2023-08-19

You ever have one of those days where you realize that your brain is just a little bit broken? I’m having one of those days. The family and I were in a local discount supermarket and as we walk past the dish soap I see that an on-shelf promotion has resulted in the shelf being absolutely cleared.

My reaction to such a sight is to immediately take a photo and post it to the team’s Slack channel at work with the caption “Looks like someone priced that wrong”. It turns out, after working on supermarket projects for nearly a year just sort of breaks your brain.

I’m not sure if I’d call it a sense of appreciation. But I don’t see it as a place where I just get food anymore. I see it as a very poorly executed optimization problem.

I’m looking at the aisles thinking that they are in the wrong order. I notice that the there’s an odd number of aisles, so that after you serpentine your way through the store, you’re left to double-back on one aisle. I notice the planogram that some stocker left on the shelf and realize that the the store looks nothing like the planogram - and they dont even have half of the right variants of Coca-Cola to even make the planogram work.

It’s all just a little bit broken.

But does anyone care?

Probably not.

I mean the staff working the store definitely don’t care. But as I watched the little one try and climb into a freezer of samosas, a watched a clearly Korean employee talk to a clearly Chinese in the semi-fluent French of an immigrant trying to get by in this world. And in this tiny microcosm of the world I marvelled at the fact that everyone is just trying to make their lives’ a little bit better.

I don’t know, I’m in a bit spaced out today. I described it to N earlier as that feeling you have coming out of a spa or a good massage. After two days of horrible sleep, thanks to the antibiotics and pain killers post wisdom tooth extraction, I feel a little stoned to have a good night of nine and a half hours of quality sleep.

But maybe that isn’t so much a reflection on my sleep as it is a general malaise that seems to have come over me recently. I don’t feel terribly motivated to very much of anything just recently. For the longest time, I have defined myself by my work - and progression within it. But everything is a bit big, a bit abstract, a bit too long term at the moment to feel like any meaningful progress is being made anywhere.

Perhaps I should take a page out of the Italians playbook. Live more like a stoic and in the moment appreciating this moment, right here, right now. Instead of this American-esque obsession of progression, developing, bettering, always looking to the future. It’s probably the healthier way to be. But it requires reprogramming a lifetime of always focusing on the next thing.

Treating everything like a knife fight. Everything is life or death. Everything is a work in progress.

Should this be time for a grand revolution, and significant change in life. Or should I shut up and put the work in to get comfortable with where I am?

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2023-08-20

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2023-08-21

How do you define successful engineering leadership?

The Philosophy

Many view technical leadership as being the “smartest architect in the room.” I see it as the opposite. My job is to build a room where I don’t have to be the smartest person because the systems, culture, and communication are so robust that the team can out-innovate me.

The Strategy

  • Alignment: Does every engineer understand how their sprint task impacts the company’s bottom line?
  • Velocity vs. Stability: We aren’t just “shipping fast”; we are building a predictable, repeatable engine that doesn’t collapse under its own weight at the next order of magnitude.
  • The Human Growth Curve: Success is when the engineering team’s capability evolves faster than the product’s complexity. If the team feels stagnant, the tech stack will soon follow.

What is your approach to scaling technical organizations?

The Philosophy

Scaling isn’t just “hiring more people” - that’s often how you slow down. Scaling is about moving from Individual Heroics to Organizational Systems.

The Strategy

  • The 3-Continent Perspective: Having managed global teams, I focus on “High-Signal Communication.” As you grow, the cost of a meeting triples. I implement “Asynchronous-First” cultures that protect deep-work time while ensuring no one is blocked by a timezone.

  • Modular Autonomy: I advocate for breaking down monolithic teams into autonomous units with clear ownership. This reduces the “communication tax” and allows us to scale the headcount without scaling the bureaucracy.

  • Automation as Infrastructure: At petabyte scale, manual intervention is a failure. I treat the developer experience (CI/CD, observability, self-service infra) as a first-class product to keep the “path to production” frictionless.

How do you balance high-growth velocity with technical stability?

The Philosophy

Technical debt isn’t a “bad thing” to be avoided; it’s a set of historical decisions that no longer serve you. Like any loan, leverage can accelerate growth when investments payoff. But if velocity and returns are slowing you need a payment plan before the interest kills you.

The Strategy

  • The ROI Filter: I don’t refactor for the sake of “clean code.” I don’t refactor a micro-service with no users. I refactor when the pain on that debt - measured in bugs, downtime, or developer frustration - starts to exceed the cost of the fix.

  • Zero-Downtime Culture: Especially at scale, stability is a feature. I implement “Guardrail Engineering” where the system is designed to fail gracefully, ensuring that a Series B growth spike becomes a success story rather than a post-mortem.

  • The 70/20/10 Rule: I typically aim to dedicate 70% of resources to new features, 20% to infrastructure/debt, and 10% to R&D. This ensures we never stop innovating, but we never stop fortifying either.