Prologue

I had it made. I’ve been telling myself for the last year or two at my last job. I could just stay there forever, and just coast through the rest of my life without really challenging myself, or trying at all really. I’ve lost track of how many layoffs I survived, I was in an important role that was probably never in danger. People respected me and my work, people listened when I spoke, and I had the autonomy to operate in whatever way was best for me. I had a great work-life balance too, and took generous advantage of the unlimited vacation policy. I think I probably took at least 5 weeks of PTO every year, and honestly, being in such a critical role, I’m pretty sure everyone else around was me afraid that me and everyone else on my small team would burn out if we didn’t take lots of time off, and that presented a very real risk of leading to a catastrophic failure for the business.

We were a small but very successful startup that had been acquired by a private equity firm, and we were on a downward spiral. When I started working there, the company had around 80-100 employees, and the engineering team was close to 20. When I left, there were 2 other engineers, and for a while towards the end, it was just me and one other engineer, and no manager. In the last ~2 years I was there, I think I reported to 7 or 8 different people, I lost count…

You’d think it would be really stressful to keep that big of an engineering organization running with just 2 or 3 people, and if this had happened to me 5 years earlier, it would have been hell for me. One of the most important things Ive learned in my career though, is that when very large, and unanticipated “all hands on deck” kind of problems happen, that’s when the best teamwork happens. In these situations, its usually no one’s fault, no one understands what’s going on, and everyone wants the same thing. This levels the playing field. All you can do it help. Everyone puts their cards on the table, some people panic, some people freeze up, sometimes someone tries to lead, but business people can’t solve engineering problems, and they might not like to show it, but they know it, and you can see it during catastrophe. The best team work happens when no one has any idea wtf to do. There is no business process to fix emergencies. Everyone has to just pitch in what they can, and work together.

I can’t tell you how many times in my career I’ve had to work through million dollar this, million dollar that, stay up all night kind of emergencies because we have to save Christmas… Yes, I have had lots of Christmas emergencies. I used to panic, I used to freeze up. I was scared of making things worse, because if I couldn’t even understand what was causing the problem, how could I possibly help? It took me years to understand the team dynamic I just described, and once I saw it, it changed everything. I was that person who was scared to cause a big failure, and I worked slower because of it.

Another cool thing about software engineering is that you can’t really punish people too badly for making big mistakes. One time it was Black Friday at an ecommerce company, and one of our devops pressed a button to clear a cache, and due to the high traffic, it took down the site for a long time, and it cost the company about $1,000,000 of lost sales during our biggest promotion of the year. Any other day of the year it would have been safe to press this button without consequence, but not on Black Friday. Wanna know what happened to him? His boss told him, “Hey, that was a bonehead move, please try to be more careful”, and that was about it. When you punish engineers for making big mistakes, they all get scared, and work more cautiously. The reduction in productivity this causes in teams is measurable. The math checks out: make people feel safe and comfortable, and they do better work.

When I really figured out the dynamic of dealing with engineering catastrophe, it taught me something really important about how I can contribute: Where I was normally scared of causing big problems, and scared to take chances… if there already was a big problem that was not my fault, then I couldn’t make things worse, and the business was willing to take chances on hacky, untested patches. This actually put me in my ideal working conditions: I could creatively problem solve on a level playing fields without fear of failure or repercussion. I didn’t know it at the time, but a big part of this was my ADHD. One of the big things about having ADHD is having a dopamine deficiency. During crisis, people tend to get flooded with dopamine, and this is what makes people act hysterical. This why we hear things like “In the event of an emergency, stay calm, walk, don’t run, to the nearest exit.” If this happens and you have ADHD, instead of getting flooded with dopamine, you actually just sort of get boosted to “normal people levels”. People with ADHD tend to act very calm and levelheaded during emergencies for this reason.

Dopamine isn’t just the happiness chemical, its the regulation chemical. It regulates so many processes and functions. During crisis, people with ADHD really can function more sensibly than is normal - compared to their own baseline and compared to others, because the dopamine flood regulates them, instead of overwhelming them. Perhaps not surprisingly, people with ADHD are over represented in various types of high energy, high pressure work environments. People with ADHD are more likely to be thrill seekers, and get into jobs like being a nurse working in an ER, or being an EMT, or a tour guide doing things like white water rafting, or take on high pressure sales jobs…

I also have Dyslexia. Dyslexia isn’t just a reading / learning disability, but that is a part of it. If you have dyslexia,  you should read the book “The Dyslexic Advantage”. Its a super power. The way it works is that dyslexic brains have impairments with very specific brain centers, and it makes rote skills very hard, like learning the alphabet or recognizing word sounds. Dyslexic brains make up for this by developing connections between various brain centers that run deeper and farther than is normal. If a dyslexic person has trouble reading, they learn to use context clues to boost their reading comprehension. It affects the way the brain is wired together, and it allows for different brain centers that aren’t usually connected very well, or at all, to work together for problem solving in novel ways. Dyslexic people see the world differently. It makes you really good at thinking in systems, and understanding how things are connected. It makes you good at piecing together clues into a story or timeline, and it makes you good at seeing things from other perspectives. It does a lot of other cool stuff too, like make you really good spatial reasoning. Dyslexics are highly over-represented in fields like architecture and engineering, and becoming entrepreneurs. I need to write an entire essay just about this. It makes me really good at figuring out how the production website broke while nobody was looking.

It came to be that creative problem solving during crisis situations became my forte. At my last job, where I was on an engineering team of 2 or 3 engineers in a company meant to have 15-20, instead of constantly being stressed out and panicking about emergency after emergency, I was riding the high the whole time, at my peak level of functioning. It was everyone around me who took comfort in my ability to stay calm, and act as a leader. It was cool, because our team was so backlogged, that in order to get any engineering time in the first place, you had to justify the ROI on paper. Every ticket I touched had the financial value written on it in plain english, so that the PM could always make sure I was doing the “most good” with the limited time I had to give. It was cool, I generally wouldn’t touch anything unless it was worth like $50,000 per day of my time. It sucked for everyone else though, who was constantly begging for help and attention, but it made me a hero, who was always saving the day for someone.

It was so chill, because of the attitude I had, and I felt like the man every day, but I hated it though. I hated that at any given time, I could put $1,000,000 of ROI on a roadmap for a single engineer to accomplish in about a month’s time, and that no matter how shitty our company was doing because layoffs, because economy, because of the private equity formula of: use acquisition to hit performance goals -> cut expenses to maximize profits -> run company into the ground -> write off the loss… no one could get the budget to for a new engineer hire to actually try to turn things around. Our whole company was a line item in a portfolio being managed according to a formula. It was bad for the company, and it was bad for me because it meant I couldn’t move up, I couldn’t challenge myself with building new things, it was just patch patch patch.

As bad as things were for the company, we got merged into a larger company, so we weren’t actually going to go out of business or anything, and while I could have stayed there for a long time, it was at the cost of complacency. I honestly spent my last year at that company in existential dilemma, trying to figure out if it was really ok for me to give up career ambition and just coast forever thriving in this weird niche of a chaotic environment. I things could be so much better, but I was settling. The erosion of my ambition spread to other areas of my life, and it became toxic.

I wanted out, but I didn’t just want another job, I didn’t want to just lose myself to someone else’s dreams again. This whole thing is a cycle of its own. I know I can build something truly amazing, and that I just need some time, some runway, some safety net, so that I can build from a place of security, and not from a place of scarcity. Doing anything from a place of scarcity is self sabotaging. I spent most of that last year trying to manifest an opportunity to allow me to create from a place of safety and security. I asked the universe for a chance to be able to build one thing of my own pure creation from a place of safety and security. And then… the most amazing thing happened… the company offered voluntary severance packages. It didn’t take very long for me to decide. It was less than hour, it might have been like 10 minutes actually, I can’t remember anymore, but I knew pretty quickly, that this was the universe giving me that opportunity, and I took it.

That’s how it started. This is the prologue.