How do you figure out if you can afford something?

How do you calculate it when some factors are unknown?
—-like the uncertainty of the current economy
—-like if you’re out of work and looking for a good job and don’t know when you’ll find one, especially in this economy

What if it is education, i.e., going back to school, which is, for the most part, always a good investment?

I’d appreciate any professional financial tips and methods, and a list of steps to take to figure this out. Thanks.

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