5-year gestalt

last updated 2021-06-26

I'm starting to write this page on my 30th birthday. Normally I don't think much of birthdays, least of all my own. But lately, I've found myself daydreaming about the future. Maybe in part due to this feeling of emergence from the pandemic's isolation, or maybe it's something that happens to everyone at the three decade mark? Either way, my younger brother Malcolm asked me a few weeks ago "Do you have any tips or examples for making a 5-year plan?" to which I replied "A 5 year plan of what? Business? Personal?" to which HE settled the matter with "Personal." The answer is: not really - aside from work 5-year spreadsheet proforma stuff, I have managed to keep planning to light {^start-of-year thematic} stuff. In the past, I've avoided heavy goals or tracking. For example I have no idea how far or fast I run; as long as it feels good, right on (although I do plan to try tracking a few things starting today, using my thirtieth as a year-0 of sorts). But this moment (this one right *snap* now) does provide a fertile opportunity for introspection. I plan to share my findings with Alejandra, my brother, and some close friends to compare notes.

So what belongs in a 5-year plan? First let's call it something else, because to think that one can sit down and devise a "plan" for the next 5 years is total crap. Leaning on the aforementioned concept of yearly themes being better than resolutions, I think the best we can hope for in planning at such a horizon is describing the gestalt of the next demi-decade. Is that too pretentious a word? Great. There are four sections that I think belong in a 5-year gestalt:

  1. Relationships: who you want to be to others, who you want to spend time with, and how you want to grow with your friends and family;
  2. Craft: what is your craft and how might that change in the future;
  3. Experiments: what experiments do you want to run, be they personal, professional, or existing outside of those realms; and
  4. Place: where you want to be, and what that placement means for 1, 2 and 3.

* The below sections are in progress *


Gosh, what a section to start with. Alejandra and I are betrothed (!) and plan to marry at Boston City Hall this autumn. We'll have a party next year. We want to have kids in the next 5 years! My most significant relationship aside, I want to have a theme of communiqué, both written by phone, with a broader circle. I currently regularly call my family and closest friends, but there are a number of folks I hope to keep close in spite of life's drift.


A lot of the daydreaming I've mentioned is meditation on what aspects of my work (both "real work" and my hobbies and {projects}) are most engaging and what about those aspects keep me creatively energized.

I suppose 5 years ago was the start of {Upstream Tech}. If my next 5 years can be as productive and "successful" (whatever that vague measure means), I'll be glad. I've been fortunate that the past 5 years of work have brought a variety pack of different roles and responsibilities. That miscellany has been valuable in starting to understand the kinds of work, from minutiae to big picture stuff, is most rewarding, and therefore what my craft, in the lifelong sense, could be.

I'd like to learn crafts that use my hands and reduce my dependency on external systems and systems that produce waste. Sewing, gardening, carpentry and "handiness", bike maintenance, and fermentation to name a few. I've dabbled in some of these, and would like to deepen my knowledge.

In terms of my work, I'd love to find ways to incorporate tools and systems that I myself might use. Upstream's subject matter is one of personal resonance, but the technologies we build are difficult for me to find excuses to use myself. I find that when I am building something that I can use, I am more creative, have a inexhaustible energy, and derive more day-to-day satisfaction. So to that end, I hope to have a theme of technological self-sufficiency or self-use to some degree. Building a few of my own tools and building technology that I myself use passionately.



The past five years, I haven't measured a run or taken note of climbing progress. I mostly just try hard and make sure it feels good. There have been brief stings of daily journaling, and Quinault and I got pretty into planning out climbing workouts around 2016/2017 when we were living together. But those have taken more the form of to do lists (a la intentions) rather than progress tracking. I've also done a poor job tracking the kinds of work and output I have on a given day, so I don't have much data to look back on to analyze. In retrospect, be it for exercise, creative pursuits, or work that kind of information would have been invaluable for a 5-year gestalt exercise.

This is to say I hope to start tracking:


I've found myself focusing a bit too much on future potential places to live over the past few years, which have prevented me from ::living in the moment, man::. When I lived in the city, I was obsessed with being closer to natural space and having room to grow food. Living in the liminal space between city and forest (aka the suburbs), I now want both a city and to live in the middle of nowhere. Helpful.

But in thinking about where to go, and telling friends and family about potential spots, it's become clear that the where doesn't matter, it's really about the who else you could convince to be there with you. If I could redo my early 20s, I would try to make some manner of blood pact with my closest friends to live in adjacent living situations (or at least the same cities) for longer. It's amazing how quickly jobs pull a thick social web askew.

Luckily for me, I've proven to myself that place is not dependent on work, and work is not dependent on place. The two are decoupled, whether I'm practicing my craft alone, growing a team, or joining another. My main criteria when I'm thinking about where to live are:

  1. ample natural space full of water, trees, trails, paths
  2. an artistic and intellectual community (having a nearby college or university helps)
  3. access to train and air travel
  4. low-to-medium cost of living
  5. resilient to climate-change
So I do forsee moving at some point in the next 5 years, probably closer to the end, but it's really about figuring out who between family and close friends will be where and who can be convinced to be there too.

⇣ (2)

Alejandra and I took the day off today from work. Unfortunately it's a scorcher - topping out at 98 degrees (although far short of what my pals in the Northwest have been dealt). It's a good opportunity to continue thinking about the {5-year gestalt}, catch up on personal correspondence, and run some errands before work all-consumes this week.

  • Intentions

  • finish {5-year gestalt}