A Career Hackers’ Classic, read the full post here.


“Should I drop out of college?”, no one but you can really answer this question for yourself. The answer is complicated; you are worried about your parent’s reactions or if you will make a mistake.

Before starting read a paragraph about Ryan’s (Writer) journey on dropping out of college:

“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.”

This may look a lot less messy than it actually was. A ton of things didn’t work out. But he got through it asking the ‘tough questions’, like ‘what’s the absolute worst that can happen?’.
And this is the solution oftentimes, asking yourself some deep and tough questions to figure out the best answer for yourself.
But remember, dropping out of college isn’t life or death.

Here are the questions you can ask yourself that will help you reach the decision and can walk you through the process.

  • Am I dropping out of college because I have something better to do?
  • What different am I going to do outside college than inside it?
  • Have you fully taken advantage of the opportunities and kindness offered to students?
  • What are your plans to continue learning after leaving college? Education is a lifelong job.
  • Have you taken any third-person perspective or information about this from people who dropped out? Take information, not advice.
  • Did you join college for the opportunity in front of you in the first place?
  • You can always go back to college. Most dropouts take a temporary leave and are just as nervous as you are.
  • Are you prepared for nobody to understand you?
  • You are most probably not going to starve unless you fuck up big somewhere.
  • There will always be a gulf between you and your friends in college. Your experiences will make you very different from your 4-years-in- dorms friends.
  • If college is hard for you, why are you sure you’ll succeed outside of it?
  • Figure out the money you need to live and find a source to support yourself to feel less pressurised.
  • Having an answer to what’s the plan if everything goes wrong?
  • Are you aware that even if you graduate you have to struggle for a job or settle for an underpaid job?
  • Who are your mentor and your support system? It’s hard to do this all alone. You need someone checking on you to survive this.
  • Are you OK with accepting your failure if it doesn’t work out?
  • If you ‘hate college’, ask yourself if college is the problem or if your major or your lifestyle that is making you hate it.
  • Are you being spoiled, petulant, entitled, reactionary, or delusional? Ask yourself. Really ask yourself.
  • Always trade space for time. Think about it. Does leave or staying in college will give you more time to develop?
  • Are you in college just because it’s safe? “Just because you’re winning a game doesn’t mean it’s a good game.” – Seth Godin
  • Think about whether is anyone going to be impressed in 15 years that you have a degree.
  • If you are scared of making the wrong choice, remember regret is a lot less of a deal than we think it is.
  • Gain more knowledge about the people who dropped out. Both the success and failure stories of people you never heard about.
  • What will your parents think? Know that it’s OK to disagree with them. Understand their perspective but do what’s best for you.
  • Think about the worth your degree will be for you. It can be worthless or it could be a stock you need to ride out.
  • Why are you taking out this big student loan debt when you are unhappy with college?
  • Read Charlie Hoehn’s Recession Proof Graduate?
  • Get rid of the notion that anything in your life is at stake because whatever happens, you’ll be fine. Calm down.
  • Are you aware that “the proportion of people without any college education at Google has increased over time”

Nothing will make this decision easy for you. This is a risk and that’s why it is a big opportunity. Everything that changes who you are for the better will be like this.

The only thing you can do is ask yourself questions and gain clarity on whether the decision is right for you or not.


A powerful excerpt from the blog-

“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.”


A Career Hackers’ Classic, read the full post here.


Ryan Holiday is an American author, modern Stoic, public-relations strategist, owner of the Painted Porch Bookshop, and host of the podcast The Daily Stoic. Prior to becoming an author, he served as the former director of marketing and eventually an advisor for American Apparel.