Career Advice From A High School Drop-Out CEO

CollegeHumor head of video and Big Breakfast president Sam Reich imparts lessons learned from an unconventional path.

Career Advice From A High School Drop-Out CEO
[Source Photo: Flickr user The Library of Congress]

I’m a high school drop out. I’m also head of video for CollegeHumor and president of Big Breakfast, CollegeHumor’s offshoot production company. (Yes, I appreciate the irony.)


People always ask me, “Would you recommend that I skip out on high school or college?”

Sam ReichPhoto: Robyn Von Swank

Let’s be clear about this: I don’t want you showing up to my house saying, “It didn’t work out, Sam. I will now make camp in the tent village in your backyard, among the other people you’ve ruined.” But if you’re going to do it—if you’re to make this trust fall into the arms or no-arms of a degree-less career—then here’s my advice.

Ask Yourself: Do You Know What You Want To Do?

College is a place where plans are formed, and so not going to college only works if you already have a plan. Also, ask yourself if what you want to do requires a degree. There’s plenty of things you can do without a degree, but dentistry is not one of them.

Negotiate Shrewdly With Your Parents

I told mine that I was into poetry, so they were thrilled when I decided to go into show business.

Find The Capital Of Your Chosen Industry And Move There

Even in this digital age, a lot happens by physical proximity.


Play Some Dungeons and Dragons

I maintain that Dungeons & Dragons is an important part in the development of any human being’s imagination and social skills.

Get A Bad Job Somewhere You’d Like To Work

Assistants are promoted to writers, PAs are promoted to coordinators, and so on. Strangers are scary, and we’d all rather work with the people we know. Former CollegeHumor writer Dan Gurewitch began as a front desk person. He now writes for John Oliver.

Write Emails To Your Heroes And Ask For Coffee And Advice

You’ll find mentors or maybe even that bad job. This is how I met Fred Seibert of Frederator, who helps me make every big decision in regards to my career.

Learn By Doing

Do whatever you can to get your practice in. Tweet, create a funny single-serving blog, get some friends together and make a web series, or whatever applies to your industry. You’ll meet people, but more importantly, you’ll slowly but surely get good.

Fake It ‘Til You Make It

It’s impossible to get a good job without going out on a limb. Fake confidence, or experience if necessary, get the job, and figure it out. I convinced the Burton Taylor Theater in Oxford to let me do Waiting for Godot by telling them I was an experienced theater director. I was 15.


Read “Getting Things Done” and “The 80/20 Principal”

Using those principles, create meticulous lists of your goals and the next action item associated with each goal. I do this in an app called Trello.

Go With The Flow

There may come a time where you want to “strategically settle.” I at first wanted to be an actor but in the end found that I was getting more opportunities—and was probably better—at producing, directing, and writing. This is hardly a concession, but it felt like one, and it led my whole, gratifying career.

Put In A Decade

The best piece of advice I ever received, from my high school drama teacher Mark Lindberg, is this: “It’s not how much you want something; it’s how long you want it for.” The odds are never in your favor, but a 100-sided die will eventually show 100. And that’s one hell of a move in Dungeons & Dragons.

Related: Tig Notaro On The Best Lesson She Ever Learned In Comedy

Sam Reich is the president of Big Breakfast, CollegeHumor’s offshoot production company, and the head of video for CollegeHumor.