I like the focus on python cli tools, using the standard argparse module, and writing good help and self documentation.

You can develop skills incrementally, starting with just one md file describing how to do something, and no code at first.

As you run through it for the first several times, testing and debugging it, you accumulate a rich history of prompts, examples, commands, errors, recovery, backing up and branching. But that chat history is ephemeral, so you need to scoop it up and fold it back into the md instructions.

While the experience is still fresh in the chat, have it uplift knowledge from the experience into the md instructions, refine the instructions with more details, give concrete examples of input and output, Add more detailed and explicit instructions, handle exceptions and prerequisites, etc.

Then after you have a robust reliable set of instructions and examples for solving a problem (with branches and conditionals and loops to handle different conditions, like installing prerequisite tools, or checking and handling different cases), you can have it rewrite the parts that don't require "thought" into python, as a self documenting cli tool that an llm, you, and other scripts can call.

It's great to end up with a tangible well documented cli tool that you can use yourself interactively, and build on top of with other scripts.

Often the whole procedure can be rewritten in python, in which case the md instructions only need to tell how to use the python cli tool you've generated, which cli.py --help will fully document.

But if it requires a mix of llm decision making or processing plus easily automated deterministic procedures, then the art is in breaking it up into one or more cli tools and file formats, and having the llm orchestrate them.

Finally you can take it all the way into one tool, turn it outside in, and have the python cli tool call out to an llm, instead of being called by an llm, so it can run independently outside of cursor or whatever.

It's a lot like a "just in time" compiler from md instructions to python code.

Anyone can write up (and refine) this "Self Optimizing Skills" approach in another md file of meta instructions for incrementally bootstrapping md instructions into python clis.