What It’s Like to Dropout of School

My list of the advantages and disadvantages of dropping out of school 

The other day a friend asked me what it was like to drop out of school. I thought it’d be a good topic for an article since it’s a question I’m asked quite often. Like many things in life, leaving school has had both its ups and downs. Here’s my list of those ups and downs:


Real world learning

One of the benefits of leaving school and pursuing my career is that I’ve been able to learn in settings where it is most conducive to personal growth. Compared to sitting in a classroom, or reading a textbook, this environment is orders of magnitude more efficient. In many ways studying and the test become one in the same after school.

An example of this is learning Bayes Theorem from the creator of Adwords and then understanding how to apply it to prototyping a product ten minutes later. Another example is learning inbound marketing from Hubspot (a company that literally wrote the book on the subject) and then managing an inbound marketing team. Switching from textbooks to blog posts has helped me learn a variety of subjects in a tenth the time and best of all, I’m not left asking the most common question in school:

“Is this going to be on the test?”

It’s always on the test.

The most up to date textbooks

In school I often questioned how up to date our readings were and whether they even mattered. In 20th century history this clearly doesn’t matter, but when it comes to marketing if you are 6 months behind a trend you can pretty much give up. Trends like Facebook Ads and SEO have short half-lives and become less efficient with time so generally I am forced to always be up to speed on the latest trends.

Health and happiness

Another obvious benefit of being an entrepreneur for the last 9 months and now working at a startup is that I get to choose my schedule. Some mornings I wake up at 8am, some mornings I wake up at 10am, but I rarely set an alarm.

All of this makes me about 10x more happy on a day to day basis than I was when I was sleeping 6 hours and waking up before dawn to get to an 8am class.


When I was running SkyRocket my goal was to reach out to (email, phone or voicemail) at least 10 people every day. So over the course of the last 9 months I’ve “touched” over 2,700 people and probably met about 500-750 of those people. Some of these people are CEOs of top companies like HootSuite and Mobify, which has its obvious perks, and others are thought leaders who I get to learn from.


Specific learning instead of general learning

One thing I loved about school was the exposure to new ideas, books and topics. For example, I never would have researched machine learning or artificial intelligence if it weren’t for my Computer Science course, but now I find it very interesting. I also don’t get exposed to much history, math or a foreign language since I primarily focus on marketing and sales (I realize some would argue this is a benefit and not a disadvantage).

One of the ways I make up for this is by writing everyday, reading a couple books a week and keeping up to date on current events, but I can’t possibly get the same exposure I would if I were in school.

Hanging out with friends is hard

Leaving Vancouver was one of the hardest decisions I had to make in 2013 because it meant leaving many of my close friends. Then when I arrived in Palo Alto I had no connection to a group of people my age. Constraint breeds creativity, but the challenge of meeting people my age is one of the hardest I deal with.

Neither here nor there

Another disadvantage to leaving school was knowing that I would be the outcast in many situations. A couple, “What are you studying?” questions into my journey I realized just how painful most small talk was going to be for the rest of my life.

The stress

People often ask me if I was scared to leave school and my usual answer is no. I don’t worry about not being able to get a job or falling behind or any of that because I have confidence in myself (sometimes too much). If an investor or employer doesn’t like the words “Did not finish school” on a resume then I don’t want to work with them anyway.

The stress that kept me up at night as a founder was not knowing whether or not I was going to be able to finish our app before the date I promised stakeholders it would be. It was looking a customer in the eye and telling them that we did not in fact hit our deadline and their $7,000 was at risk. That kind of stress topped the stress of studying for a meaningless test all day for me and caused more than a few restless nights.

All things considered the advantages far outweigh the disadvantages in my situation and I’m very happy with my decision to put school on hold and follow my dreams. It’s certainly not final, but odds are that I won’t return to school because the opportunity cost of doing so is so unfavorable.

Paradoxically, learning—which is one of my biggest passions—didn’t happen in an environment where the sole mission was to educate. In fact, I’ve learned more about myself and the world around me since leaving school than I have ever learned before.

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