Review: I Will Teach You To Be Rich

A few years ago, I saw Ramit Sethi on The Daily Show promoting his book I Will Teach You To Be Rich. It sounded very helpful and like a book I should probably read. I filed it away on my Amazon Wishlist and forgot about it for a while. Since I recently got a job with actual income, I decided to buy the book and see what it was all about.

I Will Teach You To Be Rich by Ramit SethiI’ll start by saying that this book blew me away. Since I’m busy studying medicine, I had not put much effort into learning about finance. I am still pretty young (ahem!), and I thought the topic was too complicated and something I could put off worrying about until later. In essence, Sethi wrote this book for people like me. It’s meant for people in their 20’s, and he points out a number of ways that you’re an idiot if you put off starting to save until it’s too late. While I assumed that “starting early helps,” I had no idea how much. He demonstrates with a nice chart that a person who invests $100/month for only 10 years starting at age 25 will have a lot more money at retirement than a person who invests $100/month for 30 years starting at age 35. That’s right. You have to save for 3 times as long if you delay starting for 10 years, and you still end up with less money!

The book is broken down into a 6-week program. You’re given tasks to complete each week. Tasks cover budgeting; tackling credit card debt and improving your credit history; setting up a no-fee, high-interest savings account; opening a 401(k) and an IRA; and learning to invest appropriately.

Besides just giving plain, old “good advice,” there are a lot of reasons that this book succeeds. First, he addresses perfection. Most people know they should do this stuff but don’t want to get started because the topic is overwhelming and they’re afraid they’ll do something wrong. They say, “I don’t want to make a mistake. I’ll just worry about it later.” Sethi advocates the 85% approach, wherein doing something 85% right is still a lot better than doing nothing, which equates to 0%. When addressing your budget, he doesn’t advocate being an all-around cheap penny-pincher. He proposes “conscious spending.” After socking away an appropriate percentage of your paycheck to savings and paying your bills, he tells you to consciously spend what’s left on things you love and avoid spending on things you don’t. He provides an example of a friend who spends $21,000/year on going out to bars. Granted this friend has a 6-figure salary, but Sethi makes his point. As long as you’re putting enough into long-term and short-term savings, it doesn’t really matter what you spend the rest on. He also breaks down overwhelming topics into digestible chunks and gives you timed, task-oriented directions. Importantly, he tackles a lot of common misconceptions around finances. For example, investing is not about picking stocks! He demonstrates thorough evidence that, aside from a very elite few, no person is able to consistently predict the stock market. Instead of losing thousands of dollars per year on fees to investment companies, he shows you how to create a portfolio that will return 8% on your investments long-term. This has been the average return for the last 80 years on the stock market, and you won’t do any better unless your name is Warren Buffett.

The best part about Sethi’s program is that he advocates for minimal effort. The last thing I wanted to read was a book telling me how I need to spend hours a week pouring over my finances, checking stocks, and doing financial research. In fact, it’s just the opposite. He teaches you how to make things happen automatically, so that after working through his 6 week schedule, everything is done. You’re making money without even thinking about it, doing things that you actually like, such as being with friends and family. He teaches you how to automatically direct money from every paycheck into savings so that you don’t even miss it. He teaches you how to automate investing so that you only have to think about your investments for about an hour per year (if that!).

I can’t speak highly enough of this book, and I can’t wait to put the rest of it into action. I need actual income for parts of it :). I know I’m being weird, but I want to convince almost everyone I know to read it: Sadie, my sister, my cousins, my friends. While it’s geared towards young people, I think middle-aged people could get a lot of benefit from reading this book too, especially on understanding investing and changing investments as you get closer to retirement. I can’t recommend this book highly enough. Go out and buy a copy right now. Once you’re financially secure, you can start making decisions about life and your career based on what is in your best interest, not what will make you the most money to pay the bills. Define what “rich” means to you and make it happen!


Cellphone Economics Revisited: One Year In

Last year I devised a plan to save myself a ton of money by revising my cellphone service. I was paying $576 per year (including taxes) for a mediocre cell plan from AT&T. I’m happy to report that my plan has been a fantastic success. Using this plan, I managed to pay $188.56 (including taxes) for my phone service for the entire year. That includes $162.01 for 1500 prepaid cellphone minutes and $26.55 for a 1-year Skype subscription. The Skype subscription is really the key here. I made a 30 to 60-minute phone call on average of 4 nights/week, every week for a year, for $26 total. That’s pretty amazing. Otherwise, I would have been using about 720 minutes/month to talk to Sadie on my cell every night, in which case talking to her with a regular phone plan including “free” nights and weekends would have been cheaper.

With my heavy reliance on Skype, you’re probably wondering what the service is like. To be honest, it’s better than I expected. I very rarely had a dropped call, and for the most part the sound quality was quite clear. Sadie even told me that she was impressed with the call quality, saying it sounded just as good as if I were calling from a cell.

CC-NC-ND: Jason Nicholls

Were there any downsides to using Skype? Only a few minor ones, some of which I had predicted. Unless you sign up for a SkypeIn online number ($30/year), when you call someone who has Caller ID, your number shows up as something crazy (like 0001123456789), and it’s always different. This scared a lot people who weren’t used to it, since they had no idea who was calling. Sometimes my mom still screens my calls with the answering machine. I could have also gotten around this by buying some Skype Credit, which can be used to disguise Skype calls as ones coming from my cell number. I need the credit in order to send and receive a text message from Skype to my cell to verify the number. I would have done this long ago, but unfortunately the lowest amount of Credit you can buy is $10. I would have had $9.80 worth of Credit still sitting in my account. I decided to save my money and live with the inconvenience for the time being. I also had an issue with poor call quality using my Skype-to-Go calling card, but it significantly improved at some point last Fall.

As serendipity would have it, Google Voice also launched last year. I linked my new Google Voice number to my cell number so that I can give out my Google Voice number and it will ring my cell. Then, if I ever decide to buy a SkypeIn online number, I can tell Google Voice to ring my cell and my computer when someone is calling.

So what is my plan for the future? At least for the next year, I plan to keep doing what I’m doing. I may splurge and buy a SkypeIn number and hook it up to Google Voice. It would not only stop the Caller ID problem I mentioned, but it would also allow me to receive phone calls on my computer, which would be a big help. I would say that at least half of my cellphone minutes are used because someone is calling my phone, and I can’t answer it on Skype. The only thing keeping me from doing that right away is the rumor that Google Voice is soon going to become a desktop VOIP provider and thus a direct Skype competitor. If they can offer competitive rates to Skype, I may have little reason not to use them. Of course, Skype is likely announcing an open-source client, which would be fantastic. Then it will be a battle to see who provides the best quality service, the best price, and the best open-source/Linux compatible platform. It’s shaping up to be quite a year!

On a related note, LifeHacker picked up this topic today. As I posted in their comments: Every time that I have the urge to get a smart phone, I cringe at how much more it’ll cost me every year for features that I don’t even need, and I quickly remember why I don’t already have one 🙂

Medicine in an electronic age

The following is the fifth (and probably final) post in a series entitled, “Securing your Email.” I’ve spent the majority of the series talking about logistical things like why secure email is important and how to get started with public-key cryptography. If you look back at my first post, you’ll see that the reason I went out and learned all of this (and wrote about it ad nauseum) is because I feel like it’s an incredibly interesting and important topic where medicine meets technology.

Communication throughout the world is becoming more and more electronic, and things are changing rapidly. In the field of medicine five years ago, most institutions (including very large hospitals) were still using paper records. In fact, even today a number of institutions still do. Doctors communicated by telephones and pagers, and records from other facilities were carried in by hand or faxed. With the technological advances in the last 10 years, today a physician could easily be consulted halfway around the world with a simple email, and a copy of an X-ray or CT-scan could be sent electronically. These changes in the way health care is administered presents a new set of problems to the industry.

This electronic age spawned a strong concern about health care privacy in the United States, which was addressed by HIPAA. The health care industry spends an incredible amount of time and resources dedicated to preserving people’s privacy. They spend millions and millions of dollars on “enterprise level solutions” to make sure that they can work online safely. These are not always dollars well-spent, but that’s the topic for another day. Unfortunately these solutions end up restricting health care professionals in such a way as to reduce the utility of the system. As an example, I’m going to talk about email (as you might have guessed).

As I pointed out in my first post, I’ve been thinking about this for a while. How in the world can health care institutions, who are so concerned about privacy and protection of their patient’s data, not be doing more to provide secure email solutions? I think I’m in an appropriate position to answer that question. I’m part of a committee that has been charged with selecting a new email provider for the hospital. We’re currently looking into a number of different vendors, and a question that consistently comes up is about “email security.” We’ve got a number of people on our committee including people from IS, the legal department, and human resources staff as well as physicians, nurses and students. Their “email security” questions have the best intentions. They want to make sure that the solution we choose is going to keep our patients’ data safe.

At the same time, however, I feel like there is a knowledge gap as to what they know about email security. I feel like most (if not all) of the people involved just want someone to say “your email is super-duper secure with our system.” One vendor took it a step further and started talking specifics of cool stuff that their system can do to prevent, for example, someone from emailing Protected Healthcare Information, or PHI, to someone outside of Rush. The problem I (and some members of the legal department) have is that sometimes this information needs to be sent out, for example to a lawyer’s office. From a patient’s perspective, if I request that my physician contact me via email with my lab results as opposed to over the phone, should that be discouraged? But it is, and that’s because some of the people in the IS departments across the land realize how insecure email is. So we need to make it more secure, and in order to do that, we have to understand where its security flaws lie.

The problem is that most institutions don’t look at the problem like that. They don’t get an unbiased assessment of email security. Instead they get a vendor to sell them an “email security solution” in which the vendor defines what secure email is and how their solution fits the bill. I’m not saying that all companies are giving a false sense of security, but it’s definitely a concern. It’s exactly why you have to understand the problem before you go looking for an answer. Things would be significantly different if a group of people like the “free software community” assessed a health care institution’s email security needs. In fact, the purpose of my post is to propose the following: the health care community should embrace the free software community’s model of email security.

Health care institutions have all the right resources already in place. They simply need to implement it. It would be fairly easy the create a public key server for your health care institution. When Housestaff and Physicians begin their tenure, they could easily be required to create a key pair during new employee orientation. Key pairs could be distributed on cheap flash drives for safe keeping and stored on a private server for easy access while on campus. Alternatively, keys could be distributed on smart cards. Since an institution has verified who an employee is, their internal web-of-trust will form easily. As long as someone’s public key has been signed by the company’s IS department, it can be trusted. These key servers could be made to exchange keys with those of other institutions or even external key servers, such as one set up by the NIH or the Department of Health and Human Services. Physicians also often travel to conferences, and “key signing parties” or booths could be set up to create a more full-fledged web of trust.

Having public keys freely available would make it easy for physicians to communicate more securely with one another. They’d be able to trust an email from a colleague. Plus, they’d be able to encrypt emails and attachments containing PHI. Physicians would also be able to communicate with their patients via email more freely. Patients could be given instructions how to acquire the physician’s public key and how to use it. It would be even better to set up a way to simplify the process by just emailing the patient a link so that an encrypted email could be viewed directly on the institution’s website. They wouldn’t need to worry about having the proper GPG client software installed, since they’d just have to click a link and the web page would decrypt the email for them.

Unfortunately, there are many in the health care IS industry that would rather none of this communication go on via email. They are probably smart to have a firm stance that no PHI should be communicated via email at this point since their email system is probably very insecure. The problem with their plan is that both now and in the future PHI is being sent via email and it’s probably not going to stop unless some serious consequences are put into place at individual institutions.

I have to wonder though. If the email system was actually set up securely and properly, why couldn’t PHI be sent via email? Why shouldn’t I be able to request my test results in electronic format from my doctor? These aren’t questions that are going to be addressed by any single institution, unfortunately, and this presents a very big problem in the near future. A number of other industries are currently caught in a downward spiral because they chose not to adapt to the Internet era. Does a similar fate await a health care industry that wants to deny physicians and consumers access to the PHI electronically under the guise of HIPAA and “we know what’s best” for protecting patients rights? Doing so is just going to drive the process more underground, giving them less control over the situation in the future. They’d be better off embracing the idea now and preparing for the future of medicine in an electronic age.

Safety Dance

The following is the fourth post in a series entitled, “Securing your Email.” So far in this series, I’ve done a lot of talking about the theory of secure email and why you might want to make your email more secure. If you’re not familiar with these concepts, I strongly urge you to go back and read the rest of this series. In this post, I’m going to highlight how you can get started using public-key encryption today, using only free software.

Disclaimer: It’s important that you read this entire post before attempting anything. It is perfectly acceptable to create a “test” key using a fake name and email address. Just make sure you label it as “test” and that you delete it (or revoke it) when you’re done. Also, creating a key is (somewhat) serious business. Only create one if you plan on using it and keeping track of it.

Before we begin, we need to get a few terms out of the way. First, I’ve oversimplified one point up until now. I let the term “encryption key” have multiple meanings. An “encryption key” is actually an “encryption key pair.” Each pair consists of a “public key” and a “private key.” As you can probably guess, a “public key” is meant to be shared with anyone and everyone. For example, here’s mine. It is meant to be your public electronic identity. If anyone wants to check whether I truly wrote an email that I’ve digitally signed, they can use my public key to verify the authenticity of the message. A “private key” is never meant to leave your possession. Never, ever give someone access to your private key. It is the lifeline of your electronic identity. It’s used to digitally sign outgoing messages and to decrypt any private mail sent to you. Your private key is still passphrase-protected, so as long as you’ve chosen a strong passphrase, your key is relatively safe even in the wrong hands. This is why it’s important to use an extremely strong passphrase when creating your key: uppercase and lowercase letters, numbers, and symbols that is at least 8 characters long. It is almost certain that your passphrase will be the weakest link in the security of your key. Check out this article by Microsoft to learn more about creating a truly secure passphrase.

Let’s take a minute to understand how public and private keys work together. Basically, you are the only one who uses your private key, and everyone else uses your public key. For example if I want to digitally sign an email, my private key takes a snapshot of the outgoing email and attaches a small digital signature to the message (attachment: signature.asc). The signature is tied to the exact text of my email. If the contents of the message is altered en-route, it will not validate when it reaches the recipient. When you receive my email, FireGPG or Enigmail will see the signature.asc attachment and analyze it using my public key, which will be retrieved from the Internet if it’s not on your computer already. If my message has not been altered, the signature shows up as “valid.” No matter what, the message of the email will be visible, and if the recipient does not use any GPG-capable software, the email will look normal (except for a simple signature.asc file attached to it).

Encryption and decryption work differently. If I encrypt a message to you, I want you to be the only one able to read it. So, I encrypt the email using your public key. The text of the email is encoded, and the only way to read the original message is for you to decode it using your private key. Nobody else can read the message (unless they’ve somehow stolen your private key and cracked the passphrase). Not to get too technical, but you can actually use digital signatures and encryption at the same time. For example, I want to send you a message that is meant only for you (encryption), and I want you to verify that I actually sent it (digital signature).

Ok, enough talk. To get started creating your key pair, you’re going to need to install a piece of software called GNU Privacy Guard (GPG or GnuPG for short) on your computer. Somewhat confusingly, GPG is a free software implementation of the OpenPGP standard. PGP stands for “Pretty Good Privacy,” an ironic acronym considering that it’s extraordinarily secure. Windows users can download and install Gpg4Win, which should contain everything you need to get started, including the WinPT keyring manager. I’ll discuss more about what a “keyring manager” is in a moment. It looks like a new version of Gpg4Win is due out in a few weeks if you’d rather wait, but you shouldn’t need to. Mac OS X users can install MacGPG, which should likewise contain everything you need to get started. Linux users almost definitely have GPG installed on their system by default along with a keyring manager (like Seahorse for Gnome or KGpg for KDE).

GPG by itself uses a command-line interface. Since most users want a more robust interface, they install additional applications that harness the power of GPG and make it available via a more user-friendly point-and-click interface. The “keyring managers” that I mentioned earlier provide this interface. A keying manager is an application that keeps track of other people’s public keys so that you can verify their digital signatures and encrypt emails to them. They keep track of the trust level of these keys, and they can be used to sign someone’s public key if you want to confirm their identity. A keyring manager can also be used to generate a new key pair for yourself and keep key pairs in sync with the many online public keyservers in the world. As I mentioned in a previous post, if you want to use GPG to sign and encrypt emails, you need to use a browser extension or a desktop email client. Gpg4Win comes bundled with an extension for Microsoft Outlook. Enigmail is a fantastic extension for Mozilla Thunderbird that can serve as a keyring manager and desktop email interface for GPG. FireGPG is a great Firefox extension that can serve as a keyring manager and a GMail interface for GPG. As you can see, software developers, many of whom need to send secure emails every day, have developed a great set of tools that make getting started with secure email fairly easy.

Unfortunatley, I can’t ouline all the possible ways to use this software. I’m going to go through a few examples here and provide some links to relevant documentation. In general, to create a new key for yourself you need to enter your “key manager,” for example by going to “OpenPGP -> Key Management” in Thunderbird (with Enigmail installed) or “Tools -> FireGPG -> Key Manager” in Firefox (with FireGPG installed). Then you want to generate a new key pair by going to “Generate -> New Key Pair” in Enigmail or click “New Key” in FireGPG. If you’re using Gpg4Win without Enigmail or FireGPG, you can follow this guide (although it looks a little dated, and you may want to use the WinPT key manager over GPA). Make sure you enter your full name and the email address you plan on mailing from. The “comment” field can be left blank, unless you’re creating a “test” key. It’s up to you whether you want to give your key an expiration date. (Most people don’t.) If you’re feeling adventurous, check out the advanced options. While most key managers should use these advanced options by default, you want your key to have the following options: “Key size/length: 2048” and “Key Type: DSA & Elgamal.” It will probably take a minute or two to generate your key. Make sure to move your mouse around and do something like browse the Internet, which helps create a strong key. Once your key pair has been created, you’ll be able to add additional email addresses to it if you plan on using more than one.

If you are asked whether you’d like to create a back-up your of key pair and/or create a revocation certificate, do it. If you are not given the option to back up your key pair and you cannot figure out how with the software you’re using (either “back up” or “export” your public and private keys), you may need to use an alternative key manager or the gpg command line tool. For example, FireGPG does not allow you to export a private key (only a public key, which is not an adequate back up). If you are not given the option to create a revocation key/certificate and you cannot figure out how with the software you’re using, you should create one using an alternative key manager or the gpg command line tool. You should back up all three of these files (your public key, your private key, and your revocation certificate) on a USB flash drive, external hard drive, or blank CD and store it in a safe place. This is especially true if you created a key pair without an expiration date. This will be your fall-back so that your key is never completely unusable.

I should take a minute to explain the revocation key (or revocation certificate). It can be used to “revoke” your key pair if it is ever lost or stolen. It will be used to notify public key servers that your key is no longer valid, and it will tell your friends and colleagues to no longer use this key. This is obviously something you want to keep private as well, since someone could easily revoke your key if they got ahold of it.

Now that you’ve hopefully got a functional key pair created, you’ll want to take some steps to enter into a web-of-trust. First, you have to publish your key to one (or many) of the free pgp/gpg key servers. There are likely a few built in to your key manager, like hkp:// and hkp:// You can also manually upload your public key to the PGP Global Directory (make sure it’s not your private key!). Now your friends and colleagues can use these key servers to keep track of your public key.

To get your own web-of-trust started among your friends and colleagues, you will need to exchange two numbers with them (usually in person). Your “Key ID” should be fairly apparent in your key manager. Mine is D4188BF6. Your “Key Fingerprint” should also be available through your key manager, but you may need to do a little bit of digging into the key via “Properties.” Mine is C14A 6784 162F 9C42 E404 D37F E5B6 FD50 D418 8BF6. You might notice that the last 8 digits of my key fingerprint match my key ID. These numbers will allow you to positively identify my correct key on a public key server. Thus, you can be sure that if I gave you that key fingerprint, I am in possession of the corresponding private key. If you can positively identify me, you should sign my public key and synchronize that signed key to the key server. Once I do the same for you and more of our friends and colleagues do the same, a web-of-trust will begin to form. Using this, I can reasonably trust people that I’ve never met if their keys are signed by my trusted friends and colleagues.

I realize there was a lot of terminology thrown around in this post that you probably weren’t familiar with. I apologize for that. I also apologize for not giving step-by-step instructions for individual key managers and software. I thought it would be better if I gave more general instructions that should be applicable to any key manager. There should be guides, documentation and forums available to give specifics for most of the popular key managers. If you’re having trouble with that (or anything in this entire series), leave me a note and I’ll see if I can clarify things for you or point you toward an answer.

I’m basically done with “new educational material” for this series. In my final post, I’m going to outline some ways that the medical community could use the tools described here to change the means of communication between health care providers. Since that was my original intent of this series, I hope you’ll tune in for the final installment. It may have a lot of “what ifs,” but it should be interesting to think about.

Who do you trust?

The following is the third post in a series entitled, “Securing your Email.” If you’re just tuning in and you’re not very familiar with words like “digital signature” and “public-key cryptography,” you may want to take a few minutes to read the first two posts in this series.

After reading my earlier posts, hopefully you’ve gotten a better understanding of what digital signatures and encrypted emails are and why they can be necessary. Before getting into the technical details of how to obtain or create an encryption key, you should gain a better understanding of how keys are authenticated. After all, this entire process is about learning to trust a system more than a plain old email. So why should you trust an email with a digital signature more than a normal email? How do you know whether that digital signature is even valid? Your recipients need a way to verify that your digital signature actually belongs to you. There are two competing theories (or “schemes”) about how this should be done, each with advantages and disadvantages. Both involve “verifying” that the identity of someone’s key matches their true identity in real life. A key is considered “verified” when a person or company signs the key. By signing a key, the signer is asserting two things: the person is who they say they are and their identity matches their key.

In the public key infrastructure (PKI) scheme, a certificate authority is responsible for this verification. You’ve probably heard of Verisign, the most popular certificate authority. Certificate authorities are companies who take responsibility for verifying that your key matches your identity (as determined by a driver’s license or passport) in exchange for a fee. For example, an individual “Digital ID” from Verisign costs $20/year. Thus, for a fairly nominal fee you get a verified encryption key that can be used to digitally sign or even encrypt emails. In order to do this, you’ll need to use a desktop email client, such as Microsoft Outlook Express or Mozilla Thunderbird, or you’ll need to use a browser-based plug-in for web email, such as the GMail S/MIME extension for Firefox. It’s important to realize that your recipients also need to use one of these applications to be able to check your digital signature or decrypt your email messages.

While the PKI scheme costs an annual fee, nearly all of the work and upkeep is done by the certificate authority. The user simply has to purchase the key and start using it. Cost aside, however, many people in the computer industry do not trust keys that are signed by certificate authorities simply because the companies can be easily subverted. In other words, they do not trust that the certificate authorities are doing their jobs thoroughly. People claim that for your $20, you can get a certificate identifying you as basically whomever you want. If true, this destroys the integrity of the entire system. Once they have your $20, does the company have a significant interest in whether you actually are who you say you are? You also have to wonder how much you can trust a lesser known certificate authority. For example, if you got a message from Joe, whose key was verified by Jimbo’s Certificates, would you be more likely to trust Joe’s signature? Less likely? Also, what happens if a certificate authority goes bankrupt?

As an alternative to PKI, the web-of-trust (WOT) scheme is used. Instead of a central company (or set of companies) in charge of certifying people’s identities, groups of users validate each other’s identity. You first need to create an encryption key on your computer, which I will cover in my next post. Your key will have a “digital ID number.” You then need to meet in person and exchange “digital ID numbers” with your friends and colleagues. Once you’re back at a computer, if you’re satisfied with someone’s identity you can use this number to locate their key on the web and sign it. You’re essentially saying, “I met this person, and I can confirm their identity and that this is their true key.”

Using this scheme reduces cost (it’s free), and thus eliminates the bias of companies that are more concerned with profit than actual validity. Plus, multiple validations for a given key should greatly increase your ability to trust it. If 15 of your close friends have verified Joe’s key, would you be more likely to trust Joe’s signature or less likely? A disadvantage of the WOT scheme is that without a backing company, it is usually a lot more work for the individuals. You can’t just pay someone $20/year to take care of it for you. It also usually involves meeting face-to-face with people in order to verify their identity or have them verify yours, which can be difficult for some people depending on where they live. Fortunately, with the advent of free software tools like key servers, it is really easy to assess the trust level of a person’s key.

As with PKI, you need software tools to be able to digitally sign or encrypt an email. You’ll also need this software to be able to verify someone’s signature and decrypt an email. Some examples of these tools are the Enigmail plug-in for Mozilla Thunderbird or the FireGPG Firefox extension for GMail. I will go through how to use these two applications in more detail in my next post.

Now that you’ve got a good background on how key validation works, you’re ready to get started with your own key. If you’d like to purchase a key from a certificate authority, go for it. Unfortunately, I can’t describe how to use it in detail since I’ve never purchased one, but some of the information I’ll provide may still be helpful. In my next post in this series, I’ll show you how to use free software to create your own encryption key right on your computer for free. I’ll also discuss how to use it and how to get started in the web-of-trust.

Fixing the Holes

The following is the second post in a series entitled, “Securing your Email.” Throughout the post, I am going to be referencing an analogy about mailing a letter that I described in the first post of the series. If you’re not familiar with it, you may want to take a minute to read it. I’ll wait…

There are a number of ways you can make email a more secure form of communication. One of the easiest ways to start patching holes in your current system is to look for major lapses in security and take care of those first. In my analogy, multiple security threats could be effectively eliminated by handing your postcard directly to the mail carrier and having your boss’ mail carrier hand it directly to him or her. That way, the postcard is never left sitting in an insecure location. There’s no chance for a random person walking down the street to read, copy, or change your message. If you really trust your postal workers and your message doesn’t contain too much sensitive information, this may be all the protection you need.

The equivalent in the email world is making sure you do all of your communication to and from your email provider over a secure connection. This is actually really easy to do, as long as your email provider supports it. Since GMail is fairly ubiquitous these days, I’ll use them as an example.

You want to make sure you’re viewing, sending, and receiving email over a secure connection. If you’re using a web browser to access GMail, you just need to make sure you log in using (note the https). GMail also intelligently offers an option to “Always connect using https,” which makes sure you never forget and leave a postcard sitting out by the curb. I highly recommend enabling that option if you haven’t already. If you’re using a desktop mail client like Outlook or Thunderbird to access your email, make sure you specify a TLS or SSL connection when you’re setting up your account. By making sure the connection to and from your email service is secure, you’ve eliminated a major lapse in email security. Since many email services offer (or even require) it, it’s a good idea to get into the habit of verifying that you’re communicating over a secure connection whenever you check your email. It’s also imperative that you’re using a secure connection if you’re emailing on public networks, especially insecure wireless networks.

But what if your email service doesn’t offer secure connections? Or what if that’s not enough? Personally, I don’t think it is! If you look back to my analogy, you’ll see that there are still a number of prominent security threats. For example, what if some nefarious character at the post office tampers with your message?

The best way to deal with the remaining threats is using public-key cryptography. This is a fairly complicated topic, and I’ll only be scratching the surface of it in my posts. For now, let’s say that all you need is a file on your computer called an encryption key. In future posts, I’ll briefly cover how to obtain and use an encryption key and some of the basic theory behind public-key cryptography. For now, let’s understand some of problems that public-key cryptography aims to solve.

Flickr: Zappowbang's "Seal"

Flickr: Zappowbang's Seal (CC-BY)

In my analogy, I pointed out that upon receiving your message, your boss has no way to verify whether you were the original author. In the real world, a person uses their written signature to symbolize a document’s authenticity. Unfortunately, forged signatures are sometimes difficult to spot, except by experts. To provide an extra layer of verification, important documents that have been authenticated usually bear a seal. In the old days, many important people sealed their letters using some wax that they would impress with a unique design. This ensured the recipient that a document had not been tampered with en-route. Today, an official document whose signature was verified by a notary public also bears a seal. A digital signature is similar to a seal. It asserts that all (or part) of an electronic document was verified by the signer and that it has not been tampered with en-route. Since the documents are electronic, this makes a digital signature much more portable than a paper document bearing a seal. Unlike a wax-sealed message, digital signatures do not prevent anyone who comes across the message from reading or copying it. It is simply a indicator of the author’s authenticity.

Flickr: timg_vancouver's Engima Machine (CC-BY-SA)

Flickr: timg_vancouver's Engima Machine (CC-BY-SA)

If you need to send a message that contains extremely private information, which no one but the intended recipient must see, the message needs to be encrypted. As you can probably guess, this is means that even if someone were to examine the message text, they would not be able to read it. For example, the Enigma machine was used by the Germans in World War II to encrypt messages between their armies. An encrypted message contains a long string of seemingly random letters and numbers that have been disguised using a code. Messages are encoded so that only a person who has the proper key can unlock the code and reveal the original message. This is starting to sound a bit like a Dan Brown novel, isn’t it? Aside from that, encryption is kind of boring. It does its job really well, and as long as you pick an adequate passphrase for your encryption key, your information is fairly secure. Just make sure the Allies don’t capture your Enigma machine, or you might be sunk. 🙂

My purpose here is not to convince everyone to start using public-key cryptography to digitally sign or encrypt all of their emails. My purpose is to help you understand how insecure your email is and why this extra security is used and ultimately necessary in a lot of situations. Many of us have come to rely heavily on email as form of communication. If you are one of those people, it may be time to reconsider how much trust you place in that system. The methods that I described in this post should help restore most of the trust you may have taken for granted in the past. Still, if I can get a handful of you to start digitally signing your emails when I’m through, I will consider that a victory.

Now that I spent almost this entire post talking about strange things like digital signatures and encryption keys, you might be fairly confused. Before things get any more technical, I wanted to help you understand why we use these things and how they work on a basic level. In my next installment in this series, I’ll discuss some of the theory behind public-key cryptography and how it’s used to create an extra layer of security on top of email by establishing your true electronic identity. In the future, I’ll also cover how to obtain or create an encryption key and how to use it. Then you’ll truly be on the road to secure messaging!

Please, Mr. Postman

One of my friends has the following “signature” attached to all his outgoing emails:

The materials in this message are private and may contain Protected Healthcare Information. If you are not the intended recipient, be advised that any unauthorized use, disclosure, copying or the taking of any action in reliance on the contents of this information is strictly prohibited. If you have received this email in error, please immediately notify the sender via telephone or return mail.

I’ve seen messages like this many, many times, and I feel like they really highlight a major problem with email. This message is like someone putting a sign outside of a window that says “Warning: You are not allowed to look in this window, and if you do, forget what you see immediately.” Does that message do any good at all? It almost makes you want to look in the window more, doesn’t it?

The following is the first post in a series entitled, “Securing your Email.” I’ll start the series by highlighting the dangers of insecure email and why this topic is important. Once I’ve got you convinced that every email you’ve ever read is a fraud, I’ll use the rest of the series to outline many different options you have to address the problems.

In case you are unaware, email is an inherently insecure form of communication. If you don’t know a lot about how web servers and the Internet work, that might not be terribly intuitive, so let’s start off with a pretty good analogy. Let’s pretend there’s no such thing as email. You work from home, and you need to send your boss a fairly important message with some sensitive information in it. It’s brief, so you just grab a pencil and jot your thoughts down on the back of a postcard and stick it out in your mailbox by the curb for the postal carrier to pick up. Pretty soon afterwards the message gets picked up, and it makes its way through various post offices and into your boss’s mailbox a while later.

Ignoring how slow things went, that still probably sounds like a pretty dumb way to send an important message. Unfortunately, it’s a pretty good description of how email works. To get a better picture of why it’s dumb, let’s examine some of the security flaws present in a system like the one described above. First, you left the message in your mailbox unattended. Anyone walking down the street could just open up the box and read what you wrote. Considering the message contains sensitive information, you probably don’t want just anyone to read it. More importantly, if the person had a pencil they could easily erase what you wrote and replace it with something else.

You also place an inherent trust in the postal system. If the message you’re sending truly contains sensitive information, you need to have it available in a form that only the intended recipient can read. Then, even if someone steals your letter, at least you won’t have to worry about private information getting out.

Finally, once your boss receives the message, there is no way for him or her to verify that you actually wrote it. Did the person who opened your mailbox change what you wrote? Did someone from a competing company send your boss false information under your name? The information is highly suspect unless your boss can verify that you were the original author and that the message hasn’t been altered since you sent it.

If you’ve made it this far, you may be asking yourself whether any of this is even relevant to you. Maybe you don’t make it a habit of emailing people sensitive information, but I would bet that you’re mistaken. A lot of seemingly harmless information in the wrong hands could be used to do a lot of damage. Plus,what if a criminal tried to impersonate you for their own gain? Don’t your friends and colleagues deserve to know that you actually wrote the words they’re reading? The same applies to emails you receive from your friends and colleagues. Maybe you don’t think that anyone would ever waste their time reading, copying or altering your private emails. There are a lot of good reasons why criminals would want to do this, however. The most obvious would be to make money at your expense. Plus, some of these security flaws could be used to get you into a lot of trouble at work. Is that something you want to risk?

The rest of the posts in this series will outline both simple and more complicated steps you can take to secure your email. Since my original reason for these posts was to address email security for health care providers, I’ll include a post that demonstrates how the health care community could begin implementing more secure email today. Hopefully this analogy has taught you something about the emails you read every day. Check out the rest of the entries in the days to come, and leave comments if you have questions or think I’m wrong about something!

Windows 7: Netbook killer

The following is a prediction of things to come in the next year.

I get the feeling that Microsoft is trying to kill the netbook market with Windows 7. In case you haven’t heard, Microsoft announced a new edition of Windows 7: Starter Edition. The Starter Edition is only capable of running 3 applications at once. Their purpose for this “Starter Edition” is two-fold. First, it is meant to be a sufficiently crippled version of Windows 7 so that they can sell it dirt cheap for use in netbooks. Many people will not buy it because it can only run 3 programs at a time. (Update: MS changed their minds on this after significant blacklash from the community, but Starter continues to have other strict limitations) They’ll pay a significant premium to buy a netbook containing a “normal” version of Windows 7 (Basic or Home) because it will be Microsoft’s flagship operating system. That’s different from today’s market. Microsoft can afford to give away Windows XP for dirt cheap on current iterations of netbooks because it’s already really old, and they’re busy trying to sell Vista. Buying a netbook with Windows 7 Basic or Home will increase the total cost so much that the devices will no longer be “worth it” to people unless they really want that small form-factor ultra-ultra-portable.

Second, most of the people silly enough to purchase the Starter Edition will find it so incredibly annoying to use that they will either have to pay to upgrade to a non-crippled version of Windows (again significantly increasing overall cost of the device) or they will discount their netbook as “a toy” of little value. This attempt by Microsoft to upsell the netbook market is probably going to kill it. Any way you slice it, Microsoft-based consumer interest in the market will wane.

Then, of course, we have Linux-based netbooks. By October, Ubuntu 9.10 will be available. It will likely boot on your netbook in 15 seconds or less if it has an SSD. It will come fully featured with an office suite, IM client, email client, web browser, media player, image editor, and much, much more. Oh, and you’ll be able to run every single application at once if you want to. Graphics will be performing fantastically, and the user interface will be strikingly refreshing. And of course you’ll get all of this for the low, low price of $0. Let’s just hope that Canonical can get it installed on a number of prominent netbooks whose manufacturers won’t hide it behind a curtain so that consumers will realize that they’re no longer subject to Microsoft’s crippleware. They can have an extraordinarily functional, free system on any machine they want. Ubuntu needs to capitalize on Microsoft’s idiotic move here, and I think they will.

Breathing Life Into An Old Machine

Sadie’s family has an old Gateway desktop in their basement. Up until last Spring, it was the only computer their family had besides Sadie’s college laptop, which was starting to show its age. The desktop was probably purchased before the turn of the century, and it came with the lovely Windows ME operating system. By most accounts, Windows ME was an incredibly botched product that was introduced after the more stable Windows 98 and before Windows XP (2001).

Despite her uncle having reformatted it and fixed it up a few years ago, the computer was in pretty dire circumstances. When it actually booted successfully, the boot process would take over 2 and a half minutes to get to a working desktop. You’d get a BSOD every time you shut down, and the thing generally ran as slow as molasses.

Her dad had mentioned wanting to learn to type, but he didn’t want to risk messing up their new laptop. I thought this would be a perfect job for their old desktop, but I had trouble deciding how to set things up. Things obviously couldn’t stay in their current state. I could get them a copy of Windows XP to put on it, but the machine only had 128 MB of RAM and either a Pentium II or III processor. This also ruled out putting Ubuntu on it, since I doubt that would run any faster or better than Windows ME or XP. I needed something extraordinarily lightweight. As long as it was capable of the basics, we’d be good to go. I even knew of a decent free Linux typing program, Klavaro Touch Typing Tutor.

I had heard of Puppy Linux at various websites around the Internet. I never knew much about it besides that people often mentioned Puppy as a good, lightweight Linux distro. I decided to investigate further only to find that it was exactly what I was looking for. In fact, it’s so lightweight that you can run it completely from RAM if you have more than 256 MB installed, making things incredibly snappy. I downloaded the latest Puppy Linux iso, and burned a copy. I booted from the CD, and after answering a few questions, I was taken to a nice linux desktop. Once I had assured myself that everything was working correctly, I went ahead and installed Puppy, erasing Windows. Puppy’s install wasn’t quite as user-friendly as Ubuntu’s, but I was able to install it without any problems. Linux novices might prefer a more helpful install process. Luckily, there is a decent online manual that should help with pretty much everything.

The real test came when the installation was finished: boot time. Puppy Linux cold-booted in less than 30 seconds on this machine. That was incredible! The desktop is fully functional. It contains a web browser (SeaMonkey), desktop email client (SeaMonkey Mail), word processor (Abiword), spreadsheet editor (Gnumeric), and a lot of other basic applitions pre-installed. They do have a repository for additional applications, but one frustrating thing is that Puppy Linux uses its own package type, the PETget. Using your own package type means that there’s going to be less software available for your system. Fortunately, it looks like there is a compatibility library so that Debian packages can also be installed, which means you can get pretty much any application on Puppy. I was lucky enough to come across someone who had made a PETget for Klavaro, so installing that was a piece of cake.

Puppy Linux uses the JWM window manager, which I had never used before. It’s popular in distros like Puppy because it’s so lightweight and very customizable. I’ll admit that JWM is not much to look at, but it does its job and uses very few resources. The panel along the bottom of the screen has a “(Puppy) Menu” button at the left, a list of windows and virtual desktops in the middle, and a system tray and RAM usage graph on the right. Puppy also comes with many icons on the desktop for popular applications. A nice feature of JWM is that the “Main Menu” (“Puppy Menu”) is actually available from anywhere on the desktop just by right-clicking. One thing that threw me off is that JWM defaults to a single-click destop interface, which was very disorienting for me. I was able to change it to double-click without much trouble.

I will say that the default look of the desktop on Puppy leaves something to be desired. I’m not talking about the window manager either. While it’s nice to have some icons on the desktop, Puppy goes a bit overboard. Plus, some of their descriptions of the applications are not entirely intuitive. Since when is “browse” a good title for your Internet browser icon? There is also a rather stark mountain lake scene as the default wallpaper, which I found terribly distracting.

Puppy Linux 4.1.2 after I fixed it up a bit

Puppy Linux 4.1.2 after I fixed it up a bit

Since Sadie’s dad isn’t exactly comfortable with computers, I wanted to make things as easy to use as possible. I cleared off most of the unnecessary icons and only left ones that he’d possibly use. I also made sure they had proper descriptions, like “Internet.” Even navigating the “Puppy Menu” would probably be too much for him. I really wanted to fix things so he’d be able to do everything right from the desktop icons. After organizing and cleaning up the icons and giving the desktop a new wallpaper, things started to look much better. I even looked up how to write a quick “shutdown script” so that I could put a “Shutdown” icon on the desktop. This actually took the most work of anything because I kept doing it wrong, and it would freeze the computer. All-in-all though, I think it turned out very nice.

This just demonstrates one of the great powers of Linux on the desktop. You can use it on everything, from powerful servers and supercomputers to hardware that’s close to 10 years old. You can use it breathe life back into a machine that you stopped using long ago because it wouldn’t work with the next version of Windows. Plus, it’s free! Do you have an old machine lying around that you could use for something? If it’s somewhat modern hardware, try Ubuntu. It’s the best Linux distro out there. If it’s older hardware, I can now recommend Puppy Linux as long as you’re somewhat familiar with Linux. Either way, why not give Linux a try on it, and let that hardware achieve its full potential!

Cellphone Economics

I’m relatively new to Skype. I’ve known about it for quite some time, but never really used it until recently. Sadie moved into a dorm at school for a few months to save herself the headache of driving 2 hours in the snow every day. Since she would get lonely by herself sometimes, we started finally using the video camera set we bought a few months back on a regular basis. We had tried it originally in Ekiga, a FOSS video conferencing application. Things were kind of buggy, but looking back, I think it’s because we were both trying to send video over Wifi connections, which also fails a lot on Skype. Regardless, we decided to try out Skype, and it works pretty well. They even have a Linux client available, although it’s 2 entire versions behind the latest Windows client (2.0 vs 4.0). In the end, Skype offers a pretty good service. I think the newest Ekiga would be just as good, if not better, but Skype is what we’re using for now.

If you’ve talked with me about cell phones recently, you know I’ve been pretty torn. I’m not very happy with my current plan (AT&T), which runs me $48-50 a month after taxes, and all I get is mediocre reception phone service. No texting. No Internet. I’m torn between wanting to embrace my inner geek and buy one of the new-fangled smartphones like the T-mobile G1 or iPhone and wanting to save myself a big expense that I don’t really need. The problem is that they each have a mandatory data plan that costs an extra $25-30 a month. We’d be talking $80 a month (minimum) for a cell phone, and that doesn’t even include text messaging. On the flip side, I like how inexpensive Sadie’s prepaid phone from T-mobile is. She pays $100 for 1000 minutes, which don’t expire for a year. I thought about just getting one, but since my cell is my only phone, those minutes would go awfully fast. We usually talk on the phone 30-60 minutes a day.

Also, I’m much more keen on the idea of spending my $200-300 on a netbook instead of a smartphone to use in my hospital clerkships next year simply because I won’t have to pay $30/month for data. Both my apartment and the hospital (and a lot of other places) have Wifi available. It may seem like I’m just being cheap or trying to save money. While that’s partially true, the bigger reason that I’d rather get a netbook is that I don’t feel like the current smartphone plans offer particularly good value for their money. I’d be much more willing to pay the $80/month if I was getting an exceptional service. Unfortunately despite the “awesomeness” of 3G, the Internet connection is still pretty slow. I already feel like my cell phone plan is not worth the money, so adding $30 a month for a crappy Internet connection that I’ll probably only use occasionally just exacerbates the problem.

Once we started using Skype, I considered getting a prepaid phone and just using Skype-to-Skype voice-chat with Sadie every night, but she doesn’t normally like to be tied to her computer while we talk. I had heard that Skype offered the ability to call landline phones for a fee, but I assumed it would end up costing just as much as my cell. Well, you know what they say about assumptions, right? I was talking with my friend Jimmy the other day, and it turns out that a Skype subscription only costs $30/year for “unlimited”1 calling! Jimmy even connects his bluetooth headset to his laptop, making it very similar to a phone. For an additional $30/year, you can purchase an “online number”, which is a regular phone number that will ring on your computer when people call it. I’m not sure I’d need this, but it’s a good option to have.

This made me start crunching some numbers, and here’s what I came up with. My current cell plan gives me 400 daytime minutes and unlimited nights/weekends for ~$48/month (probably an underestimate). That comes out to $576/year. Ouch! If I were to buy a prepaid phone ($30) with two 1000 minute refills ($200) and a Skype subscription ($30) with an online number ($30) it would cost me $290/year. That’s half the price. It also assumes that I burn through 2000 minutes on my cell and that I buy the online number, neither of which I think will happen. Subtracting those things would make my total $160/year!

Of course, there are some disadvantages to Skype. I can’t use it without an Internet connection. I could use it without a computer by purchasing a Skype phone ($65), which is a definite plus for my apartment. That said, I can’t use it like a cell phone, so if I’m away from my apartment, I’ll have to rely on my prepaid cellphone, landlines, or someone else’s wireless and my laptop with Skype. Like I said, I will probably be getting a netbook soon, which should ease some of the portability issues. Also, if my mother ever gets the Internet at her house, there will be very few places I go without an Internet connection. (Update: It turns out, with a Skype subscription, you also get a free “Skype To Go” number, which is a local number that works like a calling card but uses your “unlimited” Skype minutes. Awesome!)

There are also some advantages to this plan. Obviously, it’s much cheaper than my current situation. Since I’m no longer under contract with AT&T, it won’t cost me anything to cancel my cell phone, and I can transfer my number to the prepaid phone. (I only wish I could transfer my actual phone, since I really like my W810i.) I dig the ultra-portability of a netbook compared to a laptop, and I can use Skype on a netbook anywhere with Wifi, which is nearly everywhere these days. Not to mention, with an actual computer I’ll have applications at my disposal not available on a smartphone. I will still have a cell phone for when I’m traveling. Plus, if I decide to purchase a Skype phone and an online number, it will be just like I’ve got a landline phone in my apartment without that $35/month fee.

Of course, I’m also looking into other MIDs that aren’t phones. I’ve thought about the iPod Touch, which Usama got for similar reasons. The nice thing about the iTouch is that you get access to most of the fun apps from the App Store and the sleek design. There are 2 major downsides I see to it (personally). First, I want something with a physical keyboard. Since I’m going to have it with me in the hospital next year, I plan on using it for some actual hardcore typing. The touchscreen keyboard on the iTouch works really well, but it’s not practical for extended typing. This is also why I’m being picky about the keyboard on netbooks. Secondly, the iTouch only works with iTunes. There are currently people hacking solutions together to get it to work with Linux, but if Apple doesn’t want my business, I see no point in giving it to them.

I’ve got a big decision to make over Spring Break, but it seems like I’ve already kind of made it. I’ll probably be making the Skype/cell phone switch. I won’t be buying a netbook until June or July. There’s no hurry for me to get one, and newer models might bring a killer new feature. Plus, I’m hoping that good netbook deals will start popping up in the next few months.

If you’ve read this far, I’ve got a couple of questions for you. Do you think your wireless bill is too high? Are you satisfied with the service and features that you get for the price? If you have a smartphone, do you think the applications and constant Internet connection is worth the fee for the data plan? Any thoughts on my post? I feel like more people probably could be taking this route, so I’m curious as to why people haven’t. Or am I the only one who feels like my cell phone plan is overpriced for what I get?

1 – Unlimited = 10,000 minutes/month or 6 hours/day