11 Comments

Great article and I needed to hear this. The last few years have been very nice. I won't seek it out but it is good to have someone way shake you back to reality and offer the advice to not take your wins for granted.

Please check in on me often and maybe a slap across the face next time to make sure I am taking this advice all in.

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Agreed. Fantastic article that I will revisit often. I also find anything written by Morgan Housel helps keep me in check whether it be his blogs or his books. And I've also found https://moretothat.com/the-nothingness-of-money/ to be helpful. We are so fortunate to have Jack Raines, Morgan Housel and other great content providers help us through our financial battles.

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i wish I could easily forward this to every one of my clients - lot of them are tech professionals who won the lottery and instead of cashing out of most and being set, continue to buy more lottery tickets by holding onto the stock

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“But if you made a life-changing amount of money on a concentrated bet, it’s worth considering whether it makes sense to risk that now-life changing sum to make an additional, no-longer-life changing, amount.”

Brilliant — my key takeaway, and agree wholeheartedly

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Loved this. It can be really easy to think about investing risk from a purely financial perspective and forget about what those potential gains/losses actually mean for our daily lives.

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Hey, man!

I've been reading you almost since the beginning of your substack. I like how your language and writing style has evolved. good stuff!

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Great read. I will say, not having a significant allocation to crypto has never made me feel more dumb lol.

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Excellent!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

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INSIGHTFUL!

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If you haven't seen John Goodman in "The Gambler" on the "Position of F*ck You", it's worth a minute of your YouTube time. https://www.youtube.com/watch?v=xdfeXqHFmPI&rco=1

JL Collins has a lot to say about this topic as well.

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So smart! Great advice

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