Skilled Reflection

Keep a skilled eye on yourself.


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document 1: you

There are two parts to the document of yourself. The first is who you think you are and who you have been. The second is who you think you’ll be and what is likely to make or break that outcome. Spoiler, this page is going to ask you to write. Twice. If you want to read, feel free to check out an essay on the second task, here.

1. Is your life guided by you?

This is not a philosophy prompt. It’s a question-mark in front of your living self. It is there your whole life, to be answered as clearly as you can as soon as you can. The best thing to do is to take a stab at it right now. Update, work on, revise it later if you like, but now is what’s important.

Take 20 minutes to produce 250 words.

Those words should say something about these questions:

Whether your self is absolutely clear or not, now is a great time to take stock.

  1. Open any text editor, and watch the clock: 20 minutes.
  2. Have at it. Write 250 words, and if there’s time, edit them.
  3. Stop when 20 minutes of your life has passed. You’ve got other important things to do besides think.
  4. Save that document. It’s your life, however rough, or biased by what you just ate or thought you were going to do on the internet.

welcome to your life

Nothing is different. Except that you’ve just begun the process of identifying, and changing your life into whatever you want it to be.

The next step? Live some of your life.

Another day, revisit this 250 in another 20 minute session. Update it.

Notice what you thought the first time, and what you newly realize is important. You’re learning about yourself. You’re learning the difference between who you are before you started learning. You’re on the road to mastering the most important study of your life: yourself.

2. Bet your life

Where are you going? The last 250 words describe your life up until now, as if you died right in this moment and needed a summary. Now I want you to imagine the ideal outcome. You live a long healthy life. What happens in that life?

For a more elaborate introduction to this approach, check out the anecdotal essay, here.

I’ll spare you the fun plot-twists you’d get when we do this in a live session. Make sure your 250 words addresses three points:

  1. Your ideal outcome. A dream of who, where you are, and how you live.
  2. What you will do to change who you are now, in order to get there.
  3. Who you will be if you fail to get there, and what the most likely reason(s) is that cause you to fail.