Retirement

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. […]

Most of us take the safe road. We go to college, get a job, and spend the next 30 years hoping our employer doesn’t one day decide we’re suddenly redundant. I know this path well because I walked it for 13 years before I finally worked up the nerve to do my own thing in

I get investments wrong all the time. Losing money is part of the process to financial independence. But after I FIRE’d in 2012, the math changed. With no paycheck to bail me out, I could no longer afford big mistakes. This post will help you think about life after FIRE, and share why it’s critical

When you were a kid, did you ever dream of growing up to be someone’s exit liquidity? Probably not. But every time you buy shares in a company IPO, that’s exactly what you become. Whether being an early investor’s exit liquidity is good or bad is hard to say in the short run. In the

I recently received a great comment on my post, Why All Rich People I Know Still Have Life Insurance. It was the last line that stood out. Here’s what Marc had to say. I had life insurance ($1M) through my employer back when I worked full time, but since I cut back to ~10 hours per

At a poker game recently, I heard one of the saddest things I’ve encountered in a while: “$10 million is not enough to retire early.” Mind you, we were all sitting in San Francisco, an expensive city, but also one of the cheapest international cities in the world. So I get it, context matters. But

I’ve been playing poker for over 25 years, and I still love the game. Every time I sit down at a table, it feels like a time warp. Three hours can pass in the blink of an eye. The cards, the psychology, the rhythm of betting, and the social interaction all combine into something that’s

The problem with writing about FIRE since 2009 is that I’ve become completely sold on the lifestyle. I know how good freedom feels, so I have a natural tendency to want everyone to achieve it too. I’m also aware I can come across as annoying when I talk about FIRE, so I try to throttle

As I approach 50 in mid-2027, I’ve been thinking a lot more about responsibility, legacy, and mortality. What I’ve realized is that responsible adulting is hard. One misstep and you or your loved ones could be screwed for life. Ultimately, life is a series of financial quests for survival before we die. If we don’t

The decade-long advice to “learn to code” is losing its edge. With tools like Claude Code handling the heavy lifting, a basic three-month online course may be all anyone needs to build what they can imagine. The more important skill is investing. If you learn to invest, you can build lasting wealth and bypass the gatekeepers