I love planes. I always have. I love any mechanical contraption, so why wouldn’t I love planes? They’re amazing, absolutely gorgeous, technically incredible creations, that make our world so much smaller… but they have the power to terrify me, unlike any other means of transportation.

The other day, Brad Sams posted about his flight anxiety, and it really hit home for me. Brad and I have talked several times over Twitter before about the “joys” of flying, usually when one of us is actively flying. Some time before the blog post, but after BUILD had concluded in Seattle, Brad posted a picture of Montana, and commented on how gorgeous it was. I immediately had two thoughts:

1. Yep. He’s right. Montana is awesome.
2. Oh no. What happened to Brad?

I grew up in Montana – you don’t just wind up there, especially if you were just in Seattle. So I pretty quickly thought to myself, “Uh oh. I wonder if it was related to plane travel?”

As I said, I love planes. But I’ve long dealt with anxiety about air travel. Many of the things Brad mentioned are my same trouble spots.

1. I hate flying at night. Hate it. Hate, hate, hate it. It may sound silly – but I like seeing the ground.
2. I hate flying in bad weather – especially in summer, in the afternoon to mid evening, when storms are at their worst.
3. I don’t like takeoff – especially when there are heavy clouds.

In the summer of 2001, when we were working to finalize what had been named Windows XP earlier that year, I had to travel to Microsoft’s internal technical training conference, MGB (Microsoft Global Briefing). It was in Miami. It was obscenely hot, and rained regularly. I pitched the new technology we were working on (Windows PE) to the field employees gathered there, attended some sessions, and then after a few days, prepared to head towards home. I had creatively inserted a stopover in Chicago for a few days, to meet with a Microsoft customer about Windows deployment problems they were having, as well as to catch up with my brother and his wife, who were in Chicago at the time.

As I took the long cab ride to the airport in Miami, and afternoon turned into early evening, the sky got increasingly dark and cloudy. It started raining while I was in the cab, and only increased as we got to the airport, along with other aspects of summer weather one might expect in Miami in July.

I checked my fear at the gate, told myself it would be fine (statistically, it would be, and of course it was). I had already traveled a lot via plane in my life. But this flight from Miami to Chicago still holds the record as the most unpleasant flight of my life.

In Chicago, I had a great time with my family, a productive meeting with our customer, and even had an amusing conversation with a Starbucks barista who saw my Windows shirt and excitedly asked if we would ship Windows XP on time… I told him “of course we will.”

As I rode the Blue Line in Chicago out towards the airport, I was a bit anxious. Long story short, the same thing happened to me that Brad experienced. I had a really supportive call with my (now ex-)wife, and the weather was even pretty good, but it was another evening flight, and my brain and heart told me “nope”. I called my wife back, and told her that my plan was to take the Empire Builder (Amtrak’s Chicago<->Seattle route) back.

I headed back towards my brother’s place in downtown, where I explained what had happened, and bought my ticket home.

From the time I was originally riding the train out to the airport, I was beating myself up. I spent much of the ride home beating myself up. But because my options for charging my laptop were limited, I was offline, had no email, and resorted to conversations. All in all, it wound up being a good break for my brain. But like Brad, I had a point on the trip where I told myself, “I’ve made a mistake, and should have just flown”. But I couldn’t really get off and flip back to plane travel. So I rode all the way home.

I wound up traveling a few more times at Microsoft, but not much. I did wind up once sitting next to an incredible American Airlines pilot who was dead-heading home from San Jose, CA to Seattle. Sensing my fear, he talked with me most of the ride home, teaching me a fair amount about planes, wind, and turbulence. That one experience has been so immensely useful to me as a tool to fight my fear – because I can try to unwind what exactly is occurring, and why.

Living in Austin didn’t help my travel fears, frankly, and I like living in Seattle because even when we do get weather, it’s usually calmer skies than Texas or the midwest sees.

Since 2012, I have traveled to ~6 cities per year to co-present our Microsoft Licensing Boot Camps with my colleague/the co-founder of the company, who sometimes flies on the same plane with me, and basically never even notices any turbulence. Sometimes I’ll beat myself up because my head makes a big deal about the nuances of every damn flight, but Rob gets to be like “meh” about the whole thing. But it is who I am… so I do my best to logic my way through each flight, one by one. In general it has gotten a lot better over the years… but once in a while, I still have my moments. For those times, I always travel with a few Xanax pills and a couple of dramamine. (Delightful with a white wine chaser.) It’s not something I use every time, but if – like Brad mentioned – I’ve looked at the weather, the turbulence maps, or it’s a night flight… sometimes it’s what the doctor ordered.

Other than the “medications”, I’ve got a few plane travel recommendations I can suggest for the skittish flyer – I may put those in another post. But my intention with this post was to share that what happened to Brad wasn’t bad, or weird, or… anything but human, that I totally understand, and that in fact I’ve experienced almost the exact same thing.