Why Entrepreneurs Should Learn To Love Opposing Ideas


Dylan Ogline is serial entrepreneur and author known as a pervader of work and lifestyle optimizations. He is the founder of Ogline Digital.

Most people don’t like contradictions. They’re at their happiest when there’s a clear right way and a clear wrong way.

Consider Luke vs. Darth Vader, Frodo vs. Sauron, Harry vs. Voldemort, the Avengers vs. Thanos—we love to know who to root for. Even antihero stories make it clear who we’re supposed to be supporting.

Perhaps this is why so few people are entrepreneurs. I’ve found that many people prefer a predictable paycheck, an unambiguous standard operating procedure and a clear chain of command. When you’re working for someone else, you can know what the “right” thing is to do with your workday because your boss guides you.

But real life is full of contradictions and gray areas. There’s rarely one right way and one wrong way to do anything. If your temperament is to pick sides and defend that side, it could hold you back in a real way. I believe the most successful people tend to be able to see through the matrix. They aren’t dazzled by extreme positions or swings in cultural opinion. They feel comfortable with ambiguity and come to embody contradiction.

In the world of sports, for example, basketball players were often considered to be star offensive players or star defensive players. Michael Jordan is often considered the best because he was a star at both. Heavyweight boxers usually aren’t thought of as agile like lightweight boxers. Mike Tyson was devastating in the ring because he was both heavy in his punch and light on his feet.

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In the world of entrepreneurship, here are seven popular dichotomies to start breaking down in your mind. If you identify too strongly with one side, you might end up siloed and prevent yourself from achieving your full potential.

Technician Vs. Salesperson

In my experience, people often see themselves as a silver-tongued salesperson or back-room technician. But an entrepreneur must have aspects of both. No one is a better spokesperson and advocate for the product or service than the founder, but the founder also has to have at least some idea of how the product works.

Extrovert Vs. Introvert

I’ve seen people build big identities around introversion and extroversion. But the truth is, introverts can learn to have stamina in crowds, and extroverts can learn to be more comfortable by themselves. Entrepreneurs need both skill sets. They need to be able to represent their product to a big audience—and buckle down and work without social motivation.

Optimist Vs. Pessimist

Pessimists get a bad rap, but the truth is, healthy pessimism is absolutely necessary from a risk-management standpoint. Every business entails risk. You can’t let dreams of what might go right blind you to what might go wrong. Partnerships often feature an optimist and a pessimist. If you tend toward one, consider spending some time in the other role. It will give you a much more holistic and practical view of your business.

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Lone Wolf Vs. Team Player

Many entrepreneurs prize being a “lone wolf,” but I believe this is often a smokescreen for insecurity. They might not know if they can play well with others or if they can get other people to buy into their idea or their ability to execute it.

The truth is, a great team is a force-multiplier on any idea. Two people can accomplish double the work of one person, three people can accomplish even more than that and so on. If you really want to break through, stop valorizing your lone wolf status and develop yourself as a team player.

That said, keep in mind that an entrepreneur sometimes has to stand alone against popular opinion and rejection. If you feel you need other people behind you in order to move forward, start cultivating a little more of that lone wolf spirit. You need both.

Detail-Oriented Vs. Big-Picture Thinking

Entrepreneurs, especially aspiring CEOs, sometimes style themselves as a “big-picture” person in order to get out of doing the hard work. But even CEOs need to become acquainted with the nitty-gritty of their business so they can effectively lead a detail-oriented team. Meanwhile, people who get mired in the details might forget what all the hard work is for and burn out. Whichever mode you feel most comfortable in, start stretching your comfort zone for the other.

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Polite Vs. Disruptive

You can’t please everyone. To break through in business, you have to be a disruptor. That means being willing to challenge the status quo.

On the other hand, no one wants to do business with a jerk. If you’re going to be a pit bull, make sure to do it with a sense of decorum. Be fair, and don’t make a career out of stepping on other people. That always comes back to haunt you.

Passionate Vs. Rational

Passion vs. reason is an age-old dichotomy, maybe the most fundamental dichotomy of the human condition. As an entrepreneur, you can’t prioritize one over the other. Rationality is the basis of sound decision-making. If you make decisions from your emotions, you will probably be wrong an unacceptable proportion of the time. However, remember that passion is the fuel. It’s the glue. You still need to be passionate about your ideas and the impact you intend to have on the world.

Passionate people can be admirable. Rational people can be laudable. People who find a balance of both can be unstoppable.

If your instinct is to pick sides, it will hold you back. Instead, start playing both sides.


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