TL;DR: this is a repository for discussing income generation strategies optimized for free time

I hope I'm not cluttering up LW but maybe enough people are also interested in this? I graduated high school about a year ago. 

I have a lot in common with Will Newsome's self description in this post


But it's a dead thread, and there's been some interest in early retirement extreme, ( and having repositories for stuff. 

The upshot of it is that I want to optimize for free time and mobility. Need about $2,000 to live (1600 expenses 400 savings/buffer) 2nd EDIT: no I don't, I must have screwed something up when I was adding this it's more like $1600. ($1300 to spend $300 buffer). A 20 hour workweek or even shorter is what I'm going for here. Right now I'm barely functional. Even that much is a bit of a stretch for me as I am now. Plenty of advice abounds on optimizing my health and squashing akrasia though, and I'm sure that if I implemented it I could get to the point of handling part time work. But I think I would always find being a 9 to 5er unappealing.

 I'd value spending that time reading texbooks or walking around town or lazing around on the beach more than I'd value extra money. I'm also interested to hear about some more conventional part time jobs if they pay enough. I'm ok with doing somewhat boring work if the hours are light and I have time to think.

I've generated some candidate strategies if anyone here has experience at these. I don't have much knowledge of what they would entail or how to break into them. Or they might give someone some ideas I dunno but anyway:

4hww style dropship business (but success at that seems hard to set up and sustain)

freelance work at a site like odesk or elance

Own a popular app or forum

Push carts at wal mart part time (but I don't think that pays enough)

Self employment doing massage therapy (I can set my own hours but I'd need to invest time and money to get trained)

Tutoring (I might like this one. Do I need a college degree? Can I make enough with part time hours? Is it hard to find leads for clients? How would I do that?)

Online poker (but it seems kinda hard)

Does anyone here live in a yurt? And has anyone tried living in other countries to cut down expenses? 

edited to add: Did I make a mistake including numbers? They're what would be ideal for me, not strict requirements. I can work a little more or spend less. Err on the side of posting ideas, I'm sure some other people are interested in low stress work but don't value free time *quite* as much I seem to


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2,000 dollars seems a bit much for bachelor living. What are your expenses?

I currently have a monthly food budget of 200 dollars. I do this by optimizing for raw nutritional content and buying in bulk. This daily diet consists of

  • 1/2 can of beans
  • 1/2 can of corn
  • 1/2 cup of rice
  • 2 cups of milk
  • 1 cup of vegetable cocktail
  • 1 whole wheat bagel
  • 1/2 can of chick peas
  • 1/2 cup of dried cranberries

However, I work as a dishwasher and this nets a lot of opportunities to eat. The company officially provides one staff meal per shift; on days I have a double shift, I eat twice. Between these meals and the full plates of fries and bowls of untouched seafood chowder I see that would otherwise be thrown away in my work washing dishes, I have actually gone to work in the morning hungry and come home late at night full, having stowed said food away in Tupperware containers I bring with me to the counter. So my food budget is likely to drop down to 125.

Definitely puts the munch in munchkins, eh? Eh?

Become a dishwasher.

That was awful. Upvoted for that alone :) I don't actually know for sure. I live with my parents and have no expenses. I used a monthly expense calculator and input what I expected things to be likely to cost but I redid the numbers now, and it seems to come out to more like $1600
I must be an outlier then. My rent is 550 including utilities, giving a total expense of ~700. Are you in the city?
$1600 in targeted income, not expenses. The expense calculator adds up the numbers and multiplies it by 1.3 to spit out an income target. The expenses come out to $1300, (including a hypothetical car I'm seriously considering not getting) and they're padded a bit to be on the safe side.
I would be concerned primarily with rent. Getting utilities well below $150 should be doable; food for $200, $300 tops; transportation would depend on specifics, but all said I'd expect under $1000 to be sufficient, barring expensive rent or absurdly high bills (I don't know how expensive house/car payments are, and how this varies with location). To be safe regardless of location, I'd go with $2000, although I could manage on $600 in my current location if not for college debts. So I suppose the cost of living in the location in question is the important thing; average cost of living is going to be well above a comfortable minimum, I'd expect (or at least, the average cost of living in my area is over $2000/month; I believe it was a little over $2400 last I checked.).
I wouldn't recommend getting a car if your city has good public transportation/bike paths. The cost of updating a monthly pass for a bus will be exceeded once and half again by cost of your car's insurance, never mind gas, maintenance and parking. No, a car is a liability in most cases, unless you have a dire reason to visit rural areas on a regular basis. For houses I'm not so sure- on the one hand your money will be going back to you in the form of equity, but on the other hand you'd be losing a lot of said payments to interest, unless you really pumped money into the mortgage payments.One year out of high school may be too early to consider conventional housing.
Or if you live in a rural area, but I suppose you covered that with "if your city has good public transportation/bike paths." (I live in a rural area, but physically couldn't drive if I could afford it. gotdistractedbythe doesn't seem to have mentioned eir location, but judging by the way the beach was mentioned, I'm imagining one of the coastal cities that generally have decent public transportation, so I don't expect ey will need to worry about cars. However, said areas also tend to have some of the higher end costs for renting living space, as I understand it.)
Sounds like it has good perks. How's the pay?
Minimum wage. In Canada, this is 10.30
I would expect that by "optimizing for raw nutritional content and buying in bulk" you could get your food budget down to about $55/month. For $200/month that doesn't have to cover lunches at work you should be able to afford much more variety and meat/luxuries etc. (A while ago I collected lots of food budget numbers: food costs on a scale [].)
Really? What items ought I replace?
Cooking dried beans, probably in a slow-cooker, would be cheaper than using canned ones. [1] You could cook the rice along with the beans. Chickpeas would also be cheaper dry. You could probably get below $100/month cooking all your own meals that way. I'd start with dry rice and beans ($0.61/day for the beans and $0.76/day for the rice) which comes to $42/month, add vegetables, small amounts of cheap cuts of meat for flavor, spices, and luxuries for the other $58/month. [1] []
Brilliant! This will shave off ~30 dollars per month, thank you.
(Strangely: I've also worked as a dishwasher, I also bring tupperware to work to take home excess food, and I lived on ~$80/month for food for about 2 years. I think focusing on earning more earlier would probably have been a better use of my time than all of those combined.)
Some advice, written when Jeff and I were spending $170/month on groceries for two of us: []

I need about 2,000 ($1600 expenses, $400 savings/buffer) per month to live. A 20 hour workweek or even shorter is what I'm going for here.

So do a simple bit of arithmetic. $2K/mo = $24K/year after taxes. If you're working in the grey economy / being paid cash, that's your necessary annual income. If you're being paid by paycheck, you probably will need around $32K salary (depends on the state, etc.) to get to the $24K take-home amount.

A 20-hour workweek translates to 1000 working hours per year (and two weeks for vacations, sick leave, etc.).

So you're looking for a job that pays you at least $32/hour above the table or $24/hour below the table, besides being a part-time job.

Other options seem to boil down to running a small business which doesn't strike me as a low-commitment, low-stress, and high-free-time activity.

Disregard those numbers. They were bad. But the point I guess you're making is that living comfortably on low net work is hard to make happen. I know. But I want to try. Nearly half my waking hours just seems like a lot of time.
Sure. The really really REALLY long line of people who want to get a lot of money for little work is right over there. Your can start by reading the Tim Ferriss' The 4-hour Workweek book, by the way.
Keep in mind that Tim Ferriss works extremely hard. You are not as successful and prolific as he is on a 4-hour workweek. Ironically enough.
Also a fair point. I mentioned 4 hour workweek style dropship business in my list of strategies. In fact, you can more or less blame that book for this post having been written.

This takes some start-up time, but accounting can work for this. Without higher ed you can get various low-level positions in large corporations and if you're smart you work up quickly. The work process is likely to be old and very inefficient, with some computer savvy you can streamline your work and slowly phase out duplicated labor. And the work naturally comes in cycles - quarter-ends are rough, the rest of the time is fairly light. It's been a few years, but now (aside from 2 weeks per quarter) I only actually labor for 20 hours/week. The down side is that you do still have to be at the office for 40 hours, but if you can be productive at your computer, or read surreptitiously (eReaders are great), that time isn't lost. And it pays fairly well.

Thanks, potentially helpful, upvoted. Do you find the office environment conducive to doing your own reading or projects? I remember just being at school could be draining, even when I didn't do much of anything. Would you mind describing the kinds of things you're actually doing when you're working? Does it pay well enough to save up a couple years of living expenses quickly?

I can read fine, I've taken up writing, and I do most of my online-doable chores & blog reading. And reply to LW posts. ;) I suppose it depends on your office but mine is cool.

When I'm actually working it's a lot of number juggling on spreadsheets, pulling data from databases, and tracking down where money went and why it wasn't entered into our system the way it was supposed to be. About half of it requires little enough concentration that I can listen to podcasts while doing it. The other half takes actual mental effort.

The pay right now - yeah. Starting pay is lower, I've been in the game for a while. And it depends on how you live. After bonus I make aprox 66k/year, which isn't spectacular, but is more than enough for me, and seems fair based on how much free time I get at work. I've had to start investing my money, because it was piling up and doing nothing.

As a former boss of mine used to say: "Bloody five o-clocker"

I am curious... you don't seem lke a lazy person through the lens of LessWrong site, yet the impression I get from this particular post is that you would resent every one of the 20 or so hours you would spend working. IMO that really need not be the case.

Supposing you meet your stated goal - what would you spend your "free time" on? Could you make that activity generate income? eg. being a lifeguard on that beach you'd like to laze on?

Smarthinking pays about $12/hr for online tutoring work, done from home. For English, this implies reading essays of high school and college students and sending feedback according to highly standardized procedures that they train you in. ("Your essay should open with a thesis statement", etc.) They also do math, science and computer tutoring, but I know less about how they work. You choose how many hours a week you want to work and which hours (e.g., Monday 10-4) but they have to be the same each week (you are allowed skip some occasionally and just not get paid from them).

With 20 hrs/week it would only give about half of your targeted income, which might be too far. But if you think you'd find tutoring easy/fun and have problems finding customers out on your own (which would obviously pay more), you might give it or another company like it a try. (ETA: I think the company keeps for itself half of what the students pay, and certainly hiring a personal tutor must be more expensive than paying for anonymous, standardized online feedback. So getting a few students to hire you for personal lessons might give you enough to get close to your target. You would have to save for the summer though.)

I'm signed up with a tutoring outfit called InstaEDU that pays $20/hr for purely online tutoring. The hours are very irregular -- tutors make first-come first-served responses to student requests. And I find that, at least in CS, the students are often rather confused, at least to start. But their money's as green as anybody else's.

I work for Smarthinking (also as a writing tutor), and it only pays $12/hour if you have a Ph.D. If you have a Master's degree, $11/hour; a Bachelor's, $10/hour.

For what it's worth, they are reliable in supplying work hours, which is nice, and the work isn't bad.

ETA: Although they advertise and accept applications year-round, I have a suspicion that they hire/train new people only during the summer. I have only extremely limited data on this point (myself and one other person who both applied in the fall to be hired in May), but it seems worth mentioning as a possibility to be aware of. Alejandro1, what was your experience?

It was my wife who worked for them for some time she was unemployed immediately after getting her PhD. She was hired and trained in the summer, too.
Is the pay strictly by hours or by work produced? Is it possible to make more than $10-$12/hr by e.g. reading the essays faster?

Online poker (but it seems kinda hard)

Actually, does anyone know any good resources for getting up to speed on poker strategies? I'm smart, I'm good at math, I'm good at doing quick statistical math, and I've got a lot of experience at avoiding bias in the context of games. Plus I'm a decent programmer, so I should be able to take even more of an advantage by writing a helper bot to run the math faster and more accurately than I otherwise could. It seems to me that I should be able to do well at online poker, and this would be the sort of thing that I could likely actually get motivated to do to make money (which I unfortunately need to do).

Anyway, if anyone has any recommendations for how to go about the learning process and getting into playing, I'd love to hear them. I'll try to comment back here after doing some independent research as well.

I don't, but: []
The main reason you don't hear much about it IMO is that the number of hours you wind up putting in makes it only commensurable with normal decent paying jobs. You only exceed that at high levels. This is just based on searching around for info a few years ago and speaking with people who made a living at it. I myself did it part time for pocket money for awhile, but the stress got to me.
If I can do something fun, from my house, on my own hours, without any long-term commitment, and make as much money as a decent paying job, then that sounds incredible. Even if it turns out I can't play at high levels, I don't mind playing poker for hours a day and making a modest living from it. I don't really need much more than basic rent/food/utilities in any case.
I would just warn that variance is way more stressful than most people predict. It is really really hard to keep doing something when you get very strongly negatively reinforced. And things have a way of not being as fun when they are a job.
WOW. I predicted that I would have a high tolerance for variance, given that I was relatively unfazed by things that I understand most people would be extremely distressed by (failing out of college and getting fired). I was mostly right in that I'm not feeling stress, exactly, but what I did not predict was a literal physical feeling of sickness after losing around $20 to a series of bad plays (and one really bad beat, although I definitely felt less bad about that one after realizing that I really did play the hand correctly). It wasn't even originally money from my wallet; it came from one of the free offers linked elsewhere in this thread. But, wow, this advice is really really good. I can only imagine what it's like with even worse variance or for someone more inclined to stress about this sort of thing.
0ChristianKl9y [] is a decent article on learning it.

If you are in the United States, you may want to consider applying for disability. This is ethically questionable if you can support yourself working. It may or may not be a rational economic decision: see below.


  • Many part-time jobs are not designed for people with significantly and arbitrarily fluctuating energy levels/availabilities.
  • Almost no part-time job available to someone without social influence or significant skills will let you earn a comfortable living with a guaranteed income level. Some part-time jobs available to people with skills but
... (read more)
I'm on disability, and the resource limit is indeed $2000 (I don't know if that's across the board, or just in my state). I wasn't sure how much attention they pay to Paypal until you mentioned it specifically. In my case, every dollar of income would cost 50 cents of SSI, so any job that earns less than $1260/month is probably not worth it. However, what I've read indicates that this rule is specific to blindness, and the system is less forgiving to other disabilities. And I have student loan debt that costs more each month than my disability check, and my parents have been moving away from making that sustainable (at the current rate, I should be overdrawing from my checking account by the end of the year; I was expecting this to happen much sooner, but my parents paid much more of the bills in the first few months of 2013). This prevents "withdraw some cash to hide from the IRS" from being a viable strategy. Without the loans, however, I could both live on SSI and have money left over for other things, assuming I was efficient with electricity and eating. The amount received depends on how many people you're living with, marriage status, property/car/stock ownership, etc.
It wouldn't only look like tax evasion but effectively be tax evasion. You might do some online work that pays you in bitcoins.
This is only liquid assets right? A car wouldn't count against that?
I have no anxiety disorder. I'm okay with doing freelance but don't think I'm skilled enough. This could buy me some time to solve that problem until I get really good at webdev or poker or something. On the other hand, an acquaintence had trouble getting disability, and she's very bipolar and prone to full blown manic episodes, pyschotic breaks, etc. so I'm unsure of my chances of even getting it, even if I do decide I want to. I feel a bit guilty about considering it but the possibility of becoming financially independent later assuages my guilt somewhat. Can you elaborate on what qualifies in practice or link to something?
retracted until i rewrite this

Living off the grid seems to be working for open source programmer Joey Hess. Though he seems to have a fixed homestead, so there's not that much mobility.

I would be interested in resources on how to set something like this up and learn everything I would need to, if someone can make recommendations. Main issues seem to be money and effort of setting this up
The Homestead [] Reddit looks like one place for stuff about sustainable living. Survivalists are also thinking about this stuff, but you'll need to filter out the crazy there. Probably better to look for people already living outside population centers rather than the office workers who debate the number of tactical knives to have in the bug-out bag in their living room closet. Some sort of commune would help with the setup and maintenance work, but then you may get problems with freeloading, incompetence and general drama.

The 52-karma top comment of the Virtual Employment thread has been deleted. I gather that it said something about copywriting, with online skill tests for prospective applicants.

Can anyone provide a bit more information about this apparently quite valuable comment?

This has not been my experience with trying to do freelance programming on elance. I've applied for about 20 projects on there over the past few months, all of which I was very qualified for and gave evidence that I was qualified for (by linking to past projects of mine). I interviewed for one, which went well, but they went for a much cheaper programmer from India (I don't blame them; he looks like he does a good job). Most just don't respond.

I may be charging a bit too much, especially since I have no elance reputation), but on a lot of the projects I didn't even cite a price, and instead asked reasonable questions about the project and stated I needed those answers before I could offer a cost estimate. Almost nobody even replied. So I don't think cost is the only issue.

Maybe odesk is different, but I doubt it.

My impression from what other freelancers have said is that you need to do lots of networking to find good clients, and that most good freelance software development projects are never posted to job boards or elance or anything like that, they're handled by referrals. (I haven't actually successfully done this approach yet either though, so I can't personally vouch for it)

I had a similar experience with elance. I applied to a bunch of jobs and only got a reply back from one. That job ended up being not worth the time I ended up spending. However, Uvocorp ( is another freelancing site I use, and my experience there has been much better. You have to pass a pretty easy writing test to be able to work at all. Once you pass, though, you can browse all the job offers, and you are assigned the job as soon as you hit 'apply'. I'm very selective about what jobs I choose, in order to make them worth my time and to make sure I that can do a good job. Just read the job description carefully, so you know what you're signing up for. By being very selective, I've managed to keep the pay above $20 to $30 per hour. I'm competing somewhat with writers from India or elsewhere that are willing to work for less than me, but I get a premium by being a native speaker of American English and having good ratings. I've been able to negotiate the price at times because I've been specifically requested by repeat customers. There have been a couple of disputes, and the administrators have been reasonable. Disclaimers: * The payment / time varies quite a bit from job to job, so be careful what you sign up for * It involves doing homework for college kids, in case you have moral issues with that * During the busy college season they will assign you jobs without asking you. You can still decline them without penalty.
Thanks for the warning!

Tutoring- If you don't want to find clients yourself, there are companies that will hire you, and then match you up with students. When I did this, I made $20/hr with a bachelors. The problem with tutoring is that you are only working an hour or two, and have to drive there and back. If you're lucky, you can schedule two clients back-to-back, but you still are having to travel for short shifts.

Nannying- If you find taking care of kids and houses to be unstressful, this can pay pretty decently (generally under the table), be full-time or part-time, and inc... (read more)

According to a cracked article (I didn't check their sources, and comedy does trump accuracy there, so take these with a spoon full of salt), begging, busking and dumpster diving are pretty lucrative. I believe it was a top 5 or 6 article, but I've since lost the link and don't remember the others off the top of my head. (I'll edit it in if I can find it...)

Edit: Here it is. The others were sperm/egg donation and participating in scientific studies, both of which are pretty hard to get into in the US (demand for sperm donation is apparently much higher in ... (read more)

Dumpster diving and scientific studies are both MUCH more profitable near university campuses. I speak from experience.

Munchkin approach to earning money from scientific studies (if near a big university): Find out if the psychology department (and related social science departments) requires students to participate in experiments for course credit. If not, or if the student numbers are low relative to the number of researchers, there will be arrangements to pay participants. If you are near a suitably large department, as long as you show up reliably and follow the instructions without being "difficult", participation in such experiments can be a decent source of income. And less risky than medical testing in most cases. Central London (UK) is one such place where this seems to work - there are a number of "professional subjects" who work the circuit. What consequences does this have for the scientific studies? Well I said this is a munchkin approach to earning some cash.... it certainly doesn't make the participant "sample" any less WEIRD []
Why would dumpster diving be better near schools?
At specific times in the year, for universities where most students live on or near campus: lots of students seem to find it easier just to discard perfectly good things rather than move them around - especially the start of summertime when many students move back home, or start a job elsewhere. It can be worthwhile to collect useful-but-discarded things and sell them on to the next round of arriving students provided you have someplace to store them in the interim. At all times in the year, again for universities where the student population is resident nearby = relatively diverse array of grocery, convenience stores and relatively high % of restaurants, typically clustered in a relatively dense area and all of which will generate some food waste. The key is not just the availability (and diversity of products that may be found this way) but also the tendency to hire student (or recently-student) employees who may be a bit more likely to turn a blind eye toward dumpster diving, or even facilitate it by spreading the word about "desirable" items about to be trashed.
This. I never went looking for perishable foods but all sorts of perfectly good small appliances or pieces of furniture were to be found in May of each year. Apartment complexes can also be pretty good for this sort of thing. Where I live now people who move out sometimes leave their stuff by the dumpsters in the understanding that doing so means the stuff is fair game for other residents (especially recent move-ins) and the administration in the rental office will let you know if you ask about any furniture that recent move-outs have left behind inside their empty apartments. I got a couch, microwave, coffee table, and set of chairs that way for free when I moved here for grad school. Also, when universities get new equipment some departments just throw stuff out rather than actually sending it to the surplus depot or whatever. Got fully functional computer monitors and an oscilloscope once in undergrad (and gave the latter to an engineering major friend who tinkers a lot in his basement).
If there's a nearby plasma bank, plasma donations can pay around $20, a couple times a week. Not a lot, but pretty easy/low-stress if needles don't freak you out too much. To make it go faster, be sure to drink plenty of water fluids and don't eat too much fatty foods.
I forgot to ask this, but how long do these take?
About 90 minutes average. First time will be longer because of paperwork.

I'd just like to update my dishwasher scheme- a supervisor has asked me to stop eating leftovers from the plates I wash for liability purposes, so... yeah.

prostitution pays pretty well, if you're attractive.

Dealing drugs is very lucrative but fairly risky.

If you can find out and be good at keeping track of the value of collectibles such as magic cards you can make a lot of money buying and selling them.

Low level crack dealers in gangs face worse pay and conditions than workers in most minimum wage jobs. My friendly independent neighborhood pot dealer makes a good living. There is still a risk of being robbed etc. without any legal recourse, but I'd imagine it's a lot lower if you aren't selling crack in the inner city.

That leaves me with a question that they were nice enough to explicitly ask at the end of the page: Do they answer it later in the chapter?

Status-seeking, essentially. Gang leaders are very high status in some circles, dealing drugs through gangs is a necessary part of becoming one. Of course actually becoming a gang leader is extremely unlikely, but then there aren't many self-described rationalists who deal crack.

Yeah. They say that there's a slim chance of becoming a successful drug dealer and making tons of money, so people see those guys and try to be like them.

For what it's worth, I imagine that being a suburban weed dealer is an entirely different ball game. OP might want to look into that.

See, i see that question and assume the answer is probably extreme poverty and inability to make money any other way.

prostitution pays pretty well, if you're attractive.

Attractive, and female. Male prostitutes do get paid a lot less. Also, stress levels and risk levels here are likely pretty high for all genders. If one is in an area where it is legal, possibly less stress and risk, but still likely to be not at all small.

If you can find out and be good at keeping track of the value of collectibles such as magic cards you can make a lot of money buying and selling them.

This seems like an area that's already saturated with a lot of skilled people.

Running an MTGO trading bot apparently isn't too difficult. I don't know how much money they actually make, though. (Hopefully enough to pay the electricity it takes to run the computer...)
My consort says working a dry cleaner's is very easy and you get a lot of free time, though it is very hot.

I'm currently thinking of getting a commercial driver's license and doing over-the-road trucking. The research I have leads me to believe that I'd make between $35k and $45k my first year. Living out of a truck/motel rooms should save quite a bit on expenses too.

Downside is that it's a lot of hours on-duty, as well as a couple grand of loan debt and a month with no income to complete school.

I don't understand why you want to do this, honestly. Trucking seems like a very unpleasant profession from what I've seen. What upsides drew your interest?
I find driving pleasant and I'm good at it. Mostly it's a combination of low living expenses, decent salary, and getting to see the country. The independence and lightness (term borrowed from Go strategy) of the position were upsides as well. It's basically a good way to turn a year or two of my life into the roughly 40k it'd take to retire on a couple acres, a garden, and a yurt. I could even get the yurt before getting out of trucking as a fairly cheap minimal economic offering. Also, I fully expect trucking to get automated into a much cushier job over the next decade with self-driving vehicles. Instead of driving a truck for 11 hours a day, you babysit a truck-driving machine and make sure everything runs fine and gets loaded/routed properly, which is essentially a desk job. Lowered accident rates and insurance premiums pays for the upgrade, even without an increase in the allowed hours of service regulations. Not needing a college education is another huge plus, since it means I get working sooner and with less out-of-pocket expenses front-loaded onto it. Anyhow, it's not something that makes sense as a long-term plan. It's something to do to loot roughly $100k over three years after living expenses and then get out.
Have you actually done the calculations that convince you you could retire on $40k? Because that seems awfully optimistic to me. Let's make the following optimistic assumptions: (1) You will be able to invest the money so that it grows reliably at 4% over inflation. (2) You will only need the money to last you for 25 years (e.g., because after that some rich family member will die and leave you a big pile of money. Or because after that you will die and not care any more). Then, taking inflation to be zero for convenience (the alternative is to inflation-adjust all the numbers, and because of the form of assumption 1 this is equivalent but uglier), if my scribblings are correct then you can afford to spend about $2500/year. Living on $2500/year in the US seems really, really tough. And that's assuming none of the $40k actually needs to be spent on the acres, the garden, and the yurt.
The $40k was more roughly the number I had in mind for getting set up somewhere. Land, yurt, gardening tools, and food expenses for a year or two. My ongoing costs would be property taxes, food costs if gardening doesn't work out, and water/electricity (or budget for upkeep/maintenance/replacement on my own systems). Gardening can be an income stream, too - selling fresh vegetables at a farmer's market (or effective income stream in offsetting food costs). But that's probably not wise to count on - it keeps my position dependent on not failing at gardening. It's really getting the living expenses down that's important, though. If I can meet my needs cheaply enough, then it's really not that big of a deal if I have to pick up a shitty job later. The research I've done also suggests that it's fairly straightforward to get on disability. That would more than cover incidental expenses at $500/month. Anyhow, I kind of rambled for this, but that's mostly because it's not particularly thoroughly thought out. It's more out of a suspicion that it takes much less money to live a happy life than most Americans think it takes, and that the common error mode is spending too much time making money to try to fulfill your needs, rather than simply fulfilling your needs with more effort and less money.
Doesn't this lead to the risk that your pay will drop as you face competition for the position with an increasing number of willing unskilled workers?
I'll have an experience edge over recent graduates by the time that happens. Besides which, the better working conditions would more than make up for it. Worst case scenario is that I cross-train or cross-certify in truck maintenance, as "someone who can get the damn truck rolling again in an emergency" is going to get a much better paycheck than "someone who picks up the phone when the damn truck stops". Actually, the real worst case scenario is that I lose my job and get out of trucking in general.
My father (in his mid 40s) recently took up trucking to help pay off credit card debt (my parents claim to be good with money, but I do not predict they'll pay off anything in their lifetimes barring winning a lottery or living much longer than average). He also owns an electrical/construction contracting business, so he only takes a maximum of one load a week (he usually does much less; more like one or two a month). He hauls steel, primarily from Tennessee and Arkansas to Texas (other trips come up, but I haven't heard of him accepting any). I think each trip is supposed to net him $1000, although there isn't a reliable schedule on when he gets paid--basically whenever the people in charge get to him in their list of priorities. (He also wound up working for a business in which one of his high school friends has a lot of status, which probably makes it easier for him to bug them about when he's getting paid--although at any given moment they seem to owe him around $5000, from what I hear.) So just generalizing from the one datapoint, your $30-40k/year sounds about right.

I am unclear whether you are claiming that you're disabled or that you're simply lazy. So I am going to assume that you're lazy. But if, in fact, you are suffering from a medical condition, then it would be best to deal with that straightaway.

But I think I would always find being a 9 to 5er unappealing.

This seems to be the null hypothesis by which you basing your desire to work as little and as easily as possible on. I think your null hypothesis should be that developing a full time career will be most beneficial to you. A career is rewarding financia... (read more)