Do you really need to eat your vegetables? Deliberating dropping out for MIT students. 

How to deliberate a leave of absence to work on your company. For MIT Entrepreneurial Spirits.

Alex List
8 min readApr 26, 2014

I recently had a conversation with my friend Blanc, an MIT freshman whose company has been taking off. Blanc had met with MIT President Rafael Reif about dropping out. “He basically gave me the ‘you gotta eat your vegetables speech’ about taking the General Institute Requirements,” said Blanc.

Reif recently spread the word on campus that he’d like to meet with anyone thinking of dropping out. He’s been very interested in improving the undergraduate experience.

Yet something seems to make MIT incompatible with active entrepreneurship. Delian, Laura, Ishaan, Eric, Doug. These are just my friends that have gone on leave of absence in the last two years at MIT to work on their own companies. I know fleetingly few who have managed to do both.

Should they have stayed to eat their vegetables? Let’s investigate why one should be inclined to stay, and why one should be inclined to go.

You learn a lot at a place like MIT- not just linear algebra, thermodynamics and algorithms. You learn how to think. You learn how the best thinkers create a toolbox of principles -mechanical and moral- they rely on and fall-back on whenever things get tough.

You have astonishingly intelligent fellow students building and learning awesome things. They encourage you. They even teach you!

You have a fantastic center for entrepreneurship. As a founder you get supportive quirky people helping you think about entrepreneurship, the pitfalls they’ve encountered, the traps. They force you to think about fundamentals. They invite-over successful inspiring alumni. They are always encouraging.

There are even quirkier experiments that happen on this campus: the MIT Beehive, space in an old building given for student entrepreneurship, which perhaps should have required mentorship, but was awesome.

The Entrepreneurs Anonymous group, where I accompanied Romi and Delian at the Trust Center was my first entry into a shared community of practice around entrepreneurship. I had been a total loner in my prior business work. I never before had friends who were making companies.

Like it was for me, MIT is a beacon of hope for all the brilliant people in the world: you are not alone. Come and you’ll be stronger. Come and your head will be brought above the fog. Come and somewhere you’ll find your people. Come and you’ll learn something others need.

There is a primary parental concern regarding eating vegetables: “What you don’t like will be good for you in ways you don’t yet realize.” This is a valid concern, specifically relating to dangers one can’t expect.

You see, my friends who drop out to work on their own companies, usually go through some startup or fellowship thing.

My fear for my friends who drop out is that they will be rolled into some machine they don’t understand, and consumed. It seems that an MIT degree could help avoid that.

First you leave to do some startup or fellowship thing. Then even if business isn’t optimal, it looks like if you persevere for a year or two, you’ll be acquired. Then after you’re acquired, there’s a year or two incentive to stay on board to help “integrate your technology.”

Before you know it, three years have gone by and MIT won’t take you back so readily. Before you know it, people aren’t looking at you like “founders” anymore. They’re looking at you like employees. All in the guise of first opportunity, then upward mobility, then vesting.

Be careful and skeptical. Business people are successful for a reason. As successful simultaneous CEO/MIT student Romi Kadri, MIT 14' says, “the business world is full of sharks.”

By plugging into some startup or fellowship thing you give yourself an API for reuse by others. You’re like a spark plug running in someone else’s engine. When your engine fails, people are going to scrap you out for another engine.

All the some startup or fellowship thing who looked so generous on the outset are going to start looking more like sharks. And like my grandpa said, “nobody ever pillaged a junkyard looking like Mother Teresa.”

But given that, when does it make sense to get up from the table? Why would it make sense to leave school? I think it has to do with time, rate of nourishment, vision, and excitement.

Time. I cherish what my mentor in Aerospace engineering Professor Lagace told me in a meeting: “Alex, MIT is about doing things well.” In Sophomore year when I was overly ambitious, taking eight classes and flunking most of them, that helped a lot.

“Alex, MIT is about doing things well.”

Indeed, why do anything you care about in life if you can’t do it well? I’ve kept this advice in mind, even outside MIT. I’ve discovered that usually it’s not “how smart you are,” so much as time spent that describes how well I’ll do at a task. It’s true for others too. From the people I know, IQ isn’t a direct predictor of tasks completed per hour.

Thus if you want to work well on a project, you’ve got to give yourself time— I take roughly three classes. If you want to launch a product, you better work on it smart — find good partners—you’re forced to.

The trouble is, unless what you’re building is guarded by patents, good luck competing with people who can spend their entire day every day on building product. Competitors will be people whose entire life revolves around the success of their product.

What do students do when their products have competitors? And what do students do if they don’t have any competitors, but feel that their entire life revolves around a product? A lot of students go on leave.

Economically, this appears to be a fine time to go on leave of absence. You’re young and have no dependents, the economy is ridiculously strong in tech— so strong people are excited to invest in a pre-22 year old to build their vision for a company.

Whether to leave MIT because of a project is not like whether to buy a milkshake or smoothie. The following two questions have helped:

Whether to leave MIT because of a project is not like whether to buy a milkshake or smoothie.

The first question I’ve asked is “Do I know enough?” It’s meant to specify whether you need to take specific courses that prepare you to build what you want. It’s not meant to be a discouragement question, because without extenuating circumstances, you will be doing the building.

Second, I’ve asked “will I learn what I need for future bigger things?” You know you will do even bigger awesome things in the future. You need to make sure you’re positioned to do great things in the future, and you can’t let building a specific business stop you.

Companies are pretty good teaching grounds— you learn you weakness, meet people to accomplish things with, and can even improve the world.

If you leave, luckily MIT is often great about taking you back, especially within three years. Sometimes you will have to fight your way back-in, but good relationships will help bring you back.

When you really love MIT, it becomes sad that you only have one year left. You need to start thinking about what’s next, and if you’re excited, you start doing it immediately. That new thing will tug at you until it has your entire attention, leaving you dissatisfied if you’re unable to treat it well.

There is one more important question: “can you afford to do what you love?” You ought to be able to survive without significant personal risk. For example, be able to afford health insurance. Have the ability to buy new equipment if yours break.

You may not have the cash you need to afford a base quality of life without absorbing a massive amount of debt. Set yourself a debt ceiling. Don’t absorb the kind of debt that will impede you from doing great things in the future.

If you’ve saved a ton, you can really do whatever. But if you’re making a company, the best idea I’ve found is to “build something people want.”

If you don’t have the cash, it probably makes sense to go into fundraising mode, or apply to some startup or fellowship thing, and figure out how to use to leverage other people’s money — OPM.

OPM is usually smarter than your money, and by definition it’s more connected. It’s good to have a large network of people whose success corresponds to yours. Aligning incentives is why it’s often better to be utilizing OPM.

Bootstrapping can also be an okay mechanism, says Paul Graham of Y-Combinator, who suggests bootstrapping only if it ties your clients into your product. Graham’s Viaweb built others’ websites to acquire first customers for their web store platform. Graham also wrote one of the best articles on how to fundraise.

I know I have a ton to learn. Regarding business, the experimental method does seem like the best way to get experience. If the things you’d like to accomplish in life are hard, experimentation seems the only way you’ll ever achieve them.

Do you know enough to build you company? Will you learn things by working on your company? Can you afford to work on your company? Are you equally excited about your project as you were about getting into MIT?

If so — make your vision happen! Take some time off of school and throw everything you’ve got into it. You may succeed, but no matter what you’ll learn. Most importantly, you’ll feel good about yourself.

If instead you still need to learn a lot to do what you’d like, or if you need a certification— you ought to take those enabling courses. Get the degree and pass your exam, work for that architecture firm, or maybe start your own.

This world is yours too! Enable yourself to do what you want, then do what you love.

Yet know where you stand between two machines. Specifically do not be arrogant. Specifically it’s dumb to insult potential advocates for your return to MIT. Specifically don’t say: “see you later, I’m making a startup, Jerks!” Simultaneously be very clear with the people on another coast, that you “feel returning to MIT is a very strong option” you’ll consider if you company flops, so that there are fewer hard feelings if it does.

Even better, keep your ties both places. Respect everyone, and they’ll respect that what you’re doing is simply right for you. Frankly, this requires a level of maturity I just don’t see in most of my friends my age, or mostly anyone for that matter.

But I feel everyone is capable of building that courage to have respect. That’s why I support and care for my friends through all the dumb shit they say or do. My friends are the craziest most creative people on earth— but they also have the potential to be the best human beings.

What you do in life should be what you love. If you can’t do what you love in life yet, you ought to eat some vegetables. If you’ve had all the veggies you need to do what you love —or need the real world to determine the vegetables you need— it may be the right time to build a company.

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Alex List

Born-again MIT student. Apple Design Award recipient. Founder of usemagnet.com