I Blame Jorg

“Life is what happens to us while we are making other plans.”

Allen Saunders

People who work at Microsoft have a reputation for being driven and having “type A” personalities. While the truth is more nuanced, certainly we do like to be in control of things. After all, creating computer software is an exercise in control–trying to make the computer do what you want, when you want without it doing what you don’t want. It was with that mindset that we made a fateful decision in the summer of 2007. I was feeling a bit stuck in my job and our daughter was approaching pre-school age. Several multi-day day road trips to visit family in Nebraska had us thinking it might be best for her if we lived closer to family. But how to pull it off?

Redmond, Washington is the “center of gravity” for Microsoft, where you were most likely to progress in your career, due in large part of the sheer volume of engineering jobs available. Yes, we have offices all over the work but these are mainly for sales and consulting teams. If I was going to find a good engineering job in the middle of the country it was likely going to be with another company. Before giving up on Microsoft, though, I reached out to an old boss of mine, Charlie, who–last I heard–was managing internal training programs. If anyone knew of interesting jobs around the company I thought it would be he.

Unfortunately, upon connecting with Charlie I discovered he’d taken a new position and was no longer with the training org. He told me he’d just taken a position at our office in Boulder, Colorado. Excuse me?! What office in Boulder, Colorado? Oh, yes, it’s relatively new–the result of an acquisition–and, yes, we are hiring.

I’m not sure if “Wait! What?” was a meme back then but that we likely my reaction. He suggested I email his boss, Steve, and set up an interview. I did and, after what seemed like months of waiting for a decision, I was offered the job–Program Manager for Microsoft Streetside imagery. Things had come full circle. I had worked for Charlie during my time in Flight Sim where I had had to teach myself about mapping. I had now just landed my first post-simulations role thanks, in part, to my experience making maps.


I’ve been very fortunate throughout my career to have found roles where I get to learn about new and fascinating technologies. I have never been the type to specialize in one thing, perhaps because I just didn’t know better. After all, I have an undergraduate in hotel and restaurant management plus an MBA–not exactly the onramp to software development. To compensate I try to be open minded, hard working, and a fast learner. I put those skills to work over the next several years helping to design, deploy and manage Microsoft’s version of Google Streetview, which, admittedly, has been less successful than our competitor’s offering (as evidenced by the fact that you were just thinking, “Wait, Microsoft has a street view product?”).


This project gave me the chance to work with some very talented hardware engineers and computer vision scientists in Boulder and at our sister office in beautiful Graz, Austria (near Arnold Schwarzenegger’s birthplace), which I got to visit several times. Eventually I was also tasked with managing our rather large imagery production operation, which helped produce over 400 photorealistic 3D cities (“Wait, Microsoft has 3D cities?” 🤦‍♂️). Life was good. I could see myself working on Bing Maps for some time and my wife and I decided to “put down roots” and broke ground on a new home. We had plans!

Then life happened.

No photo description available.

I knew that Monday was not going to be a normal one after receiving a late-night meeting invite for a mandatory breakfast meeting at the historic Hotel Boulderado. It wasn’t the timing of the request it was that they were going to feed us. Something had to be up. That’s when we learned we’d been sold (well, not actually us since I think that was outlawed) and had a luxurious seven days to decide whether to accept a job offer from our new masters or cast off on our own.

For a variety of reasons I chose to say, “thanks but no thanks,” though I was in the vast minority. I think many viewed the Silicon Valley darling’s impending IPO as a way to cash in but something just didn’t feel right to me. Once again, fate intervened and I found work immediately in the Skype for Business team, again doing things I was wholly unqualified for–helping Microsoft launch a cloud telephony service as part of Office. In additional to filling my brain with yet more technical knowledge and acronyms (PSTN, SIP, SBC) the role did bring me closer to the world of (commercial) aviation, thanks to twice monthly trips to Seattle and the occasional overseas hop.

The decision to stay at Microsoft turned out to be a gone not only because Uber eventually shifted their strategy, necessitating downsizing at their Boulder operation, but also because the company-provided insurance came in handy when my wife almost died that New Year’s Eve during surgery to have a tumor removed from her heart (a story for another time). Still, the fun wouldn’t last. After a series of reorgs and management changes I found myself once again looking for “what’s next”. And, once again, circular pathways and my passion for flight would collide once again.

In August 2019 I caught wind that Microsoft was looking to get back in the 3D game once again and wanted to resurrect the software and processes we’d used successfully for many years in Boulder. This needed to happen fast to meet the needs of a large government customer but, thanks to the Uber debacle four years earlier, very few people with knowledge of the system were still around. Suddenly I had become singularly valuable.


About the same time I heard about how Microsoft was also planning to bring back Flight Simulator, after unceremoniously shut down the studio in 2009. In the midst of this dual act of necromancy I reached out to a former colleague from the TrainSim days–a former F-15 pilot whose name is Royal Winchester (because of course it is)–who was working as Creative Director on the game. He, in turn, put me in touch with the new head of FlightSim, Jorg Neumann, to see if they, too, would value someone with historical context. The answer seemed to be no. Because the new version was being developed out of house there wasn’t the need for as many fulltime staff. Disappointed, I thanked Jorg and accepted the Bing Maps position.

See the source image

By now, if you’ve been following along, you can probably see what’s coming. As has been widely reported, Flight Simulator 2020 combines real-world mapping data and AI-based computer vision algorithms to present a version of the real world in the game. This includes all the aerial imagery and 3D cities we created back in Boulder. As the release date approached the two teams, Flight Simulator and Bing Maps, worked closely to ensure a successful launch. I was involved because I understood how the 3D cities were built and had context for the needs of the game. They even drafted me (along with a few of my colleagues) to help produce a video highlighting our collaboration.


I began to feel like the universe was trying to tell me something. I started to discuss with my wife how the dream to fly again was being rousted from it’s career-and-family-fueled slumber. She encouraged me to pursue the dream again so, as a good program manager is want to do, I started making lists. I made lists on what I needed to do to get my pilot’s license current again. I also made lists related to building an airplane. Why build? I had always had in the back of my mind that it would feed both my passion for flying but also my general inquisitive nature and love of a challenge. The question was, could I do it? Should I do it? Those would take more time to answer but I decided at last I might as well get back in the cockpit again.

I renewed my FAA medical certificate and started searching out local flight schools. I came across Western Air Flight Academy at nearby Rocky Mountain Metro airport (KBJC) in Broomfield and made an appointment to meet with an instructor to discuss my goals. I chose Western not only because they were close by but because they are part of a larger network–with locations in Colorado, California, Oregon and Nebraska–and are also a flying club with different varieties of aircraft available to rent. My instructor, Natalie, (who is not that much older than our daughter 😆) listened patiently while I explained my situation (including how I somehow only had 1.3 hours of tricycle gear time in my logbook) and then, on a cool November afternoon, I took the controls of a veteran Piper Archer for my first flight as Pilot in Command in over 16 years!


On subsequent flights, Natalie took me through the normal suite of skills required for a flight review–ground reference maneuvers, slow flight, stalls, and so forth. The air work came back quickly. At first my landings were a bit sketchy but, in time, those improved as well. Then, with the stroke of a pen in my logbook, I was deemed once again authorized to fly!


With this accomplishment under my belt it was “put up or shut up” time with respect to aircraft building. I found a local A&P who builds and refurbishes aircraft and who also teaches a construction skills class that gives you a sense of what’s required. You learn about the basic techniques and get to practice with some of the tools creating a section of an aileron.


Attending the class provided a much needed confidence boost. I was pretty sure I could pull this off and, if I needed help, Troy was just 45 minutes away. Attending the class also got me introduce an acquaintance of Troy’s who, like me, had been bitten by the building bug and knocked out the majority of an RV-10 tail section over the course of the preceding few months. However, hopefully unlike me, he realized he wanted to fly more than he wanted to build (or least spend the next couple years building) and bought a used Piper Comanche. With the means to take flight acquired, the tail section was now playing the role of aluminum artwork in his basement. He was looking to sell. After a visit to his “aircraft factory” (with Troy in tow to ensure the workmanship was up to snuff) we shook hands (preceded and followed by rigorous disinfection protocols) and I took possession of one largely completed tail and several boxes of assorted parts, bolts, rivets, etc. I had graduated from balsa and plastic models to something that would someday carry me and my family on far-flung airborne adventures in a mere 42 years!


Looking back I am still somewhat amazed at the sequence of events that, in a relatively short time, resurrected a series of childhood (and grown-up) dreams and compelled them to take flight. If I think about it, though, it was during those meetings with Jorg, discussing the new Flight Sim, that the first inklings began to scratch the recesses of my brain. And once I had the chance to experience the game, taking in the beautifully rendered aircraft, terrain and weather, I realized I would not be content to simply “fly my desk” when the real sky was calling. So you see, Jorg, a few years from now, when I send you a bill for the thousands of dollars I spent chasing the passion you helped me rekindle I hope you understand why.

A Dream Takes Root


He who would learn to fly one day must first learn to stand and walk and run and climb and dance; one cannot fly into flying.

Friedrich Nietzsche

How many dreams stick with you since childhood? For me the dream of flight formed when I was a young boy growing up on a small farm in rural Maine. I would look up as airliners passed overhead, drawing faint while streaks across the sky, and, if I was lucky, catch a glimpse of a light aircraft meandering over the fields and forests. I became fascinated with flying machines of all types and became an avid builder of balsa and plastic models. I even replicated various aircraft designs by gluing together toothpicks (with varying degrees of success) for 4th grade show-and-tell. Building models fed my aviation aspirations before I really understood what it would take to command these amazing, complex, and magical craft.

I can’t recall if there was one moment when I knew I wanted to learn to fly or whether small events coalesced into a sense that the desire had always been there. Military aviation intrigued me but these hopes were dashed when I came to understand (incorrectly) that those pilots needed perfect vision and by age 10 my eyes were already succumbing to nearsightedness. My first experience in a light aircraft came a year earlier, facilitated by my fourth grade teacher, whose husband was a private pilot. The instrument panel of his rented Piper Cherokee towered over me so my view was limited to what I could see out the passenger window. Nonetheless I was in awe of the sea of gauges and switches. Actually being able to take the yoke and maneuver the aircraft was addicting.

As I got older I retained my love of flying and relished any chance to travel by air. When I was 12 I got to fly cross-country (alone!) to meet by biological father for the first time. As I recall, the TWA Lockheed L-1011 was roughly half full (not like the sardine can seating of today) and the flight attendants served complementary champagne to the entire cabin (with the exception of the unaccompanied minor, of course). I don’t remember if I ever seriously discussed learning to fly with my parents or whether I just assumed it was an unrealistic and frivolous desire at the time but, either way, I filed it in the “someday” mental folder. High school and college and marriage and life (and marriage again) filled my waking hours and added their constant pull to my bank accounts.

It wasn’t until I was in my mid-thirties, with a second marriage slowing drifting to an end, that I decided to take stock of life and what I had (or hadn’t) gotten out of it. By now I was working a stable, well paid technology job and had downsized from a “power couple McMansion” to a spartan one-bedroom apartment in Seattle’s Queen Anne neighborhood. I was making intentional changes in my life to create a better, more fulfilling future. So, while it sounds cliché, I finally just asked myself, “what am I waiting for?” The call of the sky hadn’t disappeared. It was time to make those past dreams real. It was time to become a pilot.

I must have also uncovered a contrarian streak because I also decided to pursue my dream a bit differently than most. About a year earlier a colleague had introduced me to the world of taildraggers. He owned a Maule—a M7-260C to be precise—and we would discuss the benefits (and challenges) of tailwheel aircraft during several scenic flights. Learning to fly a plane with a “little wheel in the back” was difficult for many skilled pilots of tricycle gear aircraft, much less someone with no practical piloting experience (beyond games and simulators). It would be much harder than training in your average Cessna or Piper. Sounds great—sign me up!

It was also during this period that I made another decision. Realizing that I was now both single and well compensated I placed an order for an airplane (a taildragger, of course). Eschewing notions of renting, co-ownership or potential problems of a pre-owned aircraft, I landed on (no pun intended) a brand-new-from-the-factory Maule which would carry the moniker N5509M. Now, unlike with an automobile, there are no “new plane lots” with rows of airplanes to browse. Research is performed at airshows, fly-ins and the occasional chance encounter on the ramp. I eventually decided on an IFR-equipped M7-235-C, the logic being I would eventually train for and receive an instrument rating. I selected options like float fittings, stainless steel cowling screws and cupholders (just kidding), submitted the order (along with a sizable deposit) and set about waiting for the factory in Moultrie, Georgia to alert me it was ready to be picked up.

Owning your own aircraft is a big commitment, both financially and in terms of your free time. As it happens, two events occurred in between placing my order and flying down to Moultrie to pick up my purchase: the dot-com bubble burst and I met “the one”. Both would have an influence on my dream’s future trajectory. My plan to rely on stock sales to fund the balance due on N5509M had to be altered and I ended up financing the equivalent of the proverbial “luxury SUV”, adding to my monthly obligations of hangar rental, insurance, fuel, maintenance and so forth. And while “her one-ness” was not opposed to the occasional cross-country flight to a worthy destination she did not share my drive to go “burn some AvGas” on any available sunny weekend.


In her defense, the square footage of my hangar was larger than that of my apartment and if we were going to get serious (and we were!) owning a house was more practical than sharing ownership of an airplane with the bank (though they never asked to borrow it, which I thought was nice). So, not long after we tied the knot it was time for N5509M to find a new home. It was a bittersweet transaction. Though I was saying “so long” to something that represented the culmination of a childhood dream I knew “she’ would be in good hands and not far away. On March 12, 2002 I inscribed the final entry in my logbook as pilot in command of N5509M for the ferry to Vashon Island. I had sold N5509M to my flight instructor George.

I felt the pangs of melancholy for some time afterward but, as it often does, time helped heal the wounds. I had a new bride, an exciting new job (more on that in another post), and a new house to finish building before our new baby arrived. Before long the demands and joys of marriage and parenthood took center stage. My consolation came from an acceptance that I had, at last, realized my childhood dream in a way few do. After all, how many people can say they owned their own airplane? Surely my dreams will now be dominated by other things and I can safety cherish my flying days as fond memories, never again to emerge so strongly.

Or can I?