If you're afraid to experiment with using a or in case you end up getting it wrong and losing access to all the things (I am), how about doing the counter-intuitive thing and start with using it only for the stuff that doesn't really matter. All the burner accounts you create only to comment on blogs and forums on whatever. After a few days/ weeks/ months of creeping up the learning curve and making noob mistakes, you can slowly include your more mission critical stuff.

@strypey This is a really good idea! I got over a lot of the initial stress by exporting the database onto a new flash drive and storing that with my identity documents, but I really like the idea of working with low risk stuff first.

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@feonixrift I figure if I start by putting passwords I can recover using my email address into the password manager, it doesn't improve my security much, but it does provide a sandbox for learning how to use the PM safely. Maybe I can try out a few different PMs while transitioning between them is still low risk.

@strypey :) I honestly think this is brilliant .. and being able to pull back out stuff I used once a year ago reliably is one of the things having a password manager has allowed me to do that I never would have been able to do without it. There is still some improvement to your security as well, since it makes using unique passwords easier, and an attacker can more trivially try reused passwords than interfere with an email-based password recovery flow.

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