Retirement

In 2012, two months before my 35th birthday, I engineered my layoff from a 13-year career in investment banking. At the time, it felt like the riskiest thing I had ever done. Was I really going to blow up my career right as my earning power was about to compound? It did not seem wise.

Ever wonder why Honolulu, Hawaii has the highest median life expectancy of any city in America? Sunshine, moderate temperatures, walkability, and an unhurried pace do wonders for your mental and physical health. As a relatively low-stress guy who doesn’t have to commute to a day job to sit in meetings all day, every time I

A neighbor across the street from my rental texted me at 3:35pm on a Saturday to say something had been beeping inside my property all day and my tenants appeared to be gone. I e-mailed the tenants, drove over, heard the sound, let myself in, and found three smoke alarms stacked on the garage floor

On Tuesday, September 8, 2026, an Anthropic researcher named Jacob Coxon resigned after six weeks over safety concerns and wrote about why. He said the leading labs are “racing straight to self-improving superintelligence” and gambling with everybody’s lives. The people building AI, he wrote, earnestly believe it could kill us all by the end of

After publishing The Untold Burden Of Being Your Family’s Financial Provider, I got this comment from a reader named Brian: “I can identify with this post as I am the family CFO / CIO. I think you are WAY overcomplicating this. What is wrong with merely investing in VTI / VXUS and chill? My returns have

There are layers to freedom, and most of us only ever peel back two. The first layer is breaking free from your parents. Some people manage it the summer after high school. Others are still depending on dad to pay their new credit card charges at 37. The second layer is breaking free from work.

Recently, I shared a sample budget of a family of four earning $408,000 a year on Twitter, the amount third-party data deems necessary to feel comfortable in San Francisco. To be clear, this wasn’t my budget and it wasn’t a recommendation. It was an illustration of how fast a six-figure household income disappears once taxes, shelter,

I toured a $9 million house in Honolulu to better understand the luxury housing market. I love real estate, and visiting nice homes for sale is one of my favorite hobbies. My parents are 81 and 78 and live in Honolulu. Like many people their age, they have a few health issues, and I’d like

FIRE is ultimately about being set for life. You build a portfolio big enough to cover your expenses, and then your one job is to not blow it up. But here’s the tension worth talking more about. The moment you give up your paycheck, you also give up your single biggest wealth-building engine: active income.