When the “Safe” Route Is Actually Less Safe

I have sometimes bought into the narrative that the conventional and “safe” route is the easiest path to success and have failed to strive for certain goals because I viewed them as being too pie-in-the-sky.

In high school, I was voted as the “most likely to become a talk show host.” For those of you who know me, I think you’d agree that I was, in fact, born to be a talk show host. Yet, because the odds of becoming the next Oprah are slim to none, I never seriously considered that career path.

Instead, I focused nearly all of my time on the more “practical” school subjects promoted by my engineering-focused high school. I poured my heart into math and science, even though I am not naturally inclined to excel in those subjects. I worked five times as hard as my classmates, yet I only achieved mediocre results. I learned the important lesson that being mediocre at anything is not a “safe” path to success. I now realize that the “safe” path for others may not be the best route for me.

As a venture capitalist, I have had the opportunity to meet hundreds of highly successful investors, entrepreneurs, and random extraordinary people who have managed to achieve success by pursuing unconventional, seemingly impossible career paths. I now believe the following principles define the “safe” route to success:

Being the best, or at least one of the best, at anything can lead to success. Focusing more time on valuing and fostering natural talent and tendencies is more effective than killing yourself to overcome shortcomings.  

Passion matters. I’ve heard many people give the advice to pursue a career to make money so you can have the flexibility to pursue your passions on the side. From my experience, I’ve seen the opposite, especially among entrepreneurs. The entrepreneurs who do work that they LOVE are far more likely to succeed than those who build businesses to make money so they can enjoy their true passions when they're work is done.

Sales and marketing make a difference. I’ve seen entrepreneurs with the best, most perfectly-timed ideas fail because they underestimated the importance of sales and marketing. I have seen entrepreneurs with ill-timed, sure-to-fail ideas achieve success through flawless sales and marketing execution. From my experience, entrepreneurs who are great salespeople and marketers – or who know how to hire great salespeople and marketers – win more often.

Oprah became “Oprah” because she pursued her passion, fostered her extraordinary talent, AND effectively marketed and sold her brand. While I never pursued the path of becoming the next Oprah, I’ve leveraged my talent for asking questions and connecting with people in my work in investing. Life has turned out pretty well for me. Yet, I always wonder where I would be today if I had had the courage to pursue the seemingly impossible path.

I’m going to keep asking myself that question each time I hit a fork in the road or hear the call of something that seems pie-in-the-sky. I hope you’ll ask yourself that question, too.