About My Path Less Beaten – Hear My Story

My Story

So who am I? My name is Jon Cantrell. I’m a father of two boys (7 and 9) and happily married for (let me check) just about twelve years. I manage a software platform at a large company that is based in Seattle. That all sounds rather mundane, where does the Less Beaten come in? It’s how I got here…

Early School

As a kid I was “gifted” in school. This started me off on a challenging path. Our society tends to focus the most resources on the under achieving and the least on the over achieving. Since we’re getting good scores, everything must be fine, right? No, one of the things I experienced was being bumped up a grade level. Sounds good, but there is a lot of physical and mental maturity in one year at that age (5-6 years old). I got bumped back. At this point I can’t honestly remember how many years I spent in K-6 but I think it was only six years. I’d had a rough start going to no fewer than four schools (as a child of a single parent, we moved a lot). Things settled down in junior high (7th-8th grade in California) and I went to the same school for two years straight. For high school, my mom didn’t like the local schools so she worked some tricks of her own and got me enrolled in a neighboring district. This meant a morning drop off at a city bus stop and an afternoon ride home on a city bus again, followed by a three-mile walk. Even in high school I was commuting almost three hours a day.

High School

High school is where it snapped. I’d had enough. I didn’t fit in socially being both younger than my year yet relating better to older students. By junior year I was taking, amongst other courses, AP Physics and French I. Mid-year I got a bad cold and missed a week of school. I came back, focused on catching up in Physics and let French homework slide (the day I came back there was a test in French and with extra credit, I scored over 100%). I was fine in Physics but I got detention for not making up my French homework. My mom again went up to bat for me but the principal chose to back the teacher’s choice of detention. This was a pivotal point for me. I had first hand evidence that proved to me school was not about learning, it was about doing time. I quit doing time.

I spent the next few months cutting class a lot. I had a friend who was in a similar situation and he lived in apartments across the street from the school. I would ride the bus in to school, cross the street and go to his place. He’d let me in and then go back to sleep and I would get on his computer. Ah computers. I was almost sixteen, it was 1993. My friend introduced me to the Internet. Yes, I was online before many of my generation were on AOL. Insert a lot of technical babble here, but the gist was… I was hooked.

Eventually, the system caught up to me. My mom got word that I was skipping and she wanted to know what was up. My brother had also left school early, but for different reasons. At sixteen, only halfway through my junior year, I convinced her to let me take the CHSPE. That’s a Californian version of the GED that you can take before you’re 18. The agreement was, I’d then go to the local junior college. Unsurprisingly, I passed the test. Later that year, I started taking courses at American River College.

Junior College

I started out with a few core classes and some electrical engineering and computer science courses. I knew I wanted to get into computer science, I just didn’t know what. I took C, Philosophy and Guitar. Soon though, I found the library. The classrooms couldn’t hold my attention. I had been burnt out on school, but in the library, I found the science fiction section! I read a lot, Asimov, Frederik Pohl, and Poul Anderson, among others. Looking back, how I didn’t find Heinlein, I’m not sure. The cracks appeared in this façade as well. The course I liked, I did enough to get passing grades. The classes I didn’t like, I dropped or failed. In the end I think my GPA was around 2. This wasn’t working. So I started working.


I had a few jobs in my youth. I engraved the plates that go on trophies. I volunteered at a natural history museum. I even had a paper route, back when papers were a thing. My first big job following my attempt at junior college was TJ Maxx. I had a lot of fun there. Because I had my CHSPE, I could work shifts that other teens couldn’t. The management noticed my proficiency and they promoted me to head cashier (the off hours one that worked mostly nights and weekends). This worked for me as that was when a lot of the other teens worked and we got along well.

I spent about a year there. I had some amazing times and, I saw how horrible shoppers could be during Christmas. Eventually, one of my cashiers, who was about five years older than me, went to work at a video store (yes, they still had VHS back then). She persuaded me to join there and there were many new exploits, but that’s not where this story finishes. All this time, I had two loves when I was outside of work. Punk and computers. From 16 – 18, I probably went to 75 or more shows. I saw Sublime, No Doubt, The Mighty Mighty Bosstones, Swinging Utters, AFI, Cake (my first concert), Phish (ugh), Goldfinger, Reel Big Fish, Less Than Jake, The Aquabats, you name it. I went to Warped Tour in San Francisco and got a blistering sunburn. I had an amazing time and to this day, many of those remain my favorite bands. But also, I had computers, and the Internet. Sierra adventure games taught me how to type. I still only use 2-3 fingers per hand.  IRC gave me speed. I connected with other kids my age online who had similar social challenges, or were just pioneers. I met people in person who I knew from the Internet when that was still considered a dangerous thing to do. I eventually found online girlfriends…


I was eighteen. I realized the video store wasn’t going anywhere. I also realized that living at home with my mom wasn’t working. I met a girl online who lived in Texas. She was about five years older than me. It was stupid. I saved up just enough money to get a plane ticket there. I moved. I got a job at a grocery store and started stocking the shelves for a day. The same day, Petco called me back and offered me a job. I no-called the grocery store on my second day, as it happened to be Thanksgiving, and started working at Petco. Petco didn’t last too long before a friend of my girlfriend introduced me to National Tech Team. I had started working deep night tech support. I was front-line on extended warranties sold at places like Circuit City. To this day, I still loathe the 144AM modem sold in Packard Bell computers. I jumped from there to CompUSA’s help desk and then on to State Farm. State Farm’s helpdesk at the time had some horribly inefficient process where there were (if I recall correctly) four specialties we were evenly divided into yet 90% of the calls came in for a single specialty.

In training at State Farm, I figured out that the people running things didn’t have it together. I hand-coded some of the support procedures in HTML and passed them around so we all could have digital and easily utilized references.

Not Fired, I Quit

I forget why, but I became disenfranchised with State Farm rather quickly. I believe it had to do with the balance of the calls we took versus the training we received. At one point, I got called into a meeting, about my performance. This was starting to become a bit of a trend for me. I recognized it was a terrible fit and I quit before they could say they fired me. A useless talking point that came back to bite me when it came to unemployment benefits.


Quite soon after State Farm, I got an interview at Microsoft, through Volt Technical Services (a staffing agency). Microsoft was about to launch Internet Explorer 5 and wanted some contract staff for support. I got the job. I also quickly questioned how much an influx they’d actually see with the launch of the new browser. My NEST (New Support Engineer Training) instructor was STEPTO who later rose to decent acclaim before departing Microsoft. I’ll put this portion on fast-forward, but while there eventually was hired full time. During my tenure, I supported Internet Explorer 5, Windows 98, Windows 98 Second Edition, Windows Millennium Edition (eye roll), FrontPage 98, FrontPage 2000, MVPs and Partner Newsgroups for Internet Explorer and Outlook Express, and eventually, my career ending Project Server.

Project Server

My last nine years (of fifteen) at Microsoft were spent supporting Project Server 2003-2013. It was a small team with some very amazing people at the top. Over the years I learned a lot and even got to the point where I was debugging source code, writing applications to aid troubleshooting, and leading my own training courses. But I got stuck. The senior roles were filled, I didn’t know what to do. I didn’t know how to advance. I got bored. I binge-watched Sons of Anarchy on Netflix. My metrics tanked. I got canned.

In Between

So, I was freshly fired, my wife had quit working to take care of our five and two-and-a-half-year-old boys. I was the sole bread winner and had lost a niche, six-figure job. What now? My wife was panicked, I wasn’t. Maybe I was numb. My mom had been recently diagnosed with terminal cancer. I even dropped a devastating line to the HR drone who delivered my exit interview “I’ve got bigger things to worry about, my mom was just diagnosed with cancer.” Like many relationships, it was over long before I exited it. So what next? I wrote my first resume in fourteen years and I started spamming everything.

A few weeks later I was back, working as a contractor for Microsoft, making more than I was when I was fired. I worked with that diverse group for about four months, when one of my old Project Server team members reached out to me about an opening at a local company for that specialty. I applied, got the interview and got the job.


I’ve been at my current employer for four years now. I’ve been through multiple reorgs and managers and directors. I’ve seen the staff on my team drop to from five to two and rise back up. We’ve gone from being a loathed group to trusted allies. Along the way, I was promoted to lead and then manager. We’re now working on a plan to upgrade our platform. The effort that previously was a $0 investment three years ago now has a budget five times my annual salary this time around. From my termination at Microsoft to now I’ve experienced phenomenal personal growth. While always going my own way in my personal life, I didn’t always apply that thinking to my career. The fourteen years I spent at Microsoft I was basically on cruise control, going from one opening to the next as my previous team evaporated. Now I’m making conscious choices and leading myself and others.