormous day for me. The enduring impressions I have of that flight are the confidence I felt and the exquisite landing I made.

My first crash landing remains memorable, and it wasn’t even my fault. I was in the right seat of a Cessna 210 from which the landing gear would not extend. A belly landing at Calgary International soon followed and we all walked away without a scratch, but with a good story to tell. Well, I hope it’s good because I’m obviously still telling it all these years later.

I proposed to my wife in an airplane. That was pretty cool and is also a good story – for both of us. Definitely a milestone, that one.

Lucky for me, many of my milestones involve other pilots. When I was a teenager I spent an afternoon with my wife’s uncle, a former US Marine Corps pilot, on a US airbase. We watched some very famous fighter and attack planes landing and taking off from just a short distance away. I reveled in all the stories he told and was proud that when he mentioned an airplane I knew what it was. It was all a breathtaking experience for me.

I came very close to joining the RCAF in the early 90’s. Instead, I chose another career path. I’ve often wondered how things would have gone had I followed that dream. To be clear, I don’t regret my choice, but making the decision was certainly a pivotal moment for me and my flying.

Other important points on my journey include buying my first plane, and honestly, each one after that. Building and flying my own airplane certainly ranks, as does flying with each of my boys and my dad. Perhaps I’m luckier than most, or maybe just more sensitive, but I feel that I’ve had an unbelievable number of epic flying adventures that I’ve shared with my wingmen. Such adventures have been stunning viewpoints along my highway in the sky.

Milestones come at the end of a flying career, too. Sometimes we know when we’re going to have our last flight, most times we don’t. It may be a medical issue, an accident, or simply a personal choice. Either way, I’m not looking forward to saying goodbye to the left seat.

Every pilot’s milestones are different, I reckon. What might be important to someone may mean little or nothing to someone else. Or perhaps someone simply can’t imagine how important a certain achievement or moment is to another pilot. A pilot who learned to fly in a mountain environment might find it tough to understand the elation a prairie pilot feels on his or her first serious foray into the Rockies. If you’ve never shot an ILS to minimums and broken out to see the most beautiful lights in the world, you may wonder what all the fuss is about.

Though pilots share certain milestones they’re all deeply personal to each of us.

I know of other pilots who seem to have run out of milestones. They’ve run out of things that enchant them in the air. They’re so familiar and experienced with airplanes and the sky, or perhaps frustrated with some aspect of aviation, that flying no longer means to them what it once did. I don’t fault them for that, I just fear it happening to me.

I reached another milestone recently. I rolled over 2000 hours of flying time. It took me thirty years and on top of my ultralight permits, I still only have a private pilot’s license to show for it, which is just fine with me. I’m rather proud of my achievement because I got there one hour at a time and it was all at my own expense. I also enjoyed most every minute of it.

Interestingly, the first thousand hours came over the course of twenty years, while the next thousand happened in only half that time. I’ll have to sit down and analyze that someday.

Realizing I’d hit 2000 hours took me by surprise. I was simply perusing my log book, noticed some numbers and did a bit of math. Then I wondered why we tend to celebrate round numbers. Why is 2000 a more important number than, say, 1677?

Regardless of the fact that I hit 2000 hours, there’s actually something about it that’s even more important to me. When my personal Hobbs meter slipped past 1999.9, my wife was right there beside me, just as she’s always been, in one way or another, since that day in the sky when I first asked for her hand. Sharing this with her, well, that’s the best part of this milestone.