How to Resist the Temptation of the Road Well Traveled

Everyone talks about the road less traveled, and the idea of the road less traveled—the idea of adventure and mystery—is definitely exciting. Yet often when we find ourselves “where two roads diverge in a yellow wood,” it is fear of the unknown and the temptations of the road well traveled that triumph over our decision.

In my last post, I talked about Dr. Ariely’s research on how we have difficulty sealing off options, even when it is detrimental to keep them open. Yet what was even more interesting: Dr. Ariely and his research partner discovered that the tendency to want to keep doors open was not a desire for flexibility, but rather an aversion to loss.

While taking the road less traveled might not be the best decision for everyone, if it calls you, you should face that fear and answer it. And given that naming a fear makes it easier to face, here are some of the things we fear to lose by taking the road less traveled:

"Security"

When people talk about “security,” it’s usually a euphemism for money. And yes, money is a difficult thing to turn down. I used to think that anyone who made a decision based on money was shallow or materialistic, but after spending a year living on the sharp edge of the poverty line, I am aware that that was the misguided perception of someone who has never wanted for life’s basic necessities. Money does buy you a certain degree of freedom: freedom to visit those you love when they need you (or when you need them), the freedom to take a cab home when you feel in danger, or the freedom to quit your job because it's sucking your soul away.

“Security” can also mean health and dental benefits. The job I just quit had excellent benefits. I received my health insurance card in the mail after I finished my last day, its $5 co-pays for doctor visits attempting to mock my decision. I just smiled and knew that I had conquered a fear.

Knowing What Comes Next

We fear the unknown, so naturally, it feels good to know what we’re getting ourselves into, to have a clear path. Becoming an investment banker, a lawyer, or a doctor involves following a previously charted path. They are definitely not easy paths, but there is a certain security in having that road map, as opposed to making it up as you go along. Even if it is difficult to walk the road, knowing what’s ahead is comforting.

Praise, Recognition, and Prestige

One of the hardest things about deciding not to go to law school was turning down the potential praise, recognition, and prestige. My passionate soon-to-be lawyer friend couldn’t believe that with the LSAT score I had I was throwing away my chance to go to a prestigious school. And a good LSAT score is a form of praise, as well as the promise of more to come—if you continue to perform as the test supposedly predicts you will. Deciding not to go to law school also meant forfeiting a degree that could have convinced people to take my opinions more seriously, and feeling that you will be respected, your ideas considered, is a huge draw.

So how can we resist these temptations of the road well traveled? I can only offer two strategies that I have used, but I hope others will contribute their own in the comments section:

Focus on the Cost of Regret

If what really motivates our decisions to “keep our options open,” isn’t a want for flexibility, but an aversion to loss, we should focus on what we lose by not taking the road less traveled: an opportunity, perhaps a dream, or even self-respect. I don’t know of anything that can fill regret. If you try something and fail horribly, it won’t be the end of the world. You’ll learn something valuable and you’ll move on, but you’ll never have to lie awake wondering, “what if?"

If Possible, Avoid Temptation

One way I’ve resisted temptation is through avoidance. After a curious twist of fate found me working at an investment bank for a summer, the wonderful people I worked for suggested that I come back after graduating to be an analyst—one of the most lucrative jobs a recent graduate can have. I could have made a ton of money to put away for future projects, but I also knew that between my need to excel at whatever I do and the almost-instant rewards system for analysts, I would be seduced into a career that ten years later I would realize I didn’t want. I took away the temptation: I didn’t apply.

Likewise, my friend, Hannah, is a teacher who is passionate about maps, world cultures, and geography, a subject that usually falls in the same category as history, government, and social studies—all of which she hates teaching. While getting certified in social studies was the most marketable option (meaning that she could teach any of those subjects), she decided to certify in geography specifically. She knew that she would have to be tougher in her job hunt, working harder to find and compete for fewer jobs because of her specialized certification, but she also knew that when she found that job her students would find her passionate and engaged—not lackluster. As she puts it, she “happy-proofed” her job. She knew herself and what would make her a fantastic teacher, and she wasn’t afraid to self-limit her options in order to push herself to get there. It may seem counter-intuitive, but one of the best strategies might be to identify your temptation before you have to face it—and then avoid it, if you can.

Facing our fears of losing and resisting the temptations of the road well traveled might be one of the hardest, and perhaps most important aspects of our journeys, but doing so is ultimately empowering. As my wise friend Sarah Miller—who is embarking on her own adventurous road less traveled—says, you must “embrace the uncertainty,” of struggling to find your way, and just roll with the punches.