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Reading your post, I feel like you're me, except I haven't worked at startups. Addressing your first two points:

* If I don't like a situation, I will leave it. After all, the easiest way to change your environment is to escape it.

I feel conflicted with this one. While what you say is true I can't help but feel, when I try to apply to certain situations in life, like I'm quitting... or that I'd beat myself up for "being a quitter who didn't try hard enough to make things better" at a particular job or relationship or something of the sort. There's something to be said about the potential payoff relative to the amount of effort involved in making things better, of course.

Your second point is something I've been personally stuck in for awhile, mostly given the economic downturn and seeing friends go unemployed for quite a long time. Still, I probably have to make that jump sooner or later.

Oh, I try to change things. However the reality is you're working against a much larger force. It's difficult to create enough inertia to force real change.

Regarding the second point, I quit my job in early October. I had my first offer in hand in 23 days, and three in hand after the first month. Income was $0, which was a good motivator.

Though the amusing thing this time around is my former employer is now looking to become one of my clients (the place loved me, I just didn't like them).

I understand your point, but I think it might not always be possible to improve the work situation enough to justify staying there. I think it's always worthwhile to give it a try and see how much change you can effect, but there is a practical limit.

As far as unemployment - I only know of one friend who is currently unemployed, and that's by choice! Not that this is indicative of North America as a whole; but it does reflect what I've heard others say in regards to there always being good jobs available for good people who are skilled.

Yeah, that's what I was referring to when I talked about the potential payoff. I certainly have skills and a decent resume, but have had trouble getting interviews my way.

"* Fear of failure is a great motivator. When you quit without having another opportunity already lined up, you have a lot of obvious motivation to find a new job since your income is $0. I've found it easier than lulling myself into complacency by continuing to get my income from the source I hate."

This is true - but this has to mean that you also manage your finances properly on the side. People who are one late paycheck away from a cascade of payment failures and personal financial chaos can't operate this way. (So they should fix their financial management first, then follow your advice!)

No, I've done it when it wasn't prudent either. People who look at my salary history tend to have their jaw hit the floor when they look at the first 8-to-9 years. I used to have my own bosses tell me every day that I was "getting screwed". We're talking 25-33% of market rate, which traps you into slightly less crappy paychecks going forward and initially being typecast as an idiot. That was my fault for being a doormat in my teenage years -- I didn't think it would follow me until I was 26.

Fortunately I was smart enough to fix it at one point, and got a 70% pay increase upon starting another job. That takes a few tricks, though, including being hard-nosed enough to call the CxO of a company out on the politics of his negotiating practices.

It has forced me to live simpler overall, and not waste money. That's stuck with me. But when you don't have much to fall back on, you'd be surprised at how fast you're able to find a decent step up.

Just a question out of interest - how/why are people looking at your salary history?

Formal job applications.

"* Fear of failure is a great motivator. When you quit without having another opportunity already lined up, you have a lot of obvious motivation to find a new job since your income is $0. I've found it easier than lulling myself into complacency by continuing to get my income from the source I hate"

Just remember that you are a more desired candidate if you are actively employed, and that other available jobs might be just as bad or worse than your current one. Also, if you don't absolutely loathe your job, you can use job offers as leverage in your current role.

>Just remember that you are a more desired candidate if you are actively employed

This doesn't apply in all industries.

>and that other available jobs might be just as bad or worse than your current one

This also only applies if you aren't the one in control. I could get a substantially better job, and I knew it, not fearful if I could get any job at all.

Which industries does that not apply to?

You may be more desirable to a dysfunctional employer if you are actively employed, but working for another one of those is not the goal. A rational employer would judge a candidate on his/her ability to add value to the company, regardless of how they have chosen to spend the majority of their time recently.

Remember that all employers hire based on imperfect information. Being employed signals that you can add value to at least one organization, which is a pretty strong indication that you can add value to them.

Absolutely. Being employed is one of many possible indicators of your worth. Hopefully one's portfolio contains a few items more persuasive than merely being employed.