The advantage of the two-job route is that it lets you jump over obstacles. The landscape of possible jobs isn't flat; there are walls of varying heights between different kinds of work. [7] The trick of maximizing the parts of your job that you like can get you from architecture to product design, but not, probably, to music. If you make money doing one thing and then work on another, you have more freedom of choice.
Which route should you take? That depends on how sure you are of what you want to do, how good you are at taking orders, how much risk you can stand, and the odds that anyone will pay (in your lifetime) for what you want to do. If you're sure of the general area you want to work in and it's something people are likely to pay you for, then you should probably take the organic route. But if you don't know what you want to work on, or don't like to take orders, you may want to take the two-job route, if you can stand the risk.
Don't decide too soon. Kids who know early what they want to do seem impressive, as if they got the answer to some math question before the other kids. They have an answer, certainly, but odds are it's wrong.
A friend of mine who is a quite successful doctor complains constantly about her job. When people applying to medical school ask her for advice, she wants to shake them and yell "Don't do it!" (But she never does.) How did she get into this fix? In high school she already wanted to be a doctor. And she is so ambitious and determined that she overcame every obstacle along the way-- including, unfortunately, not liking it.
Now she has a life chosen for her by a high-school kid.
When you're young, you're given the impression that you'll get enough information to make each choice before you need to make it. But this is certainly not so with work. When you're deciding what to do, you have to operate on ridiculously incomplete information. Even in college you get little idea what various types of work are like. At best you may have a couple internships, but not all jobs offer internships, and those that do don't teach you much more about the work than being a batboy teaches you about playing baseball.
In the design of lives, as in the design of most other things, you get better results if you use flexible media. So unless you're fairly sure what you want to do, your best bet may be to choose a type of work that could turn into either an organic or two-job career. That was probably part of the reason I chose computers. You can be a professor, or make a lot of money, or morph it into any number of other kinds of work.
It's also wise, early on, to seek jobs that let you do many different things, so you can learn faster what various kinds of work are like. Conversely, the extreme version of the two-job route is dangerous because it teaches you so little about what you like. If you work hard at being a bond trader for ten years, thinking that you'll quit and write novels when you have enough money, what happens when you quit and then discover that you don't actually like writing novels?
Most people would say, I'd take that problem. Give me a million dollars and I'll figure out what to do. But it's harder than it looks. Constraints give your life shape. Remove them and most people have no idea what to do: look at what happens to those who win lotteries or inherit money. Much as everyone thinks they want financial security, the happiest people are not those who have it, but those who like what they do. So a plan that promises freedom at the expense of knowing what to do with it may not be as good as it seems.
Whichever route you take, expect a struggle. Finding work you love is very difficult. Most people fail. Even if you succeed, it's rare to be free to work on what you want till your thirties or forties. But if you have the destination in sight you'll be more likely to arrive at it. If you know you can love work, you're in the home stretch, and if you know what work you love, you're practically there.
[1] Currently we do the opposite: when we make kids do boring work, like arithmetic drills, instead of admitting frankly that it's boring, we try to disguise it with superficial decorations.
[2] One father told me about a related phenomenon: he found himself concealing from his family how much he liked his work. When he wanted to go to work on a saturday, he found it easier to say that it was because he "had to" for some reason, rather than admitting he preferred to work than stay home with them.
[3] Something similar happens with suburbs. Parents move to suburbs to raise their kids in a safe environment, but suburbs are so dull and artificial that by the time they're fifteen the kids are convinced the whole world is boring.
[4] I'm not saying friends should be the only audience for your work. The more people you can help, the better. But friends should be your compass.
[5] Donald Hall said young would-be poets were mistaken to be so obsessed with being published. But you can imagine what it would do for a 24 year old to get a poem published in The New Yorker. Now to people he meets at parties he's a real poet. Actually he's no better or worse than he was before, but to a clueless audience like that, the approval of an official authority makes all the difference. So it's a harder problem than Hall realizes. The reason the young care so much about prestige is that the people they want to impress are not very discerning.
[6] This is isomorphic to the principle that you should prevent your beliefs about how things are from being contaminated by how you wish they were. Most people let them mix pretty promiscuously. The continuing popularity of religion is the most visible index of that.
[7] A more accurate metaphor would be to say that the graph of jobs is not very well connected.
Are Software Patents Evil?
(This essay is derived from a talk at Google.)
A few weeks ago I found to my surprise that I'd been granted four patents. This was all the more surprising because I'd only applied for three. The patents aren't mine, of course. They were assigned to Viaweb, and became Yahoo's when they bought us. But the news set me thinking about the question of software patents generally.
Patents are a hard problem. I've had to advise most of the startups we've funded about them, and despite years of experience I'm still not always sure I'm giving the right advice.
One thing I do feel pretty certain of is that if you're against software patents, you're against patents in general. Gradually our machines consist more and more of software. Things that used to be done with levers and cams and gears are now done with loops and trees and closures. There's nothing special about physical embodiments of control systems that should make them patentable, and the software equivalent not.
Unfortunately, patent law is inconsistent on this point. Patent law in most countries says that algorithms aren't patentable. This rule is left over from a time when "algorithm" meant something like the Sieve of Eratosthenes. In 1800, people could not see as readily as we can that a great many patents on mechanical objects were really patents on the algorithms they embodied.
Patent lawyers still have to pretend that's what they're doing when they patent algorithms. You must not use the word "algorithm" in the title of a patent application, just as you must not use the word "essays" in the title of a book. If you want to patent an algorithm, you have to frame it as a computer system executing that algorithm. Then it's mechanical; phew. The default euphemism for algorithm is "system and method." Try a patent search for that phrase and see how many results you get.