The Great Tiltfile Migration: A Comedy of Errors

Or: How I Created a Museum for a Single File

Today I discovered that I had created an entire directory structure (platform/infra/tilt/) for a single Tiltfile, complete with FDD.md documentation and .gitkeep files. What started as a simple development tool somehow evolved into a full museum exhibition for one configuration file.

The Setup

Picture this: You're a developer. You have a Tiltfile. It's a single file. Where do you put it?

If you're a normal person, you put it in the root directory. If you're me, you create an entire architectural monument to house this precious artifact.

The Architecture

Behold, the masterpiece that was platform/infra/tilt/:

platform/infra/tilt/
├── Tiltfile          # The actual useful thing
├── FDD.md           # Because we need to document why we moved a file
└── .gitkeep         # The cherry on top of this architectural disaster

Three files. THREE. WHOLE. FILES.

It's like creating a whole museum wing to display a single spoon, complete with:

• The Spoon (Tiltfile) - the thing people actually came to see
• The Plaque (FDD.md) - explaining why this spoon deserves its own wing
• The Security Guard (.gitkeep) - ensuring this "architecture" is preserved for posterity

The Reasoning (Or Lack Thereof)

Why did I do this? Great question! I have absolutely no idea.

Maybe I thought:

• "This file is too important for the root directory"
• "It needs its own dedicated space to breathe"
• "Future developers will thank me for this organizational clarity"

Spoiler alert: Future developers did not thank me. Future me definitely didn't thank past me.

The Comedy Gold

The best part? The relative paths. Oh, the relative paths!

Because the Tiltfile was buried three levels deep, every path became a beautiful symphony of ../../../:

# What it should have been:
deps=['domains/mercury/backend/src']

# What it actually was:
deps=['../../../domains/mercury/backend/src']

It's like giving someone directions by saying "Go back to your childhood home, then forward to where you are now, then to the grocery store."

The Plot Twist: "Future-Proofing"

But wait, there's more! Past me, in a moment of what I thought was brilliant foresight, added these scripts to package.json:

"tilt:up": "tilt up --file platform/infra/tilt/Tiltfile",
"tilt:down": "tilt down --file platform/infra/tilt/Tiltfile",
"tilt:args": "tilt args --file platform/infra/tilt/Tiltfile",
"tilt:ci": "tilt ci --file platform/infra/tilt/Tiltfile"

I literally hardcoded the path to the problematic location!

This is like installing a fire extinguisher and then chaining it to the thing that's going to catch fire. The "preparation for the future" was actually preparation to make the future migration more painful.

I created convenience scripts that were inconveniently cementing the exact architectural decision that would later become the problem. It's beautiful in its complete lack of self-awareness.

The Revelation

The moment of clarity came when debugging why Tilt wasn't restarting services on code changes. The conversation went like this:

Me: "Why isn't this working?" Also Me: "Maybe the paths are wrong?" Still Me: "Wait... why is the Tiltfile in a bunker?" Finally Me: "This is comedy gold material."

The Fix

The solution was revolutionary in its simplicity:

1. Move Tiltfile to root
2. Delete the entire platform/infra/tilt/ directory
3. Update the docker-compose path from ../compose/ to platform/infra/compose/
4. Enjoy not having to explain this architectural decision to new team members

Lessons Learned

1. Sometimes the simplest solution is the right solution
2. Over-engineering can happen at any scale - even with a single file
3. Future you will judge past you - make sure it's for good reasons
4. Every mistake is potential standup material - waste not, want not

The Moral

If you ever find yourself creating a dedicated directory structure for a single configuration file, ask yourself: "Am I solving a problem, or am I creating a museum exhibit?"

Because sometimes, the best architecture is no architecture at all.

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This blog post is dedicated to all the developers who have ever over-engineered a simple solution and lived to laugh about it. May your Tiltfiles be in your root directories and your relative paths be short.

Special thanks to Gemini 2.5 Pro (fessional fuckup) and over-engineering assistance. Sometimes the best comedy comes from collaborative disasters.

P.S.: The .gitkeep file was the real MVP here. It ensured that this architectural masterpiece would be preserved in git history forever, serving as a permanent reminder of this decision. That's commitment to the bit.

P.P.S.: If you're reading this and thinking "I would never do something like this," just wait. We all have our Tiltfile moments. Mine just happened to be very, very literal.