The great external achievements of my life have been my family, my friends, and my fortune. I never became famous or won any great prizes, so I can’t give advice on those types of goals.
These stories are about what it takes to be successful as seen by others, and to enjoy the process. It’s called working hard and playing hard.
They come in three groups. Money is about making it, investing it, losing it, spending it, and knowing when you have enough. I went bankrupt before I got rich, so there’s advice here on both. Productivity is about getting things done: procrastination, email, being on time, keeping your word, making decisions, and what to do when a business you thought was running itself suddenly isn’t. Relationships is about family, friends, strangers and the people you work with, including how to find great ones and when to let the wrong ones go.
Some of the stories are about the consequences of success, things to watch out for, rather than how to get there. Think of them as how to avoid failure, which I believe is just as important as how to achieve success.
Money
- Win at Life By Understanding Asymmetric Risk “You win some, you lose some” is for losers
- How to Make Big Money Without Taking Big Risks You have to spend money to make money, but you don’t have to spend it all at once
- The Real Meaning of Persistence: Getting Better At Quitting You have to fail to succeed, and that’s the way it’s supposed to be
- Share This Article With Anybody Who Owes You Money People don’t get mad because you don’t pay them back, they get mad because…
- How to Make Money Investing In Startups What Naval Ravikant and other top investors already know about investing in tech startups and getting rich
- My Best Startup Investment: A Peek Inside Y-Combinator Dumb luck can be an investment strategy
- The Biggest Financial Mistake I Ever Made Make all your mistakes at once, I always say
- You Can Be Wealthy Right Now Self-promotion is all about choosing what to emphasize, not outright deceit — usually
- Spending isn’t How You Go Bankrupt
- My Quest to Get the Coveted American Express Black Centurion Card Oh, to hear the satisfying clank of status
- More is the Enemy of Enough Quit while you still have a head, I always say
Productivity
- Avoid Procrastination by Breaking Down Daunting Problems Procrastination is just psychology ganging up on you like a bunch of mean cheerleaders
- Dealing with Your Email Inbox What it taught me about managing my email inbox
- Stop Being Habitually Late How I learned to take (and give) a good old slap up side the head to a colleague
- Doing What You Say You’re Going To Do Is a Superpower The trick is to match your promises to reality
- Start With the End in Mind Terrified of public speaking? There’s an easy hack to make sure you say something others appreciate
- Look to the Past to Get Inspiration for the Future
- Don’t Listen to Bullshit Advice Because it Sounds Good When I was a kid, my mother would scare me with viscerally terrifying warnings.
- Make Better Decisions with 5 Unique Rules of Thumb You might want to skip this one if you’re a cat lover
- Moving from Engagementstan to the Republic of Gettingshitdone Not sure if this is a vacation, a sabbatical, or a permanent exile
- An Espresso Martini Won’t Solve All Your Problems — But Two Might These are the times my mother warned me about
Relationships
- My Mother Is Trying to Kill Me A continuous glucose monitoring murder mystery
- From Man Cave to Dad Save: The Sweet Solution to Sibling Rivalry It’s not about the candy, it’s about winning and losing
- What Tom Brady and My Son Can Teach You About Success — It’s Not About What You Do What the gurus never mention about swimming with the big fish
- Why You Should Bribe Your Friends and Family To Watch the Super Bowl The key to happiness is surrounding yourself with people who like the same things you do, like sports and cake
- I Finally Read Tuesdays With Morrie and I Don’t Get It What is life’s greatest lesson, did I miss it?
- On Not Knowing What to Say I’m not proud of how I’ve reacted during times of pain and conflict
- On Not Being the Fool in a Conversation Politics just isn’t a safe space
- This is Why You Shouldn’t Talk to Strangers A chance encounter in a tire dealership
- Why Do People Play Pickleball? Some choices are sexier than others
- Vegetarians are Evil (and Other Hard to Digest Truths) It feels so good to get this off my chest. I hope you don’t choke on it.
- 3 Rules to Get Away with Anything Actual tips to help you never get caught in another lie, that don’t involve telling the whole truth
- I Was a Guy Pretending To Be a Girl, Pretending To Be a Girl This is going to get a little weird
- Unlock Your Hidden Potential With Your Hidden Network When the aspirant is ready, the network will appear
- 5 Ways to Recognize the Best Person for the Job Learn how to make spotting greatness your superpower
- People Adore Simon Cowell Because He’s Not Afraid To Tell Them To Go to Hell And they’ll like you more if you do the same. That’s because dissension can be a force for good
- Surrounding Yourself with Great People Starts with One Hard Thing Cutting out the wrong ones