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Frustration Management

One of the most frustrating things I’ve ever had to deal with in life is losing my data backups, most of the time because I’ve forgotten my password. I’m too cheap in order to pay up for an iCloud subscription, and so far I’ve been too cheap to pay up for a third-party cloud backup solution, so typically I back up my iPhone to my MacBook Pro, and my MacBook Pro to an external drive. This is a bad idea, especially because as a software engineer I already know about data integrity/loss prevention best practices.

I’ve mentioned my usage of this productivity app called Productive before on this site. I’m sure the staff building and maintaining this application are doing the best they can, but despite their best efforts, the app kept crashing for me this morning. I didn’t really know what to do, so I deleted the app in order to try and re-download, because iOS has this weird thing where the app build with version downloaded fresh from the App Store differs in behavior from an app installed previously and upgraded through patches (likely for backwards compatibility reasons or such). Productive is extremely privacy-focused, and so ties together user data and the app’s existence locally, with only iCloud backups available at all, and many buttons asking whether you wish to delete all app data. One click and all my app data got deleted, around 6,500 habits and all habit schemas and migrations.

Okay. So there’s my iPhone backup on my laptop. Except that I forgot the password, and after searching through the entire apartment, realized I didn’t write down the backup password anywhere, store it in my macOS keychain, or add it to my password manager. Can’t brute force it either, since I choose relatively long strings for passwords (min 8 characters). Tried all common passwords and they failed. So the backup didn’t work. And if the password has failed, then all backups are invalidated and useless.

Okay. So set a new password. Except you can’t, unless you reset all user settings in your iPhone, which clears out a bunch of configuration stuff (including Apple Pay, Passcodes, Screen Time, etc.), in order to set a new password for backups. So those are now gone too.

This isn’t Productive’s fault at all, by any means. It’s mine, especially since this has happened before. I had a bunch of photos stored in Google Photos. After the identity theft incident last year, and random people trying to brute force my Google account, I took down my original personal email and downloaded a dump of my original Google account contents onto my local computer’s hard drive. Except that I didn’t download everything, so a bunch of my spreadsheets, like who I should stay in touch with, got lost. Then I had forgotten about the dump and the fact it wasn’t backed up anywhere, and factory reset my desktop in order to get around some pesky NVIDIA driver settings. So I lost all my photos from high school and college, to the letter. Memories, friends, good times, they all just live in my mind now. So I guess I should hope I have a good long-term memory.


This isn’t a pity party for myself. I’ve already implemented certain processes for myself, like the usage of a password manager in the first place with automated password generation and 2FA/MFA support, and I should add on others, such as using a NAS backup with Backblaze B2 or something. I’m also probably going to quit Productive entirely, and switch to a platform that has native multi-device support and data export like Remember The Milk or Todoist. But getting over the feelings of loss and regret after the fact are hard, however simple they may be.

I have learned some coping mechanisms for dealing with hard times:

  • Figure out the worst-case scenario, realize the worst case actually isn’t so bad, and then apply layers of reason to work your way back to something more logical and less lossy: Okay, I lost all my data over the past two or three years with one fell swoop. How much worse is it going to get? What can the world possibly do to hurt me more? Not much more? Yeah that sounds about right. I also have X, Y, and Z, so it’s not actually the worst case scenario.

  • Positive self-talk and self-reinforcement: This actually works. I couldn’t really do this just a few short weeks ago, but some clouds have lifted and I realized that I am fortunate for a good deal. And when you can look forward and see the sunlight ahead, or look up at the clouds and make yourself believe that the sun exists somewhere, that surprisingly helps out quite a bit. Identity is quite tied with self-perception.

  • Keeping busy: If you lose all your memories, then you shouldn’t just stand there. Go out and make more happy memories, and start filling in the wiped drive with new backups (and your backups password checked into a password manager). Keeping busy helps keep the monsters at bay.


All this helps undergird the importance of moving forward, of setting actionables and deliverables, and getting the future you want.