What's important to you? (career-wise)

Should I stay or should I go now?
If I go, there will be trouble
And if I stay it will be double
- The Clash

I normally stay away from blogging about career advice, or advice in general, but sometimes you get thrown a curveball - something like "The Offer" and have to come up with a way of dealing with it.

It's a very generous offer. It also shows strong commitment by leadership to an idea or ideal; especially when the ramifications are large enough to potentially reinvigorate, or decimate, a fortune 500 company. Unfortunately, is it too good of an offer? I'm not going to go into the tech landscape at Zappos, but there are many confounding factors.

What I want to talk about though is, "As a software engineer, how could I process a major decision like "stay or go"?

Do we:
Break out the some spreadsheets and calculate financial outcomes using future value of money formulas?
Mash it up with the expected probabilities of various events?
Go with a gut feeling?
Just blindly invest in someone else's evolving vision?
Ask your friends what they're doing or for advice?

Is it even necessary to evaluate the attempted transition to self-management/self-organization? Or, is there an easier heuristic for this decision in the first place?

Lets look at Maslow's work on hierarchy of needs, usually pictured as a pyramid. Roughly paraphrased, Maslow posited that there are two groupings: deficiency needs and growth needs. Deficiency needs are things that must be satisfied before you can move to the next higher level. Growth needs can only be acted upon after deficiency needs are satisfied.

From the bottom of the pyramid to the top, the first four are deficiency needs: Physiological -> Safety/security -> Belongingness/Love -> Esteem.
After that are the growth needs: Cognitive -> Aesthetic -> Self-actualization -> Self-transcendence

(Self-actualization is something like "finding self-fulfillment and realizing one's potential", while self-transcendence is something like "helping others find self-fulfillment and realize their potential")

Is there something similar to this hierarchy of needs for a career? Where would self-management and self-organization fit in?

I'm going to suggest that these ideas that we're being asked to buy into fall somewhere between self-actualization and self-transcendence, as I don't think anyone can argue they're a deficiency need.
Since it's not a deficiency need, and deficiency needs must be satisfied first, what are your deficiency needs? Or put more plainly, "what's important to you?"

Figure out what is important to you in your career/profession and what you need from your place of employment

That might be earning enough money to live comfortably, job security, a good work/life balance allowing you to spend time with your family or traveling to exotic locales, a short commute, growth opportunities, etc. It doesn't matter WHAT those are, just figure out what goals or things are important to YOU in your career. Once you do that, it may help you evaluate large decisions like this.