Now that the smoke is clearing and Smile’s dastardly attempt to charge more for its product has been “adjusted,” we can talk about more important aspects of this transition. Specifically, Gabe describes Smile’s decision to not encrypt TextExpander snippet data as:

A design choice like that has consequences that I’m not comfortable with. It’s not something I want to use or recommend.

The word “recommend” zeroes in on the fundamental thing I’m struggling with as more developers abandon Dropbox and iCloud in favor of their own syncing platforms. It’s not really about the cost of the services to me. That’s something that I feel I can objectively evaluate myself.

The more difficult decision process now is:

  1. Am I OK using it? And if yes,
  2. Would I recommend it to someone else?

Before data privacy became such a thing, Decision No. 2 was almost always naturally a yes if Decision No. 1 was a yes. It’s not so simple now.

An even better case study than TextExpander is YNAB, which shifted from a pay-per-upgrade / desktop app / Dropbox sync model to a subscription / web app model earlier this year. While I’m using the new YNAB and still feel that it is lightyears ahead of any other personal finance software because of its budgeting philosophies, actually recommending the new version is a far more complex decision than it was when user data wasn’t stored on YNAB-controlled servers and bank data didn’t sync “through the cloud.”

Now, the recommendation decision is a function not only of the benefits of the software but also the risk management implications on the data side. The reason that I am ultimately comfortable with the tradeoff has less to do with my perceived security around the YNAB servers and more to do with:

  1. How selective I am with which bank accounts I sync
  2. Other backstops I have in place at the bank level (transaction alerts, fraud alerts, how I distribute savings across different accounts, and even my decision to keep my credit frozen)

I can’t expect that other people will have the same things in place, but those things are now inextricably linked to my personal experience of the software—making my experience far more singular, nuanced, and much less “lift and move” to someone else’s life.

So. Software is getting better. Software is maybe getting more sustainable through subscription pricing models. But the psychological benefits and costs of using software have never been more complex. As I’ve said before, software is fundamentally a knowledge resource—an abstract layer on top of the physical universe created by humans for humans to grapple with. Software is truly as human as it gets—a medium through which problems are solved and as many new ones are born.

And software and data are now more inseparable than ever. This was inevitable: They are made of the same stuff. Software is a developer’s knowledge; my data are my knowledge. Where should they be allowed to play together? The developer’s house? My house? Or some sandbox in the sky?

I can answer these questions for myself. But for someone else?