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You Are Not the Horse: Rules for Entrepreneurs

Doing something new isn’t only hard. It’s risky.

Sure, there’s the risk of failure. However, the fear of failure itself isn’t actually the scariest part. For most people, the scariest part is the fear of looking foolish, slipping on the proverbial banana peel, leading a parade with no one following.

Managing that risk, psychologically and financially, is central to the art of the start.

To be an entrepreneur, whether you’re looking for a multi-million-dollar start-up investment or simply proposing an innovative idea to your team, requires that you step out into the unknown – not just once but repeatedly and habitually exposing yourself to risk.

Everyone has a few novel ideas in the course of a career. But that doesn’t necessarily make one an entrepreneur. An entrepreneur doesn’t take that step into the unknown once. They do it again, and again, and again. This means that over a long enough time, every entrepreneur acquires a long list of wins, losses, goofs, and if you’re lucky, a few truly magical projects.

The inherent value of the entrepreneur is not the possibility that they might hit it out of the park once or twice. Instead their value to an organization, or society in general, is that they know how to keep showing up for each and every game – ready to try something new and take their best swing under a multitude of conditions, not just the ideal ones.

Whether your entrepreneurial adventures are already underway, or you’re considering a new career pivot into the great unknown, here’s some advice that has served me well.

Find new rooms.

You need to hang out with people who are going where you want to go.

As Confucius (might have) said, “If you’re the smartest person in the room. You’re in the wrong room.”

Surround yourself with people who are thinking about the same new ideas that you are thinking about. If you don’t know anyone who fits the bill, find them. After you find them, do whatever you need to do to spend more time with them. Is your idea going to require entry into a new market or social setting? If so, you will need to find out where these people gather and how you will find or chisel a doorway into that world.

The easiest way to do this is to start with who you know now. If you live in British Columbia and your dream is to start a surf shop in Maui, who do you know who has been there or lives there? Do your friends know anyone who has surfed that area? Where do surfers and shop owners hang out online?

Maybe you’ll find a friend-of-a-friend who runs a hotdog stand in Honolulu. It’s not Maui, but you could probably still learn a lot about doing business in the islands. Don’t just schedule a call with them or chat occasionally on Instagram. Make friends with them. Go and meet them. Build the relationships in the present, that you will need to succeed later. Start inhabiting the life you want to enter from where you are now.

You are the rider, not the horse.

Perhaps one of the greatest dangers for entrepreneurs, just as with artists, is the possibility of losing the distinction between an idea and yourself. Sure, to bring something new into the world you need to be passionate about it. You need to invest part of your psyche into it.

But remember, that idea is not actually you. It’s just an idea, a hunch, a hypothesis that “something” you’re considering might be of value to others.

It might pan-out. It might not. You could find out that a hundred other people are doing the same thing better than you probably can, or that there’s a fundamental flaw in your grand plan that you hadn’t considered.

Sometimes, a truly great idea just doesn’t catch the right wave. It happens.

When this does happen, remember that an idea is just a horse. Some horses don’t perform the way you’d hoped, regardless of how much you spent on them. Some just unexpectedly fall over and die. Again, it happens. However, you are not the horse. You are the rider. You are unique. The horse is replaceable. So, go find another horse and try again.

Hedge your bets.

In the great book, Originals: How Non-Conformists Move in the World, Adam Grant shares one of the great secrets of entrepreneurship:

Though often hailed as wild risk-takers, successful entrepreneurs are actually experts at hedging their bets.

A more accurate way of saying this is that you should be very strategic about how and where you allow for and manage risk. Mortgaging your home, betting your child’s college fund, and setting out for Maui with naught but your passion for the sea, is a very bad idea. Again, most new ideas fail.

You need to plan how you will take multiple risks on new ideas over time, not bet the farm in a onetime high-wire act.

Starting small and thinking about the minimum viable audience is a good way to test your ideas, maximize your joy, and minimize your stress.

Then, when you have more positive data and hard-won experience, be willing to take a deep breath, put on your big-person pants, and scale it up.

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