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Legacy systems drain budgets and block AI adoption. A pragmatic modernization roadmap for engineering leaders who need results, not slide decks.
Senior Freelancer & Technical Lead
Working as a Golang developer since 2020. Working as a mobile developer since 2013.
Focussed on architecture, testability and clean code. Open minded & product driven. Based in Rhede, available world-wide
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Here's a number that should bother you: organizations that modernize applications during cloud migration see 40% higher ROI than those doing lift-and-shift. Yet most companies still fork-lift their monolith into EC2 and call it "cloud transformation."
That's not modernization. That's moving your problems to someone else's data center — and paying more for the privilege.
Three things changed in the last 18 months:
Not everything needs to be modernized at once. Here's what actually matters, in order:
You can't improve what you can't see. Before touching a single service:
Cost: days. Impact: immediate. You'll find problems you didn't know you had.
If deploying takes a ticket, a meeting, and a prayer — fix that first. Everything downstream (containers, Kubernetes, microservices) is meaningless if shipping code takes a week.
Target: push to main → deployed to staging in under 10 minutes. That's table stakes in 2026.
Don't containerize everything. Find the service that's:
Containerize that one. Get it running in a managed Kubernetes cluster or a simple container service. Learn from it. Then do the next one.
The Strangler Fig pattern works. Route new traffic to new services, keep the old system for everything else, gradually migrate.
Rewrites fail. Partial, incremental replacement works. Every time.
Splitting databases is the hardest part of any modernization. Do it last, when you actually understand your domain boundaries. Premature database splitting creates distributed monoliths — worse than what you started with.
| Week | Action | Outcome |
| 1–2 | Audit current state: deployments, incidents, costs | Baseline you can measure against |
| 3–4 | Set up observability stack | Visibility into actual problems |
| 5–8 | CI/CD pipeline for top 2 services | Deploy in minutes, not days |
| 9–12 | Containerize first workload, deploy to managed cluster | Proof of concept, real production traffic |
After 90 days you have: visibility, fast deployments, and one containerized service running in the cloud. That's enough to make the business case for the rest.
Cloud modernization isn't a technology project. It's an organizational one. The tech is the easy part — changing how teams ship, operate, and own their services is what takes time.
Start small. Measure everything. Expand what works. Kill what doesn't.
That's the whole roadmap. No 200-slide deck required.