5-year gestalt

last updated 2021-12-31

I'm started to write this page on my 30th birthday, and am returning and revising it now on the last day of 2021. I don't think much of new years or 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 "Do you have any tips or examples for making a 5-year plan?" to which I replied "A 5 year plan of what? Business?" He was in pursuit of a 5-year personal plan, and aside from 5-year spreadsheet proformas for work, an exercise I endure with a grimace, my life has been light on "plan." 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. To think that one can sit down and devise a "plan" for the next 5 years is total crap. In both personal and professional goals I've found that themes, applied consistently, can be more powerful than hard, quantified goals. 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 want in my 5-year gestalt:

* The below sections are in progress *


Gosh, what a section to start with. Alejandra and I got married on November 5th, 2021. We'll have a party at some point once things chill out. 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 and by phone, with a broader circle than those on my current "speed dial". 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.

Over the last 2 years I've fallen into a stasis of social isolation, which given the circumstances, is not too outside of the norm. But as folks start to emerge from our collective cycles of reclusion, I have been slow to revise my modus operandi.


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.

Early in my career my measure for whether I was doing the right kind of work was "rate of learning." If that rate plateaued, I would adjust my work. In work now there is no shortage for new lessons, in fact the rate of learning has never been higher - all of the parts of business operations (fundraising, management, accounting, etc) that start getting interesting at a certain scale are in full swing. But optimizing for "rate of learning" isn't enough if you're learning things you are apathetic about. The challenge that lies before me is to determine how to balance:

This will be the pivotal question for me to answer this year.

{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.

Outside of work, 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", and fermentation to name a few. I've dabbled in some of these, and would like to deepen my knowledge.


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.

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:

So I do foresee moving at some point in the near future, 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.

Compiled 2024-04-21