What you can learn from innovative entrepreneurs you’ve never heard.

By Alexa Clay (Co-author, The Misfit Economy)

Growing up, I was always interested in iconoclast and outlier-type personalities. Joan of Arc and Henry Thoreau were some of my heroes. I was impressed by those who walked the road less travelled, individuals who honored their inner voice and conscience regardless of how much that voice might have been in conflict with societal norms. These were people who made history, or died trying.

As an adult, my captivation with misfits never waned. Over the past three years, I’ve traveled the world speaking to fringe innovators: performance artists, hackers, Somali pirates, maverick entrepreneurs and gangsters. And what I harvested were some important lessons that any entrepreneur or corporate rebel should take to heart.

Don’t be Afraid of Rabbit Holes

All great journeys start by stepping into the unknown. The ability to tolerate ambiguity, and take risk even in the face of self-doubt is what sets the misfit apart.

Following your intuition and just doing things because they feel right will set you on an extraordinary path. Don’t be afraid of rabbit holes; rather, seek them out. Steve Jobs’ love of calligraphy and LSD might be viewed by many as “distractions,” but were notable inspirations behind Apple. Catherine Hoke’s venture into a prison, started a whole new career for her as the CEO of Defy Ventures, a non-profit that brings entrepreneurial training to ex-con populations.


Hustling is about spotting an idea and going for it. It’s about using whatever tools you have at your disposal to achieve whatever it is that you want to achieve.

Most critically, it’s about being highly resourceful, dogged and determined. Walking the misfit path also means practicing the art of resilience. Take plenty of time for self-care so you don’t burn out.

Hack the System

Go against the grain and take on the establishment, but make sure to spend the time truly understanding whichever system it is that you’re looking to effect change in. Too often agitating misfits will rail against a system, without understanding why certain protocols or norms exist.

The best types of hackers are ones who know intimately the systems they are trying to penetrate. Hacking is also about not waiting for permission, but taking matters into your own hands. Give yourself permission to be the change you want to see in the world.

Lean Out

You are not a job description, a cog in the wheel. Let yourself loose from others expectations and start listening to what drives you on the inside. Don’t readily conform to cultures and organizations at the expense of your own values.

And don’t check yourself at the door. So many go into the workplace not fully bringing their most authentic selves into their jobs. Find room for your passions and bring an entrepreneurial mindset into everything you do. Don’t just climb the corporate ladder. Be courageous enough to define what success means for you.

About the guest blogger: Alexa Clay is a storyteller and leading expert on subculture and the co-author of THE MISFIT ECONOMY. She is the co-founder of the League of Intrapreneurs, a movement to create change from within big business and the founder of Wisdom Hackers, an incubator for philosophical inquiry. Alexa initiates projects through the collective The Human Agency, which aims to create communities of purpose around the world.