I’ve been programming for the better part of a decade, and I’ve been programming in Python for the better part of that better part.

As loathe as I am to assume the mantel of “X Engineer”, if I were to describe my career in relation to any technology it would be “Python Engineer”.

It is the language I feel most comfortable with; it is the language I reach to first when starting a new project; it is the language I write daily. It is as frictionless as English.

And yet I still find myself losing hours to things I thought I had mastered.

The other night, I played with the idea of bumping Buttondown to Python 3.6 from 3.5 — I wanted cooler types and faster dictionaries, and it seemed like a painless process, so I ran brew upgrade python and was off to the races.

Except something broke: there was an issue with how I was using grequests that was fine in 3.5 but not 3.6, and I decided to revert.

So I hit up pyenv to try and grab 3.5 (since it was no longer the latest thing installed on my machine) and use that to recreate my virtualenv.

Except now psycopg2 was broken for some reason?

It kept on throwing a bizarre error that had like, three matches on Google total:

ImportError: datetime initialization failed

So, I do what I’ve learned to do: nuke everything and start over.

Except now virtualenv is broken, looking for a global python installation that doesn’t exist: no such file or directory, it snaps back at me.

After a few hours of fruitless Googling and tinkering, I do the thing I’m not supposed to do: I just re-install the old version of Python with brew:

brew install https://raw.githubusercontent.com/Homebrew/homebrew-core/ec545d45d4512ace3570782283df4ecda6bb0044/Formula/python3.rb

And suddenly everything works. I recreate the virtualenv; I reinstall the dependencies; I get back to work.

There’s no big lesson here. I probably should have stuck with 3.6 and figured out the grequests issue; I probably should have been more disciplined with installing 3.6 through pyenv and managing my environments.

But I think it feels good to get lost in a sea of arcana and development hell for an afternoon. I mean, it sucks in the moment — there’s no denying that. But once the moment passes, you’re reminded about how much left there is to learn and to master.

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