The Password Conundrum – Part 1

Obligatory password-blog-post lock picture. We can all breathe easy now that the status quo has been upheld.


This is the first part of a three-part article in which I’ll discuss managing online accounts and password security. In this first part, I’ll talk about the embarrassing state of my own account management – or lack thereof, what prompted me to get my act together and form a realistic account management strategy, and a brief note on what my personal needs for account and password management entail.

In the second part of this article, I’ll go over some of the tools and strategies that I researched while I was figuring out how I was going to manage my accounts. I’ll cover password managers, using complex passwords, and multi-factor authentication.

In the third part of this article, I’ll discuss my overall account management strategy: what I did and didn’t do, and also my rationale behind each choice. I hope that by the end of this article, you’ll have a good idea of what is available to help you get your accounts under control and to also make informed choices regarding what methods and technologies that you want to use to help keep your accounts and personal information secured.

A shameful tale of woe and regret

I’ve been an Internet user for about half my life now. That’s been enough time to collect many, many accounts. I have at least 3 email accounts, accounts on the usual social networking sites, and a slew of random accounts for online stores and services. I figure that I have somewhere around 30 personal accounts that I’ve set up over the years. There are many others that I’ve lost track of, consigned to the briny depths of the web to be forever forgotten.

It’s time for a confession dear readers: I have committed a grievous evil. I have re-used passwords for multiple personal accounts with wild abandon. On top of that, before this article, I had not changed passwords on some accounts for years. What’s worse is I know better than this; I follow best practices for passwords in my professional life obsessively. Seriously, there was an intervention and everything. I guess it would be at this point where I’d say something about the cobbler’s son having no shoes.

This was pretty much the extent of my super sophisticated personal password scheme. Luckily, I kept the post-it note under my keyboard where no one would ever find it.

Continuing down this cliche’d path, I’ve heard that people don’t change until the pain of staying the same is greater than the pain of changing. For me, the pain came just a few days ago when I received an email from The email stated that they’d been compromised and that the attacker had gained access to their database of usernames and encrypted passwords.

I have an account on Had I used the same username and password on that I used on other sites? I couldn’t remember. *CRAP*! Time to put my big boy pants on and get this password mess sorted out.

First, I had to figure out what sites I had accounts on. I started a list of all of the sites I could immediately recall, then I went through my archived emails and found several more sites. I have A LOT of accounts.

Over the years I had halfheartedly skimmed many articles (like this one) that provided advice on proper account and password management. All these questions started popping into my brains: Should I set up a password manager? Which password manager should I use? How complex does my password need to be? How can I set up multi-factor authentication and how well does it work?

It was about this time that I started to become overwhelmed. I needed to do some reading. I researched and read way too many articles and blog posts and here is the strategy that I found would work for me. Others may not have the same security needs, so, as always keep in mind that YMMV.


I spent some time thinking about what my needs were and how I access my accounts. I use a variety of computers and devices. I have multiple beat up, old computers running Windows and Linux based OSes in varying stages of obsolescence, an iPhone, and a broken iPad which I may replace in the distant future. I access email and other accounts from my own, trusted systems and other’s that I don’t trust.

It would be nice to be able to access my various accounts easily and securely, regardless of the computer or device I am using. I need to be able to remember my passwords. At the very least, the passwords for my most important accounts – Email, banking, etc. need to be different from each other. Services like Linkedin, Dropbox, and Twitter get “hacked” with some regularity, so being able to easily come up with secure, memorable passwords without repeating old ones is a necessity too.

So this concludes the first part of my three-part password conundrum saga. Check back soon for part two where we dive into the tools, methods, and concepts behind building a solid account/password management strategy.