I'd imagine these weren't the only opportunities that presented themselves to you.
How did you choose which threads to pull and which to leave alone?
How did you know when to give up on things like Prolific or SEO?
I'm at a stage in life where a whole host of interesting, ego-stroking, curiosity-inducing, and financially fulfilling opportunities are coming my way. But I'm having trouble triaging what I should take and what is just resistance in disguise.
love this question - my favorite heuristic here is like a future-casting intuition : what will make the best story? What will help you come alive?
Practically speaking - you could get scientific, too -- read up on some design thinking methodologies (Burnett and Evans are good enough), and run some prototype experiments :) I don't think these are the kinds of decisions you can make in the abstract. you've got to get your hands dirty to know if you want to play/invest in Garden Bed X or Shit-field Y :)
Sounds like serendipity intersecting with curiosity and opportunity. To your awesome benefit….
I admire the photo. It seems to be a perfect visual representation of what someone told me many years ago would be his ideal retirement project: hole-in-the-wall beach bar. Is this an actual photo of a place like that? If so, where is it located?
Having watched Nat's online journey the past decade or so, I suspect he has a really strong intuitive mindset. Whether that's learned or innate, I'm not sure. But in general he's a learner and a tinkerer and let's curiosity take him in all kinds of directions. In a sense, this tinkering manifests as mini-experiments. He then has a strong intuitive sense of product-market fit and has the confidence and diverse skillsets to move very aggressively when he senses traction. At least that's what I've observed from afar.
If we assume this can be a learned skill, I'd recommend reading "Optionality" by Richard Meadows.
The whole idea that exploration justifies itself after the fact is so real—you don’t need a perfect reason upfront, just curiosity and momentum.
I’m wondering—do you think this whole “failed thing leads to better unexpected thing” pattern is just how doing interesting work works, or is it more about how certain people see their work? Like, if someone else had made Prolific and it flopped, they might just write it off as a waste. So the ability to "sell sawdust" or at least see it as something sellable seems to be a very useful, cultivatable skills!
The balance between Exploration & Exploitation is essential (some thoughts here https://www.strategicstructures.com/?p=1583), and it appears at all scales: ants foraging (there is even an agent-based simulation for that), any resource allocation strategy, markets, companies (slow learners, J March) and clear in the Viable System Model (S4, here and now vs S4, then-and-there tension); reinforcement learning now used in most LLM, mostly in Claude and DeepSeek) and so on.
I'd imagine these weren't the only opportunities that presented themselves to you.
How did you choose which threads to pull and which to leave alone?
How did you know when to give up on things like Prolific or SEO?
I'm at a stage in life where a whole host of interesting, ego-stroking, curiosity-inducing, and financially fulfilling opportunities are coming my way. But I'm having trouble triaging what I should take and what is just resistance in disguise.
honestly I have no idea, I have no system for this, the best answer I can give is "intuition"
Opportunities without an audience account for nothing.
love this question - my favorite heuristic here is like a future-casting intuition : what will make the best story? What will help you come alive?
Practically speaking - you could get scientific, too -- read up on some design thinking methodologies (Burnett and Evans are good enough), and run some prototype experiments :) I don't think these are the kinds of decisions you can make in the abstract. you've got to get your hands dirty to know if you want to play/invest in Garden Bed X or Shit-field Y :)
Sounds like serendipity intersecting with curiosity and opportunity. To your awesome benefit….
I admire the photo. It seems to be a perfect visual representation of what someone told me many years ago would be his ideal retirement project: hole-in-the-wall beach bar. Is this an actual photo of a place like that? If so, where is it located?
and before cameras, nintendo started as a playing-card company back in 1889... waiting for the Musashi episode :')
Having watched Nat's online journey the past decade or so, I suspect he has a really strong intuitive mindset. Whether that's learned or innate, I'm not sure. But in general he's a learner and a tinkerer and let's curiosity take him in all kinds of directions. In a sense, this tinkering manifests as mini-experiments. He then has a strong intuitive sense of product-market fit and has the confidence and diverse skillsets to move very aggressively when he senses traction. At least that's what I've observed from afar.
If we assume this can be a learned skill, I'd recommend reading "Optionality" by Richard Meadows.
https://amzn.to/42R8yQX
The whole idea that exploration justifies itself after the fact is so real—you don’t need a perfect reason upfront, just curiosity and momentum.
I’m wondering—do you think this whole “failed thing leads to better unexpected thing” pattern is just how doing interesting work works, or is it more about how certain people see their work? Like, if someone else had made Prolific and it flopped, they might just write it off as a waste. So the ability to "sell sawdust" or at least see it as something sellable seems to be a very useful, cultivatable skills!
The balance between Exploration & Exploitation is essential (some thoughts here https://www.strategicstructures.com/?p=1583), and it appears at all scales: ants foraging (there is even an agent-based simulation for that), any resource allocation strategy, markets, companies (slow learners, J March) and clear in the Viable System Model (S4, here and now vs S4, then-and-there tension); reinforcement learning now used in most LLM, mostly in Claude and DeepSeek) and so on.