You'll never be ready for anything that matters

The author describes making a series of major changes in 2022 while unprepared: he was an alcoholic, had a newborn baby, was running a startup, and decided to ride a bicycle from San Francisco to Los Angeles for AIDS/Lifecycle. He says the decision was selfish, thanks Chelsea for supporting him, and explains that he needed to change himself rather than wait to feel ready.

He says he was not ready to be sober, to be a father, to start a company, or to ride the bike. He also admits he rode the first 100 miles with two flat tires because he thought all tubes needed exactly 12 PSI.

Reading notes

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• In 2022, he took on sobriety, fatherhood, startup work, and a long charity ride while not feeling prepared for any of them.
• He presents the bike ride as a commitment that made little sense at the time, even if the charity itself was good.
• He credits Chelsea with supporting his ambitions and forgiving his mistakes.
• He frames the choice as a way to force personal change instead of waiting for readiness.
• He ends by saying people will never be ready for such things and should do them anyway.