It’s the question you’re asking yourself…and now, pretty regularly, you’re asking me because my article on leaving school somehow became #1 Google result for “dropping out of college.”

I’m not going to give you an answer, because no one can really answer that but you. But I can walk you through the process, through the questions you’re going to need to ask yourself. Because most of the emails I get are from kids struggling with the same basic issues: School is not what they thought it would be, they aren’t happy, they want to do something different. Yet they’re worried what their parents will think, they don’t want to make a mistake and they want to hear from someone who has been in their shoes.

I remember those shoes well. I remember pacing in a parking lot—a 100+ degrees outside in Riverside, California—listening to the same song over and over again as I thought about it all. I thought I would have an anxiety attack. I was petrified of making a mistake. But then I made the leap.

As I said about my own journey:

When I dropped out of school, I was betting on myself. It was a good bet at the time, based on a lot of factors. Honestly, the outcome surprised even me. In less than 3 years, I’d worked as a Hollywood executive, researched for and promoted multiple NYT bestsellers, and was Director of Marketing for one of the most provocative companies on the planet. I had achieved more than I ever could have dreamed of—the scared, overwhelmed me of 19 could have never conceived of having done all that. And since then, I “dropped out” of many other supposedly required things, from six figure jobs to entire career paths.

Of course in hindsight this seems a lot cleaner than it was. I was often terrified, worried, and didn’t know how things would work out. But one of the ways I got through this period was by asking myself the tough questions. Questions like, “What’s the absolute worst that can happen?” By doing this I was able alter my perspective and see that this obstacle that stood in my way wasn’t really an obstacle at all all, but an opportunity to see what I was made of. I was able to see the possible consequences of my decision without all the hysteria and drama that comes with it when you’re stuck in your own head or listening to bad advice.

So, what I often do when people ask me about dropping out of school is respond by asking them questions back, because I’ve found that’s the best way of finding answers for yourself. So here are some questions you should consider if you’re thinking of dropping out of school, and remember it’s not life or death.

So here are the questions (but of course if you have specific ones, you can always email me):

-Am I dropping out of school because I have something better? Or is it because I can’t cut it in school?

-What am I going to be doing outside of school that I couldn’t do inside?

-Have you fully taken advantage of the unique opportunities that are offered to students? Because let me tell you, the world is much kinder to students. The second you leave you’re now competition.

-What are your plans for continuing your education? You’re 20 years old…you don’t know shit. Leaving school might be the right thing, but do you have a plan to keep learning? Like I’ve said before: education is hard, it’s a lifelong job and the responsibility to do it rests solely on you.

-What other smart people in your life have you asked for information about this? I wrote information, not advice, for an important reason. Most people give horrible advice and will lead you astray, no matter how successful they are.

-Do you know what the sunk cost fallacy is? Basically it means that just because you started something, doesn’t mean you have to finish it. Instead, decide if you want to do it right now and ignore what you’ve put in so far. It is, logically and statistically, irrelevant.

-This opportunity that is front of you—is it what you were going to school for in the first place? For me, that was it. I wasn’t going to stay in school for another year, graduate, and then cross my fingers and hope to get offered a similar job again. Fuck the marshmallow test—sometimes you have to take what’s offered to you right now…because later might not happen.

-You know that you can always go back right? Most drop outs don’t actually “drop out”—they just take a temporary leave of absence (which gives them the option to return). The certainty is a projection, they were just as nervous as you are. So try to relax. I know it feels like life or death but it isn’t. This is a first world problem. You will be fine.

-Are you prepared for nobody to understand? Especially your parents?

-You’re not going to starve—you know that right? And you won’t end up working at McDonalds unless you fuck up somewhere. Unless you make numerous, repeated, unnecessary and deliberate mistakes that are far removed from whether you drop out or not. You live in America, it’s going to be fine whatever you decide.

-There will forever be a gulf between you and your college friends. Is that something you’re OK with? It will be like Raul’s piece about the fundamental difference between Millenials. You might not be going to war…but your experiences will make you very different from your 4-years-in-the-dorms friends.

-If you can’t cut it in school—which is run a lot like the corporate world—why are you so sure you’ll succeed outside of it?

-How much money do you need to live? Have you thought about this? Do you know how to support yourself? Try to have a few months money on hand. It makes you feel less pressure and gives you more power in negotiating situations.

-If everything goes to shit, what’s the plan? It could be just as simple as “I’ll re-enroll” but have an answer.

-Are you aware that if you graduate you’ll still probably have to beg for a job? Or accept a shitty, under-paid one? Fifty three percent of recent college grads are jobless or underemployed. A degree is not a guarantee.

–Who is your mentor? What is your support system? Who has your back now that there is no one checking to see if you turned your work in? You’re going to want this locked down. Don’t tell me you plan to do this alone. Honestly, I don’t think I would have survived it without two people: my girlfriend (now fiancée) and my grandfather (I also had great mentors).

-If it doesn’t work out—which it might—are you OK with accepting or admitting failure?

-A kid once emailed me about wanted to drop out of Liberty University because he “hated college.” I had to ask: Are you sure it was college that was the problem? Maybe it’s just your college. Or maybe it’s just your major. Or just the way you’ve been living. Make sure you’re not throwing the baby out with the bathwater. There’s no law that says you can’t make changes. There are a lot of drastic changes you can make between here and leaving school. Make sure you’ve explored them. Don’t pull the grim trigger straight out.

-Are you being spoiled, petulant, entitled, reactionary, or delusional? Ask yourself. Really ask yourself.

-There’s a saying: Always trade space for time. Think about it. Does it apply here? Because it can—in either direction. Does staying in college give you more time to develop? Does leaving give you a chance to get a lead on your peers?

-Are you staying in school because it’s safe and comfortable? “Just because you’re winning a game doesn’t mean it’s a good game.” – Seth Godin

-I was talking to a friend the other day who was doing his resume. He’d never actually graduated from school but none of the jobs he’d applied for had actually known this. Why? He just put that he’d attended school for however many years and they’d assumed. This isn’t really a question, just a funny illustration of how it works in the real world.

-In 15 years, is anyone going to be impressed that you have a degree from [insert your school]? Sometimes the answer to this question is yes. Dropping out of Harvard is very different than dropping out of a state school.

-Scared about making the wrong choice? Have you heard of cognitive dissonance? It’s a weird phenomenon but it means regret is a lot less of a deal than we think it is.

-I’m sure you’ve thought of all the dropout successes—Bill Gates, Zuckerberg, etc—but have you taken a second to consider the people you’ve never heard of? On both ends…I’m talking about the quiet successes who you never even know don’t have a degree. And of course on the other end, the people who failed miserably. The survivorship bias can be deceptive. Take a second to think about what it is hiding from your view.

-What will your parents think? They will probably want you to do what’s safe. But I want to say this: you know it’s OK to disagree with them right? Understand why they feel what they feel, but then do what’s best for you. I mean, forty five percent of recent college graduates were still living with their parents in 2011, so college is more like a coin flip.

-A degree is just a piece of paper. But how much is that paper going to be worth to you down the road? Think about it. It’s worthless now, but depending on your field, it could be a stock you need to ride out.

-If you’re unhappy with college, why are you taking out the equivalent of home mortgage to get a degree? Odds are you’ll never pay it back (it will never be forgiven). Student loan debt is at $1.1 trillion and rising, which is more than American credit card debt.

-Have you read Charlie Hoehn’s Recession Proof Graduate?

-“First, you get rid of the notion that anything about your life is really at stake. Whatever happens, you’ll be fine. You’re not deciding whether to opt for chemo or not.

That is to say: calm down.”

-“Get information, not advice. See most people—no matter how wise or successful—give horrible advice. They’ll send you astray. So don’t ask for advice. Ask them for information that you can translate into advice.”

-Are you aware that “the proportion of people without any college education at Google has increased over time” according to a New York Times interview with their senior VP of people operations? Something to think about.

Nothing will make this decision easy for you. Nothing will make it clear either. It’s a risk, it’s a gamble. But that’s what makes it such a big opportunity. All the big decisions in your life will be like this. All the things that change who you are for the better will be like this.

I can’t tell you whether you should leave school, just like no one could really tell me. But they did help. I was leaning one way but when I was asked—and asked myself—the right questions, I figured out the choice that made the most sense to me.

And here’s the kicker: in retrospect, I realize that had I made the opposite decision I probably would have ended up in more or less the same place. People who do great things aren’t held back by school or not school. For the greats, obstacles only serve to fuel the fire of their ambition and determination. They use adversity to turn their obstacles upside down and create opportunities. And the same is true for you.

Ryan Holiday’s new book is The Obstacle Is The Way.