How to Be Free | Letter to a Friend #13

Hey friend,

Currently posted up with a friend at a rest stop in a box truck in the middle of a thunderstorm in Pennsylvania. Drove from Boston to NYC yesterday and making it all the way (hopefully) to Chicago today. Up since 5, probably going til midnight at least as the truck is having intermittent problems (like going 30 mph instead of 60 on inclines). Flying out of Chicago tomorrow morning back to Hawai`i.
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We are listening to the Elon Musk biography which I first read at around 17 and consistently credit with seeding my ambition to live an "extraordinary" life. Basically, it was this book that really made it clear to me how much shit you can do, and how most of the rules which we imagine prevent us from pursuing certain paths do not actually exist.
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IMO, the primary "rule" that actually guides these beliefs is a fear of failing publicly, and the best way to overcome this fear is to subject yourself to it. This is why I value this newsletter and the Youtube videos so much: They put me out in public and make me progressively more comfortable (i.e. indifferent) to what other people think. I feel I am slowly earning my freedom from fear of public embarrassment with every piece of content I create, particularly those that are more personal/vulnerable.
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​If I am fine with someone hearing about my daddy issues, publicly failing in a business venture suddenly isn't so bad. As this fear of public failure lessens, the number of opportunities I pursue and risks I take grows and my life becomes more exciting and fulfilling.
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My goal is to continuously reduce the time between idea and execution. Many people might have great ideas, be it for a business or a crazy fun adventure, but the time from idea to execution is infinity (i.e. they never act on it). Ask any successful person and they will tell you the key is to simply keep taking swings, to keep executing.
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So this is my goal for the summer: To say yes and take as many swings as I can, be it pursuing businesses, people, adventures, or anything else. Who knows how many will hit, but I will never know unless I try, and if I miss I'll be in the same position as I am now.
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As always, I invite you to do a lil reflection and consider what swings you can take that you might be afraid of. The worst case is usually never as bad as you imagine, and the upside might be greater than you could ever hope for.
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Happy failures!
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Much love,
Ryan

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