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Upgrade Paths


Patrick Rhone’s The Best Upgrade is You essay is a nice set of thoughts about building mastery and being consciously (and eventually, effortlessly) efficient. Patrick followed up on the post asking for recommendations of “apps and tips for upgrading yourself,” resulting in this cool list.

While I like and use a number of the apps on that list, I also think that the real insight in Patrick’s original column was that he wasn’t necessarily pointing just to new tools but focusing on the value gained from getting really good at the tools you’re already using. in fact, he put that most strongly with the exhortation

Force yourself into the mindset that this is all you have. In other words, imagine this is the last working technology on earth. How would you still get the job done? How would it help you create? How would it help you work? How would it help you survive?

So I wonder if the message of getting better at what I have is somewhat misplaced in the enthusiasm for new tools. This strikes me as highlighting an interesting tension, between the do one thing well and the be deep and complex schools of thought. What Patrick writes about Mail.app falls into the latter category: It’s a complex application whose usage is deeply enhanced by knowing its keyboard shortcuts and extensive preferences and plugin possibilities. (See also software like emacs, which I have returned to at work for the endlessly customizable org mode.)

At the other pole are applications like iA Writer, which I am using to write this post: Apps with no preferences and no plugins, and which are built to excel at a single core function. Not surprisingly, these apps seem to be most common in writing, where single-focus tools have long been in vogue. The strength of these tools is that they don’t have any depth to learn; the upgrade to borrow Patrick’s term is at once simpler but more difficult: to get better at the work you do with the tool.

To be sure, these things are not at all mutually exclusive: effectively using a complex tool also requires more than any deep technical competence, and neither model helps without the spark of creativity or passion or drive or whatever moves us to really apply ourselves to our work. Or, put differently, org mode may help me capture notes and make sure I follow up on them; and iA Writer may help me focus on one thing at a time; but neither one, by itself, will make me a better co-worker or writer.

But as someone who has spent what was undoubtedly an unreasonable amounts of time refining my grad-school-era workflow for R, SWeave and LaTeX (and dived into similar wormholes on all sorts of toolchains since), I do have a feeling that knowing when to turn to the simple tool, or when to turn to the complex one, and knowing when my level of proficiency with either is good enough to get my work done, is a key capability of its own.