2023-09-20

I’m not sure if I’m actually any good at this whole journaling thing. I’ve been doing the attempted daily thing for about a month now and I’m not entirely sure what my hit rate was like. It was okay. But it was certainly far from the daily target I would’ve liked. But in the words of Meatloaf “two outta three ain’t bad”.

I think crucially it’s been enough for me to cross the inertia threshold and for it actually feel like a new habit. If I get to the end of the day and I haven’t done it yet then I feel like I’m looking for it. And that is unusual. Few things have ever gotten that far. The last notable thing that I felt my body looking for was lifting some weights. But just recently with life commitments and a focus on getting myself ready for the run, I’ve barely touched the weights and the yearning disappeared disturbingly fast. But I’m sure it will come back. It always has in the past.

However, perhaps I’m looking at all of this wrong. Maybe journaling shouldn’t be objective based. Perhaps this should be one of those things I do in life just for the sake of doing it.

Ironically, I found myself giving nearly identical advice to one of our ambitious, junior developers yesterday. I was there telling him that he needs to learn to enjoy the process and not be so focused on the results. After all, the process, the journey is how we spend our lives. For instance, with the supermarket project I spent nearly a year of my life associated with it. But when it’s all said and done, the team and I spent only an hour reminiscing about a job well done before we got back to it on the next thing.

Why is it so much harder to implement advice in our own lives?

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2023-09-18

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2023-09-21

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.