Hi Reader, Happy Hanukkah, Merry Christmas and I hope you're all getting a two week "unplug." I want to thank you all for your support over the past *checks notes* decades! It is a real gift to be able to share these ideas with you and grow as individuals, together. I'm truly grateful. Thank you. And if 2025 is the year you're going to make a bold career pivot, I'd love to be your co-pilot. We're filling out our upcoming group coaching cohort and will be hosting a free information session on January 9th.
Here are this week's top reads: // oneA rule for lifestyle creep: live beneath your assets6 minutes | Money with KatieTLDR, it’s Total Annual Spending = [ (4% of liquid net worth) + income ] / 2. Spending rules always seemed too 1-dimensional, either as a % of assets or income. But when there’s a huge spread between the two (as in our case) what’s a good rule of thumb? // twoWhen ‘middle age’ arrives in your 20s5 minutes | Wall Street Journal“20% of younger people ages 25 to 34 feel middle-aged.” Wait, wutttt? What if middle age is just a recalibration of expectations — which, technically, is age agnostic. // threeAre you overreacting?9 minutes | The New YorkerAre we drowning in a world that demands a reaction to everything? From YouTube commentators to political outrage, our days are chained together by endless provocations. Perhaps true freedom isn't about unplugging entirely, but learning to react authentically rather than as part of the reactive mass. Stories from my lifeI recently pulled up a chart of the S&P 500 since I began investing 25 years ago. Am I lucky? Hell yeah. But when it comes to investing, it's easy to talk about things with the benefit of hindsight. Someone pointed out my relative good fortune: Here's what I remember: it was 2009 and I was looking at my principal invested (around $200k) and seeing that I hadn't made any investment returns in 9 years. In fact, many of my Gen X peers got out of the market at that time (remember, the S&P was down 50%) and have tried timing their re-entry points ever since. It hasn't been pretty for them. My strategy has been simple: the best decision is a non-decision. Lucky? For sure. But this is a game where time usually works to your advantage. This Week on The Examined Life PodcastThis week's episode: Should you move out of the US? Below the Fold
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One of the cardinal rules of investing is: If it’s too good to be true — it probably is. When it comes to AI, I don’t think it falls in the “too good to be true” category. Yet. But it’s damn good. And I use it all the time. Yet I don’t want to be blind and naive about its limitations. And while I want to understand what is happening under the hood — I have no appetite for the super technical details. Andrej Karpathy was on the founding team of OpenAI and has the most incredible video primer...
Hey Reader, We made it back stateside after an incredible trip to Japan. Lisa and I even managed to squeeze in an Omakase date night in Tokyo. Here's one of our last pics from a swanky rooftop bar. I'm starting a small mastermind for finance professionals looking to master AI. Learn more about the program below ⤵️ Apply for the Mastermind → Here are this week's top reads: // one What happens when you leave your career (and identity) behind 20 minutes | Andy Johns Substack Occasionally, I...
Hey Reader, Greetings from Japan. We're fully immersed in yakitori, micro pig cafes, Zen gardens and 7-11 pork buns. It's awesome. I've also been writing two posts a week on AI developments over at Future-Proof Your Career with AI. It's totally free, check it out (it's a separate newsletter). Sign up for free → Here are this week's top reads: // one You should be setting rejection goals 10 minutes | Vox What would life look like if we didn’t take rejection so damn personally. Our fear of...