As the host of the Successful Dropout podcast and website, I have had the pleasure of interviewing an inspiring and successful dropout every week. Most have been entrepreneurs, as well as a few individuals (and many more to come) who dropped out to land their dream 9-5 job.

Entrepreneur or dream-job-lander, they all have one thing in common: they had the guts to design their own path to success, and because of that, they are most often wealthy, living life on their own terms, and influencing other dream chasers to follow suit.

Although they all have different stories and backgrounds, there are some common themes I’ve started to identify.

Here are five things I’ve learned about Successful Dropouts:

1.    They are natural born rebels

By far the most common trait I’ve noticed with the Successful Dropouts I interview is that they are natural contrarians. They don’t have to think about thinking outside of the box, they just do. When everyone else is going one way, red flags and alarms go off in their heads, and they see it as a challenge to find opportunity in the opposite direction.

They understand a fundamental law of success, and that is; if you always follow the status quo, you will never facilitate change, and change is what drives progress, opportunity, and influence.

One of the greatest fears a Successful Dropout has is that they won’t shake things up. They dread anyone calling them a “rule follower” or a “conformist”. If they can lead change, revolutionize their industry, shatter long-held beliefs, or spark a trend…it’s a good day…it’s a good life!

When asked how they perceive college, they view it as a mostly archaic and stale system designed to produce a common mentality. There are, of course, certain programs and university that are outliers, but in general, they view the system as too steeped in the past and in politics to stay innovative. To them, a degree is just an incredibly expensive piece of paper that is rapidly losing it’s return on investment for many career paths.

Because they are natural born rebels, the decision to drop out of this traditional system and build their own success is just a natural manifestation of their ambitious and innovative personalities. They can’t help but question the system, and they find it lacking.

2.    They understand the power of focus

Following one course until success (did you catch the acronym there?) is a common habit among Successful Dropouts.

As an entrepreneur, or just a “go-getter” in general, you are always looking for new opportunities, great ideas, and the “next big thing”. It’s easy to get Shiny Object Syndrome and chase after something new and exciting in hopes that it’s better than what you are doing right now.

Successful dropouts understand that in order to succeed; you have to commit to something and exercise relentless perseverance until the end goal is realized.  Focus and consistency are the keys to success.

For some, this habit came naturally, but for many, it was a learned skill.

Michael Fisk (episode 8) for example chased different opportunities for several years, never sticking with one thing long enough to make it a true success and turn the original vision into reality. It took being broke, and having to panhandle for money for him to realize he needed to pick one thing and stick with it. Once he did, he built a six-figure business in a matter of months, and he is now on track for seven figures. 

At some point, Successful Dropouts learn the value of focus.

The myth is that if you have multiple irons in the fire, if several fail, you might have one that takes off…you’re hedging your bets right?

The reality is that you are spreading yourself too thin, which causes you to move too slow in a world where speed, quick decisions, and laser focus moves the ball forward.

3.    They are “just in time” learners

This is a huge one. Too often people associate the term “dropout” with someone who hates learning…why else would they drop out of school?

It’s the opposite, actually.

Often, these Successful Dropouts are better learners than their friends in college.


In high school and college, you are focused on learning things “just in case”. You develop a skill for remembering information just long enough to regurgitate it and receive your paper reward.

Is that really learning? 100% of Successful Dropouts say no.

Smart learning is absorbing knowledge relevant to your pursuits in life only when you need to in order to take action and move forward in achieving your goals. In other words, learning is always done in the context of driving real world results. If it’s not, you should view it as recreational learning for fun.

Successful Dropouts understand this, and never learn anything “just in case”. Instead, they learn “just in time”, and because of this they retain more knowledge, are more efficient with their time and money, and accomplish more.

4.    They stay “hungry”

Successful Dropouts are never 100% satisfied with what they have achieved in the past to the point where they don’t keep looking to the future.

When they achieve their goals, they set new ones, always adding rungs to the ladder. They keep expanding their visions and questioning what is possible.

They reject the “retirement mentality”, meaning they don’t build, work and make money just so they can retire and never work again. To them, retirement is simply the excuse one gives when they run out of ideas and the will to pursue them.

Staying hungry doesn’t mean that they never enjoy or celebrate past or present successes, they simply do so with an eye towards the future and what can be accomplished next.

An unquenchable thirst for ambition goes hand in hand with successful individuals who defy the status quo, lead change and build a legacy that lasts well beyond themselves.

5.    They are self-aware

Last but not least, one of the most noticeable traits of Successful Dropouts is that they have an incredible sense of self-awareness, which is no wonder! Leaving a tried and true path forces one to become introspective, looking deep inside themselves to discover who they are and what they are made of.

The Successful Dropouts I’ve interviewed can tell you without hesitation what their strengths and weaknesses are, and they know how to go all in on their strengths and supplement their weakness, making them incredibly efficient.

They have also clearly defined what they want to be, do, and have in life. They can tell you in a heartbeat what their goals are and what vision they are striving to turn into reality.

This ability to clearly define your abilities and aspirations is a major key to success. Yet, it is often suppressed in a traditional college environment. Not completely…but enough.

It’s Parkinson’s Law in action. With four years of “just in case” learning ahead of you, there’s no significant pressure to “figure it all out”. Instead, you are liable to graduate six years and thousands of dollars later and you STILL will be wondering what exactly you want to do with your life.

Leaving the tried and true path is perhaps the strongest catalyst for personal growth and discovery.

The Successful Dropouts I’ve had the pleasure to interview are only the beginning of a new generation of awakened world changers.

Here’s to the ones who dare to dream, and act on their dreams.

Stay hungry, stay foolish.