Time, space and geography have collapsed, what we are doing right now would have seemed like a magical thing to somebody from just 20 years ago - Jim O’Shaughnessy
I keep thinking about The Great Reshuffle happening all around us:
Power decentralizing away from institutions
Proof of work replacing credentials
Geography no longer matters as much as it did
Legacy career paths are losing status and utility
Looking past all the political bullshit, these are exciting times! We’re experiencing a global realignment of talent, capital, and creativity.
With things accelerating so fast and all this unpredictability from one day to the next, I think it’s the perfect time to zoom out and be open to new experiences.
Or put more bluntly, FAFO.
New experiences & FAFO — that’s the theme of this weeks Sunday Serendipity…
I first realized things were changing when I read "The 4-Hour Work Week" by Tim Ferriss. I was miserable at my 9-5 corporate job, trying to figure out a way to escape and move to Spain.
In the book he talks about building online businesses, geo-arbitrage, and outsourcing work to virtual assistants. At the time, it was all so foreign to me. I had no idea how to implement most of what Tim was talking about. This was in 2018, pre-pandemic days, before the digital nomad boom.
Still the book opened my eyes to a whole new way of work. I could see the light, and I was curious to follow it. So I saved up enough money to last me for a year and moved to Barcelona. I don’t recommend this for everyone, but sometimes you can jump and the net appears.
After a year long sabbatical and having no idea what I wanted to do with my life, I stumbled into a remote sales position through my warm network and that was the catalyst for so much of what I do now. I didn’t really have a plan, but I was open to new experiences, and it changed my entire life trajectory.
Now I’ve been working online for six years and the world of remote work has become my native language. I went from building solar farms in the middle of nowhere to building out CRMs and Client Success systems for online businesses.

A couple generations ago, it was normal for people stayed at one company in one industry for 40 years until retiring. The next generation typically moved between companies, but within the same industry.
In our generation, during The Great Reshuffle, it’s common to switch industries, reinvent your career multiple times, and follow a non-linear path. This is why I like the idea of retiring often and zooming out to see if the path you’re on is really the path you want to continue down.
Instead of going to university and learning one specific skill to perform for the rest of your life, I think it will be common to take breaks between jobs and learn new skills.
Because we live in a non-linear world:
Instagram famously only had 13 employees when it sold to Facebook for $1 billion in 2012.
The internet and AI gives infinite leverage to anyone anywhere.
Company headcount is getting smaller while revenue continues to skyrocket.
So, how do you open yourself up to new experiences and ideas?
Find the others
One of the ways I’m dealing with the Great Reshuffle is I’ve been finding creators I resonate with and joining their communities.
Similar to
, I’m looking for the dope corners of the internet.I love what
is doing over at helping people navigate the next step in their journey through both online and offline community events.I’ve been a fan of
and his approach to work, so joined the Pathless Path community a while back.And last week I enrolled in
’s Sovereign Artist Program.Joining these niche communities is a great way to open yourself up to new ideas and experiences. It’s how I manufacture serendipity. Plus it’s a great way to just see what other people are doing and what kind of unconventional paths are out there.
Build in public
Another thing I've found useful is writing here on Substack.
I’ve noticed my gravitational pull for serendipity has increased. The more I’ve shared, the more opportunities and like-minded people have come into my orbit. About a month ago,
from reached out to ask me about my transition from engineering into remote work.Now we’ve been meeting regularly to collaborate on a course I’m building out to help others get through the Great Reshuffle.
The beauty of the Great Reshuffle is that the gatekeepers are gone and friction has been reduced. You can just do things. It doesn’t take as much up-front capital as it used to to take an idea to market and test it out.
In this Infinite Loops episode with
and , Jim describes his experience opening his first business in 1987. It took him months because nothing was digital, everything had to be done analog, in-person:You couldn't simply whip up an LLC. You had to go to the lawyers, meet with the lawyers, multiple times. Everything was very viscous, it was not easy, it was very difficult to actually form a company. Today, I could tap out something on my cell phone and we'd have an LLC all set up before the end of the day.
This is Moore’s Law in action. Welcome to the Great Reshuffle my friends.
Until next time,
<3 B
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I'm already looking forward to our next meeting. Sure, there's a lot we can worry about during the "Great Shift"––and rightfully so––but there's just as much opportunity when you're open to it. I feel lucky cause when you find people who keep you open, everything starts coming together.
Also, I clicked on the first hyperlink, and I was really hoping for "You gotta "fuck around to find out how [to cultivate serendipity]" line somewhere in here.
I agree with the idea of a great reshuffle. I also share some of your enthusiasm about changing career paths throughout life.
But I’d also question a couple of your points.
"Power decentralizing away from institutions." Is that so? Or is it even more centralized but toward new institutions?
"Geography no longer matters as much as it did." Maybe, for some of us who are the privileged few. But what about the Sub-Saharan African trying to cross the Mediterranean or the Latino migrating to the north? Geography has had an indelible mark on their existence.
What do you think? If you’re still in Barcelona, we can grab a coffee one day and continue the conversation.