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How Being Less Realistic Made Me A Better Entrepreneur

Every business leader’s success rests on bold ambitions, even if they don’t seem realistic at first.

How Being Less Realistic Made Me A Better Entrepreneur
[Photo: Flickr user Candida.Performa]

I used to call myself a business realist. I did my best to look critically at others’ ideas and check them against my own beliefs and experiences. Anything that didn’t seem to measure up I dismissed as out of touch. “That won’t work in practice,” I typically thought. But when I decided to become an entrepreneur around a decade ago, and started reading intensively about other successful entrepreneurs, I noticed they had the reverse instinct. Rarely did they ever say “no no, that won’t work.” If they had anything in common, it was that they were all optimists.

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I realized my “realistic” attitude was actually a pessimistic one, thinly disguised. I decided that if I was going to have any luck with my own venture, I needed to be more optimistic–perhaps even “unrealistically” so.

Optimists aren’t delusional, but they do view the world and everything in it through a positive-tinted lens. They seek out opportunities rather than analyze the challenges to achieving them. They maintain their confidence rather than succumb to doubt and insecurity–even if they have legitimate doubts and insecurities–and they consider what’s possible rather than what isn’t.

Cliché as it now is to point back to him, Steve Jobs is the nearly unavoidable example of an optimistic business leader in the tech world. He was convinced iTunes would revolutionize how consumers listened to and paid for their music. In order to continue improving and growing iTunes Jobs was convinced that music would have to be DRM-free. Rolf Schmidt-Holtz, Sony music’s chairman, disagreed, but Jobs dug his heels in. Despite Schmidt-Holtz’s resolute opposition, Jobs moved ahead on his belief. It may not have seemed realistic at the time, but he succeeded anyway. What if he had given in to realism instead?

Ultimately, optimism is riskier. But it will catapult you much farther than any “realistic” viewpoint ever will. So how do you make yourself into a more optimistic entrepreneur? Here are three strategies.

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1. Master Your Inner Voice

When a new opportunity arises, think about how you’re inclined to think about it. If you begin skeptically, automatically running through doubts and reservations, don’t throw them all out the window, but press pause. Before you get too far down that pessimistic path, take a positive turn. What needs to occur in order to turn the probably impossible into the probably possible? “That can never happen” becomes “How can we make this happen?”

2. Rethink Who You Hang Out With

Pessimistic people love to congregate with other pessimistic people. They thrive on convincing one another that their reality is the one the rest of the world lives by but just doesn’t recognize. Sometimes looking at circumstances dead on, with an eye toward limits and liabilities, can be a huge asset in business. But it should never be all-engulfing. And whenever you hang out with people who think this way too much of the time, you’ll be overcome by that attitude and might miss out on opportunities.

So just do the reverse: Seek out more optimistic friends and associates who support your goals, including–and especially–some of the more ambitious ones.

3. Manage Your Media

What information are you saturating yourself with in your daily routine? So many media outlets today serve up heaping portions of shocking and negative content–disaster stories, health warnings, news about failures and missteps. To be sure, the world is full of those things, but they tend to get more time in the spotlight because they grab more attention–more clicks, more views, more shares.

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So be conscious of the media you expose yourself to. Listen, watch, and read stories about achievements, successes, breakthroughs. Make a conscious effort to lift your spirits during the day. Give yourself a daily dose of inspiration. More than just instilling a more positive outlook, that can help give you a better understanding of the ways people and organizations find to overcome unlikely odds to do something great.

Ultimately, whether you’re mostly pessimistic or optimistic is really up to you. Pessimists might deal with fewer disappointments, but optimists–especially entrepreneurs–can wind up not only with more successful careers but more fulfilling lives, too.

Shawn Casemore is the founder of Casemore and Co, Inc., a management consultancy. He helps CEOs empower their businesses to improve productivity and profitability. Shawn has worked with dozens of recognizable companies that include Honda, Tim Hortons, and CN Rail.

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