Do People See Entrepreneurs as Cowboys?

Tim Ferris, author of The Four-Hour Work Week, posted an interesting piece on his web site recently that talked about the “myth of entrepreneur as risk-taker.”
I think what he means by that is the idea that entrepreneurs are wild cowboy risk-takers, leaping boldly off cliffs in search of a dream. Ferris includes a fairly long excerpt from Rick Smith’s new book called The Leap that argues … as if it’s a new thought … that entrepreneurs typically make small, calculated steps that lead them in a particular direction, instead of bold, rash leaps. From Ferris’s review of the book, I gather that its author uses that point to encourage people to change their career paths by showing them that there isn’t such great, scary risk involved in the process.
I haven’t read the book. But I had several reactions as I read Ferris’s piece. First, I found myself wondering if people really see entrepreneurs as cowboy risk takers. Like Ferris, I don’t know a single entrepreneur who approaches their ventures with the cavalier attitude of a bungee jumping “cowabunga, dude!” wild man (or woman). Every entrepreneur I know thinks hard about each choice and directional shift, balancing strengths and desires against cost and potential downsides. They may be overly optimistic in terms of market reaction or product popularity, or the time frame or work involved in getting their idea to market, but few get very far without a good plan.
I also agree with Ferris that few entrepreneurs I know are “double-down, bet-everything-on-a-single-strategy,” high-stakes gamblers. They start out with an idea, invest a bit to develop it, and see what partners and interest they can garner for it, all the while keeping one eye on potential applications or opportunities that might not have been their initial destination, but might be more successful to pursue. (see my post a couple of weeks ago about finding success in an unplanned direction).
But calculated risk taking is still risk taking. More than 70% of first-time entrepreneurial businesses fail, at least in their first iteration. And even if they succeed, financial profitability can be a long time coming. My father started his own business with a partner when I was 10 years old. It was in a field where he had contacts, experience, and they had a really good, new idea. He still went three years without a paycheck while they built the business. And then the global economy shifted, and the market for their product went away. Not everybody is up for that. Even if, as my father has said many times since, that experience taught him an extraordinary amount and gave him the experience he needed to make his second entrepreneurial venture (15 years later) highly successful.
It is possible, as the book’s author says, to mitigate the risks in entrepreneurial ventures by playing to your strengths, finding good partners, being open to new directions, and taking small steps while still hedging your bets. But often, there does come a time when you have to fish or cut bait: quit the old job, mortgage the house, or take some other fairly scary option to make the new direction work.
A friend of mine, an experienced lawyer and a partner in a big law firm, was unhappy with her work situation. A fellow lawyer approached her about going into practice together. They looked at what clients might follow, and what new clients they might be able to get. They looked at the costs of a start-up, versus the profits they were losing to the big firm overhead. The numbers looked good. But there still came that day when she had to decide to leave the safer world of her firm, cut the ties, and venture out alone. It wasn’t an easy day for her, and she and her husband didn’t take any vacation for a while. She’s now happy she made the move. The rewards were worth it. But making that move was scary, hard, and it did entail risk. To say otherwise would be disingenuous.
It’s also true that some people need more reassurance about change than others. At a Design Thinking conference in June, Prof. Jeanne Liedtka from the University of Virginia’s Darden School of Business advised businesses with managers who were reluctant to try new ideas to try conducting small experiments first. The results of those experiments could provide the reassurance the reluctant managers needed to feel more comfortable with the new idea or approach.
In some fields, people can also try out a new career path part-time, in the evenings, or on a freelance basis, while still holding onto their “day” job. As the business builds, it gets easier to make the leap away from the old job and into the new venture. So experimentation and small steps can be great tools.
But if more people don’t “leap,” I’m not sure it’s because they see entrepreneurship (or flying, or mountain climbing, or any other adventurous path) as wildly risky. I think they just see it as containing more risk—or even just more discomfort—than they want to take on. Even if you’re checked your parachute 10 times, you’ve been well-trained, and it’s a relatively straightforward jump, it’s still hard to jump—especially for the very first time.
Consider how we teach people to fly airplanes. You teach a student pilot how to handle the airplane, how to read the winds, how to figure out what to do if the engine quits, and how to land. You take them up and practice landings with them, building their confidence as well as their skills. All of that is risk mitigation. But there still comes a day when the student has to take that machine off the planet by themselves. And there’s not a student pilot out there who wasn’t terrified the day they soloed, risk mitigation or not. Those who go on to become pilots do so not because it’s easy, comfortable, or risk-free, but because it’s worth it.
Leaving a set paycheck and forging your own way in the world is never as comfortable as staying where you are. It’s just often more rewarding. And if you’re unhappy where you are … then perhaps the discomfort of a new venture is no more uncomfortable than the discomfort of a miserable, soul-depleting rut. With the potential upside of a happy, rewarding career and life. So if you’re unhappy where you are, it absolutely makes sense to try to figure out how to parlay what you love and want to do into a new career. It also makes sense to seek out potential partners, leverage your strengths and connections, and explore possibilities—and then to mitigate the risk of leaping through experimentation, either in discussion or in small ventures.
But in the end, while risk mitigation is just smart business, the decision to leap isn’t about low risk. It’s about high reward. No matter how many times your instructor tells you you’re ready to solo, and you’re going to be fine, it’s not a reassurance of low risk that gets a student pilot to gather the courage to go out on their own for the first time. It’s the pull of all the rewards that lie waiting, just the other side of fear and discomfort, that tilts the balance in favor of the leap.
Lane Wallace is the Editor and Founder of No Map. No Guide. No Limits.