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How I Broke My Workflow Trying To Automate Everything

If there's one thing developers love, it's automation. We want fewer manual clicks, less repetition, and more time for the fun work - building, shipping, and (let's be honest) refactoring code that didn't need refactoring.

But here's the trap I fell into: I tried to automate everything. And instead of speeding up my workflow, I ended up with a house of cards that collapsed under its own weight.

This post is about what I learned from that experience: what worked, what failed, and how you can avoid the mistakes I made.

The Dream: One Workflow To Rule Them All

At the start, I had noble intentions.

  • Git hooks to enforce linting and commit conventions.

  • CI/CD pipelines to auto-test, build, and deploy.

  • Scripts for local setup, environment variables, and data seeding.

  • Slack bots for deploy notifications and code review nudges.

  • Even cron jobs to sync docs and dependencies.

The idea was: if something could be scripted, it should be scripted. Manual = bad. Automation = good.

Where It All Started to Break

1. Hidden Complexity

Automation is code. Code has bugs.\
Every script I added was another moving part that could (and did) fail.

For example, my CI pipeline had three separate jobs just to handle dependency caching. It shaved ~30 seconds off builds when it worked, but when it broke, it ate hours of debugging.

Lesson: Don't forget that automation itself needs maintenance. Sometimes "boring manual steps" are safer.

2. Over-Optimizing for Speed

I set up pre-commit hooks that ran full lint + test suites. The idea was: catch everything early.

The reality? My commits took ~45 seconds each. That killed my flow. I started skipping commits, working in huge messy branches, and ironically introducing more bugs.

Lesson: Optimize for developer experience, not just process purity. Lightweight checks locally, full checks in CI.

3. Poor Documentation

When you automate everything, you end up with a system that only you understand.

New teammates would try to run npm start and instead get: missing .env.production.local

...because I had buried half the setup inside a script nobody else knew existed.

Lesson: Document your automation. If your workflow is clever but opaque, it's not a workflow - it's a trap.

4. False Sense of Security

Automation made me lazy. "The scripts will handle it," I thought.

But scripts only handle the scenarios you wrote them for. Real life has edge cases. A cron job silently failed on a dependency update, and I didn't notice until production started throwing 500s.

Lesson: Automation should assist you, not babysit you. Monitoring and visibility are just as important.

What Actually Helped

After a painful reset, I rebuilt my workflow with a more pragmatic mindset. Here are the things that genuinely worked for me:

  • Use Makefiles or Task Runners: Instead of a forest of bash scripts, I consolidated into a Makefile. Anyone can run make setup and understand what it does.

  • Automate What's Stable: CI tests, code formatting, dependency caching. These don't change often and are worth automating.

  • Keep Local Dev Lightweight: Pre-commit hooks now only run linters and type checks - fast, non-blocking.

  • Focus on Observability: I set up logging and alerts for cron jobs instead of assuming "no news = good news."

I also adopted the philosophy: if automation saves me < 1 hour/month, it's not worth it.

When Automation Gets Serious

Here are a few useful things I wish I'd known earlier:

  • Containerize your workflows: Tools like Docker and Podman aren't just for deployment - they make automation more reproducible.

  • Infrastructure as Code: Even if you're not on AWS, using tools like Terraform helps keep infra automation transparent and version-controlled.

  • Event-Driven Automation: Instead of brittle cron jobs, look at event-based triggers (GitHub Actions, serverless functions). They fail less often.

  • Secrets Management: Never hardcode tokens in scripts. Use something like Vault or Doppler.

Security Beyond Code

One of the biggest lessons I learned is that automation doesn't fix bad security hygiene.

In fact, it can make it worse - because when things are automatic, you stop thinking critically about the risks.

This came up in my crypto projects. I realized I was still using a regular Gmail account for some Web3 logins and sensitive data. Big mistake. Emails are often the weakest link.

That's when I started looking into secure, encrypted crypto email.

Why? Because standard email ties you to your personal identity and metadata, which in crypto is basically painting a target on your back. A dedicated encrypted mailbox (like Atomic Mail in my case) gives you:

  • End-to-end encryption for sensitive comms.

  • Aliases so you're not reusing the same identity everywhere.

  • Zero-access architecture - even the provider can't read your messages.

For devs dealing with wallets, dApps, or even just client contracts, this is the kind of "automation" you can trust: it reduces human error instead of adding complexity.

Finding the Balance

Here's the truth: automation isn't about "doing everything automatically."

It's about choosing what's worth automating and what's worth keeping manual.

  • Automate the boring, stable, low-risk stuff.

  • Keep visibility high on automated processes.

  • Always prioritize developer happiness over theoretical efficiency.

And most importantly: don't forget the human factor. Automation should make you feel lighter, not trapped in a system you built yourself.

Wrapping Up

If you're about to go down the "automate everything" rabbit hole, pause for a second. Ask yourself:

  • Will this actually save time in the long run?

  • Will other people understand it?

  • Does this add resilience - or fragility?

And don't forget security. Because at the end of the day, automation is just code. And code should serve us - not the other way around.

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