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    #106 Pick your freedom battles

    Most people don’t really want the freedom to do anything they want, in other words, a life without constraints.

    They want the freedom to set their own constraints.

    To decide, “I want to spend my time writing,” instead of saying, “I am supposed to become a lawyer because that’s what we do in this family.”

    To decide, “I don’t drink alcohol,” instead of saying, “My social circle forces me to have a glass when I’m out.”

    To decide, “I want to live in that house, drive that car, and go on that exotic holiday, and I’m going to make it happen,” instead of saying, “I’m constrained by my talent, potential, current job, or where I grew up.”

    To decide, “I have time to learn a new language because it’s important to me,” instead of saying, “I’m too busy, I can’t (or don’t deserve to) do anything nice for myself.”

    Good or bad, beneficial or misguided, constraints are always there.

    Because life constantly forces you to make decisions, and every decision leads to a new constraint.

    Since it’s challenging to be aware of your decisions and their long-term constraining effects, which constraints do you consider important enough to set consciously (and spend considerable time and effort doing so)?

    Where do you allow others to dictate the constraints you live within?

    Who do you allow to dictate the constraints you live within?

    Pick your freedom battles.

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    #227 Could a changed past set me free?

    Which conclusions did I draw from past experiences?

    Have I overreacted to petty events, and ignored beautiful moments?

    Have I deleted memories? Maybe invented some?

    Have I built stories based on generalizations?

    Most importantly: how does the past I still feel affect my actions today?

    And if I know a lot of it was my own interpretation… could I change my past, or at least what it means to me?

    Would that set me free?


    I was undoubtedly in a pensive mood when writing this.

    I guess, given the daily letters I send you, you might conclude I’m in a pensive mood every day.

    And you wouldn’t be wrong.

    But pensive moods can be useful – when they’re coupled with conclusions and insights. Maybe even with Tiny Trust Builders.

    And if any of these questions help you re-interpret your past and set you free, too, I’ll be a happy man.

    A wistful win-win.

  • #319 Starting silly small

    Start small.

    Very small.

    So small, it might feel silly at first.

    For example, if you’ve committed to writing every day, don’t start by aiming to write a thousand words. Start with something you can absolutely, positively achieve.

    Maybe that’s writing one sentence. Maybe it’s opening your notebook. Maybe it’s just holding a pen!

    Your goal isn’t to produce fantastic prose, but simply to show up and write something.

    After all, before it can be about the content, it must be about the consistency.

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