[practicingdev]

The web of foundational skills for software development is vast enough that you can't really build it out from the bottom up.

What you can do though, is start with small projects and try to understand every piece involved in them, and why you did things the way you did.

Repeat this with increasingly complicated projects, testing and synthesizing what you learned.

[awkward_yeti]

So cross reference the common experiences from different small projects. That does make sense.

Have you done that ? Or are you doing it at the moment ? because some hints of those projects ideas will be awesome.

[practicingdev]

I am the author of the essay, so... yes!

The context I currently apply this in is that in the apprenticeship I'm running.

So for example, we work on business applications and some amount of complex analysis is needed because we work with raw problems (i.e. it's necessary to interview the users/customers directly, collect raw data, etc... collect and transform raw data from many sources before we can even start on a project, etc)

I would start by trying to give my apprentice small chunks of the work we were doing, at a task-based level. She would do fine when I could break it down into well-defined tasks, but not do as well if I just gave her some raw materials and said "OK, implement something that will solve <HIGH_LEVEL_GOAL>"

So we circled around that a lot, and realized part of the issue was the challenge of thinking rigorously and synthesizing lots of details. We dug into Gilded Rose kata together to practice that a bit...

( https://github.com/NotMyself/GildedRose )

Then after that, we went back to some more realistic work, talking things through... taking notes... etc. It helped for a little while, but then we were still hitting issues related to rigorous problem solving / analysis.

So then we went back and did some more exercises. This book chapter gives some examples of the sort of "fundamental lessons" that can be pulled from specific exercises, so long as you're looking at them with the goal of seeing the deeper ideas behind the work you're doing:

http://tinyurl.com/pbp-rigor (PDF)

This is the sort of stuff I've been working on lately, because I don't think there's a direct path towards getting the big picture if you don't have someone guiding you, aside from a ton of hard work and patience combined with continuous practice.

That said... keeping a journal does help. My apprentice has been working with me since the beginning of the year, and she writes notes daily on what she does, what she studies, what she struggles with, etc. Periodically going back through those is how we figure out what to do in practice and study sessions, and I imagine even if working solo... you could try that.

Hope that helps!