Aleen Mean

Sometimes You Have to Begin Again

Apple’s developer conference was two weeks ago. The conference’s keynote is Christmas for the Apple developer community every year; those of us who geek out over new operating system features usually get some great presents. This year, I was especially excited to try Swift Playgrounds on iOS, but it’s only available on the iOS 10 beta. Running early betas like this one can be a quick way to experience a lot of computing-related pain.

I managed to make it a week before I decided to sacrifice my iPad in the name of learning Swift via Playgrounds and, while I was caught up in the NewShiny! excitement, I upgraded my computer to the beta Mac operating system.

Turns out, that wasn’t the best choice. After a few days, it became clear that it would be a good idea for me to downgrade to OS X 10.11. The problem was that I didn’t clone my SSD before installing Sierra and my Time Machine backups were toast. Oops.1

This is the second time I’ve needed to wipe my computer and start over again in a the last few months.2 The first time I embarked upon this journey in recent memory, my friend Casey Liss was kind enough to share his starting-over list with me and it really helped me get up and running pretty quickly. I should have made my own version at that time, but I figured it’d be a while before I’d need one again. Oops.

I don’t always learn from my mistakes, but this time I decided to make a list of my own as I got everything set up again. I use 1Password Families to keep track all of my important information. It seemed pretty logical to put these details there, since 1Password is one of the first things I set up on a new device and it syncs almost instantly.3

Starting Over Secure Note in 1Password

I started a Secure Note and started documenting everything I installed or set up as I muddled my way through getting my Mac back up to spec. I’m still making edits to the note. For example, it was a few days before I worked out of the house and realized I hadn’t yet set up the VPN.

I made sure to use Related Items to help speed up setup in the future since I just need to click on the Item’s name to go to it directly.4 I also took the liberty of writing the text in Markdown in the hope that support will be added soon!5

Now the challenge will be remembering to update the note when I make big changes to my processes and preferred apps…and finding a text editor I really like.


Here’s the full text of my Secure Note, in Markdown, if you’d like to copy and paste and/or can’t read the image:

1. Change computer’s name in Sys Preferences > Sharing. Also enable Screen Sharing, File Sharing, Remote Login
2. Download 1Password and set up Families
3. Enable FileVault
4. Set up Dropbox and let sync (give at least 8 hours)
5. Set up backups
6. Set up mail.app (use password authentication for outgoing mail)
7. Make sure messages originate from phone number
8. Set up VPN (VPN Type: L2TP over IPSec, Send All Traffic Over VPN, Show VPN status in menu bar)
9. Download: Alfred (set up powerpack!), aText, Audio Hijack, Bartender, BetterSnapTool, Chrome, Dropshare, Fantastical, Skitch, Skype, Slack, Ulysses, and the text editor du jour

## Set up AleenMean.com

### Homebrew, Ruby, Jekyll, etc.:

http://jekyllrb.com/docs/troubleshooting/#jekyll-amp-mac-os-x-1011

### Set up SSH keypair:

* mkdir ~/.ssh
* chmod -R 700 ~/.ssh
* _copy public key to pasteboard_
* pbpaste > ~/.ssh/id_rsa.pub
* _copy private key to pasteboard_
* pbpaste > ~/.ssh/id_rsa
* chmod 644 ~/.ssh/id_rsa.pub
* chmod 600 ~/.ssh/id_rsa

### Test keypair:

* ssh (redacted)
* exit (if 👍)
  1. It’s fine, really. I wouldn’t have risked it if I wasn’t willing to start over again.

  2. Way back in the late 90s, I’d reformat my computer’s hard drive for fun. Starting over was a lot easier then. All I needed to do was reinstall a bit of software and configure our dial-up Internet before I was ready to take on the virtual world again. Things are more complicated for me now so I start from scratch far less often. I’ve really only wiped everything out a handful of times since I got my first iMac in 2008.

  3. Reminder that I worked for AgileBits for nearly two years, left on excellent terms, and have a ton of friends who still work there. I’m not entirely unbiased, here :)

  4. I wish that there was an easy way to go to a previous item. As it is, I have to make sure to add my Starting Over note to each Related Item I add.

  5. I have no inside information on this, but it was an oft-requested feature when I worked there!