539: Jack Raines - Playing Infinite Games, Living Life Backwards, Building Your Platform, Traveling More, & Writing Young Money

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Aug 6, 2023

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Jack Raines

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ADVICE

Do Time-Sensitive Things Now

Think about what you'll regret on your deathbed and prioritize experiences now when risk is low.
Use life seasons to schedule high-opportunity actions like travel while you're unencumbered.

INSIGHT

People Hate Bad Work, Not Offices

Younger workers don't inherently dislike offices; they dislike meaningless work and forced presence.
When an office enables real collaboration and purposeful work, people prefer being there.

ADVICE

Write To Clarify Thinking

Write to clarify thoughts because ideas stay vague in your head until you put them on the page.
Edit ruthlessly to remove fluff and reveal the core idea.

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Jack Raines is a student at Columbia Business School and the writer of YoungMoney.co – Young Money is a finance blog that covers a wide variety of life topics like why we should travel more, timeless advice, the use of humor, the 6 types of wealth, and infinite games. Jack is one of my favorite writers on the internet…

Infinite Games – "The focus on outcome over everything leads to us discounting 99% of our lives for the sake of a few, small, fleeting moments that might provide some sense of satisfaction before the cycle begins anew."
- It's not about getting to the top of the mountain, it's about the person you become along the way.
Why We Should Travel More – Rolf Potts, Vagabonding. "The explorer has no goal other than exploration itself."
The Opportunity Cost of Everything – The Journey IS the Destination. Life isn't a Pixar film. It's not a television series. Our life isn't some chain of events and decisions that leads to a climax. A final moment of victory. Life is the chain of events itself.
- "Someday isn't a day."
The purpose of Jack's finance blog: "I write a finance blog that is really, like, idk? Maybe 40% finance? The rest is existential musings, satire, the occasional exclamation that Americans seriously need to travel more, and whatever random stuff comes through my brain."
Jack's LinkedIn satirical posts: "I take nothing seriously, but I do take the serious things pretty seriously. Linkedin isn't one of the serious things."
How Jack built a large following online: "I have published approximately 450,000 words of content in an 18-month period." Whatever it is that we want to do, in order to get good, we have to get going. We have to get the reps…
The Case for Living Life Backwards – "You should write your obituary, and then try to figure out how to live up to it."