2025/07/03 - Three years

The start of summer has marked my three years of working in the world of DevSecOps. I thought this would be as best a time as any to do a bit of reminiscing on my time in this sector.

The journey so far

Here's a rough overview of the eras and how this adventure has progressed so far:

Bright eyed and bushy tailed

Join a monetization team. Full steam ahead on monolith decomposition. All the billing APIs. Ugh Salesforce.

Oh no layoffs

Bye-bye mentors, guess I need to be some form of authority now? New team, new name, new friends, new funnels.

Hey, platform is over there

Notice where the cool things are happening and where the skilled people are operating. EDA and OAuth sounds like more fun. Lets go be a platform engineer!

Leveling up

Wow some of these people are damn efficient, gotta get up to par.

Company says no

Re-org because priorities change. Projects shelved, new division, new mission, a patchwork team. Developer Experience is our god now.

Greenfield

Guess I'm working on source control integrations? New service, all the Kafka, data pipelines. Build our little wonderland, wait how am I a mentor now?

EA, GA ... AI?

Hype cycles drive the market. Call the MVP prod ready, the great AI rebrand is upon us. Debt creeps, bottlenecks show themselves at scale.

Polish and strip

Investigations, new ideas, team comes together, analytics, enhancements, challenges! Oh wait, new layoffs? Lost mentees.

What now?

A little summary

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  teams: 4
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The highlights

  • Enjoyed working alongside some brilliant folks who made me reconsider how I was approaching problems/solutions and pushed me to get up to speed.
  • Had my brain formatted by various managers with unique approaches to handling engineering teams and career progressions (weaponizing Conways Law for the greater good).
  • Took a greenfield domain and led it from first commit to GA'd with a highly motivated team.
  • Fought the impostor syndrome and started taking the lead more, successfully pushed back against the feature factory habits when critical.

The lowlights

  • Definitely wish I could have worked longer with certain people to soak up more of their knowledge. May have missed some growth opportunities there.
  • Hyperfocus on trend following causing projects to be identified as "completed" by the business. I've never seen such a wicked amount of debt accrued in such a short time.
  • Incidents happen, lots of incidents shouldn't. System instability for velocity is a bad tradeoff and could have been avoided earlier in hindsight.

The takeaways

Throughout this time, I had the pleasure to pick up a bunch of new skills as well as work with a myriad of interesting people. Although being far from an expert in any of the subjects, it has been a joy to become proefficient with both Kubernetes and Kafka. Diving deep into these systems and maintaining solutions that leverage them tickled my brain frequently. By proxy of working in this space, it has also exposed me to a plethora of other projects (Envoy, External Secrets Operator, ArgoCD, Kyverno, Istio, etc.) all with their own approaches and design philosophies. This had the benefit of opening up my horizons quite significantly.

On a organizational standpoint, I've definitely felt the instability of working in tech. Frequent re-orgs, employee churn, not being able to spend more than 6 months in a team or on a project, etc. This led me to realize that a fundamental skill is to maintain vision from the bottom up even if the company is unclear as to its own priorities. Defining where we want to be in a years time as well as spiking and experimenting should be a strong focus alongside the habitual responsibilities of implementation, maintenance, and support. It sometimes feels like folks are a bit overwhelmed with the amount of facets to the industry and we tend to fall into a "Business as usual" mindset without challenging the internal status quo. Basically ask for forgiveness instead of permission and constantly push to do better.

Next steps

As I re-evaluate my career trajectory, I think my renewed focus will be on a couple of key aspects:

  • Championing observability to sleep better at night.
  • Extracting and cleaning more data to ensure success criteria are traceable early in the SDLC.
  • Improving local dev setups for better momentum later in projects.