Hi AE, I'm babysitting renders all day and I wrote you a book of pure unsolicited advice. To preface it: I don't *know* if what I'm recommending is the right thing for you. Maybe it's garbage advice for who you are. Most people only give reasonable advice, and I see one of my roles around here as on of the folks who gives
unreasonable advice to bring some Balance to the Force.
The rest of this post is written as if I'm some life coach who actually knows you, just because I'm too lazy to go back and edit it to be more obsequious. I don't actually presume to know what's best for you... you know what I mean.
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In that post of mine you quoted, I wrote it as if the process was linear. I don't think it needs to be and I definitely don't think it "should" be. The point there was just to not neglect the fundamentals -- don't think you can jump to WL7 and skip the step where you figure out how to clothe yourself for less than $1,000/year. I don't think you have to have all your fundamentals dialed in order to do work on figuring out your Freedom-To motivation though.
If figuring out what your freedom-to is is your current primary goal, farting around with figuring out how to force yourself to go to the gym/do kb swings in your living room might be a distraction, AND figuring out your freedom-to motivation might actually be the shortest path to a healthy, consistent exercise practice, as well as all the rest of it.
The thing that comes to my mind when catching up on your journal is the notion of environment design. Certain environments make certain actions/lifestyles easy, and others harder. If you live above a donut shop in Indiana, it's going to be massively difficult to curb your sweet tooth. If you live in an ashram, it'd going to be massively difficult to *not* meditate several hours a day. If you have a really comfortable computer setup in your house with enterprise class internet, it's going to be really difficult to not spend a lot of time on your computer. Particularly if you've been in a "computers: it's what we do" groove for years.
When I read what fundamentals your trying to work on, I see patterns of actions that are in alignment with your environment. You spend a lot of time on screens because you have a dope setup with fast internet in your home, and your work is screen-centric. Etc etc. Also, it seems like you've been doing the same basic thing for a long time. You're probably bored AF. I think you're dead on about being conditioned to do things that suck - I absolutely was as well. In fact I took pride in it, being the guy who could handle more suffering than anyone else. Gets old after a while, doesn't it?
My recommendation is to significantly change your environment. It sounds like a big lift, but it's just one decision, and then your actions will come into alignment with that one decision-environment change. Instead of fighting against the current of your present environment with a dozen different little bits and bobs of lifestyle tweaks and improvements. I often feel that doing some big-seeming thing is way easier than doing a hundred small things in the same old environment.
The environment-as-design-factor idea is one thing, and then there's this thing:
Range by David Epstein: wrote: When she compiled her findings, the central premise was at once simple and profound: we learn who we are only by living, and not before. Ibarra concluded that we maximize match quality throughout life by sampling activities, social groups, contexts, jobs, careers, and then reflecting and adjusting our personal narratives. And repeat. If that sounds facile, consider that it is precisely the opposite of a vast marketing crusade that assures customers they can alight on their perfect matches via introspection alone.
Probably you have some idea what you want to do, some vague sense of direction. Or maybe you just have some obvious "no's". Either way, combining the environmental design notion with the "we learn who we are by living" notion, my recommendation is this:
Change your environment to something different, but do it in a way that you're not locked in to it. Do it for 3-6 months. Then do something else, a different environment. Learn as you go. Don't worry too much about getting it "right" on the first guess - in fact, expect not to. Go for breadth. You'll learn a ton about yourself in a short amount of time, and your guesses will get better. At the beginning you'll mostly learn all kinds of things you never want to do again, but that's part of the process. Your life is art, and you've only done like three or four sketches so far. You need to produce more stuff to get good at it.
Some nuts and bolts considerations:
Your net worth is half a million, and iirc you own your house/apt outright. Quit your job/close out your active projects, rent out your house/apt, leave, and take a "gap year". You can come back to work if you want to later. Or see if you can get a long leave of absence, if the idea of quitting fills you with enough horror to prevent you from actually doing it.
Change your environment drastically. If you have any notions of anything that sounds cool, do that. If you don't, have a good friend pick something for you. Or we can. Or make a script where you enter a bunch of ideas into a database and it gives you one at random. Have a "my next adventure" party with a colored smoke flare thingy (don't set your state on fire though, please).
I can't possibly tell you what you ought to change your environment *to*, but the key is it has to be different. Don't just move to an apartment in some other city and set up a dope computer rig there and keep doing the same thing. Four walls is four walls.
Google "james altucher ten ideas a day", the tl;dr is write down ten ideas a day, even crazy ideas, just get 'em on paper. But write down ten ideas for how you can change your environment drastically. Do this for a week you have 70 ideas. You'll probably start to see some patterns.
Making the call to quit/take a gap year is hard. I actually wouldn't know exactly how hard it is because I never pulled it off. I had to wait around to get laid off, the coward's way out. Sounds like you're actually a valuable employee so you can't count on that method. Don't be like me; pull the trigger yourself.
Here's 10 ideas for what you could do from me: they're probably all terrible. Crank out 100 ideas, though, and a few might get into your brain and in four months later you're there.
1. WWOOF somewhere else. No/few screens, the work is exercise, and you meet cool people who are into healthy stuff.
2. Go vanlife. Don't build out your own - just buy a used van already kitted out, try not to trash it, and then sell it for basically what you paid for it in a few months.
3. Buy/rent a little shack out in the New Mexico desert like Mike whatshisface, and read books and walk around.
4. Sign up for a training session for something you've always wanted to do or maybe just been a little curious about - motorcycle riding, western pistol shooting, skydiving instructing, rafting, ice climbing, horsie riding, archery, gardening, welding, woodworking, sculpture, weaving, whatever, and then set up your environment so you ONLY DO THAT THING. Get a motorcycle and ride around North America. Sign up for the wester pistol shooting tournament series. Get a job at a dude ranch. Go live in an urban garden/some homesteaders land. Sweep the floor of a makerspace in exchange for shop access and sleep in the loft. The training helps you a) not be such a damned noob for so long, which is painful, b) gets you invested in the thing, and c) gets you connections in that world that you can leverage for the rest of your thing.
5. Volunteer at an ashram.
6. Get a job as a pastry chef.
7. Get a job - any job, front desk person is fine - at a gym.
8. Come up with some kind of strange quest (Chris Guillabo, the happiness of pursuit) and just get after that.
9. Volunteer for organizations that you're into - homeless shelter, trailwork, etc.
10. Throw a dart at a map and walk or bicycle there. You don't need to train for long journeys, you just need to start, go slow, and you're in shape by the third week or so. "To Shake the Sleeping Self" is a solid read along those lines, as well as Alastair Humphreys.
11. For any of the ideas that don't involve shelter, but involve staying in one place, make sure the shelter you set up is different than what you're used to. Move into a housing coop, group house, ecovillage, squat, or at least a place with roommates, the weirder the better (i.e. DONT move in with a bunch of techies. Find some people growing weed in the basement and playing in funkpop bands at night, rollerderby people, starving artists, hippiepunks, anything but people you're used to).
My list was a little dirtbag centric because, well, that's just the sort of stuff that floats around my head. I don't mean to imply that only dirtbaggy or "out there" ideas are what you *should* do - do whatever you want, as long as you're getting a big environment change.
I don't recall if you consider yourself FI or not. It's possible that your gap year / environment change / living as learning experiments, if it results in you figuring out what your freedom-to actually is, will show that your freedom-to costs like $400/mo, or even is some kind of activity that people actually pay you for. In either case, bam, you're FI. If you figure out that you actually need a bit more money to pull off your freedom-to, fine, go back to work and crank it out - but now you've got your motivation properly set.