The problem with this is that it moves in the wrong direction. You spent all this time learning how to earn more money for your time. Then what do you do after you earn a bunch of money? Figure out how to trade your time for money again, just in different arenas? Why, so you can avoid having to spend more time doing what you specialized in? This isn't the direction of leisure.
The MMM types always are quick to say that they actually enjoy all these little things they do to avoid having to put out more money for daily essentials. Cloth diapering and seems the be the poster-child for these sorts of things. Also using single-blade razors. Working on your own car.
Doing these things properly requires learning more skills. But time spent learning these skills is time not spent engineering. It almost seems more of a irrational reaction against modernity than it does an actual path towards greater impact.
You need to be trading the money you're making through specialization for time not spent learning more skills to be going in the direction of more actual leisure. (what I call "fuck you time". Much better IMO than fuck you money.) You use some of the freed-up time to make more money, and the rest of it towards leisure activities. It's possible for your skill-set to be so valuable that you can maintain ridiculous incomes on, as Tim Ferriss puts it, four hours a week.
Every dollar I can spend on not learning a new skill is a minute I can put towards pushing my flywheel.
Yes. Part of enjoying life -- at least for most people -- is taking part in challenges and endeavors in a wide range of activities. If you can work for 4 hours a week and maintain a high income, this would fit the bill but probably not realistic for most people (do you have suggestions besides managing a portfolio of capital, or free-lancing?). MMM is not saying we should do everything ourselves, but to be smart about what we do save have more time for other activities. This is how humans have been biologically desired over millions of years -- to be adaptable and have a wide range of skills. Legs for running, hands for climbing and building and fixing physical objects, noses for smelling. Skills that are unnecessary for simply writing code but useful to use. The flywheel sounds a bit too mechanical and less in tune with our biological needs.
"A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly. Specialization is for insects." — Robert Heinlein, Time Enough for Love
If you want to make the most money to be able to work the least hours over your lifetime, then focusing on those skills making the most money at the expense of other skills (and paying someone else with those skills when necessary) is the best strategy by far.
If you enjoy fucking around with plumbing, then by all means fuck with it all you want. But if making less money and fucking with plumbing is your plan to free up the most time for other things (neither making money nor plumbing), then I think it's just plain dumb.
Tim Ferriss' extremely valuable skillset is being a flim-flam man / borderline scam artist who markets questionable pesudoscience nonsense: https://en.wikipedia.org/wiki/Timothy_Ferriss#BrainQUICKEN
I'm not necessarily saying you're wrong... but what has he done that's actually bad? He says himself that the things he writes about worked for him, and he shows how he measured it in his own life. That doesn't mean it's scientific fact and will work for everyone necessarily.
Personally, I refuse to give up my life today for the possibility of a life tomorrow. There's too few guarantees that there will be a tomorrow.
MMM's point is that, if you live well within your means and can save 50% of your income (however you choose to define that, but most people do after-tax), you can "retire" after a short number of years. "Retirement" is very much however you want to define it, but the core is that you don't have to work for money anymore, since your previous investments can take care of your lower-than-average expenses. Lots and lots of people are financially independent (don't have to work for money) and still work a normal job because they like it.
MMM promotes freedom, in the sense that you can change some small aspects of your lifestyle and in a short amount of time free yourself of the requirement to sell your time.
Here's something you can take away from MMM even if you don't agree with everything he says.
Based on your post, these are the things that are important to you (or at least a start):
- Newer car - owning a house over 300 sq. ft. - Traveling to Arizona to visit relatives.
Maybe there are a dozen or so other things that are important to you that you could add to that list.
Now open up your bank account and find out how much spending happens on stuff that isn't important to you. 50%? 80%?
If you can dial down the spending that doesn't make you happy or the spending you do that just out of habit then you would be able to do more that does matter to you... nicer house, nicer car, more frequent and longer trips to AZ.
I don't think it was about the size of impact but about fixing your work/life balance. When it's skewing too much towards "all work/no play", most people burn out. By changing to learning something new and different, they get refreshed.
Personally I think I may have to write an article called "Join the Leisure Class, Leave the Engineering Class".
For me, I stopped working in engineering and life is awesome. Having made enough to pay off the mortgage and with leftover savings, I don't think I will need to work again. But when I was working I actually did get a certification in a completely different field of welding/machining.
It doesn't just apply to household stuff. A business has to be able to scale beyond your personal efforts as well. To do so you have to be able to remove yourself from a lot of equations. Large impacts to society and the world don't really happen without institutions, and institutions can't get built any other way.
What I love about engineering is the personal value curve is so steep, that it starts making sense a lot sooner to outsource drudge work. It becomes a question of, how big do you want to grow, and how fast do you want to do it?
If you don't have any skills, you have to pay a plumber to come fix it, for maybe $200. That's already four hours of working at $50/hour. Plus, you have to be home to let in the plumber which is most likely during business hours, so that's maybe another 2-4 hours that you're not at work. Total time cost: 8 hours.
How long does it take to learn how to fix a toilet? Remember, you're a freaking engineer. A toilet is not that complicated. You should be able to watch a youtube video and learn just about everything you need to know in 10-15 minutes. Time spent learning to be self-sufficient pays itself back very quickly.
There's also additional risks to being overspecialized. What if the thing you specialized in becomes obsolete? Now you have no way to trade your time for money and you're absolutely useless for doing anything else.
For me, single blade razors offer a better shave. The fact that it's cheaper is just a bonus.
http://earlyretirementextreme.com/
His book is especially interesting.
Granted, the author of this book is quirky and ends up doing a lot of work that you could hire someone to do for $10 an hour. But the author stressed that- at least for him- he'd rather spend his team mending clothes or fixing his bike that being in academia (his prior career).
Cloth diapering (as currently practiced, with fancy diapers and washing machines) is not cost effective at all; it's (arguably) environmentally responsible, extra butt padding, and cute.
I'm married with 5 kids. We live in rural Wyoming (no income tax, bought a comfortable house for $86k). We've always lived well below our income so we have no debt and sufficient savings.
I mostly choose to work on "products". That helps me focus on problems that people actually care about without any of the startup pressures. Although, I've also written several open source libraries that I thought the community might like.
I started by telling my employer that I would only work 4 days each week. I spent Fridays working on a cool idea my brother and I had. That idea proved useful enough to pay the bills so I quit my job.
I'm much more relaxed now and spend better quality time with my kids. In hindsight, it would be worth almost any sacrifice to get to this point again.
> I spent Fridays working on a cool idea my brother and I had. That idea proved useful enough to pay the bills so I quit my job.
Regarding this, it sounds like you already had a good idea of what your expenses were, and I think people underestimate how important this is.
I recently quit my job and have jumped into the unknown. Firstly knowing where all my money was going, and secondly spending about 12 months trimming off all the fat was an important part of the process to give me the confidence to try this. These days I live in one of the most expensive cities in the world with my wife for about $2000/month (and over half of that is rent). We want for little. Several years ago this figure was closer to $4000/month.
Given the typically high salaries in the dev world, working part-time is an easy path to maintaining a work/life balance which provides time to pursue personal projects.
I work from home so I can move anywhere, and a more rural/calm place, earning less and having more time does appeal to me, but all the good schools here are in the city and I'm not brave enough to risk my kids future on my dreams of today.
Having said that, my wife and I place much more emphasis on independent learning and life experiences than on formal schooling. Because my wife and I have plenty of time, we are able to encourage their education in ways we couldn't if we lived in an expensive city. Our lower living expenses also allow us to take trips and have experiences that we feel are more valuable than book learning.
I have never regretted the lost income from reducing my work hours.
I had money saved up, and for visa reasons had to spend a year outside the USA. Seemed like a perfect time to indulge in some risky ideas, especially those which were a little idealistic.
It ended up being incredibly depressing and I got very little done.
It's hard enough to build a product when you're in a startup or a smart team. In my opinion it's nearly impossible if you're going it alone. And unless some of your friends have an exactly coincidental amount of leisure time or extra energy, you probably won't make progress.
It's especially bad if you're taking on something that you think is good for the world, because now you have extra pressure, but no extra motivation.
Plus, things that are good for the world tend to be products, and not just tools. Those are harder.
I know you, the reader reading this, are exempt from this, and you're an island of personal productivity that needs no human inputs. That's how I used to think, too. Or at least, I told myself that I was more capable than others who said the same thing and who similarly failed.
The main problem is that you think you're freeing yourself from distraction and you're just going to have 100% of time to work on something. But in the process you might also free yourself from people to tell you you are overbuilding, from customers to tell you you're doing it wrong, from the social interactions that make the day brighter. And you might feel the urge to keep it all behind the curtain until The Great Unveiling. This has the effect of making all your small progresses, in the meantime, feel useless. Success recedes further and further away, and human emotional feedback loops don't usually work in those situations.
So I suggest if you're going to use your money and time this way:
- Take on something small. REALLY small. Then cut it to 10% of that size. Then release it. Iterate if it seems to be working out and building a community.
or:
- Be very young and with enough privilege to not have to worry about debt. You have leisure time, few expenses or commitments, and extra energy, and so does almost everyone you know.
or:
- Make sure others are invested in your success and have a commitment to it that's at least in the same order of magnitude as your own. A funded startup is a wonderful way of focusing commitment like this, and ensuring that you have to talk to people all the time. But there are other models.
I gave up after 8 months and got a job. Now all I have to show for it is some source code, and a gap on my resume to explain.
I don't think these things are hard, at least they certainly aren't things I would doubt myself to be able to do. These are just things I'm sure I could do today if only I had more time, and at least to me these are definitely worth thing for one reason: they make me happy
The idea that everyone should want to have a job all the time seems like a strange distortion in the labour market.
This week I started using Trello with a basic kanban arrangement. When I'm ready for a break from one task, instead of goofing off I just switch to a different one. Eg., if I need a break from coding, I'll read my current book for a while; at the moment I'm going through a stack of books on UI design.
I've built one proof of concept, made a lot of progress on another, did each in a language I didn't know before, and I'm working now on another idea using Meteor, which I also didn't know before. Several projects are from ideas I had after starting all this, and I think they could become marketable products.
I guess you could say I'm not exactly doing the "leisure" thing since I'm working towards real products, but it's not a definite startup yet either. But now I'm focusing more on the easier projects so I can get something into production. It's been nice working in an ivory tower for a little while, but I'm getting an itch to show people results.
And I'm having a great time doing it all. I'm pretty introverted so I don't need that much social interaction, but I have a girlfriend I see every day, do lunch with my old coworkers every week or two, and make sure I get good food and exercise. Several times a week I wake up early enough and watch the sunrise.
All of which is just to say: YMMV.
Working by myself, without any deadlines or goals, I become unmotivated and pretty depressed.
I updated my skills, learned new tech, and tried stuff I never would have got to try in a normal work situation. I got to dick around with pretty UI on Monday and backend performance on Tuesday.
So a sabbatical of sorts wasn't a terrible idea -- I'd just do it differently. Ensuring a good iterative environment (social context, regular advisor meetings, customer contact) would be my #1 priority.
Certainly, one way to manage all this is to not live in a place like San Francisco. But I think it is important to make sure people know that lovely luxuries aren't really what forces people with families to focus on money, and that if you do try to raise a family in SF on the median developer's pay (about $114k a year in SF), you'll find engineers don't really have "more money than <we> need", though of course there's always a version of poverty or struggling that would make raising a family on $114k in any expensive city a cakewalk.
Just keep in mind, the median price for a house here is over 1 mil, and that 1 mil will get you a 2br, maybe 3, south of 280 or maybe the outer sunset. OK areas. Full time childcare is about $24,000 a year. Those are really the whopper expenses (that and health care).
Are those "lovely luxuries"? Well, maybe living in SF is a lovely luxury. I like it here, though I'm really here because I grew up here, have two kids in school, and have so much family around that I'm sort of superglued at this point. But yeah, I could leave. All in all, I think there are better places (no, I'm not like some pac northwester trying to get you scared of the rain, if it's your choice to live here you should be welcome in SF, but I really do mean this, I'm really not sure SF is worth it if you have the option of living somewhere else).
I'm not trying to be hard on the author of this piece, but I do think it's important for people to know that engineers in SF even in dual income families struggle with housing and child care payments, not with luxury cars, expensive vacation, lovely luxuries.
From: http://www.nytimes.com/2015/01/31/upshot/letter-from-the-edi...
I'm not saying you are not making a good use of your money - I make similar tradeoffs. But we have the choice. Our income affords us that choice. There are people who do not get to make those tradeoffs, they do not have the choice of living in "OK areas", or paying for childcare.
Choosing to work in a locale where a median home price is a million dollars is a luxury. Engineers could pick from other metro areas, and get fairly close to $100K/year with much lower costs of living (Austin, Dallas, Durham come to mind, there are many more).
And have their potential job prospects cut in half or worse.
Although oddly enough both probably cost about the same.
You don't pay this on "a median developer's salary". Most children have two parents.
Thinking about these things made me kinda appreciate why the rich want to get richer. Even if I'm earning more than strictly necessary for subsistence under normal conditions, our economy / society is set up so that the only source of a safety net for my family is my own productivity right now. I wouldn't mind growing that safety net to infinity, so long as it imposes no externality on my own family. This is what keeps me in the rat race.
A better safety net would make people think less about going to such extremes.
I'm lucky to have a mentally rewarding job with minimal "price" in terms of things like office politics and bullshit. My opinion might change if this situation changes.
That said I feel much happier now being able to focus on a project that is my own creation. I was frequently angry everyday I had to split my time between paid work and my own project, leaving even less time for my family. (To be honest, in terms of total work, I got more done, but was miserable.) I frequently think about the consequences if my project ends up being a failure, but if I never tried to create something on my own, I'm pretty sure I would regret it on my deathbed.
My advice is to do this engineering leisure time before you have a family to support.
<shamelessplug> If anyone wants a preview of what I'm building, please check out https://solveforall.com/. It's a hackable search engine that can be enhanced with user-provided data, programs, and third party APIs. I'm currently working on making it much more customizable and private, so hopefully I'll be able to publicly announce it in a 2-3 more months. </shamelessplug>
One problem as mentioned in another thread is that it is very hard to get feedback while working alone. Everyone is so busy these days caught up in the rat race and their families, and I don't blame them. It would be nice to have some tech friends at work to bounce ideas off of. If anyone has any feedback for me, I'd greatly appreciate it!
Also, it seems like eventually you'd run out of money unless you can just retire early, in which case, you have the issue of explaining why you've been out of work for so long and proving you still are up to the task.
The last issue I have is that things I want to enjoy in my leisure time are costly. For example, I'd love to finish my degree and study music, but these things cost money. I want to continue studying piano, but pianos cost money, getting a house costs money, and lessons cost money. I'm sure I would still program and do projects, but it's not the only thing I happen to enjoy. Maybe not everyone has expensive hobbies like I do but I bet a lot of people, for whatever reason, want kids. Those things are expensive!
Also, I take issue with the author assuming that we spend money on luxuries just because we make more. At least for myself, this is not true at all. I've had jobs that were very stressful, and getting things I liked was my means of destressing and justifying staying at my job instead of just becoming a teacher or something (Not that teachers don't have stressful jobs, I just wonder if I'd enjoy it more). I think I'd have trouble keeping some jobs if I couldn't enjoy spending some of what I made.
- I don't personally have enough money to pay for my current living expenses for the 70-odd years I hope to remain alive. It was an important shift for me when I stopped thinking this was necessary. I have enough money to glide for several years, and I'm confident that either some money will come my way during those years (and I believe it's a little easier to make money when you're not worried so much about it), or I will at least have enough time to notice I'm running out and adjust course. I'm not too worried about the "hole in my resume". If you do interesting stuff with your life, you'll always have a good story to tell. Maybe your story isn't optimized for going up a certain career ladder, but who cares?
- I don't think luxuries are bad, and I think you spending money on a piano could be an awesome use of your time on earth. I just think we don't realize quite how many choices we have. I know lots of poor musicians find ways to get access to pianos, and owning a house out here in 29 Palms is certainly not too costly. But that doesn't mean you have to do it that way!
- I also spent more money while I was working long hours in part to "de-stress". While I don't think it was strictly necessary, I don't think it's crazy. It's just useful to remember that those "de-stressing" costs disappear when you leave the stressful situation.
I completely agree with all your points! I'm definitely looking to find ways to start saving so that I'll be able to spend some time not working sooner. And I am sure that once I stop working I won't have to de-stress as much!
I am sure it will be glorious.. being able to do things just because you feel like it! That's the dream
You can live pretty cheaply out there but you also have to deal with all dumb crap out there. It wasn't very pleasant growing up in the schools there.
Given the difficulty people experience in getting rid of pianos, and the constant flood of pianos, a piano might not cost you much money; you might even be able to get paid to take a nice piano off someone's hands: http://www.nytimes.com/2012/07/30/arts/music/for-more-pianos...
If you get a poorly maintained piano, it could cost several thousand dollars to restore it. Just replacing the actions of a grand costs something like $4k-$5k from what a technician told me.
Someone in my area sold me an old Roland RD-500 in excellent condition, two amps, and a stand for $500. Total cost including van rental to move it, music stand, and a bunch of sheet music: $700-800. Not sure what an equivalent setup would cost new, but I'd wager somewhere in the $1.5-3k range.
I actually have a digital. In fact I have something somewhat better than a digital: a hybrid (Yamaha N1). It has the action of a grand but I can still use it in an apartment.
I also thought this would be good enough, but after taking lessons it's obvious that it's really not. Even though the action is supposed to be that of a grand piano, the reality is that when I actually try to play on a grand I can't play it. My teacher has also said that I really need to get an acoustic piano.
I'm not entirely sure what it is, but I think the main difference is that even if the action feels like that of a real piano, it doesn't react quite the same. There are a lot more subtleties that you can get from a grand piano that's just not possible from a digital with the touch and especially with the pedal.
Note that this is for classical music, I don't know a thing about Jazz or pop music.
I really do appreciate your trying to help though!
I.e. The itch we instinctively don't bother scratching when we are too busy working. We need to value that itch so we take the time to scratch.
I don't get why the world thinks software engineers are so rich...
>>I don't get why the world thinks software engineers are so rich...
Last year I lived in Austin TX, owned a car, ate healthy, lived 15 minutes from the city center and made 29000 before taxes. Of which I managed to save 15000.
The world doesn't think software engineers are so rich, we think anyone above 50K is rich, because for a lot of us thats double what we make a year, and many of us are supporting families on that. The idea that some one making 75-100k could be living paycheck to paycheck is fucking baffling to the half the population making less than 42k per household.
Everybody know how much a programmer makes in Silicon Valley, and think everyone in the industry is paid accordingly. Also, high cost of living in SF area is not that well known (or at least, not understood to be correlated) by the masses.
It's a bit like saying every football/basketball player is a millionaire. Those that play in the professional leagues, yes. The ones that end up coaching pee-whee teams, not so much.
...and if you want to talk global, $100k/year is beyond the wildest dreams of most everyone on Earth. (For that matter, so is starting a capital-intensive business.)
You can probably see where this perception comes from.
Not needing money is incredibly liberating, I advise everyone to just try it for a year.
Having the 'standard' car, house, and family are unnecessary luxuries. It's fine if you choose to do these things but it's silly to me that people feel poor making 50k+. I would argue that if you are struggling with those types of income, your lifestyle is severely out of whack. You don't have to keep up the Jonses to lead a very happy, healthy life.
The benefits of living cheaply are pretty obvious and already pretty well covered. The ability to work on whatever I want, whenever I want all without ever having to think about the personal finance side of it, is just incredibly freeing.
$100/mo for rice and beans, $70/mo for water,trash,electric,heat,telecom ; $400/mo for rent, ???
Do your kids have their own jobs? Your spouse doesn't, because someone has to watch the kids, and that is over $600/mo alone.
The article is idealistic bullshit.
As i understand it, the situation in the US is that there is Silicon Valley, where the salaries are high and the rents higher, and then half a dozen other places where there are significant concentrations of software jobs, and more reasonable living costs.
This is not really the case in the UK. There's London, there's a ring of big corporate offices just outside London (Guildford, Cheshunt, places like that), and that's more or less it. You pretty much need to live in London or its commuter belt to work non-remotely in software.
If that doesn't work out then I will find something fun to do that may not pay. This will be some combination of taking Tactition Programming seriously, and working on open source lab specific software that my wife uses for crystallography.
Am I wrong in thinking that, in fact, all major open-source projects continue to thrive because there are big established companies supporting them? Where corporate support is lacking, the project doesn't do too well in the long term (I'm mainly thinking of the OpenSSL case from a few months back).
I.e. switching jobs (or having none) doesn't affect whether a hospital will treat you or not.
From an american perspective, that sounds like some sort of unattainable utopia.
If you're part of the lucky privileged elite that actually has money to burn, then yeah, go for it. For the rest of us, though, saying "you should stop working for a paycheck so you have more time to do other things" basically translates to "you should stop eating, drinking water, and breathing oxygen so you have more time to do other things", which is plain nonsensical unless one happens to be a robot (which, while I'd love to be a robot, isn't really in the cards right now).
For example, if you have a nanny part-time, you will have to figure out nanny taxes - assuming you're doing it the legal way - or pay an outside party to manage the nanny's payroll.
That overhead may be easier to justify when the nanny is allowing you to work a full time high paying job, less so if the nanny is only coming a couple days a week. In this case, you might consider a part-time day care center instead.
And unless you have a lot of energy or hired/family help, you will be so tired in the first few years of your child's life that you likely won't have the energy to do anything beyond growing a few token tomatoes and potatoes, certainly nothing at the scale needed to make a dent in a family's food costs.
For clothing, tap your friends-with-kids network to get into the hand-me-down stream. Babies and toddlers grow out of clothes faster than they can wear them out, and new clothes are $$$.
Also, you mention you have a spouse. I know it is terribly unfashionable to say this, but have you considered being a single income family? Sounds like that would give you the best of both worlds.
In my case, we are a single-and-a-half income family. Once kids go to school, there's no much reason to keep an adult around home all day. I am officially the bread winner, and my wife has the lifestyle job, but considering how much she has accomplished just by working part time, we might need to revisit that decision sometime down the road.
At the moment I'm exploring other directions with it, such as having it as a story telling platform, but the original idea was a startup/engineering sounding board. With reply videos able to be added to the existing videos there, and smart conversations happening through video replying to video.
In parallel to the skill acquisition there is a change in mindset, replacing the ideal of comfort with the ideals of strength and self-sufficiency.
- Depending on what kind of problems you enjoy solving, you're going to be miserable even if you are able to do this.
I love working on my own at times (exploring new concepts and ideas, new languages, or even "toy projects" with no real-world applications), but in the end, I find working on bigger problems, with a team of great people to be a lot more fulfilling.
- Constraints are useful in that they force you to rely on something other than pure will power. This can go both ways: _if_ you are going without a regular source of income (as opposed to retiring after winning the [startup] lottery), you'll need to sacrifice time for money. On the other hand, a full time job provides a good deal of constraints as well (both for what you do _at_ work and what you do outside of work hours).
Gene Wolfe[2] kept a full time job and wrote an hour each day. That had two constraints: he didn't need to rush or alter his work in order to sell (his books are fulfilling and rewarding but not a "easy, fun read" that brings in great royalties right away) and since he only had an hour each day to write, he knew he had to make the best of it (one thing said about him, is that he doesn't waste words: he's got a whole CNC machine milling Chekhov's guns...)
- Burnout is an entirely different matter, one shouldn't generalize from "this helps deal with being burnt out" to "drop everything, do this, and you'll never be burnt out."
- Finally, it isn't a feasible option for most:
First, one can't insure against economic catastrophe, savings and a low burn rate are great, but ultimately the _only_ financial insurance one is there ability to earn an income[1].
That ability is predicated on ability to contribute and the amount of people willing to pay for your contributions. In other words, if you're a great developer and you live (or can relocate to) a fluid job market, your risks are lower than those of an average developer (note: assuming a normal probability distribution, 50% of developers are _below_ average, and most fall within a standard deviation of average...) in a less fluid job market.
Areas with fluid job markets tend to have higher costs of living. Unless one is extremely talented (and in many cases, even if that is the case), one doesn't become a great cut above average overnight. One generally starts off with a job in an area with a fluid job market (hence greater expenses!) and over the time develops ties to the area (friends, family, pets, etc...) and can't easily drop everything to move to a cheaper area for their "leisure time" and then -- if something goes wrong -- easily return to the area to take advantage of the fluid job market.
All else being equal, a developer of equal skill, in an equally fluid area, that did not "take a year off" will hired over one that has, _unless_ they've done something extra-ordinary with this time. Best prediction of being able to do something extra-ordinary is... having done something extra-ordinary. So at the least, do something extra-ordinary on a smaller scale first before going full-time on it. Zuck and billg didn't drop out of Harvard with a blank emacs window (in billg's case, perhaps it was a TECO window, not sure if TECO EMACS was around in his days...).
- In a capitalist system, money does one thing well: if you have more money than you have a use for, you can give it to someone who has the time to make the most of it. Marginally, a dollar spent donating to someone _very good_ working on a project I care about (a programming language, infrastructure for open source projects, a social cause, etc...) goes _much further_ than a dollar "spent" by foregoing income to work on most of those projects full-time. As for the exceptions to this, I can usually incorporate them into full-time jobs.
Conversely, I'd suggest this heuristic:
1) Can you afford it without putting people who rely on you into jeopardy? (Are you going to demand that your wife end a rewarding career to move to a cheaper area with you? Are you going to make your kids move to an area in inferior schools? If either is true, stop right there and then...)
2) Marginal value of dollar spent metric above: if someone can do a better job with the same resources, help provide the resources for them. Concrete example: since my username doesn't begin with a 'p' and end with a 'g', money I contributed to Clojure project (when it was in dire financial straits) probably had more impact in creating a Lisp-1 with a good macro-system than if I were to quit my job and work full-time on a Lisp-1 (likewise, while pg can afford to literally work on anything he wants to, he chooses to invest[3] in teams capable of building things he careers deeply about, but isn't quite good at building himself).
Otherwise, try to make the "leisure" activity part of your day-to-day job as well.
3) Otherwise, if you can do something awesome with your time -- you probably don't need someone named after a function that may never return in a memory-unsafe language's standard library to tell you that :-)
[1] Investments under-writing "early retirement" may collapse. "Social insurance" such as universal healthcare, pensions, unemployment benefits, etc... can be voted or sued out of existence.
[2] If you're an SFF fan, pick up Gene Wolfe's Book of the New Sun tetralogy sometime, but be warned that once you start, your dreams of doing anything else with your time will be over.
[3] Investing is not the same thing as donations, but I don't believe any angel/seed investor invests purely for the money.
Stop coupling "enjoyment" with "non-productive".
It seems like the opposite considering he's advocating working on an idea for no pay, which is something you'd only do because you enjoy it and can easily be seen as being productive.
By considering "use of free time for enjoyment" too narrow. Supposedly because he thinks that "meaningful" is distinct from "enjoyable".
