On the why of adventuring and how I’m approaching my new direction in life

3 min readJan 22, 2024
road sign pointing in two different directions

I just read this line from

in his newsletter:

I slowly gained more awareness that these people were top-down thinkers, people that need to know the destination before they head out. I’m the opposite, a bottom-up thinker, and I actually enjoy not knowing how things are going to end up before I start something.

…and it really resonated with me.

Back in the nineties as I took up work as a systems administrator and worked through a college (but I think Ilearned more working for the university and volunteering with other students, than I did going to classes) education in liberal arts and computer science, I was continually digging into the assignments from the bottom up: JUST START CODING!! This led to a lot of unfinished projects, but also was regularly a lot more fun than the commonly accepted “right” way of creating a top-down thoroughly outlined plan before writing a single line of code.

On the other hand, the complex project which went “the best” by conventional standards was one I did with my friend

who was a very methodical thinker. He practically forced me to sit down at a whiteboard for more than one session to plan out our complex, multithreaded project (the assignment was to use threads for a complex simulation), and while I may be misremembering a little bit, as far as I can recall, once we got to code, our project basically worked on the first try, while other students found theirs deadlocking and undebuggable.

Still, I’ve always felt more like a “scruffy” (“do it quickly, create a draft attempt / minimum viable project, and then see if you need more”) than a “neat” (“do it right and thoroughly from the start”). I guess I learned about those terms from some of my dabbling in AI (which was somewhat theoretical and far off from where the “industry” is today), and wikipedia has a history of those terms in that context in case my explanation doesn’t resonate or make sense to you: https://en.wikipedia.org/wiki/Neats_and_scruffies

Now, on this soul-searching adventure, I am more interested in figuring it out as I go than having an overarching plan. I suppose you could view the plan such as it exists for my trip as top-down, I see it more as a framework from which to adapt to whatever seems interesting as I go. The forethought I’m doing is more around long-term logistics (do I have enough money? the right gear? Am I considering the weather appropriately?) than exactly where I’ll travel to each day. It does focus a LOT on incorporating what matters to me — connections with my friends along the way and ensuring that my parter is part of the journey as much as she can be within her constraints — and less about “I’ll do an average of 63 miles per day and arrive in Atlanta on exactly the 14th of May at 3:27pm” (though now that I wrote that, it will be a giggle to judge my actual arrival in Atlanta against that completely arbitrary datestamp).

So, thanks again for coming on this adventure with me as much as it interests you. But also, thanks in advance for sharing in response what resonates and whatever “and then!?” moments you have, which you think I might be interested in, inspired by, or even just adjacent to. One skill I developed in my 30 years or so of perusing system logs and too many details from computers and customers is a sort of speed-readiung filter, so please don’t worry that your suggestion or mention of something that “maybe fool will find relevant” is a distraction — I promise that it won’t be too much to process! And, I do really look forward to the happy accidents that are inspired by an overlap, virtual or physical, with my communities and the ones I’ll pass through and nearby.




I’m just a guy who likes stuff, like riding bikes, facilitating joy, building community & the culture of customer support,