On February 12th, 2020, I boarded a flight from London to my childhood home in Puerto Rico. My partner and I had sold almost everything we owned (not much) and had an empty schedule ahead of us. It would be 6-9 months of exploration after a decade of standard career development.
What I learned over the next year and a half was invaluable. The experiences, although mundane, changed the course of my life and have allowed me to connect with a new form of ambition: unhinged curiosity.
My partner and I had discussed the concept of a sabbatical over many years. I think it appealed to us through the lens of carefully curated Instagram aesthetics - beautiful landscapes and no worries. This, of course, was a facade of escapism.
We had delayed going on sabbatical for almost two years. Each of us would have a reason to wait: a promotion, a bonus, some important event. Eventually, in late 2019, we set the plans in motion. Looking back, there were a lot of fears driving our procrastination. The top ones, which I remember clearly, were around stalled career progression, decreased retirement savings, and just overall putting “life” on hold. All of these are clearly standard scripts and could be viewed as corporate propaganda.
Turns out that no one I spoke to ever regretted time off, or seemed financially or professionally impacted by the time off. So, at least anecdotally, my fears didn’t seem to have any basis in reality. It’s been about two years, and I can confirm that my experience was similar. My financials are better, my health is better, my life is better.
This weekend, AbstractFairy tweeted about levels of ambition and I immediately realized that I had undergone a profound change that I hadn’t been able to articulate. Specifically, prior to the sabbatical, I had Ambition Level 1, and then now I had Ambition Level 2.
Could I describe what actually happened?
The combination of the experiences during the sabbatical awakened in me a sense of unhinged curiosity, which is well articulated by AbstractFairy’s tweet: “fuck the money, we here to do what has not been done before, to build greatness (the bottleneck is imagination and skill, not money)”.
When I had originally thought about curiosity, many years ago, I had always tied it to asking questions and finding answers. Now, I think of it as much more: curiosity is an orientation of the world, not an activity or personality type.
Similar to Ender saying “the enemy’s gate is down”, curiosity is “the world is here to be explored”. By awakening curiosity, I changed the game. It was no longer a rat race, it became an open world MMORPG.
This newfound orientation of the world came in three mutually interacting phases: Deload, Reorient, Build.
Today, I find it absolutely insane that the average American only takes 2 weeks of vacation a year. European’s fare a bit better, with most countries having 20-30+ days off per year. If we are meant to prevent burnout, how much time does it actually take to reset? How much time does it take to deload from ongoing work stress?
First off, let’s unpack this concept of “deloading”. I can describe it now, since I’ve experienced it, but wouldn’t have been able to prior to the sabbatical. This is an oversimplification for contrast:
For me, this process took an intentionally open calendar for 3 to 4 months, supported by COVID curfew and restrictions. I’m not sure exactly when the full adjustment happened, as it’s a bit of a progressive experience. By the end of May, a deload mindset dominated my life. Here’s a rough calendar of the progression:
It’s important to note here that there wasn’t anything “special” happening. Or a better framing, the specialness was the nothingness. I remember looking at myself in the mirror “I don’t have bags under my eyes wtf”. My partner commented, “I don’t think I’ve felt this rested since before high-school”. We are in our mid-thirties for context.
It was a bit odd, with everyone in the world focused on COVID, no one really was pressuring me to “get back to work”. I started getting a new sense of anxiety around the second month, driven by boredom. As my own worst critic, I kept thinking “I need to do something don’t I?”. However, one of the people I had connected with had warned me: “Get comfortable being bored and make sure you push through it.” And so, I did.
While waiting for my boredom to subside, and not being aware of my current state of deload, I started looking around for something to do. I started a few books (which I quickly abandoned) and then noticed how the house was full of things, made by people. This was the first instance of conscious curiosity. I remember asking: “I wonder what’s the Island’s history regarding artisanal work”. It turned out that I had forgotten my curiosity. It had been mostly replaced over the years by algorithmic suggestions of interests.
Being bored had reset my forgotten conscious curiosity. My natural interests started to surface again. It was only within boredom that curiosity showed up. At first, it was not very refined (“what would a run feel like today?” “why is this picture fading?”). Over the course of about a month, the questions became more complex.
The complexity of the curiosity was the trigger for a re-orientation of how I saw the world. Whereas the initial question I had regarding artisans prompted a book buying-spree, more complex questions started changing my behaviors.
There was a particular moment in late May or early June that serves as an example:
I was reading a coffee table book on artisans, looking at gorgeous photographs. Each photograph was the size of a full page or more and accompanied by descriptions of the artisans. The crafts were unmistakably embedded with soul. I was reading the names of the artisans and thought “I wish I could speak to them”. And in that boredom, in that space of imagination, I thought “I mean, why not?”.
It turned out, that I could. And if I could speak to them (which I’ve done many times since), I could help them. And if I could help them, I could shape the world to be a better place. I remember this epiphany: I could do. I can act within the world based on what I’m interested in. It was a rebirth of personal agency. How had I lived so long without understanding I could just reach out and touch the world? Maybe I had understood it and forgotten?
Prior to this, I had thought the different levels of ambition were concentric circles of awareness. I considered the levels a stepwise function: I must first want a career, then I will want enough money, and then, after I have all the money I need - I will be free.
What I realize now, is that this is the wrong framing. Each ambition level is a different orientation. Level 0, a job, is about “getting and keeping a job”. Level 1, “fuck-you money/wealth”, is about “getting and growing wealth”. Level 2, “we here to do what has not been done before”, is about “play your own game.”
The sabbatical, rather unexpectedly, had given me space and time to find out what games I’m naturally interested in. This, which can only happen by allowing your curiosity to lead, is not trivial - at all. I would be foolish to suggest it “just happens”. However, there are definitely things that I did that helped increase the chances of it happening - even if I didn’t know I was doing it:
By mid-June, I was pursuing what would become my two main games. The first was related to artisans and helping preserve local culture. The second was related to a long-term curiosity - organization design and internet subcultures. In both cases, I followed the same playbook:
I’m not sure what the cost of coordination would have been 50 years ago. Now, there’s something magical online. The friction to connect with others is so incredibly low. For example, I listened to a podcast with Venkat on organization design (March 2020?), found their blog (ribbonfarm.com), joined an online community experiment (yakcollective.org), and joined a regular reading group.
This bridge between consumption to participation took less than a week. I am still in awe at the availability of experts online. By speaking to the people I admired, I became conscious, like waking up for the first time in a long decade of career progression: “I can make my curiosity my career. I can make my curiosity my life.”
Now, two years later, Venkat wrote about the work I’ve been doing, in the same newsletter that had initially inspired me.
To make curiosity my career though, it took more than just an orientation. I needed the work to build over time and then transform into something I could get paid for. As they say, “hindsight is 2020” (pun intended).
Here’s what I learned:
Most people get stuck because they only focus on gathering niche knowledge and then get frustrated when that expert knowledge isn’t recognized or rewarded financially. It can be especially frustrating if you can’t make your passion your full-time job. At least for me, this was true for the entire initial decade of my career.
Over the last two years, I ended up learning that I needed three pieces to complete the puzzle:
The magic is not in the aggregation of information (collecting and reading books/links), it’s in the curation of the feeds and in the synthesis of common themes. Staying up to date is the wrong objective! Instead, focus on finding, reading and understanding the most influential pieces of work - and curate a feed of the highest quality work.
A few things that helped me: moving to a place with nature, playing video games without ads, limited internet.
I can’t stress enough though - this needs to happen AFTER long periods of uninterrupted leisure/nothingness. The magic of gathering information only shows up by connecting new curiosities to what you’ve learned over time.
“You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something - your gut, destiny, life, karma, whatever.”
In addition, it’s important to note that the volume of information doesn’t matter nearly as much as the methodology of gathering quality information. It’s not about “knowing”, it’s about crafting a reliable resource pool. What you want is not “know it all”. What you want is “I can likely find the answer to this topic because I know who to ask and where to look”.
I didn’t realize the importance of the second piece until much later. It turns out that curiosity isn’t satisfied by collecting knowledge, it’s rewarded by actually understanding the itch.
You can know the name of that bird in all the languages of the world, but when you're finished, you'll know absolutely nothing whatever about the bird. You'll only know about humans in different places, and what they call the bird.
Becoming a true expert has two benefits. First off, it satisfies curiosity in a way that I can’t put into words. Secondly, and importantly, it creates credibility. This credibility will be really useful later when you ask to get paid. With enough credibility, you don’t even have to ask to get paid - people will offer you payment.
How do you become an expert?
Well, I would suggest two steps (which happen in parallel):
A path of research is different than gathering information. Research requires two pieces: (a) creating a framework of thesis and (b) synthesizing what you now have learned into something you can communicate to others. Both are done by learning to write essays and sharing what you’ve learned with family, friends, and other peers.
Interacting with other experts is self-explanatory. You need to schedule lots of calls and send a lot of cold-emails / direct messages. The tricky part is that you need to get comfortable with your incompetence. We are often taught that our value is only based on the knowledge we can prove to others. This is false.
There is monumental value in shared interests. Don’t let anyone tell you otherwise. This is the reason why there’s a multi-billion dollar hobby industry. And so, the pitch to connect with other experts should appeal to the shared muse (curiosity!), not on a quid-pro-quo exchange.
Following this, I would recommend three parts to conversations:
I really think I had misunderstood the value of interacting with experts. I think pop culture and media portrayal of competency porn had just rotted my brain. The goal is not to be “productive”, it’s to join a network fueled by passion. You do this by sharing your passion, not by exchanging the latest research.
If you do these activities, you end up becoming an expert - not by trying to be an expert, but by allowing your curiosity to be fed (research) and shared (conversations). This is like an orthogonal activity set to an academic Ph.D. Your goal isn’t peer-reviewed publishing, it’s peer-supported adventuring.
“I’ve heard people compare the knowledge of a topic to a tree. If you don’t fully get it, it’s like a tree in your head with no trunk—and without a trunk, when you learn something new about the topic—a new branch or leaf of the tree—there’s nothing for it to hang onto, so it just falls away. By clearing out fog all the way to the bottom, I build a tree trunk in my head, and from then on, all new information can hold on, which makes that topic forever more interesting and productive to learn about. And what I usually find is that so many of the topics I’ve pegged as “boring” in my head are actually just foggy to me—like watching episode 17 of a great show, which would be boring if you didn’t have the tree trunk of the back story and characters in place.”
Source: Wait but Why
Morning pages helped a lot (although I did this after my curiosity had been recentered), where you force write first thing in the morning 1000 words. I did that for 60 straight days in months 5 and 6.
And yet, even the combination of quality information and an expert network isn’t enough. To truly build curiosity into a core piece of your life, you need to become a merchant. You need to be able to trade curiosity for financial reward.
It was during this exploration that I recognized the previous decade of work had not gone to waste - I had skills. I just hadn’t used them for me — I was using them for others. It was time to use my curiosity for others, and get paid for it.
This final piece is why so many passions lead to starving artists. You can’t be afraid of money, to charge for it, to use newfound knowledge to transform the world (this is totally not ironic, this is pretty serious btw).
In the age of the internet, this is solved in two ways:
I would argue this is the absolute hardest part of this entire journey. Connecting with your curiosity and maintaining it is hard, but this part is way harder. I’m still figuring out how to best do this, and I’m not sure I have a good playbook for either piece.
At the moment, I would recommend talking to someone who knows more about this piece than I do. I’ve ended up blogging as a way to package what I’ve learned and following a sort of amateur indie-consulting path. In theory, though, I can imagine how this might transform into an actual product (physical or software).
For the distribution part, I’ve been using Twitter, with some success. Most of my reputation has been developed through replies, DMs, and ongoing conversations. This is fragile though, especially because I have tied my success to a specific digital identity. I think, in a perfect world, I would want to sell my curiosity, not my identity.
I’ve mentioned multiple times how lucky I was to go through this process. It has not been easy, and I hope this walkthrough helps others. That being said, I have to reiterate that I’m not sure if this is the right model. I think it’s useful, but probably far from “right”. There are pieces I’m missing and I hope others might be able to share their own stories to fill in these gaps.
In many cases, it’s likely that following these steps won’t lead to any breakthrough. It takes more than space and exploration, it also takes a supportive community. In this adventure, I was constantly encouraged by my partner, tpot, and friends who served as unconscious role models.
I’m still deep within this journey. One thing is certain though -- I no longer feel restricted by the script of a career. I’ve deeply internalized that I’m happier (and wealthier) by channeling my curiosity into all aspects of my life.
I feel unhinged, and it’s wonderful.