Annual review 2023 - 2) Best of

This post is part of my annual review process for 2023. This year, I’ve committing to writing a more comprehensive review, but to do so I’ve structured myself into particular areas that I think are important to cover.

To read more,

  1. Intro
  2. Best of and memories
  3. Career
  4. Relationships
  5. Health
  6. Personal growth

Best memories

Best Surprise Axe throwing for my birthday

Best Meal Gourmet, fine-dining steak experience in Mexico. The best steak of my life.

Coolest New Experience Swimming through a limestone cave (cenote)

Favourite Weekend Flying into Vancouver for a long weekend and hanging out with some friends, that I dearly miss and should appreciate more

Favourite First Meeting Many new friends at this year’s SwordPunk

Favourite New City Cancun, Mexico. First time in Mexico, first time in Latin America

Favourite Sports Moment Crossing the finish line of this year’s Montreal half marathon

Favourite New Walk What’s old is new again, but walking the North Norfolk Coast around Blakeney with my parents was pretty special

Favourite New Friend Xavier. Placed together to face a near impossible task at work, he quickly became my work wife and more besides. Now if only the kids could stay not sick for one weekend, we’ll have ourselves a nice little place date

Favourite Day Tough one to call. First day of Cancun was pretty special. But best day, I think goes to the first day of SwordPunk. After driving across the country to find a Doug ready with beer and a BBQ surrounded by some picturesque camping. Yeah… that’s hard to beat.

Most Intense Week Maybe this last week just gone. Having a client at work ask you what exactly they’ve spent millions of dollars on is never a great conversation to be had.

On the family front, well we had the week where the little guy had surgery, or the week of atrocities and war being declared in Israel. Definitely not the best week I’ve ever had.

Favourite Artist By Spotify listens, I think Thrice takes it. By actual connection, I’ve kept coming back to the post-rock. Namely, Maybeshewill and Athletics

Favourite Song Lost - Linkin Park. There’s something about hearing a song recorded 20 years ago, by a man, now long dead, and it still sounds like it came out yesterday.

Favourite Concert A good year for gigs. I managed to get to a lot. Some notable highlights were Bullet for my Valentine, Tool, Thrice. But the hands down best was Avenged Sevenfold supported by Alexisonfire.

Favourite Quote Still hard to beat that old Mike Tyson quote

“Everybody has a plan until they get punched in the face”

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.