Writing by Geoff Roberts.
For the past 8 years, my wife and I have spent six months out of every 24 months living abroad. Six months abroad, 18 months in San Diego—rinse and repeat. It's become one of the rhythms of our lives and is one of my favorite parts of my life. The idea here was always simple; if we kept up this routine, we'd end up taking more than 20 Trips of a Lifetime . Tomorrow, we leave the US again—but for…
My biases and personal values aside, here s my rational case against voting for Trump
In the week since Donald Trump was relected as President of the United States, Republicans have loudly celebrated the death of "wokeness." That may be true, but as I've analyzed the festering feelings inside of me I've come to realize that something far more problematic has risen in its place. The era of Fake Principled People is upon us. Fake principled people go to great lengths to convince you…
Has been taken over by fitness cyborgs
Today I: Woke up at sunrise in a beautiful place. Worked diligently for 6 hours. Answered support tickets while sitting in the sun on volcanic rock, with waves crashing around me. Drank two beers. Smoked a joint. Swam around with a sea turtle. Had a great meal. Actively missed my wife and kids. Felt immensely grateful for it all.
I believe that we should be less tolerant of assholes. Collectively, it would benefit us all. It's funny... I think most people go through an arc in life where they are fiestier and more combative when they are younger. As they get older, they let a lot more slide. In most cases this represents a person maturing. You realize you need to pick and choose your battles, and some battles you'll never…
I had breakfast this morning at Ground Zero—the park that now sits at the site of the attacks that occurred on 9/11. A bit hungover, I sit in silence taking the place in through squinted eyes and scalding hot coffee. Where the towers once stood there are now two large pools. Water falls into each, then further down into a smaller pool in the center of each of the larger pools. The water just drops…
My first impressions of suburban life in Sweden
I am the guy that doesn’t move the goalposts—I can promise you that. Like any founder, I have goals for Outseta —both personal goals and team goals. And I'll work more diligently, over an extended period of time, than almost anyone to meet them. But when I do, I’m on to a different game—I can promise you that. I see so many tech founders make $20M, only to focus on making $100M. They’re rats on a…
The technology world is going absolutely bonkers for AI at the moment. I get it—AI represents a technological innovation quite unlike any that I've seen before. Admittedly, I don't know that much about it. I haven't thrown myself into it by any means, but I've certainly explored it a bit and I've taken the course that I usually do with emerging technologies... I've tried to consider the…
The endless barrage of goal setting frameworks, process improvements, and life optimizations are increasingly making people miserable
Most people who read anything that I post online know me via my start-up, Outseta . But outside of work a lot of my free time and energy goes into scheming... scheming up where my next adventure will take me! My wife and I have settled into a routine where we travel for 6 months out of every 24. We both love to travel but we now have twin 3-year old boys, so a fully nomadic lifestyle simply isn't…
There are times when I feel a swell of gratitude building up in me—so much so that it becomes all encompassing. It happened to me this morning, clearly triggered by a pristine morning, kids that were actually behaving themselves as they played happily on the beach, and the upcoming Thanksgiving holiday. As the rest of the world increasingly looks at many aspects of American culture with a critical…
Somewhere in the depths of Silicon Valley—not far from Sand Hill Road—there’s a Monday morning mastermind group of tech CEOs who practice poor corporate behavior. The sessions are led by a well known executive coach, who facilitates the discussion as each CEO updates their colleagues on their most recent conquests. “We exclusively hire Stanford MBAs now,” one CEO boasts. “We reduced churn by…
I recently tried to buy a beeper. I literally couldn’t find one that I could actually get service for. I looked high and low on eBay, mobile service providers, etc—no dice. Turns out the only people using beepers these days are nurses. Bummer. At first the thought was something of a novelty. Imagine you’re at dinner with a friend—you hear beep-beep-beep as they check the number to screen the…
There are lots of people who write beautifully about lifestyle design. But for all the insights these writers share, almost all of them begin sharing their wisdom on how to live a happy and fulfilling life only after they’ve become quite wealthy. “I made millions and it didn’t make me any happier,” is a common theme, followed closely thereafter by a nudge to work less, live in the present more,…