10 Signs You’re an Eccentric Entrepreneur (and why you should embrace it)

Taylor Ellwood
9 min readMar 1, 2016

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When I was a kid I remember one day having a conversation with my dad. He asked me what I wanted to be when I grow up and I told him I wanted to be eccentric! He said, “Taylor the only people who are eccentric are rich. Otherwise you’re just weird.” And I said, “I guess I’m weird then.” But deep within me I knew I really wanted to be eccentric, because frankly then and now I’m a person with a multitude of interests and passions (Thus why I own 3 businesses) and weird just didn’t do it for me.

The identity of the eccentric isn’t one restricted to a 7 digit (or higher) income, but what the rich eccentric shows us is that being eccentric plays a huge role in their success. Instead of treating eccentricity like an obstacle, they treat eccentricity as a gift that provides insight and opportunities that grow their success and businesses.

Embracing your weirdness is what makes you an eccentric.

And why not embrace that weirdness and make your life and business more interesting as a result? When people try to fit in, try to play it safe, life gets boring. I know this because for a long time, I did exactly that. I tried to look conventional when I went to networking events and I didn’t share much about myself because if I did, well they’d figure out I was weird and if you’re weird that’s not good (or so I was told).

Yet the most successful people I’ve known in my life and the ones I’ve observed are eccentric and let their weirdness for all the world to see. Clearly they are onto something.

Howard Hugh’s Spruce Goose, which everyone claimed couldn’t fly (but it id). Picture courtesy of wikipedia

Let me share with you 10 signs that can help you identify that you’re an eccentric entrepreneur.

1. You own a business or want to own one and that business is your opportunity to geek out about something you love. Eccentric Entrepreneurs own businesses that let them be the geeks they want to be. Whether you’re geeking out about yarn or business systems or magic, or something else altogether, your business becomes an outlet for your geekiness (and a way to turn that geekiness into income).

And what’s fascinating is that when people turn their geekiness into a business, they discover other people who share that geekiness and want to support it. If you have enough passion to turn your geekiness into a business you will also discover the people who have enough passion to support you because your geekiness lets them bring their geekiness out.

2. Eccentric entrepreneurs recognize that money follows weirdness. When your openly weird, it may not seem like money would follow, but eccentric personalities attract people because they are larger than life.

The Eccentric Entrepreneurs on Shark Tank are an excellent example. Whether it’s the 5 investors or the people pitching, all of them are eccentric in their own way. If they hid that eccentricity it would be harder for them succeed. By openly embracing their eccentricity, they become larger than life and people want to know more.

When you openly embrace your eccentricity you become larger than life and people want to know more.

3. Being eccentric is part of your identity and you use it to market your business. Marketing is where most business owners stumble, in large part because they’re trying too hard to create a polished version of themselves and the business that is fake. People see through that pretty quickly.

Take your eccentric interests and actively make it part of your business identity and brand. Take all your imperfections, your fears, etc., and make that part of your business identity. When we step fearlessly into who we actually are, people respond to your choice to step into who you are and the reason is because they can identify with you.

Me stepping into my identity as the business wizard for eccentric entrepreneurs. Courtesy of Dax McMillan Photography

You know that saying, “People do business with people they know, like, and trust…” There’s a lot of truth to that saying, but what they don’t tell you is that what makes people know, like, and trust you is you stepping into your eccentricities and your internal authority and showing it to the world, inviting the people who connect with those qualities into your life.

When you make your eccentricity part of your business identity it makes your business stand out.

4. You actively step into your fears and doubts and use to them push you out of being safe. Being safe is boring. And it’s actually not all that safe for your business, because your business doesn’t stand out.

Eccentric entrepreneurs take risks, starting with choosing to be openly eccentric. The reason they take risks is because they know a successful business involves some risk. The risks they take are ideally calculated and planned for, but there’s always the element of the unknown and the eccentric entrepreneur embraces the unknown instead of settling for the relatively dull stasis of safe, which never changes and kills the creativity of the eccentric entrepreneur.

To take risks you have first learn how to step into your fears and doubts. It is your fear and doubt that keeps you in a “safe” place. But when you step into your fear and doubt, fully and lovingly embracing the fear and doubt, what you discover is the narrative underneath your emotions. That narrative tries to justify keeping you safe by saying such things as “what you’re doing won’t be good enough” or “People won’t like what you offer”

That internal narrative doesn’t really keep you safe. It just keeps you stuck in a rut. The eccentric entrepreneur recognizes this and boldly embraces their fears and doubts, turning them into allies by fully choosing to feel and accept them. In the acceptance of your fear and doubt lies your freedom from your fear and doubt.

5. You love using your weirdness to start a conversation. When you embrace your weirdness, you feel shameless about flaunting it, because it’s awesome to be weird. Not everyone will react favorably but the whole point of being weird isn’t so you can get accepted by everyone.

Fly your freak flag proudly to find the people who actually are a good fit for you and can appreciate your weirdness and how it shows up in your business. Those people will also likely be the people who need your services and products. When your weirdness shows up in your services and products they’ll appreciate that weirdness and how it helps them with their needs. And they’ll remember you much easier than someone else who isn’t putting their weirdness on display.

6. You’ve felt like you had to compartmentalize parts of your life because of how people might respond. Eccentrics who don’t fly their freak flag for fear of how people will respond are compartmentalizing themselves. I know how that feels because for a long time I did just that. I tried really hard to fit a conventional image of business and the entire time I was miserable.

If you find yourself holding back when it comes to putting your weirdness on display, you need to find out why. Dollars to donuts, I’m willing to bet it’s because you’re afraid people will judge you for being eccentric. But guess what?

People judge you all the time.

So if you’re going to be judged, why not be judged for who you really are? Better yet, don’t stress it if people do judge you, because those aren’t the people you want as friends or clients. You want people who accept you as you are and don’t feel the need to box you into their labels and categories.

When you’re openly eccentric it’s hard to be boxed in. So fly you’re freak flag and be the eccentric entrepreneur you are meant to be.

7. When you were young people told you that you were weird and treated it like it was bad. Another hang-up eccentric entrepreneurs have is that the words weird and eccentric have baggage with them. When you’re a young kid and you’re called weird it’s usually not meant as a compliment. And whether it’s other kids or your family, it’s usually a judgement.

The only way to get over this baggage is to embrace your eccentricity and flaunt it madly. For example, I flaunt my eccentric interest in magic by calling myself the business wizard. Regardless of what other people think that means, for me what it means is that I am letting my eccentric interests be part of the conversation around my business services.

Wizard courtesy of clipartcotttage

By flaunting my eccentricity I embrace all the judgments I was given with it and let them go, no longer allowing them any purchase on who I am. I revel in being told I’m weird because it means I’m showing up.

If you want to show up, let go of the baggage around weird and eccentric and reclaim those words on your terms.

8. You know that eccentricity is your gateway to divine inspiration about your business. Being eccentric is allowing yourself to be touched by divine inspiration (which can be its own form of madness). Being eccentric is a form of madness, but it’s only when you go mad that you actually find sanity. Your sanity.

Your sanity may not be everyone else’s sanity. In fact, it usually isn’t anyone else’s sanity. But it is YOUR sanity, your terms of existence, and your rules for living life.

What your eccentricity gives you is the permission to go mad (by societal standards) and discover what your sanity really is. When you discover what is sane for you, it may defy conventional wisdom, but it will also enlighten you about what your calling is and show you the direction you need to go towards to fulfill that calling and yourself.

9. You love taking risks on doing what you love instead of doing something safe. The eccentric entrepreneur is drawn to taking risks, because the eccentric entrepreneur understands there’s no such thing as safety. Safety is an illusion and holding on to it by trying to fit in will slowly but surely kill your eccentric spirit and creativity.

When I used to play it safe, what I found was that being safe held me back. I wasn’t putting my best foot (or anything else) forward. And while it might’ve made other people comfortable, it made me uncomfortable. I was stuck in a rut.

One of the reasons I chose to openly embrace my eccentricity was because I knew I was taking a risk. That excited me as much as it scared me. I know that every time I’ve taken a risk it’s worked out because the risk has always felt right. Whereas as every time I’ve played it safe, it hasn’t worked out, because playing it safe doesn’t feel right.

The eccentric entrepreneur doesn’t want to be safe. The eccentric entrepreneur wants risks because with risk comes reward.

10. Choosing to be openly eccentric is allowing you to realize the potential of your identity and your business. When you are openly eccentric you are telling the universe you are ready to turn your potential into reality. The eccentric is able to see opportunities where other people don’t, discover trends that other people ignore, and turn possibilities into reality, when other people claim it’s impossible.

Being openly eccentric challenges you to wrap that weirdness around your business and turn it into part of your brand. In turn that brand makes your services and products (and you!) more memorable.

Let yourself be openly eccentric. Let that eccentricity into your business and watch as you attract the people to you that are your best clients and your community.

Taylor Ellwood is the Business Wizard of Imagine Your Reality and he helps eccentric entrepreneurs design successful businesses using a combination of business smarts and wealth woo. Learn his dangerous secret to marketing your weirdness that gets you raving fans and grows your business.

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