What questions should I be asking?

At first I thought asking yourself what you should be asking yourself was redundant. It isn't. Without this question, you wouldn't ask any others, so it gets top billing. It creates an alert, thoughtful mind state, ideal for ferreting out the information you most need in every situation. Ask it frequently.
Is this what I want to be doing?

This very moment is, always, the only moment in which you can make changes. Knowing which changes are best for you comes, always, from assessing what you feel. Ask yourself many times every day if you like what you're doing. If the answer is no, start noticing what you'd prefer. Thus begins the revolution.
Why worry?

These two words, considered sincerely, can radically reconfigure the landscape of your mind. Worry rarely leads to positive action; it's just painful, useless fear about hypothetical events, which scuttles happiness rather than ensuring it. Some psychologists say that by focusing on gratitude, we can shut down the part of the brain that worries. It actually works!
How do I want the world to be different because I lived in it?

Your existence is already a factor in world history—now, what sort of factor do you want it to be? Maybe you know you're here to create worldwide prosperity, a beautiful family, or one really excellent bagel. If your impressions are more vague, keep asking this question. Eventually you'll glimpse clearer outlines of your destiny. Live by design, not by accident.
How do I want to be different because I lived in this world?

In small ways or large, your life will change the world—and in small ways or large, the world will change you. What experiences do you want to have during your brief sojourn here? Make a list. Make a vision board. Make a promise. This won't control your future, but it will shape it.
What is my body telling me?

As I often say, my mind is a two-bit whore—by which I mean that my self-justifying brain, like any self-justifying brain, will happily absorb beliefs based on biases, ego gratification, magical thinking or just plain error. The body knows better. It's a wise, capable creature. It recoils from what's bad for us, and leans into what's good. Let it.
What potential memories am I bartering, and is the profit worth the price?

I once read a story about a world where people sold memories the way we can sell plasma. The protagonist was an addict who'd pawned many memories for drugs but had sworn never to sell his memory of falling in love. His addiction won. Afterward he was unaware of his loss, lacking the memory he'd sold. But for the reader, the trade-off was ghastly to contemplate. Every time you choose social acceptance over your heart's desires, or financial gain over ethics, or your comfort zone over the adventure you were born to experience, you're making a similar deal. Don't.
Where should I break the rules?

If everyone kept all the rules, we'd still be practicing cherished traditions like child marriage, slavery and public hangings. The way humans become humane is by assessing from the heart, rather than the rule book, where the justice of a situation lies. Sometimes you have to break the rules around you to keep the rules within you.
Are my thoughts hurting or healing?

Your situation may endanger your life and limbs, but only your thoughts can endanger your happiness. Telling yourself a miserable mental story about your circumstances creates suffering. Telling yourself a more positive and grateful story, studies show, increases happiness. Wherever you are, whatever you're doing, choose thoughts that knit your heart together, rather than tear it apart.
Really truly: Is this what I want to be doing?

It's been several seconds since you asked this. Ask it again. Not to make yourself petulant or frustrated—just to see if it's possible to choose anything, and I mean any little thing, that would make your present experience more delightful. Thus continues the revolution.