It’s been a busy and interesting weekend. Our company organized a holiday party (I know, a bit early, but they managed to reserve a premium lounge during a hockey game, which I think was a good idea, and it proved to be a really big draw among staff). A friend whom I was supposed to stay with had the flu (or COVID, he thought), so I ended up getting a last-minute Hotel. Usually, when I’m in town for work, I’ll be there Monday to Wednesday, so this is my first later-of-the-week trip (I was there Thursday to Saturday), which means people were more relaxed, and I got to spend the weekend in Edmonton.
I organized a pizza lunch on Friday, and about 40 of the engineers in my org showed up. We just mostly socialized and recapped the year (so far, I know it’s still 5 weeks till year-end). People seemed to enjoy themselves, and a few shared their professional and personal achievements (I provided a “pass” opportunity for folks by letting them call “pizza”). Nothing hurts introverted engineers more than public speaking. I was speaking a bit as well. People were giving a lot of positive feedback (well, unless they just try to kiss up to the big boss. 😂) I guess introverted leaders organized better public events because they leave the team with quiet space to breathe, and they know when to push people out of their comfort zone and when to respect boundaries.
I had a couple of strategic discussions and build sessions with my VP of products and his portfolio managers as well. It was productive and forward-looking (we’ve been very busy with daily operations, so this was a nice change of pace). It’s funny because I’ve only been here 16 months, but I have a tremendous working relationship with these people. I have their collaboration, but most important of all, their respect as well. “We are able to plan for the forward-thinking projects that we can today, largely thanks to the work that you do and your support. I feel your two predecessors don’t see the business and the values of engineering the way you do,” a portfolio manager said
In the evening, I had dinner with (only) my direct reports (managers and team leads), and it was a great opportunity as well to get to know them. People are so different from people outside of the office, so it was nice. Getting able to share life experiences and career coaching (with some of these people who are older than me) was a surreal experience. People and growth are at the center of what I do in my work, and I’m proud to be practicing my values daily
During the holiday party on Saturday, staff were coming up to me and asking questions, be it industry, career advice, DEI initiative, data science, or even just my experience. I was telling people about my time at Blackline and how I used to travel all around and building amazing tech (and going to hockey games and sales events like these). And one of my HR managers asked, “That sounds amazing! So why did you leave?” So I told her, ” I felt like I’ve hit a plateau at that point and I want to go further. I want to be a CTO of a tech scale-up”. And she was like “holy shit Jason, you’re almost there”. It gave me pause, because as focused as I am and as hard as I’ve been working towards my goals, I haven’t really had people externalize my progress before. I know there’s still a path ahead and I will have a lot of work to do, but for a brief moment, I felt tremendous pride in what I have achieved this year and so far in my life.
On Saturday, I went to the farmer’s market and West Edmonton Mall with a friend (just frolicking). At least two women stopped us and complimented my outfit. 😂 One of them said, “You guys are Glory. You look so glorious and unburdened and free”. Ok, for context, below is what I wore, and my friend has long red hair like the girl in Brave, and he was wearing a full floral sweatshirt and pants like he just came back from Sunday yoga in California. We were sharing an open box of poke while walking and chatting. I can’t remember a time in my life when someone described me as unburdened and glorious and carefree. But I also can’t remember a time when I used to be a scared, closeted young man who would be terrified to be even seen near someone dressed like my friend does. Authenticity is a funny thing. It’s empowering and it’s addicting. It’s grounding and it’s elevating. It’s such a strange thing to be recognized for by strangers, yet it’s an amazing thing to recognize it in myself.

So it’s been a bit of an introspective weekend. I’ve come a long way in my life, in my love, in my career. And coincidentally, even when I’m not actively seeking validation for it, people are recognizing that. And for that, I’m grateful.
Thank goodness.
