International Travel Mistakes I Must Never Make Again

I screwed up big time with my travel this christmas. With the Ontario snowstorm, a whole lot of people had it worse, and the good news is that I got to each of my destinations (my parent's house in Canada, and my home in the USA) within 12 hours of my target arrival time. But I missed connections and had to stay overnight in an airport hotel both ways, went through security 6 times and customs 4 times, and both ways my body experienced more stress than it ever has since my thesis defence.

What really stings is that these were all avoidable mistakes, some of them even mistakes that I've made before. I must not make them again.

I planned my departures for later in the day than they needed to be.
I had a 3 pm departure for my long day of westbound travel, which I was pleased about because it seemed nice and relaxed. But that meant that there was no wiggle room for missing flights, which can cascade, and in fact I missed the last flight to my final destination. Then I did the same thing with leaving at 10 am eastbound. Early morning travel to airports suck, but it provides a margin of error. I would even consider red eye flights now, since they have the whole day for delays.

I had more connections than were absolutely necessary.
Every connection you make increases the misery and risk exponentially. I would now pay hundreds more dollars to avoid what I went through happening again.

I connected through snowy places when I didn't have to.
 Does everyone else but me know this tip? In any case this happened to me 3 or 4 years ago with Calgary - why didn't I learn my lesson back then! Thank god I didn't connect through Toronto this year anyway.

I connected through Montreal Airport.
This is only two experiences to go by, but it's enough for me to want to avoid the Montreal airport from now on. Both times that was where I missed my critical connection, and both times I and fellow passengers were given misinformation that resulted in suffering, respectively: 1) standing in a line for 2 hours and 20 minutes, and 2) sprinting for 15 minutes with my carry-on. Both unnecessary, and the latter especially brutal considering a 76 year old priest was given the same advice. A staff member also screwed up my electronic ticket, in a way that caused a delay at my next connection and could have screwed up my return voyage too if the counter person hadn't caught it. Finally, the Montreal airport is the only place I've heard airport staff joke around at the expense of passenger misfortune, and that happened once each way.

I checked baggage for international travel.
If you have a checked bag, when you travel between the US and Canada (and some other types of international travel) you often have to pick up your baggage at the carousel and put it through security. I had a lot of presents to bring there and back, so it would have required some ingenuity to do without checked luggage, but I know for a fact that I would not have missed my connections both ways if it wasn't for the bag. I am definitely buying one of those wheeled maximum-allowed-size carry-on bags, a la George Clooney.

Given that I checked baggage, I made the connections too tight.
Since I'm my own travel agent (and doing a poor job of it), I have the power to decide how much time to leave for my connection. If I have to check luggage, I will leave no less than 90 minutes, ideally 2 hours, on the international leg. Remember that you will also need to go through security again, and potentially also customs.

I gave up on connections before I should have.
After I got my baggage, I saw that it was already the departure time for my flight. However, while I waited in the endless line to rebook my ticket, I noticed that the airplane was delayed 20 minutes, then another 20 minutes. From now on I'm going to proceed directly to the gate no matter what the time says, and only accept that I've missed it from the people at the gate.

I didn't talk to airport staff as much as I should have.
On at least one occasion I was reluctant to get the attention of a harried airport employee, and ended up doing the wrong thing. Ask them questions, early and often - some of them don't know what they're talking about, so you have to double and triple check.

I didn't use a checklist to pack.
I can't believe it, but I forgot to pack the one item besides my passport that I absolutely needed: my work visa. In the weeks before my flight, I remembered to buy presents for all my roommates, and christmas cards for my work mates, but I didn't remember that! If you want to know what happens when you are forced to go through customs with only a printed facsimile of your DS-2019 (because the US postal service lost the international overnight package with the real thing), I will tell you. First of all, as I suspected, it is entirely random and based on the whim of the particular customs official. I know this because I went through US customs at the same airport (the Montreal airport) twice, twelve hours apart. So here are two things that can happen:

1. The customs official talks to his boss for 30 seconds and then lets you through with a warning.
2. Your passport and boarding passes are taken away and, without explanation, you are taken to a different area, where you wait for 40 minutes. When you get to see a Department of Homeland Security officer, she threatens you with a $325 fine, disbelieves that the US postal service could have failed, and tells you, "if you're such a smart guy, how could this happen? You are not taking these documents seriously." Once you have grovelled for a sufficiently long time, you are let through (without the fine).

I'm sure there are much worse possibilities. It's all a roll of the dice. So I will use a checklist, that I store between trips and customize for each trip. I will physically check off each item, even if it seems unnecessary. I'm starting my checklist with the things I actually have forgotten on trips, much to my dismay: Visa, underwear, phone charger, swimsuit.

I didn't keep every piece of travel documentation.
I threw out a used boarding pass and my luggage tag, thinking they would only get in the way. However in the nonsense that followed, it turned out they would both have slightly smoothed the way. It's important to keep them organized, but hang on to everything until the journey is done.

Lessons I already knew (because of past screwups):

• Don't plan multi-airline trips - way too risky. This way Air Canada had responsibility for rebooking my flights and putting me up when I missed my connections.
• If you are late for a flight, talk to someone about shortcutting the security line.
• Holiday travel just sucks. Chill as much as you can, and don't depend on arriving at a certain time.
• Cling to your passport and boarding pass with all your might. I once dropped mine on the causeway of Lester B Pearson airport and was only saved by another passenger happening across it.

My experience this time is enough to almost make me want to go back to travel agents (if they still exist). Once I travelled to a conference instead of a professor and got to use his travel agent, and it was amazing. Not only were all the flights easy and comfortable, she figured out how I could get two nights in Amsterdam with no extra trouble, and all for a $60 fee. Even if I don't try that, I now have a huge respect for travel knowledge - it's easy to book your flights online, but booking them so that it isn't an ordeal is a trick. I paid for this knowledge, and I'm going to hang onto it.

Some Etiquette Tips (Mostly in the Form of What Not to Say)

I think a lot about social gracefulness, and how to be pleasant to hang
out with. To that end I think etiquette is very important, in a broad
sense of taking the perspective of the person you're talking to, and
trying to not do things that they would find annoying or tiresome
(unless you have a good reason). So I maintain a list of tips for
casually interacting with people, mostly as a reminder for myself. I
don't like that almost all of these are negative, what not to do, but it
doesn't take a lot of effort to avoid them, and you can get a long way
just by doing that. Very many of the tips boil down to not saying to
someone the dumb thing that people who meet them say all the time, and
that they are completely sick of. Like jokes about their name.

It's a work in progress - as are my manners - and these are only my
theories. Also, I definitely break these rules, sometimes for legitimate
exceptions and sometimes not.

Several of these come from my friend Jim Davies, and others, such as the
disabilities and divorced people ones, are adapted from internet sources
(as I say, I compiled this for myself originally, so I didn't keep the
credits).

-----
When you hear someone's major, especially if it's in the humanities,
don't ask "what are you going to do with that?" Most people's jobs have
nothing to do with their major. Also, it's okay if people don't know
what they want to do with their lives when they're still in college, so
knock it off.

Don't tell people they look tired. If they feel tired, they know it, and
don't want to be reminded. If they don't, it will make them feel tired.
The same goes for "sick", "worried", "stressed", "upset".

Don't ask a graduate student what their thesis is about or when they're
planning on finishing by.

Don't ask people who just got married when they're planning to have
kids. Don't ask an engaged couple if they've set a date.

Don't ask veterans whether they killed anybody.

Don't make a joke based on someone's job that they just told you.

(Not everyone agrees with this one:) Never make a big deal over
someone's name. Don't make a joke about it, don't call it unusual, don't
compliment it, take care to get the pronunciation right without making a
fuss. The one exception: if they chose it for themselves, recently.

Try not to say things that imply the person you're talking to is an
idiot. Don't imply that the other person's actions or thoughts are part
of a bigger trend, or are because of a group they belong too, or have
been manipulated. Don't imply that the person doesn't know their own
mind. Especially: never attribute a woman's emotions on her menstrual
cycle or menopause. You may express only mild agreement with her if she
suggests it.

Don't second guess people's decisions that have already been irrevocably
made. (e.g. major purchases, career choices, creative choices for
published things, tattoos)

Don't interrogate people about their ethnic makeup. Especially not
people who appear to be of mixed race, since strangers literally come up
to them on the street and ask them, "what are you?" (I'm shocked that
this is the case - it's so incredibly rude)

If you have just met someone from a minority or country or alternative
sexuality or gender presentation that intrigues you, do not try to get
them to educate you about it as though they're the representative for
that group or country. Or at least take it easy on that until you've
gotten to know them in other ways.

There's almost never a need to tell someone that they already told you a
joke, fact or story before.

Don't ask kids what they learned today in school. I find it hard to
remember what I was doing at work the same day, and kids live even more
in the present, so talk to them about things that are closer at hand.

Never feed someone's pet people food without asking the owners first.
Same goes for kids.

Don't tell people that they look like someone else (whether celebrities
or real people). I know this one is hard.

Rarely leave voicemails. Send an email instead. Never leave second
voicemails with no new information.

Don't criticise your significant other, students or employees in front
of other people. Don't talk about a problem you're having with an
employee or student of yours to another employee or student.

Do not tell parents you hate kids; do not tell pet owners you hate pets.

Things that you can easily overestimate how interesting they will be to
other people: dreams, baby stuff, pet stuff, your travels, youtube
videos you saw.

Don't ask people questions that are traps.

Don't talk about getting older with people who aren't within about 5
years of the same age: both younger and older people find it irritating,
for different reasons.

Don't compliment people on losing weight, or otherwise get enthusiastic
over their appearance relative to their previous appearance.

Don't comment on makeup.

Don't ask a working mom, how do you juggle it all. (implies she's
screwing it up)

Don't question people's subjective impressions: how can you be cold?

Don't refer to people or groups as "exotic".

If someone is forced to wear a nametag for their job, don't use their
name off it (dick status move, where you are in effect pointing out
their lowliness relative to you)

Don't apologize except when you understand you've done something bad to
someone, and plan to change your ways. Or are forced to by some other
rule of social conduct.

Divorcing people
1. Do not congratulate them.
2. Do not tell them how you always knew they weren't going to make it.
3. Do not give them theories about the demise of the marriage.
4. Do not give them a timeline for when they "should" start to date/stop
crying/feel awesome/whatever.
5. Do not tell them to feel better because your aunt/friend/mom had a
horrible divorce.

Blind people or people with low vision:
- Try not to act embarassed or apologetic - this can be a way of
pointing out that you're making an extra effort for them.
- Say "may I shake your hand".
- When saying hello, especially for the first time, say who you are.
- Tell the person you're there, and tell them if you're leaving.
- Don't say "guess who this is"
- Don't worry about using sighted language, like, "See you later"
- Describe your gestures
- Speak at a normal volume and pace.
- Don't bring up the idea of heightened senses to compensate.
- Don't interrogate them about their exact level of vision impairment,
e.g. can you tell how many fingers I'm holding up?

Hard of hearing
- Face directly and enunciate a bit more, while not talking down to them.
- Don't ask interpreter to do physical assistance.
- Don't give something for each hand and then ask a question.

People with disabilities
- If someone uses a wheelchair, sit down to talk to them so they don't
have to crane their neck.
- Ask before you help, especially taking hold of someone's wheelchair.
But never ask someone in a wheelchair if they need help getting into
their car.
- Don't call people brave, or your inspiration. Don't say I wouldn't be
able to handle that.
- Talk to the person, not to the attendant.
- Don't touch, move, or lean on mobility aids.
- Don't ask people when they got disabled, or probe the exact extent of
their disability.
- Don't say, "you don't look sick". Keep in mind that many people have
disabilities that are invisible (e.g. arthritis of the hip in a young
person, torn ACL)
- Don't assume that they spend a lot of their time wishing they didn't
have their disability. (e.g. don't ask if they think about it, or what
they would do if healed)
- Don't say, at least it's not X.
- Don't question the wisdom of having kids.

A Book Everyone Should Read: The Dip

I've been trying to get many people around me to read this book, The Dip: A Little Book That Teaches You When to Quit (and When to Stick) by Seth Godin:

http://www.squidoo.com/theDipBook/

It's expensive for how extremely short it is, but the one idea it contains is so powerful and important that it's well worth it. Basically the idea is that when you start some new thing, there's a period of exciting growth and reward, but then eventually it becomes an unrewarding slog (the dip). But if you pour enough energy into something for long enough, eventually you climb up the other side of the dip, and things get super awesome. That sometimes takes a ridiculous amount of energy, which means quitting a bunch of other things that are consuming your time and energy but where you're not determined to get out of the dip.

Having this idea in my head has changed the way I see so many things, and is already affecting the way I live my life. Most of all I want to stop the pattern I've had of starting things and then getting fed up when they start to require a massive investment just to make a tiny bit of progress - and then feeling resentful when I see the people who did put in that investment rather than quitting, and made it to other side of the dip where their life looks awesome. I'm going to start to value that period of grind for some small number of things, and for the rest quit them intentionally and cheerfully.

Here's a good companion piece to the book, with some additional handy terminology:

http://ihack.us/2007/05/25/dips-dead-ends-lotteries-and-quests/

How to be Easy to Talk To: Turning Against, Turning Away, and Turning Towards

Why are some people really pleasant to talk to and some people not? Sometimes it's easy to put your finger on why, but not always. I think a lot of the strange friction we experience when talking to certain people can be explained by some concepts I read in psychologist John Gottman's book The Relationship Cure, that have always stayed with me.

He says that we often pay too much attention to what we say and do and not enough to how we respond to what the other person says and does. When someone tries to communicate with you, he calls that an "offer" (very similar to the improv usage), and there are three basic classes of response to offers: turning against, turning away, and turning towards. These are great terms, because you can guess the meaning from them, and also guess which ones are likely to hurt your connection with the other person and which ones are likely to strengthen it.

But it's not always obvious which one you're doing, so I'm going to use an example to show some types of reaction that are more subtly abrasive.

Your friend Matt: "Hey, I just saw Pacific Rim! The robots were fricking cool."

Your response:

TURNING AGAINST
This is turning the person's offer into an opening to attack them, in a way that might make them wish they hadn't said anything. But this might not be large or overt, or intentional. For example:

- "Yeah, all my nerd friends I've talked to are really excited." You're implying that his reaction is because of his membership in a group, not his own perceptions. (calling him a nerd might also be insulting, depending on the person.)

- "Ha ha, I haven't heard 'fricking' in a while." You're jumping on a surface aspect of his quickly-improvised speech, rather than engaging with the contents. The same goes for pointing out a grammatical or word usage error.

- "I have to remember you haven't seen that much Kaiju. The robots in Neon Genesis Evangelion are even cooler." You're using this as an opportunity to flaunt your own knowledge, and imply that he's something of a dupe.

- "That movie had a terrible script." You're attacking the thing he's trying to express enthusiasm about, without anything to transition or soften it.

- "I'm not really into the summer blockbuster thing." Again, implying that Matt is a dupe, and you're on a higher plain.

- "Um, those are not really robots. Technically, they're cyborgs." You're challenging facts in his statement that aren't that relevant to what he's trying to say. (again, keeping in mind the "quickly improvised" aspect of this)

or

TURNING AWAY
This is simply failing to acknowledge or engage with the person's offer. For example, checking your phone, mumbling something noncommital without making eye contact, continuing with what you were saying before, or interrupting them in the middle to make a joke or comment on their means of expression (which might also constitute turning against). A subtler example of turning away:

- "That reminds me of this awesome tin robot I bought at the flea market." You're wrenching the conversation away to something that's on your mind, rather than engaging with what they said.

or

TURNING TOWARDS
What's the best way to respond to an offer? Of course in some situations you want to be a dick to someone, and sometimes it's fun to be a pretend-dick to a good friend (although you have to be careful that it's on a strong background of affection and respect). In many cases something may be more important than the pleasantness of the conversation, like getting a job done. But you have to be aware of when you're turning against and turning away. Even if the other person seems not to notice, or even laughs at what you said, there's a good chance they're annoyed, though maybe below the threshold of consciousness. If you want someone to feel closer to you, and trust and like you, you have to resist that every time. Gottman's idea was that relationships are built step by tiny step: every time you notice someone has made an offer to you, which usually happens many times in a conversation, and restrain yourself from turning against or turning away from that offer.

Instead you have to turn towards the offer. That means listening carefully to the intent behind it, and at the very least acknowledging that you've heard that. In this case, all you would need would be to make eye contact, smile and go, "Cool, man!" That's it. If you wanted to go further, you might ask Matt open-ended questions, even just in the form of "oh yeah?". You could also ask, "tell me about one you liked!" And then keep your mouth shut. If you don't get the feeling he's dying to expand on the initial statement, you could talk about your own thing, if it connects with the *emotion*. So in this case, the emotion is appreciating or finding something cool in art. "I love how good special effects are now. I wish they'd been able to make monsters like that when I was a kid." But in general it's a lot of active listening, and letting the person get through all of what they wanted to say - even leaving a little pause to be sure - then acknowledging it at the end.


The response doesn't necessarily need to be positive. You could disagree, but in a way that acknowledges their offer and shows respect for the feeling that prompted it. "They didn't work for me that well - too many gadgets for my taste."

***

So much of social skill is just noticing when someone is reaching out to you, and making them feel glad they did. That way they'll want to keep doing it. It seems simple, but I see nerdy guys especially mess this up all the time (and I'm including myself in that). Even if you never have clever things to say, if you acknowledge the person's intent (turn towards) and don't jump on their words (turn against) or ignore what they're trying to say (turn away) people will find you easy to talk to.

Note that this applies to electronic communication just as much, maybe more so since you've theoretically taken time to compose it. Leaving an email sitting there for a long period of time can be a type of turning away, and often you're better off writing a shorter reply sooner, with the goal of aknowledging their offer as soon to the moment of writing as possible.

How to Keep Files Private on Your Hard Drive

Sometimes you need privacy on your computer. Maybe it’s you and your partner having certain photos you don’t want the computer repair place to find, maybe you need to keep sensitive records from work safe, or maybe you just want a “partition of one’s own” as I describe in my essay about creativity, a space on the hard drive where you can feel free to experiment without shared users of the computer happening across it. In this age of operating systems automatically scanning and indexing the contents of files, and multiple menus showing the most recently opened documents, it’s not enough to give a file a misleading name or hide it in an obscure folder. Sooner or later it will pop up.

The only solution is cryptography: using powerful mathematical techniques to scramble the contents of a file so that only people who possess the password can open it. And this type of protection is within your grasp.

If the file is a Microsoft Word document, you can use the Password to Open feature, which is found under the File -> Preferences and then the Security tab. According to Wikipedia this is very strong protection if it’s Word 2007 or later (and earlier is probably ok for discouraging kids or non technical people in your life from breaking into the files).

If you’re using a Mac, then a simple, built-in way to do this is through an encrypted disk image. This is a file that, when opened, acts like you inserted a USB stick into your computer, presenting a drive on your desktop that you can move files in and out of. A nice thing about using a disk image is that if you do all your work within it, there’s nothing to clean up when you’re done - it even locks back up automatically when you shut down your computer. To create an encrypted disk image, open the program called Disk Utility, which is found in the Utilities folder, in the Applications folder. Go to File -> New, and choose Blank Disk Image... Pick a size that can reasonably hold what you want it to hold, and where it says Encryption choose 256-bit AES Encryption. When you click Create it will ask you for a password.

If you’re not on a Mac, and it’s not a Word file, the best thing to do is to use the powerful, free encryption tools that go under the label GPG. To get set up, which includes making what are called a public and a secret key (but for our purposes amounts to a password), check out the instructions I wrote, and follow steps 1-3 for your platform. Then to encrypt the file on a PC, follow the instructions halfway down these docs for gpg4win, where it says “18.2 Encrypting and decrypting files”. Basically right click the file, choose Sign and Encrypt, and then Encrypt. Make sure your key is on the list. Click Encrypt. (On a Mac, using GPG Tools, right click the file, and choose Services, then “Open PGP: Encrypt” from the submenus. Again, make sure to choose yourself as one of the people who are allowed to open it!)

You should now have a file with the extension .gpg. Just to make sure it's valid, do a trial decryption of it, by right clicking and choosing the decrypt command for your platform, and checking that you get the same thing you put in (don’t delete the original until you’ve done this - so there should now be two copies of it). If you have multiple files, you can zip them first.

(Note that these are practically all the steps needed for making an encrypted file that others can open too, without having to exchange passwords. You just need to have imported their public key (step 4), and added them to the list of valid openers in a previous dialogue box.)

You’re not done yet. You have to get rid of the original. When you delete a file on a computer, it doesn't actually disappear: the data is all still there on the disk, it just is marked as blank and ready for reuse. So there are plenty of tools that could recover it, and might do so even inadvertently, e.g. if your hard drive crashed and you brought it to a computer shop. The information has to be deleted in a special way to actually get rid of those bytes, typically by overwriting zeros or random data. On the Mac there is something called Secure Empty Trash, right beside Empty Trash, that will probably do the trick. But I believe on the PC you need special software. I don’t have a firm recommendation, except that one called File Shredder is free and apparently not sleazy.

One caution is that it’s very difficult to keep the *existence* of secret files a secret, especially if you access it regularly (because of “Recently Opened” menus and the like) Typically the best you can do is to give things nondescript names, and rely on any shared users respecting that everyone needs a little private space. But it's a problem.

How to Become a Creative Person

1. FIGURE OUT WHEN THE WORK IS GOING TO GET DONE.

2. WORK IN AN ARTFORM THAT YOU CONSUME VORACIOUSLY

3. FOCUS ON FINISHING THINGS, RATHER THAN ON MAKING THEM GOOD

4. PLAN TO FINISH A LOT OF SMALLER PROJECTS

5. KEEP PROJECTS SECRET UNTIL SOME VERSION OF THEM IS DONE

6. MAKE MORE THINGS THAN YOU SHOW PEOPLE

7. DON’T WORRY ABOUT MAKING THINGS THAT EXPOSE YOURSELF OR OTHER PEOPLE, OR THAT ARE THAT ARE OBSCENE, PSYCHOTIC, BORING, OR UNORIGINAL

8. HANG OUT WITH PEOPLE WHO ARE MAKING THINGS ALL THE TIME

9. SEEK RELIABLE FEEDBACK AT SOME POINT, BUT DON’T TAKE IT TOO SERIOUSLY

10. TAKE CARE WITH HOW YOU SPEND THE REST OF YOUR TIME

When I say creative person, I don’t mean a character trait of creativity (which I don’t believe is a real thing). I mean very specifically a person who a) make things that are b) cultural products, c) consistently. When I say cultural products, I mean things that have the potential to expose the creator. Writing scientific papers or making crafts requires creative problem solving, but does not tend to reveal important things about yourself, in the way that a play, a painting or a serious memoir might. The consistency part is important too: everyone has made *something* at some time or another, but I’m interested in the case where it's a regular part of your lifestyle - now, not at some time in the past.

I would say about half my friends are creative people: they are making cultural products all the time. Of the half who don’t, most of them are just fine with it. However this post is for that slice of people who would be happier being a creative person, but aren’t for whatever reason. They consume cultural products all the time, have strong opinions about them, and have fantasized about having things of their own that they made, but are not doing it.

I recently started making stuff, and I want to share how I got past the barrier. These will be most useful to people who have similar brains to mine, and are being blocked by similar things. I’m going to expand on that list at the beginning of the post, at great length, but first a few words about the question: why make things?

Here’s why not to do it: to get approval. As in, praise or attention or status. First of all, when you first start making things, you’re basically a baby, and chances are it’s not going to turn out very well. If you’re older, you’ll definitely progress faster, and have a lot more life experience to draw on, but it’s still going to take a bunch of years before you’re making things that people outside of your immediate circle are going to want to look at. In terms of money, it’s always been hard to make a living making culture, and it gets so much harder all the time, so you can’t even think about that. Second, if you’re thinking about approval, it can block you up from exploring wilder things you might want to explore. Third, there’s just the practicality that it is hard to get things in front of the right audience for it. There’s a whole other set of skills that come into play, basically marketing and hustle.

Basically it takes a lot of both experience and luck to make something that turns out well and gets acclaim - just think about the most successful and well-established artists you know, and how even they can’t control how everything they make turns out. So how much harder is it going to be for you? It’s a whole separate thing from what I think you should be deriving satisfaction from, which is being productive and following the regime you’ve laid out for yourself. You just have to make things and not care whether they turn out well.

(If I had to venture a theory of what it takes to make things that turn out well, it would be a) making enough things so that some of them hit the mark b) making so many things over time that you build up powerful skills, and most of all c) coming back to a particular thing over and over and over and over, making it better each time, and showing it to different people to get different kinds of feedback. Just investing a huge amount into redoing something. Notice that none of these are innate talent, or having an amazing idea).

Making cultural products is making a million decisions, one after another, and concentrating hard over a long cumulative period of time. I’m going to focus on the scenario of making things without a partner and without a deadline, because that’s as hard as it gets. (collaborating can’t be a *break* from the responsibility of making all those decisions - that’s how crappy, lazy things get inflicted upon audiences - so it’s better if you are ready to shoulder the whole burden)

So why put in that effort, if not to get praise, or any money or recognition whatsoever? (I’m a believer in the Onion model for creative hobbies)

1) To engage more with the world. This seems paradoxical, but for me anyway going away into my lair to make cultural products encouraged me to pay more attention to the world, and become a better observer. Things you see in regular life can be much more wondrous and amusing when you’re thinking about how to use them in your creations. It can become a habit. I think of Philip in Of Human Bondage, challenged about the value of studying painting when he ended up dropping out: “I learned to look at hands, which I'd never looked at before. And instead of just looking at houses and trees I learned to look at houses and trees against the sky. And I learned also that shadows are not black but coloured.”

2) To engage more with art. When you start making things, you’ll find yourself much more appreciative and forgiving of cultural products - you’ll see that flaws are often need to be there for other parts to work, and that many little bits are done wonderfully even if the thing as a whole isn’t so successful. There are always things to learn from, and apply to your own creations, and you’ll be able to see much more deeply into the heart of the art you love once you’ve tried to solve similar problems in your own work. The growth of your taste will accelerate, and how much you learn from each thing you take in will multiply.
WARNING: That said, starting to try to make a particular artform will destroy your ability to enjoy it in the same way ever again. Consuming it will now feel a little bit like homework, and you might find yourself avoiding it as a fun-time activity. This is a genuine downside to making things.

3) You can make your own action. When there are no texts and your social networks are silent, you can do something that feels real and positive, and not like it’s just killing time. When a creative project is really rolling, it’s like an invisible forcefield against boredom, loneliness, discomfort, and heartache. Any tedious meeting can be an opportunity to work out problems. You might appear to be sitting quietly on the subway, but there are whole worlds turning around in there. It’s important to know that creative projects won’t feel like that all the way through, but at certain times you’ll be absolutely on fire.

4) It’s fun to see what comes out. I’ve found less than half the creativity is in my initial inspiration, and more than half comes out when I actually sit down to try to make it. It’s amazing how your brain will come up with something to instantly fill holes that are created as you go along, holes you didn't even realize were there until you tried to set it down. On a different note, your final product will necessarily be composed of the kind of stuff that fascinates you and is on your wavelength, and works through the things that are concerning you. It's not hard to create at least the *type* of art you would love to happen across - if not the quality.

5) You’re building creative muscle that may be of practical use. I don’t want to play up this one, since if it’s for your job, say, there are probably way more efficient ways of using the time to hone your skills or knowledge, but if you’re having a good time because of 1-4, there’s no reason why not to receive this benefit. The skills in expressing yourself might be useful for your job or other hobbies, and simply practicing making yourself do the hard thing of filling a blank canvas, over and over, is such an important thing.

Therefore, onto my tips. Most are not really original, being inspired by writings by Keith Johnstone, Ira Glass, and many other people, but this is the way I’ve synthesized them for myself - this is a manifesto for me, who is only beginning to make things, even more than for any potential reader.

1. FIGURE OUT WHEN THE WORK IS GOING TO GET DONE.
It takes an astonishing amount of time to finish even the shitty first version of something. I mean just for the time to actually do the typing, move the brush, etc, not counting the time for planning, and for bashing your way through problems. And not getting into revisions at all, which take a multiple of the original time. So just to get started, you have to figure out when you’re going to put in that time. And it’s likely going to have to be focused, uninterrupted time, which is hard to come by in big stretches for most of us.

But the good news is that if you can figure out how to put in solid half hours on a frequent basis, that can accomplish an enormous amount over time. You might write for half an hour before breakfast every morning - my friend Jim Davies wrote an entire book that way, which is now being published. Sunday evenings are a good time for me. Any kind of regular schedule can be helpful, because your body and mind will rev up to do the work at a certain time (so it doesn’t require so much willpower), and you’ll start to have ideas in anticipation of the session, while not having to feel guilty for not working at other times. That kind of regularity isn’t always possible, but the work has to keep getting done - I would say aiming for no more than a week between sessions, even if it’s just a 20-30 minutes engagement.

Once in a while you’ll feel inspired and want to work on it long into the night. But the reality is that putting in time on your creative projects isn’t always going to feel fun. In the words of Paul F. Tompkins: “Having written? That is the best. The part where you have to tell your fingers to tap the appropriate keys on the keyboard? Blegh. You can keep it.” Often, many other things you could be doing seem more attractive - and definitely a lot easier. If you’re really trying to finish things, and not just ending up with a bunch of half pages of ideas, sometimes you’re going to have to force yourself to work.

Basically any trick or advice you can find, from any source, is worth considering if it will help you a) start working and b) keep working during the time allotted. One of the only ways I’ve been able to consistently put in time on personal creative projects is using a program called Freedom, which shuts off your computer’s access to the internet for a set period of time. I’d feel sad that I need that, but apparently Jonathan Franzen does too. Besides the reduction in temptation, it also acts as a handy timer, so I know, “hey, I put in 30 minutes of solid effort”. Other approaches might be to get a buddy to check in on you, or use an automated system to track your production. One novellist I heard interviewed said that she puts on the soundtrack to Mortal Kombat every time she sits down to write, and that helps her to shut out the world and signal to her brain that she is now in work mode. Experiment on yourself. Try everything.

2. WORK IN AN ARTFORM THAT YOU CONSUME VORACIOUSLY
When thinking about yourself as a creative person, it’s tempting to imagine yourself working in an artform that is considered prestigious, or at least “normal”. Like a poem, a painting, or a realistic novel. But is that what you voraciously consume? If you read supernatural romances practically every day, and have strong opinions about the good and bad ones, something in that ballpark is what you should work on. You probably have highly refined taste for that artform, which I think is an important step to making something good, or at least having no trouble finding ideas you want to play with. Take prestige and approval out of the equation.

Of course it is possible to shift your interests, by changing your consumption habits. But will it ever run as deep as the things that you’ve been consuming for many years? Maybe getting really good at making animated gifs will be your creative outlet. Or tweets. Anything can give those kind of rewards if you put some willpower and longterm commitment into them.

3. FOCUS ON FINISHING THINGS, RATHER THAN ON MAKING THEM GOOD
This is important for people who have the same hangup that I do, which is basically vanity. It’s uncomfortable to watch my fingers type something that’s not good. I want to be making good things! But I believe in this rule for a few reasons: first, as soon as you actually finish a thing, it becomes dramatically more useful. You can give it a name, show it to other people to get help, and make use of even this not-so-good version in a surprising number of applications. You certainly can give yourself credit for it at that point.

Second, it will jumpstart your creativity for the project. It’s a lot easier to improve something than to start with a blank piece of paper. And your draft serves as a map of the territory, clearly showing the areas that need a lot more thought and care - which also helps you to estimate how much more work is needed. The combination of pride and shame whenever you think of that complete draft will drive your subconscious to beaver away on the outstanding problems. Third, when you get a version of an idea down, it frees up that slot in your mind to have another idea. So you get a boost to creativity *outside* of that project too.

Note that there’s a difference between finishing a version of a piece that’s not so good, and not properly finishing it. You’ll know it in your heart. Like avoiding tackling a section you know will be a pain in the butt. Much better to fill that in with a shitty version, than to leave in a line that says “insert cool action sequence” (or a 100 word version of something you know should be 500 words). That attempt to tackle it, even if a failure, will pave the way to future victory.

4. PLAN TO FINISH A LOT OF SMALLER PROJECTS
Many people have had success with setting up a schedule to finish smaller things on a regular basis. In fact, being forced to produce something regularly, like a radio show or comic book issue or television episode, is how a lot of famous creative people built up their creative strength quickly. It’s great if you can find a structure that will force that, but if you do it on your own, then you’re ahead of the game. Every time you finish a smaller project, you get a little motivation boost. If it’s a total dud, no big loss because you’re finishing another one next week. And you get to try a lot of different things.

What if the artform you truly love is novels, or some other longform creative product? This is risky when you’re first starting out, because you might be committing to an idea for a novel that’s not going to work. Maybe you’re okay with abandoning novels 50 pages in, over and over, but many people would find that sapping their motivation after a while. This is why I think the National Novel Writing Month is flawed, despite being a great fit for many of my points here. Why not National Write 20 Short Stories Month? As a last argument for trying shortform, most novellists I know published short stories before novels, and in the field of science fiction half the classic novels are expanded short stories (Ender’s Game, Permutation City, A Canticle for Leibowitz, Blood Music) or even just a bunch of short stories stapled together (City, The Martian Chronicles).

One tip from the David Allen school for finishing is to draw a clear line between projects you are and aren’t committed to. I would suggest a literal list of projects you are seriously trying to finish, that you update weekly (as in, take things off or put things on). You can collect ideas for the ones you’re not committed to, but until they’re on the list you have to be disciplined about not spending your serious work time on them - that’s a form of procrastination. Also if you take care to formally ditch projects you’re not keen on anymore, that frees up psychic energy for the ones you really want to finish.

5. KEEP PROJECTS SECRET UNTIL SOME VERSION OF THEM IS DONE
When you tell people about something you’re planning to make, you get a portion of the reward, without the effort and risk it takes to finish something. If you’re not careful, that can be a loan that won’t get repayed: it might sap your will to actually sit down and finish things. It can also be a trap to show people unfinished things, for the same reason. Plus unfinished things are less satisfying to consume, and you can use up the goodwill of your readers or viewers (whose attention you should be very grateful for). Also, potentially super embarassing, especially in the eyes of people who never make art themselves and so don’t understand how awkward things look in their early stages.

But how to keep your unfinished or sensitive work secret? If it’s work that’s done on a computer, I advocate using cryptography, which puts a very secure lock on your private files. That way people sharing your computer won’t accidentally run into it, nor will it turn up on searches. Even if you die suddenly it’s likely that no one without the password will be able to access the contents. It’s a little room of one’s own where you can feel free to explore to whatever extremes you like.

6. MAKE MORE THINGS THAN YOU SHOW PEOPLE
This helps to dissociate approval from the satisfaction of finishing things. You can’t count on liking everything you make well enough that other people should see it. Sometimes you need to sit on things a while to know whether you’re ok with sharing it. And some things you’ll want to keep private for good.

7. DON’T WORRY ABOUT MAKING THINGS THAT EXPOSE YOURSELF OR OTHER PEOPLE, OR THAT ARE THAT ARE OBSCENE, PSYCHOTIC, BORING, OR UNORIGINAL
The previous two are prerequisites for this one. These are all things that I think are tremendous blocks to creativity for some people, to even sitting down in the first place, even more than being afraid of making things that aren’t good. But if you keep projects secret until some version of them is done, and make more things than you show people, there’s no reason not to try everything that might inspire you. Let’s take these individually:

- Expose too much of yourself. If your creativity comes from your own experience and your own emotions, as it should, it may expose things that don’t fit with the image of yourself you would wish to present to the world. Like say you write eight short stories, and the first one is about a lonely mushroom, and the second about a lonely acrobat, and the third about a lonely seahorse and so on. You would be embarassed for someone to see them all, because together they seem to reveal that you’re very lonely. And yet if that’s the mood you’re inspired to write about, that’s what you should write. Once you have finished it, you have the power to show some of them to people, or none of them. Things you make might reveal that you’re uncool, or uncultured, or ignorant about some important things about the world, or that your life sucks. You might find out things you don’t like about yourself. You have to be ok with that.

- Expose too much of other people. You may be driven to make things inspired by real people, that would hurt them if they were to see it. Or at least make things weird with them. If you create in secret, you can get it out of your system, and decide whether to change details to conceal who it is – or merely use parts of them to inspire future fictional creations. This is one reason why I think blogs can be a trap as a creative outlet: your mom will probably find it. And so you become a politician, and can never quite say what you’re dying to say, and those thoughts are lost even to your own memory eventually. I’m a big fan of Harriet the Spy, and its message of how valuable it is to be able to write what you really want to write, no matter how potentially hurtful. As her mentor Ole Golly says, “Sometimes you have to lie. But to yourself you must always tell the truth.”

- Obscene. If you grew up in a household that was fairly modest, and never really rebelled against it, then this can be an invisible barrier. It can be very freeing to write something with elements that are extremely sexual or gruesome, or that feature an immoral or destructive character. Maybe your ambition isn't to become Clive Barker or Barbara Gowdy, but knowing that you have the ability to go to very dark or passionate places might unlock your creativity. There are plenty of well-respected artists out there fantasies at least as messed up as the worst thought that’s crossed your mind, and most of them that I’ve read about are perfectly well adjusted in their personal lives.

- Psychotic. “This thing I’m making is the dumbest, most insane thing I’ve ever seen. If my friends saw this, they would think I’m having a schizophrenic break.” Again, this might be the place you need to go. A good exercise might be to make the most obscene, psychotic, self-exposing thing you can imagine. That you would be horrified if anyone were to see it. It might turn out interesting, and it might unlock something. (This makes me think of U and I by Nicholson Baker, a book-length essay about how much he wishes he were friends with John Updike. Someone asked him if it was embarassing to write, and he said, “Oh yeah! I had to force myself to type every word!” And yet this is an actual published book, and an entertaining one too.)

- Boring. On the other side of the coin, you can’t get hung up on whether your imagination is too tame or boring either. You just might not be that extreme - or, more likely, your version of extreme might look different than the stereotypical kind. You have to follow the thread of your own interest, whereever it may go. Since I mentioned Nicholson Baker, he wrote an entire book about card catalogues, and another which is a novel about mundane observations during a single escalator ride. And they were not boring. As long as you find it compelling, you can’t think about whether other people will judge you as boring for it.

- Unoriginal. This one is almost as big as self-exposure. If you consume a lot of art, you might be really blocked up by how hard it is to come up with something genuinely new. Don’t worry about it. If you’re not looking to earn money, or win praise for how original you are, you can start from whereever feels exciting to you. For example, fan fiction. Many people grow to become strong storytellers, and find interesting things to say, writing Harry Potter fan fiction or other such things. Though this is a secondary argument, very many recognized artists write fan fiction, in the form of authorized spinoffs. Every tv writer and comic book writer who isn’t the show’s creator is essentially doing this too. (Is the creativity involved in building a fictional world more praiseworthy than that of telling a story in an existing world? I would say that’s highly debatable.) Never abandon an idea just because you hear it’s already been done. (and never tell someone their idea has already been done) Never question whether you’re creative enough. You should also feel free to repeat yourself. You might hit the same idea again and again for years, never quite nailing it, until one day, you’re ready. If you’ve made enough stuff, especially if they’re secret, you can loot them for parts, or just let them fertilize something new.

Of course, even if you take some time to sit on a project before releasing it for other people to look at, things still might be revealed through them that you don’t want people to know, or else false impressions you’re not happy with might be created. But if you’re making things all the time, that’s not your only chance to make an impression, and what you are trying to get across will eventually make it.

(Note that while this whole post is heavily inspired by improv teacher Keith Johnstone’s books Impro and Impro for Storytellers, the title of this point is very close to his quote: “The truth is that the best ideas are often psychotic, obscene and unoriginal.”)

8. HANG OUT WITH PEOPLE WHO ARE MAKING THINGS ALL THE TIME
The big reason for this one is to make it seem normal to be making things. The reason is not to have people from whom to get approval. (nice things said about your work by your friends should probably be given the same weight as Facebook “likes”: a mixture of real feedback and social courtesy, and you never know how much of each). Sometimes you’ll get the reaction from someone that it’s amazing that you’re making things, “I could never do that.” I think this is often a mild social sanction: they’re saying what you’re doing is special, but a little abberent. Enough of that and it could undermine your resolve. And that’s assuming you have nice people around you, and not shitty, judgmental people who will tear down your work (and are probably not making things themselves). Much better to hang out with people who are not only supportive, but finish things all the time.

In an improv class, every person in the class creates things constantly. They’re not preselected to be super creative, it’s just that it’s expected. It doesn’t matter what you choose, as long as you choose something. Every once in a while I have to stop and marvel at how rare that is in the adult world. Many of us can go years without making something that risks exposing ourselves. It’s great when you can be around people where it’s expected, and you don’t get approval just for the *intention* to make things. You should seek out environments where you can’t possibly get any points just for calling yourself a writer or artist.

Note that *it doesn’t matter whether you care for everything these folks make*. It might even be inspiring if you see problems in the end products. *Not that you should ever tell them about it.* Nor should you offer calibrated approval. I believe the best approach is to cheerlead your friends in a generic way, encouraging them to finish things, without passing God-like judgment on the final product (the very same God-like voice in your head that makes it hard for you to create). Sure you might have the drive to give strong and sincere praise for something that they made. But then if you don’t care for their next thing, will you stay silent? Or fake the same level of enthusiasm? Praise the process and the commitment, not how it turns out.

9. SEEK RELIABLE FEEDBACK AT SOME POINT, BUT DON’T TAKE IT TOO SERIOUSLY
It’s obvious that feedback is critical for making things better. But I’m in favour of finishing a version of the thing first, as I said earlier. And like I said in the previous point, friendly acquaintance feedback is not real feedback. On the other hand, you will develop a small circle of trusted friends you can show things too, who can give suggestions for how to make it better, while respecting your feelings and the integrity of the work. That’s a precious thing.

It can be tempting to latch on to a guru or mentor, and in fact someone like that can accelerate your progress. But it’s also dangerous if you become dependent on that person’s approval (and some mentors will seek to cultivate that dependence). Ultimately you’re trying to develop your own taste to a high level, and please yourself, and what other people can offer is an outside perspective. Therefore any collection of smart, trustworthy people with good taste should do. Oh, and they should be making things, even if in a different artform.

The thing is that if you have your factory going, no one criticism can clam you up: there’s plenty more of your work coming down the line, and plenty more chances to try it again. Your ego isn’t tied up in any one thing. Feedback might give you a course adjustment, but you have plenty of momentum on your own. You’re not looking for somebody else’s permission to proceed.

I’m considering the advice that when it comes to that point, far down the line, you should actually weight objective feedback more heavily than that of acquaintances. Things like: YouTube or webpage views. Laughter of strangers in a club. Real, competitive awards. Acceptance of your book for publication. How much you can sell a piece of art for. Obviously these are extremely noisy measures, and everyone can think of examples of things that unfairly did or didn’t receive those credits. But they should be able to tell you when you’re truly onto something good, or when you’ve wandered far off track, which the people around you won’t necessarily do. The one critical point: do not compare these metrics with other people’s - only with those of other things you’ve made.

10. TAKE CARE WITH HOW YOU SPEND THE REST OF YOUR TIME
By far the most important thing is making the time to sit down and work on your projects, which is why I made it number 1, but it might help to examine how you’re spending the rest of the time. I’d like to say it’s the time spent going out and having unique experiences in the world that will provide the most inspiration, but it is hard to say in general what is a good or bad use of your time: a YouTube deep dive into Tamil vampire movies might be exactly what you need to get fired up. As with your own work, you have to listen to what you find compelling, and follow that thread deeper into it.

A caution is that if you don’t yet trust yourself to finish things, it’s a bad idea to explicitly start projects with research. It can be a way to avoid making all those millions of choices. Instead, just start writing, and do the research afterwards, or simultaneously. E.g. if you want to write a historical story set in Egypt, just make it all up out of what you already have in your brain, and then fix it later based on research (which will be very fun and engaging, because you will know just where you can use things).

As far as time spent consuming other people’s cultural products, here’s my ranking of them in descending order of how inspiring I think they are:
- Cultural products from my friends
- The highest quality cultural products
- Terrible, or just random, cultural products
- Mediocre cultural products (Man of Steel)

I’ve come to see new mainstream movies as a pretty low efficiency use of your time, if you want to improve what you’re making. Before any movie comes out, there’s a giant military campaign of hype that is trying to make that movie seem alluring, and even necessary. But you’re just having the same prepackaged experience as everyone else, so it’s not going to make your mind or art more interesting. Not to mention the fact that it’s probably marketed to your precise demographic slice. So it would almost be more valuable to close your eyes and take a DVD at random from the store to watch, and become intensely involved with its world and what it does well or poorly. But it’s still better to make up your own stories, alone or with friends - pay attention to the balance of time you spend creating vs consuming. (and movies are only a 90 minute investment of time - spending hours watching a heavily hyped TV show seems like an even bigger potential misuse of a time, unless what you’re writing is screenplays).

It’s also important to leave room for boredom. With portable electronics, it’s possible to be entertained basically all the time. But your brain needs time to chew problems over, which it can’t when it’s being entertained. A lot of people have said that they get their best ideas in the shower or on their commute - time when they are not forcing themselves to think about the problem, but rather to just move things around and put them next to each other, and otherwise follow little byways in a much looser way (randomly, I published a book chapter about this very topic!) Screenwriter Alex Epstein mentioned that he gets his best ideas 10 minutes after he’s stepped away from his work. Which probably wouldn’t happen if those 10 minutes are full of Parks and Rec.

I have a theory that it can be counterproductive to listen to too many interviews with highly successful creative people. You can get hints from it, but it also puts them on a pedestal, often above the people making art around you, which could make creating seem like something only special minority of people should do. Plus people being interviewed often give what I think is a misleading account of their creative process, making it seem like they had a clear destination in mind and travelled directly towards it, whereas the real road to a final product is very windy, with more collaboration than is usually admitted to. If you’re not careful, listening or reading to too many interviews with successful people can become a kind of self-indulgent fantasizing, and not a great use of your time. The same thing goes for reading books or blogs of advice: take it easy on those until your engine is well in motion.

--

There’s nothing wrong with deciding not to put energy into creative projects - many people don’t have that energy to spare, or have no secret desire to make things. But consider whether it’s something that might give you a lot of satisfaction, and whether you are only held back by fear, or just not making up your mind to do it. I’ll finish with a couple of inspirational quotations:

“Practicing an art, no matter how well or badly, is a way to make your soul grow, for heaven’s sake. Sing in the shower. Dance to the radio. Tell stories. Write a poem to a friend, even a lousy poem. Do it as well as you possibly can. You will get an enormous reward. You will have created something.” — Kurt Vonnegut.

“You are not imaginatively impotent until you are dead; you are only frozen up.” — Keith Johnstone

Joss Whedon's Advice on How to be Prolific

My hero, and someone who knows how to work (he wrote 7 seasons of Buffy the Vampire Slayer, and wrote and directed The Avengers):

http://www.fastcocreate.com/1683167/how-to-be-prolific-guidelines-for-getting-it-done-from-joss-whedon

Holy cow, he's a fan of David Allen! (he wrote the book Getting Things Done, a big inspiration for me to start this blog)

" For me, it boils down to specificity, knowing exactly what I’m trying to accomplish, because if I have three projects, it’s ‘Oh, maybe I’ll work on S.H.I.E.L.D. or maybe I’ll work on this or this.’ You know, it’s so easy to just get nothing done, but you’ve got to rock a little David Allen out to be able to get things done and break your list down into next actions. And this is true of producing and directing but even of writing. It’s like, Okay, today I am going to figure out this action sequence. Today, I am going to watch a shit ton of other action sequences, whatever it is, but that would be the other side of it after the specificity of knowing. Don’t just say, ‘Oh, I need to work on that.’ Say, ‘I need to work on this element of that.’"

More advice that resonated with me:

" Absolutely eat dessert first. The thing that you want to do the most, do that.... I always believe in just have as much fun as you can so that when you’re in the part that you hate there’s a light at the end of the tunnel, that you’re close to finished.”

“I have a reward system. I am the monkey with the pellet and it’s so bad that I write almost everything in restaurants or cafes [so] that when I have an idea, I go and get chocolate." He doesn’t wait to flesh out the idea and then reward himself, he rewards himself simply for having the idea. "I’ll write it down and then get some chocolate. I have the idea, I get my pellet . . .

"The last piece of advice on that level is fill the tanks, fill the tanks, fill the tanks. Constantly watch things and things you don’t [normally watch]. Step outside your viewing zone, your reading zone. It’s all fodder but if you only take from one thing then it’ll show... that was my vacation from Buffy, which was two weeks. I got two weeks every year, and in that vacation I read, in 14 days, 10 books. My wife and I saw like nine plays, and that’s all we did. We just filled the tanks."

"This comes from Kai, my wife, who produced the film. She [quotes from] Rio Grande: ‘Get it done, Johnny Reb.’ It’s like, don’t make excuses. There aren’t any anymore. If you’re talking about it, you should be doing it and she doesn’t like to see talent go fallow. She doesn’t like to see people repeat themselves. She likes people to get it done, purely out of love of the person and then joy for the product itself.

Also a charming (and relatable) personal note: “I always enjoy conversation more if there is some substance to it--which is a just incredibly hilarious thing for me to say because for many, many years I was the guy whose only contribution to any conversation was, ‘There was a funny Simpson’s joke about that.’"

How to Set Up Public Key Cryptography

Cryptography refers to the mathematical and technological techniques for keeping information secret. What’s wonderful is that we’re now at the point where very powerful cryptography is available to everyone, for free. But it still takes an investment to educate yourself and get set up. Why might you want to set up cryptography on your computer?

- For sending emails secure from snoopers enroute. Not only Google and the NSA but many other parties could potentially read your emails in transit or when stored on your computer - I have heard the level of security compared to that of a postcard.
- For transmitting files to other people that you don’t want intercepted or scanned en route.
- For keeping files secret on your own hard drive, in case of shared users of the computer.

There are a lot of approaches to cryptography that require sharing a secret password with another person, but that can be tough - obviously you can’t use email to exchange the passwords, and it’s not always possible to meet in person. Therefore I’m going to advocate an approach called public key cryptography, and show you how to set it up on the Mac, the PC, and an Android phone.

I suggest starting by reading a little background on public key cryptography on Wikipedia and on the PGP website.

But in a nutshell, public key cryptography involves the creation of two strings of data, called keys, one which you keep secret and one which doesn't have to be kept secret: you can give it to your friends, colleagues, post it publicly on the internet, etc. People use your "public key" to encrypt files or emails before they send them to you, and then you decrypt the files using your "secret key". The way I think about it is that it gives you a magical locked box, with a slot in the top that anyone can drop something into. But no one can get things out, except for you, who possesses the magic secret key.

You already use public key cryptography every day, every time you use a banking or email website which has a little picture of a lock in the corner of your browser beside the URL bar. But for a long time it was out of reach for personal use unless you were an expert. It turns out that it’s a little easier now, thanks to a set of software called Gnu Privacy Guard (GPG), which is available for both the Mac and the PC, and in fact produces encrypted files that are compatible between both. (you will also see the related terms PGP and OpenPGP thrown around - for my purposes it's good enough to call the technology GPG)

Besides the ease of use, why choose GPG? It is both open source and popular, which is a winning combination for security software. Open source means the guts of the program, the source code, are available for anyone to inspect. That creates a real disincentive for putting in sneaky code that could steal your data or compromise your privacy in other ways, because they're likely to get caught by people auditing the code. It should nearly always make you trust a program more. And, the fact that GPG open source allows security experts around the world to check the code make sure the authors haven't made any mistakes that would compromise security, and even contribute quick fixes themselves. Finally, the fact that it's popular means people actually care enough to do so. My understanding is that GPG is the strongest, most trustworthy cryptography available for any amount of money - and  it's free.

A note about passphrases. The passphrase is the string of characters that protects your secret key as it sits on your hard drive. Really it's exactly the same as a password, except it's supposed to be longer. The reason being, people with physical access to your hard drive and some time and computational resources can presently break passwords of 12 characters or more (according to wikipedia), and much more easily if it isn't truly random (i.e. if you use words that are in the dictionary, or even the slight variations that are often recommended online) And once your private key is cracked, it can be more serious than a password for an email account or the like: all the files you've encrypted in the past are now vulnerable to be read. The problem is that if you plan to decrypt files more than once in a long while, a long passphrase is hard to type, and very hard to remember. You'd probably end up writing it down physically, or using some kind of password manager (like the mac's built-in Keychain), which can pose its own security risks (for example there’s not much point if it’s shorter than the passphrase).

My take is that as long as you keep your secret key only on your hard drive, a medium-strength passphrase provides excellent protection against snooping on files and emails en-route. It unlocks the much, much longer and more random key that protects your file as it flies across the internet. Only someone with access to your hard drive can attack the passphrase, and as long as the choice of passphrase isn't completely dumb, it would take at least some expertise to crack it even then. So I suggest for this particular medium-to-low-security purpose, using the type of password you use for your regular accounts (though not the same one!).

I’m going to focus on how to get set up to exchange encrypted files - a later entry will talk about setting up email. On each platform I describe how to do the following steps:
1. Install the software.
2. Create your public and secret keys.
3. Send your public key to your friend (so they can encrypt things for you to open).
4. Install your friend’s public key (so you can encrypt things for your friend to open).

FOR THE MAC

1. Download the installer and install gpgtools.
2. Once installed, it will pop up the GPG keychain access application, and ask you to create a key. Enter the passphrase you came up with.
3. When the key is generated, select it from the list and choose File -> export. Binary or ascii should both be fine. Make sure "Allow secret key" is unchecked. Then email your friend the file that's created, which is your public key.
4. Import your friend’s public key. Go to File -> Import, and choose the file that they sent you, e.g. by email

FOR THE PC

1. Download and install Gpg4win. At the step where it says “Define trustable root certificates”, check “Root certificate defined or skip configuration”
2. Launch Kleopatra (the key manager). Choose File -> New Certificate... and choose "Create a personal OpenPGP key pair”. Enter your name and email address and click Next then click Create Key. Enter the passphrase you came up with.
3. Try Send Certificate By Email... to send me the public key. If that doesn't work (because there isn't an official email program set up), click Finish. Choose File -> Export certificates, and save the resulting .asc file somewhere. Email that .asc file to me as an attachment.
4. Import your friend’s public key, which they sent e.g. as an email attachment, which you have saved to your hard drive. Open Kleopatra (the GPG key management program) and go to File -> Import Certificate, and choose that file. More here: http://www.gpg4win.org/doc/en/gpg4win-compendium_15.html

FOR ANDROID

This one is trickier. The thing is that you can't directly create a public key/private key pair on an android, so you have to create it on a Mac or PC first and then import it to your android. (you probably  want to use the same key for your desktop computer and your phone)
1. Install the app APG, for Android Privacy Guard.
2. To add your own secret key to your android:
- Create your keys on the PC or Mac using step 2 described above.
- Export the keys, in such a way that you export the private key as well. On the mac, the option is called "Allow secret key export".
- Move this file to your Android phone. Take care with it! Don't email it anywhere! Delete it securely!
- Launch APG, and open the options menu (vertical ellipsis in the corner). Choose Manage Secret Keys.
- Hit options menu again, and choose Import Keys. Select the key file you moved onto the android, also checking the box Delete After Import.
3. Follow step 3 from the mac or PC versions to send the public key you created on your computer to your friend. This time, make sure “Allow secret key export” is unchecked!
4. To add your friend’s public key, first move it onto your phone as in step 2 launch APG, and open the options menu. Choose Manage Secret Keys, hit options menu again, and choose Import Keys, then find it on your hard drive.

To decrypt a file on the Android, go into APG, press the Decrypt File button, and choose the file to decrypt. You may need to have an app installed like File Manager if you can't type in the full path from memory. Click Decrypt. You’ll be asked to enter your secret key passphrase. This is where you find out how hard it is to type on an Android keyboard! Another wrinkle to the passphrase complexity tradeoff.

The result is that the decrypted file is saved to a directory of your choice, by default the APG directory.

Now you're ready to encryp files on your hard drive.

The Best Email Filter Ever

I finally hit on a solution to the trickle of annoyance caused by
institutional emails. I'm sure I have it easy compared to a lot of
places, but I still get dozens of emails a day about irrelevant things
to do with my institution. Since I subscribe to the GTD/inbox zero
principle of email management - and have
a problem with checking my email too often - this bugs me.
For a long time I tried to fight the tide with subject: and From:
filters, but it only helped a little.

So I tried a different approach, which I now realize is a devastating
weapon in the fight against institutional spam. I simply filter every
email that doesn't have my address in the To: or CC: line into a folder
called "nottome". I have a couple of additional folders and rules for
specific mailing lists, but that's the heart of this strategy. I also
mark the message as read, so it doesn't come up as a new message icon in
Thunderbird (my preferred email client). The result is blessed quiet.
And I am missing nothing important - once a day or so, when I'm
slacking off, I will peek in that folder and find the occasional important message,
but mostly marvel at all the nonsense I'm not interrupted by. So far absolutely
 none of it has required an instantaneous response.