A Prompt Response
Today’s Prompt
Describe a random encounter with a stranger that stuck out positively to you.
I’m a fairly introverted person. I don’t often end up in conversations with strangers, would almost never speak to a stranger unless spoken to, and don’t like mingling with crowds of people I don’t know. The only time I even voluntarily end up in situations like that are either playing in front of crowds when I was a musician, or the poker room. And in both of those cases, I have a reason for doing the thing I’m doing. And luckily, neither require recreational conversation.
In March of 2017 I was a few weeks away from starting at Amazon. I’d already accepted the offer and was waiting for my official start date. I was coming off of a six month break after leaving my previous company, CoStar, and hadn’t really pursued Amazon specifically, but when the chance came to interview I prepared and was able to nail it. Regardless, I was still nervous about the idea of working for a FAANG company after 17 years of sustained success in a fairly stable, predictable environment at LoopNet and CoStar.
My uncle and I went to Las Vegas for one of our patented annual getaways. We’d spend four to five days playing poker tournaments at Caesar’s Palace. I often did well; of the 15 or so tournaments we would play I’d place quite a few times, and win a couple. The fields weren’t super deep, maybe 100 or so, and it was a good way to get away, relax, see one of my favorite people in the whole world, and play some poker.
The last night of our stay I hit a bit of bad luck and busted out of a tournament early. I wasn’t too sad; earlier that night I’d managed to win one and I felt like I was playing pretty well. So I took my tournament winnings and requested a seat at one of the $2-$5 no limit cash games.
I ended up sitting next to trio of friends at one of the tables, with a woman in her late 20s immediately to my right. To her right was one of her friends, a tall man about the same age. As I mentioned, I don’t talk much socially, not even at (or maybe especially at) a poker table, but during a slow run of cards the man asked me what I did for work. I told him I was about to start at Amazon as an engineering manager.
The woman’s eyes lit up and she told me she was a software engineer at Zappos, a company that Amazon had acquired the year before.
We spent the next hour or so chatting about engineering, software, Amazon culture, Zappos, and anything else that mattered, and in doing so, the woman slowly eased my concerns about my new role and new adventure. We may have even played a pot or two. To this day it remains one of the few social moments where I didn’t care about what I was saying or how I was being viewed or anything else that would set off my internal introvert…just two software engineers talking shop at the poker table.
Eventually, my uncle was also knocked out of the tournament, and came over to let me know it was time to head out. I turned to the woman and thanked her for the conversation and the information and the enjoyable company, before getting up to cash in my chips.
The shock on my uncle’s face was blatantly obvious, and in many ways, almost as rewarding as the reassurance provided by the hour of shop talk.
This post is one of many in my responses to random prompts surfaced by the application that tracks my website statistics, as well as any others I encounter.
My Path To Engineering Manager
Often, a manager role is a “reward” for competency or natural leadership ability. Some will actively seek it out; others actively avoid it; and others just organically end up there, often by business need or an absence of leadership in their space. I fall in the latter category; I’ve never been one to seek out promotion or differing roles, as my goal is always to make the best decisions I can at the time they need to be made. One might say I could have pressed my career further, but I am fairly self-aware and have a pretty solid handle on what I need to be the best version of my professional self regardless of the role I happen to inhabit at any particular time.
My initial management role was in retail. At the age of 19 I was promoted to an Area Manager at the local Bradlees department store in Keene, New Hampshire, where I was working after graduating high school. I’d been there almost three years at that point, having joined just before my junior year. That experience informs a lot more of my viewpoint than you might expect. I was young, not the most mature, and was promoted over several of my peers. That was the most difficult part, to be honest…trying to lead people who the day before had been people you treated as peers and friends. That led to a lot of difficult conversations, a tough adjustment period, and changes to my social circle, including changes in the dynamic of my larger friend group. It often put my role as a friend and young adult in direct conflict with my new professional responsibilities. Not something I’d recommend, even to this day, although I did help transition a direct report from IC to manager in that exact situation. Eventually I left that position and role.
Several years into my technical career I was a Chief Architect for Marketplace Verticals at LoopNet. We were a small team of about six. My manager, who I had a great relationship with, decided that we should try out the new Scrum and Agile methodologies and strongly suggested the role of Scrum Master should fall to me. Little did I know he was positioning me to take on more leadership for the team, as he was considering taken other roles within LoopNet. Eventually he did decide to move on to a different role, and I was given a probationary period to lead the team ahead of a role shift to Technical Manager.
I refer to this as “being dragged into management against my will.” I didn’t choose this path; I didn’t seek out management roles; yes, I was a natural technical leader, but that’s definitely not the same thing. Later in my career, many Individual Contributors (ICs) came to me to ask my advice on whether they should move into management or not. The Kindle teams frequently shifted engineers to manager roles in the same way that I had, at times with little regard for the engineer’s best interests. Each time I would ask the IC why they wanted to become a manager, as often in cases like this, the person changing roles doesn’t know why, and doesn’t understand the depth of the difference in the roles. The most common answer I got was that the person shifting wanted to have more control over outcomes and more say so on what was happening on the team. I would often tell them that that was not a good reason, as managers don’t have any control; they can really only influence the quality of the behavior and decision making. Yes they can give “direction”, but at the end of the day the key to successful managers is their ability to look around corners, properly manage technical decisions and disagreements, earn a high degree of trust, become excellent communicators, effectively set expectations, and effectively coach their team. Control tends to not be a thing.
My role at LoopNet eventually ended at Senior Technical Manager with a team of 13. I then took a bit of a break to determine next steps, and ended up at Amazon as a Software Engineering Manager. Much of what I learned about being an effective manager came from that experience; at the time, Amazon’s Leadership Principles were still a primary input into culture, and they blended well with my natural leadership abilities. In particular, Ownership and Customer Obsession resonated with me, and without having to code in addition to my management responsibilities, I was able to develop to the level that I was part of the group training new SEMs as they joined Amazon.
Occasionally I wonder what would have happened if I’d stayed an IC. I’ve never lost the drive to create; I still leverage it in my music projects and at times my own technical projects at home. But I do think that my experiences since LoopNet, at Amazon and now at Atlassian, have shown me that I have much to offer in the way of guidance to the teams that I manage, so in a sense, I’m now building people rather than software, and many days that’s just as rewarding if not more.
Medical Technology Update – The OmniPod 5
One of the more interesting psychological challenges I’ve had during my time as a diabetic has been an underlying belief that any change in treatment was to be considered a failure. When you are actively managing an illness in the way diabetes requires, your vigilance, resilience, and willpower are constantly at risk. For quite a while now I’ve resisted the idea of using an insulin pump rather than giving myself 4 to 5 injections a day; it felt like all of the effort I’d put in the last several years to get myself basically “normal” blood sugar wise just hadn’t been enough, and that I’d still failed.
This was especially true early in my battle, before 2018, when I found a new doctor and was first exposed to continuous glucose monitoring systems such as the Dexcom I still wear to this day. I’ve spoken about this in two earlier blog posts, one from that period in 2018 and one earlier this year that updated my technology usage and its success. Before that, cycling through doctors and medications and periods of simply bad health had left me feeling as though I was in a losing battle.
That feeling can be hard to shake even when one succeeds for a sustained period of time.
For the past few years my doctor, who is incredible, has asked about possibly using an insulin pump. There are several benefits, including no longer needing to carry insulin pens when out and about. I had always resisted because of the seeming permanence of a device, as well as the psychological acknowledgement that we’ve crossed another line in our defense, potentially the last line. One step closer to failure. In addition, most modern insulin pumps require tubes, and that just felt…overreaching.
Two months ago at my quarterly check in, my doctor again asked about using a pump, and mentioned there was a new kind of pump that was compatible with my Dexcom and did not use tubing. The OmniPod 5, while relatively new, was constructed for people with both Type I and Type II Diabetes.

With my success with the Dexcom, the compatibility of the OmniPod with my Dexcom, the smallish profile of the device, and the lack of tubing, I finally decided to take a shot at using an insulin pump.
What a game changer.
Although learning how to apply the device requires a training session, once you have it down, application is relatively easy. The device is a bit larger than I expected, but it’s light and once you’re used to it it’s not too bad. The biggest adjustment has been sleeping on it without feeling like you’re pushing it. The insertion of the needle is quick and relatively painless. I flinch at times but it’s no worse than a normal insulin injection. The pods last about 3 days, so you’re replacing them often, but what it solves is permanent availability of insulin without needing pens or needles.
I haven’t missed a pre-meal insulin in the first three weeks of using this device. It uses AI and an initial dosage from my doctor, giving me a few units every hour as a maintenance dose, and then I can override as needed. I never have to interrupt myself to inject insulin. I control the device right from my iPhone, making eating meals out as easy as eating at home. The device effectively removes any reason to not be on top of my insulin levels every waking moment.
The results are astonishing. My average glucose level has gone down from ~140 to ~115. My in range Dexcom readings went from ~80% to ~98% in range; I went seven consecutive days at one point without a single Dexcom reading outside of my high or low range parameters.
My projected A1C has dropped from 6.9 to 6.1. That’s basically normal for a healthy human.
There are a few cons with this. I mentioned the device size, and sleeping adjustments, but I’ve made those. Changing every three days or so has been manageable. The one thing I don’t particularly like is having it on the same arm that my Dexcom is on; the bluetooth connections between my Dexcom and Omnipod aren’t strong enough to work unless they are within a few inches of each other. In addition, because the needle is a bit bigger than what the Dexcom uses, I am actively rotating positions, which means I’m alternating left and right arms as I change Dexcom sensors. The device is also big enough to be obvious in short sleeves, so I’ve taken to wearing long sleeves just to keep myself from being too self-conscious.
These “cons” are really minor inconveniences that don’t outweigh the major benefits of not having to carry insulin with me, not having to interrupt life to go take shots when I’m out or even when I’m home, and my ability to manage my insulin levels from my phone.
I suppose the moral of the story is don’t let your fear of failure interfere with success….but it could also be that everything is worth a try. In any case, I’m glad I was able to recognize when the parameters of trying a pump made sense to me personally, and I’m feeling very positive about my future as a diabetic.
