I’ve been doing these two exercises almost yearly since I was 18 (nearly 20 years ago). I should’ve kept the results and collected them in a notebook.

The Death Letter Exercise

You’ll need:

• Pen and paper
• A timer

We’re going to do a little solitary roleplaying exercise. Let’s pretend that you are going to die in five minutes. There is no possibility for survival, but your death will be quick and painless. Also, you remembered (as always) to bring your trusty pen and pocket notebook.

Set the timer for five minutes and write a letter to the people who are important to you. This is your last opportunity to say the things that need to be said.

The Obituary Exercise

You’ll need:

• A word processor with word count
• A timer

It’s three years from now, and you’ve just died (perhaps the same way as in the previous exercise). This isn’t the same you that you’d be if you kept doing the same boring stuff you’re doing now. This is the ideal you that you’d become if you got off of your ass and started working toward doing the things you really want to do.

Now pretend you’re the rookie reporter tasked with writing your obituary. You have a limit of 250 words and 30 minutes until your deadline. Your only restriction is that you have to be realistic in that what you write could possibly happen. Don’t pretend that you’ll suddenly become rich or have lots more discretionary time.

Here’s the thing: three years is enough time to learn to do nearly anything you want to do. Actually, if you apply yourself and focus, you can learn to do something reasonably well in a year or two. You can learn to paint or play a musical instrument. You can write several novels. You can lose weight and get in shape. You can fall in love, get married, and have children.

You can do all of these things in three years. Especially if you stop wasting the majority of your day on Facebook and watching television that you can’t even remember tomorrow.

What now?

If you practice GTD, and you should, incorporate reading these exercises into your weekly review. If you’re struggling with the higher-altitude stuff, these exercises will help you clarify your vison and values.

Today marks the beginning of Thing-A-Day month, and I have several hours of guitar lessons to teach after I get home from work, so I don’t think I’ll have time to draw or record a song before midnight. Instead, I spent part of my lunch hour compiling a number of rules I’ve come across over the years that help me stay sane and productive as an artist.

It isn’t done until you’re proud of it.

My friend Joe McDalno wrote this in a blog entry a couple of years ago, and it’s resonated with me ever since:

The world has a ton of artists, of art, of games, of bands, of professionals. The amount of stuff we produce and participate in is astounding. And, as a result, the world has no need of things which are good enough. And I reproach myself for going to press with something that I told myself was “good enough.” If it isn’t something that you’re unwaveringly proud of, there’s zero need for it.

What doesn’t enhance detracts.

I believe Henri Matisse said “whatever doesn’t enhance a picture detracts from it.” I’m sure I’m paraphrasing, but I couldn’t find the original quote after casual searching.

Make art you want to experience.

Don’t worry about being original, or if your work is derivative. All that matters is that you like it, that you’d be impressed by it if you heard it on the radio or saw it hanging in a gallery.

Create much, reveal little.

For every work of art I release for public consumption, there are dozens that no one but me will ever know exists. Even so, I should be a little more careful about what I release. Your audience will think you are as good as the worst piece you show them, so choose carefully. Maybe spend a little time removed from the work before you make the decision to let it out.

Find inspiration in the classics.

There’s a reason the classics are the classics. Helvetica is over 60 years old, Futura is over 80. Kerouac’s On the Road and Miller’s Tropic of Cancer are still subverting young men and women after half a century, and Miles Davis’s Kind of Blue will still blow your mind.

Don’t be boring.

You can be cool, elegant, sexy, flamboyant, dramatic. But boring will bore your audience.

Challenge your skills and polish your craft with each piece.

When you are writing an arrangement for the guitar, try to write something you can’t play without a little practicing. If you’re drawing something, and you always have trouble with hands or foreshortening, consider making those elements an important part of the composition.

Style results naturally from skill & taste.

Don’t worry about developing a personal style. You can’t help it. After awhile, if you ever get good enough, you’ll begin to see your style as a product of your limitations rather than your skill.

If you’re the best whatever, you’re in the wrong wherever.

You will learn little, and find little inspiration if you’re the best in your circle of friends. You need to be a bit uncomfortable to grow, and surrounding yourself by people who are better than you are at something you think you’re really good at is a great way to make yourself uncomfortable.

The only way to master anything is by doing it over and over again.

I don’t believe in natural, God-given talent. I’ve spent years teaching myself to draw and design, and have labored over countless mistakes. I’ve logged about 33,000 hours playing the guitar, over 20k more than the Gladwellian Virtuoso Threshold.

Speaking of Malcolm Gladwell:

Talent is the desire to practice.

Your art is what you do, not who you are.

I’ve had a lot of problems resulting from defining myself as an artist. There’s lots of ego inflation and deflation going on, and I think that might partially explain some of the weird mental states many artists find themselves in. You have to try to remember that being a great artist won’t make you a better person, it won’t make people like you more, and it won’t make you feel better about yourself. If anything, you’ll be so absorbed in your work that you’ll neglect those who love you, people will think you’re aloof and elitist, and you’ll constantly torture yourself over tiny details of theory and technique that most people, even most of those who participate in your particular discipline, don’t know exist.

I know it’s hard, but try to separate your self-esteem from your work. Don’t forget that the most important things in the world are relationships with the people you love. They’ll be the ones who pick you up out of the gutter of deep existential depression when you can’t seem to draw that nose quite right.

Make something every day.

Which is why you are here.

The day is the atomic unit of your life. If you make something every day, you’ll have lived a lifetime of making things. And, to me, that is a life worth living.

Athletes don’t eat the same way regular people eat. The food they consume is carefully considered for the effect it will have on their performance. An athlete’s body is his medium, and if he wants to compete at their maximum potential, he has to treat his body like it is as important as it is.

The artist doesn’t consume media the same way regular people consume media. The artist knows that the quality of work he produces is directly proportional to the quality of media he consumes, so he chooses carefully the things that enter his brain to fuel his imagination. The writer who only reads inside his genre and the songwriter who only listens to the music on the radio won’t be able to produce important, vital art.

The gradual, unintentional sacrifice that I’ve made as an artist is that I no longer seek entertainment. When I watch movies, read novels, or listen to music it is with the singular purpose of fueling my imagination. There are few best sellers in my reading queue. If I, as an artist, am to compete at my maximum potential, I must fill my imagination with images, mythology, and philosophy that will ferment in my subconscious, then randomize and recombine as inspiration.
I must treat my imagination like it is as important as it is.