Separating Yourself from a Mac without Erasing the Drive

In some places, you don’t have control over the computer supplied by your employer. It’s locked down and you may only install and use the apps they provide. But because working for a church is a lot like working for a small business and because my boss was confident of my general competence, my expertise with the Mac, and my personal and corporate loyalty, I was given a lot of flexibility and leeway with how I used my Mac.

So over the past two years, my work iMac became an extension of my personal Macs and iOS devices. I used my personal Evernote account to store work files. I logged into my iCloud account and used my App Store account to download software for me to use.¹ I also connected my iTunes, FaceTime, Photos, and Messages accounts over time. I synced my Omnifocus database to Omnifocus running on this iMac. I logged into my Google account and used my Google Chrome extensions. I had 1Password vaults, including my personal vault and a work vault, installed. The list goes on.

I wouldn’t necessarily recommend that anyone else do this at their place of employment. For one thing, your employer owns your computer and thus would have a right to investigate and see any data you have on that computer. It’s also possible that your job ends with you being dismissed and escorted from your workplace without an opportunity to disentangle yourself from your work computer. I explicitly and implicitly trusted my boss and was willing to take that risk.

It’s also possible that you do work in a small business or even home environment where you’re passing your Mac on to a co-worker or a family member who needs to pick up your old responsibilities where you left off.

How do I disentangle myself from my Mac?

So given all that, what steps did I take to prepare for my departure?² The easiest thing to do would have been to format the drive and leave it in a factory-fresh state. Another option would have been to create a new user and delete the old one. But those options weren’t available in my case because I wanted to leave certain applications and files in place for someone else to continue some of the duties I had been performing (namely creating the church bulletin each week.)

Instead, I methodically worked through the following steps:

1. Log out of iCloud account in System Preferences > iCloud. This is a very important first step because you don’t want to start deleting accounts and end up deleting them from the cloud and thus all your other devices.
2. Log out of Dropbox, Transporter, Google Drive, Omnipresence and all other cloud syncing services in their syncing apps. For the same reason as above, I didn’t want changes made here reflected back into the cloud.
3. Move work files to Documents. After logging out of the cloud syncing services, I want to move the work files I’m leaving in a standard location for the next person to find. I use Dropbox and Transporter on my Macs as a simple backup system, but also to allow me to work on any Mac or iOS device as applicable. But not everyone works that way, so I move the files back to the Documents folder.
4. Delete personal Internet accounts in System Preference > Internet Accounts. I deleted all my email, Twitter, Facebook, Flickr and other personal accounts that had been populated here by iCloud, even though I had disabled them when they first showed up here.
5. Clear login items. In System Preference > Users & Groups, look in your current user account and click on “login items”. Delete all the items that are connected to your personal software that you will be deleting in the next step.
6. Delete Applications and their files in Application Support, Preferences, Containers, etc. For this task, I prefer to use an app uninstaller, like CleanMyMac, which will grab all the bits and bobs related to the software, wherever they are. You can also use it to reset an application by deleting the preferences and caches without deleting the software itself, essentially leaving it as if it was just installed. Also be sure to delete your Photos library and iTunes library.
7. Log out of FaceTime, iMovie, Messages, iTunes. These apps keep you logged in separately from your iCloud account. Also, in iTunes, be sure to deauthorize this Mac from your list of 5 available computers and from your Audible account, if applicable.
8. Delete 1Password vaults. Password stores its password vaults in a couple places. The most visible is in the sync folder. As long as it’s had the Vaults feature, I’ve kept separate work and personal vaults. The personal vault syncs to all my devices through iCloud and so that is taken care of when I log out of iCloud on my work iMac. But subsequent vaults, such as my work vault, syncs through a folder on Dropbox. So after I turn off syncing in the 1Password preferences, I delete the syncing vault in the Dropbox folder because the real vault is still contained internal to 1Password. However, even though I’ve turned off iCloud, I still need to delete my personal vault from my work iMac. I do this by opening 1Password, switching to my personal vault (as opposed to All Vaults or my work vault) and then under the 1Password menu, selecting “Delete (NAME) Vault…”, where (NAME) is the name of my personal vault. Update: This may be different if you use 1Password for Families or Teams so be cautious on this step to ensure you're not deleting the vault in the cloud.
9. Delete backups. I kept both Time Machine and clone backups of my work iMac. The only way to do this effectively is to erase the Time Machine drive. If Time Machine is on a directly attached drive, open up the Disk Utility software, select the correct drive, and click on “Erase”. For clones, it depends a bit on the software you use to do the cloning. I use Carbon Copy Cloner, which makes incremental backups for my cloned files. This means that I have personal files scattered in many folders on the backup disk. If I have the time, I can tediously search them out on the drive. Or I can wipe the drive and do a new clone after all my files are gone. Better, might be to get a new hard drive to do the cloning and Time Machine and then take the old drive with me. The last option depends on how your old employer feels about you taking some work files with you. Mine was okay with it.
10. Log out of Chrome and Safari. Google Chrome and Safari sync your preferences and extensions and other data, sometimes including passwords and credit card data if that’s something you’ve allowed, among your various devices. Be sure to log out of your Chrome browser. You’ll log out of Safari when you log out of iCloud, but your data doesn’t get deleted unless you do an application reset a la CleanMyMac.
11. Delete Keychain entries. The last bit of your data you want to make sure to delete is in the Keychain, which is where OS X stores passwords and certificates and encryption keys and the like. Open up the Keychain Access software, which is in the Utilities folder. Search for entries that include any of your personal accounts, your iCloud email address, or the titles of web sites that you only visited for personal business.

That’s about it. If you use other kinds of software or use your computer differently, there may be more files that you want to delete or remove. Be sure to think it out.

Like I said, this whole process is a lot more tedious and time-intensive than simply reformatting the drive and reinstalling the operating system. But if you need to leave your Mac mostly intact, just without anything personal on it, this should work just fine.

1. I have interpreted Apple’s licensing rules to mean that I can use these apps on my personal work iMac for my personal, non-commercial use, which would be the uses I put them to. But this is my own non-legal-professional opinion so take it with a grain of salt. ↩︎
2. These steps were applicable as of MacOS X El Capitan. For later operating systems, some steps may have changed so be cautious. The principles should still apply regardless.↩︎