Tenacity, Risk, and Failure

An entrepreneur I know is looking for investors. According to his research, he thinks he’ll be able to secure a funder for every 50 people he pitches to. Think about how much work that is– that’s 50 potential funders he needs to tap his network to identify, successfully contact for a meeting, arrange a time to meet, pitch to, and then probably not hear back for weeks or months. If he hears back, he’ll have to meet with them at the drop of a hat, even if it means hopping a train or a plane to meet. He would be a fool to miss an opportunity. He’s been doing this for months. So far he’s met with six.

Is his research accurate? It doesn’t matter. The point is that he’s willing to meet with tens, if not hundreds of eccentric rich people before he finds a single one who might help him build his business.

This is a case-study in tenacity. The ability to retain your composure, your dedication, and your sense of perspective day after day in this way is a crucial ingredient to success. This much I know. Yet so many would get discouraged far too quickly and decide that entrepreneurship isn’t really for them.

One way to manage this is to retain a sense of playfulness in the whole matter. You’re not doing anything serious, you can tell yourself. Nothing important is at stake. Life, health, or morality. It’s just business. Just money. Just work. It will make the tough decisions less tough, because they seem inconsequential, and reversible if they need to be.

Everything, from the hardest business problem to the most intimidating social situation to the knottiest math problem, can be made more solvable by acknowledging that the challenge at hand does not require boldness if it does not entail risk.

In other words, if failure and success feel equally acceptable, then the pressure it off. By asking yourself at each juncture, “What happens if I fail?” and answering honestly, failure loses its scare power. It’s probably not really that bad. Boldness becomes less heroic, and therefore less intimidating.