The Journal of the Wandering Engineer

How to Decide What to Do With Your Life: Models and Heuristics

Thus it was that I began a task which has absorbed my efforts for many years: trying to manage my life, not according to tradition, or authority, or rational theory, but by experiment.

~Marion Milner, A Life of One’s Own

The thing about FU Lifestyle Design is that it’s not worth living for. It is a method for achieving freedom-from — freedom from feeling leashed to a job, freedom from financial ruin in the case of job loss or large unplanned expense. My FU Lifestyle has delivered me to a place where it’s safe to calmly ask “well, what now?” but it is unequal to the task of answering that question. It’s also a bit juvenile and self-centered. It is good to move beyond it quickly.

Carving out some breathing space for myself in the crushing maelstrom of 21st century western hustle culture is an excellent stance to arrive at, but I can’t stay here forever. I’ve got to, like, do something, eventually.

I find myself standing in a field. I was sprinting along on a freeway, and then jogging a dirt track, and then I dropped to a walk on a faint path, and now I'm in the middle of a field gaping around and there is no path in any direction I look. It's up to me. Well, it's always been up to me, but until now I had some real momentum that I was going along with, that was providing the bulk of the direction in my life.

It is not the case that I have no idea where to go from here. The world is not as open to me as when I was 18. I have 17 years of experience, learning, failing and winning behind me. It's maybe trivially true that I could do anything, but I'm not going to do anything, I have a sense of the sort of thing I'm actually going to do, based on the last seventeen years of my life. But exactly how I'm going to do it, and exactly what it's going to look like, I now have an enormous amount of agency towards that.

And I have an enormous amount of time to figure it out, thanks to frugality and a smidge of personal finance sense. This is both a good and a bad thing. Projects tend to expand to fill the time available. If I think I have five years, I might waste five years farting around and then make up my mind all in a rush at the end. I'd like to avoid that.

I'd also like to avoid introspecting my way to The Answer, to try to Figure It All Out analytically and then simply (ha!) execute The Plan. That's a recipe for endless analysis paralysis or tense control to a rigid plan, two states of mind I’m all too familiar with.

My aim is to decide not on The Plan, but the Principles, the heuristics, the lenses, the philosophy, that I'm going to use to decide how to guide my action in real-time. Solvitur ambulando - it is solved by walking.

A Latticework of Models

Over the past seventeen years, I've absorbed a number of frameworks that I think of as "systems that lend guidance towards deciding what to do with your one short little precious life". They range from metaphysical/ultimate in scope, to very nuts and bolts daily tactical. Many of these overlap (ERE in particular).

A visual metaphor for mental models

A visual metaphor for mental models

“What I want to do with my life” is necessarily informed by these frameworks, both consciously and unconsciously, and integrating these models in my mind will provide guidance as to what sort of paths I want to explore from here. I don’t think that attempting to explicitly cohere all of these models is remotely possible and I’m not going to try, but letting an intuitive internalization of them guide my experiments in living is what I’m after. I do think that running “spot checks” of frameworks against actions and plans is worthwhile.

Absorb what is useful. Discard what is not. Add what is uniquely your own.

~Bruce Lee

Here are a few of the frameworks that I have running in my head. The descriptions are my best attempt to convey what I intuitively hold in my head when I think of each framework. They shouldn’t be thought of as a True description of what that model is All About; it’s just what’s stuck on to the inside of my head at the moment.

ERE. Free yourself from Plato's cave of consumer culture via frugality, systems thinking, mastering personal finance, and the Renaissance Ideal (broad skills and knowledge). Bonus: your consumption will fall to socially equitable levels as a byproduct.

FIRE (Financial Independence/Retire Early): Working for The Man sucks! Build up your NW so you can quit early and live off investment income.

Getting Things Done. Free your mind and achieve a state of relaxed alertness (ready for anything) by getting your thoughts out of your head and organized into a system that you trust.

The Deep Life (Cal Newport). A life of focus is inherently meaningful, will make you good at stuff, and people will pay you to do that stuff. Also, social media is a machine for turning human brains into sludge that off-gasses ad revenue for massive corporations. (Thomas Sterner’s The Practicing Mind is an excellent complement here.)

Rapid Learning (Scott Young). It’s possible to learn things very quickly using principles like active recall, project-based learning, and good learning project design. The standard pace is for chumps.

The Art of the Advantage (Musashi, Takuan Soho, Sun Tzu, etc). The end of the journey is the beginning. You must learn the rules/numbers in order to internalize and forget the numbers, arriving again at beginners mind. Sublime powers are to be had by understanding and working with the mind.

Eastern spiritual traditions. Suffering = (Reality - Expectations), the self is an illusion, and suffering can be mitigated by contemplative practice. Everything is god.

Christianity. Blessed [wealthy] are the poor. Forgive, and help, people. Who the hell are you to judge anyone? If Jesus can get himself nailed up to a tree for the sins of all people, surely you can manage a dismount from your high horse. What ye do to the least of these, so ye do unto Me. We are to be wise stewards of the Earth. Everything is god.

Anti-consumerism. Consumer/capitalist culture is destroying meaning, spirit, and goodness in humans. Humans live lives of quiet desperation when they are turned into commodities, and the system of resource extraction into cheap crap that is quickly thrown away is destroying the planet.

The political philosophy of Murray Bookchin. Hierarchical dominance of human over human is the root of all the bad stuff we've got going on, including dominance of human over nature, which is why we're in this particular ecological pickle we find ourselves in.

The Strategic Theory of John Boyd. Winners can make snowmobiles, losers can't. They who can execute decision/action cycles with greater rapidity and unpredictability, with a better/more accurate mental model/map of reality, while remaining a more unsolvable cryptogram to adversary, triumphs. A noble vision, coherent story, is needed in order to pump up friendly resolve and attract support from the uncommitted and erode adversary morale.

A Critical Perspective on Complex Civilization (let’s go with Chris Ryan, Daniel Quinn, Catton, and Tainter for this one for starters). Industrial civilization is destroying the ecosphere, humanity is in overshoot, capitalism is irreformable, and modern consumer culture is commodifying every aspect of human life, turning experience into this shallow haze of meaningless action riding like scum on top of layers and layers of quiet (and sometimes not so quiet) despair and loneliness as we helplessly watch it all burn around us while being told that everything is fine, carry on, nothing to see here.

Conan the Barbarian. What is good in life is to crush your enemies, see them driven before you, and to hear ze lamentations of zeir women.

Dirtbaggery. Chase your stoke; forget everything else. It's worth it to forsake the comforts and securities of normal society to do whatever makes you hear god whisper “this is what I made your for” in your ear.

A Grab-bag of Heuristics

A heuristic is just any approach to problem solving or self-discovery that employs a practical method that is not guaranteed to be optimal, perfect, or rational, but is nevertheless sufficient for reaching an immediate, short-term goal or approximation (Wikipedia).

I used to think that the best way to sort out what to do with my life was to create A Plan, complete with schedule and milestones. Some projects call for that level of design, but most things in life do not. The application of an evolving set of heuristics, iteratively over time, is a powerful approach due to its simplicity and adaptability. You don’t need to maintain in your head some long sophisticated plan or strategy - just follow the methods.

Here are some heuristics that I’ve pulled from the above frameworks:

  • Spend very little money. Mentally decouple "spending money" and "quality of life". Frugality is magic. Jesus was on to something. Figuring out how to spend almost no money is worth it - and the difference between going from a 30k burn to a 6k burn is qualitatively different than going from 60k to 30k. There's a point at which you "tunnel through the frugality barrier" and the lifestyle forces something different. Extreme frugality pushes the move to postconsumer lifestyle.

  • Focus deeply on one thing at a time. The experience is inherently meaningful, and vastly more impactful than shallow multi-taskedness.

  • Stay off social media or use it according to strict intentional guidelines (i.e. posting work/autoposting blog posts/etc).

  • What's the next action? (projects stagnate because they haven't been broken down enough)

  • Get thoughts out of your head, and into a trusted system. Your brain is for having ideas, not for holding them.

  • Don’t decide whether or not to DIY something based on your hourly rate. Comparative advantage is a trap to get you to specialize like an insect and be made vulnerable to systemic failures.

  • Seek competence in diverse, non-correlated categories of skills (the Renaissance ideal).

  • Avoid heterotelic behavior. Know your goals, values, and vision, and evaluate the things you spend time on for if they're getting you closer to or further from that goal, and whether or not certain activities are in conflict with other activities.

  • Seek dynamic/pulsed equilibrium, not static balance, which is impossible.

  • Seek a barbell approach to risk; cap downsides, never risk more than you can afford to lose, and set self up to benefit from unexpected circumstances. Don’t participate in activities that entail ruin.

  • Don't assume the future is going to look like the past. Don't pin happiness or assets to any circumstance that requires a stable economy, government, society, or climate. That ship appears to have sailed.

  • Seek to be useful to other people. Make sure you’re adding value to any situation you find yourself in, not subtracting value. If you find yourself in need of help, be gracious.

  • Practice unilateral virtue, meaning, give first, go first, smile first; let go of getting.

  • Avoid toxic people. Don't fight them, try to fix them, point out the error of their ways, or any other thing. Either remove them from your circumstance, or remove yourself from the circumstance that they are embedded in.

Well, I didn’t get to the point of figuring out what to do with my life specifically, but I’ve daylit some of the models and heuristics I have running through my head. That’s a solid start.

Something to Fight For

FU Lifestyle Design