A chapter ended…

May 25th, 2022 was my last day at Stripe, 82 day shy of 7 years. Leaving on a Wednesday is weird, but it was the last day of school for my kids and it was fitting. I’m taking the summer off to focus on family, and recenter some parts of who I am. I’ll think about what comes next in September, but hopefully not a day sooner.

When we entered the pandemic, I had two middle schoolers. We uprooted them, moved a thousand miles to a new city, new climate, and a new experience while I started working in an office. I’d been working remotely their whole lives. While Stripe’s Seattle office was growing, they were growing into teenagers. Then the pandemic hit and we abruptly came back to Vegas. My parents are our neighbors, and I’m so happy my kids have an extra generation of wisdom, experience, and love so near. It helped make a tough time easier.

I deeply appreciated my time at Stripe, and it was my favorite job by far. It’s not perfect, but it was very good for me. I continue to miss the work, and can’t help but think more about it and unfinished projects and opportunities. This is the right choice to leave, though. My life at the moment, outside of work, has a closing window of opportunity. I’m teaching my son to drive, and he’s learning what early adult life looks like as he starts thinking about colleges. My daughter is a bit younger, no college plans yet but we have a ton of fun baking, gaming (she carries me in Valorant), and creating art. I just did my first watercolor painting, and looking forward to doing a lot more. Both of them continue to teach me a lot, but I have to be a patient student because I’m not a very good student so they’re usually not very efficient lessons.

I love to travel. Now, for the first time, I have both the financial means and the time. As much as we can do safely, we’re going to travel (and what we can do safely! There is still a pandemic). Summer in Las Vegas is miserable so I have extra motivation. My goal is to spend as little time here as we can, starting with a long trip in Seattle to reacquaint with our friends there. My wife and I have a lot of other things planned, and it’s a great perk to have not just family so close, but family we enjoy being with who also enjoy watching the kids.

Over the next 3 months, I’m going to be thinking about how life changes when so much of my time and energy isn’t focused on a job. I’ve always liked working, and I’m excited to see how the lines of being productive and being helpful move further away from doing that mostly at work. I don’t know what it looks like at all.

I wanted my last day to be celebratory and exciting. It was overshadowed by the entirely preventable, avoidable, unnecessary tragedy in Uvalde. My kids have grown up doing lockdown drills, hiding under their desks, wondering when the next shooting will happen. They both know people impacted by the mass shooting here in 2017. Gun violence is an expectation for this generation. We can stop this if we choose. I don’t mean “we” as in Democrats, I mean “we” as Americans.

We can fund groups like Everytown, so they can compete with the $60 million dollars the NRA spends in lobbying efforts every year. We can continue to demand gun safety and we can reduce the number of shootings and the number of deaths. We can vote for, and fund, people like Jessica Cisneros, ousting politicians that aggressively defend the status quo. We can stop making the deaths of so many children a divisive political issue. It will always be political, because to resolve this will require changing our laws.

The feedback I wish I got

Yesterday my son and I were out shopping for his science experiment and he got distracted by some of the wood assembly kits. He said, “I really like building things!” I agreed and asked why he didn’t spend more of his time building things. He really does enjoy it and when he is doing it he obviously enjoys himself and he loves to show off what he created. He doesn’t start projects very often, though.

I realized I’m the same way about feedback cycles. I love feedback, reviews, and really love getting helpful feedback. But every time feedback cycle rolls around I drag my feet.  This is a good signal that something isn’t aligned in my head. If I value giving and receiving feedback what is the reason the current structure isn’t motivating me to act?

I was talking about this feeling and came to the conclusion that it’s because I feel the people I choose to give me feedback are likely to either confirm my strengths or my weaknesses. The process will not grant me insights into how people see me and my work. Many feedback questions focus on areas of strength and the kindly named “growth areas”.  As I advance in my life and watch others do the same, I've noticed the ability to be more self-aware of strengths and growth areas improves. Feedback at this point is a useful tool to verify the accuracy of my self-awareness but rarely provides new insights.

In talking more about this, my friend and I came up with a few questions that will hopefully provide new information. Not just any new information, but the most wonderful of new information: how others see me. I think these questions are also more lightweight than the typical feedback questions that happens during a performance cycle at work. They're also not bound by work! Friends can also provide very interesting insights here.

What motivates me?

I know what I’m motivated by, but I’m guessing most other people don’t quite think about it as much as I do. This question I think is especially important because I’m sure there are moments where someone thinks we’re motivated to get to the same point and perhaps competing with each others. We may be, but we may not — knowing this for sure would be helpful.

Most importantly, though, is that this question invites the discussion about my goals so the people around me can help me succeed. Or they can say my goals are dumb and I should do something different. Either way, everybody wins (by everybody I mean mostly me).

How predictable am I?

I firmly believe in a culture of no surprises. At work, at home, everywhere.  Birthday and Christmas surprises are ok. I have the benefit of being inside my own head so, obviously, I am never surprising. Turns out I’m wrong.

My wife has expressed many times that she usually becomes frustrated when car shopping with me. I love cars and love getting new cars. When choosing my current car I went around and drove nearly every 4 door sports sedan on the market. This went on for weeks and weeks, then I sat in my car and drove it for 3 blocks and decided it was the car I wanted. So I got it right then and there. She was surprised and couldn’t see how I leapt from just browsing to buy, buy, buy! In my mind, all I was waiting for was that one car that felt just right. She can’t feel my just right and the entirely opaque process was frustrating purely because of the surprise. She was perfectly fine with the car and it was in our budget. She was unhappy feeling left out and surprised. That lesson sticks with me and I don’t think many people in a work setting would talk about feeling left out and the negative experience of being surprised at a decision.

Am I doing what you think I should be doing?

This one may be a bit slanted towards work but I think it can be adapted to friends fairly easily.

If someone sees my strengths and skills in a different way they may know of an opportunity better suited for me. This is almost an extension to being predictable, though, because if I’m working on something others don’t see the value or connection to my goals I want to hear about it. That means something about my behavior and choices is surprising and I should understand what that gap.

This also opens up a conversation about what I'm doing to improve and grow. Often times feedback has questions along the lines of, "What could this person do better?". Carrying this sentiment up I think brings us to this question. I may be willingly giving up on something so I can do better in another area that is higher priority or more urgent. Or maybe I don't see the importance and that information will help. I believe understanding what others think I should be doing that I'm not it will help me and mitigate problems that I may be entirely unaware of.