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Be confident that you can follow the road less traveled

Andrew Roberts
4 min readNov 22, 2019

Two roads diverged in a yellow wood,

And sorry I could not travel both

And be one traveler, long I stood

And looked down one as far as I could

To where it bent in the undergrowth;

Robert Frost

When I was young, I was convinced of a story. The story goes that if you keep doing what you’re told, and you keep doing well in school, and you keep following the path laid out for you, then you will succeed.

This story is embedded in our culture. It’s a story of which many in my generation are acutely aware (you can thank our parents). What you don’t get told is that it’s mostly a fantasy — intended to spirit away your concerns and placate you into a sense of security and meaning, despite no one having a clue where you will slot into the world, least of all you.

I was living that story, maybe you can relate, it looked something like this:

You’re finishing up high school with a desire for <insert profession>, and during your senior year you tell your counselors, your teachers, your parents, and your friends.

They give you advice about where you should apply, what you should study. You research the best schools to study <profession>. You talk to the universities about their <profession> programs, weighing the pros and cons of each. Eventually you end up in university where you spend two years taking <vaguely-but-not-really-related-to-profession> classes at a mostly comfortable pace, wondering when they’ll teach you the skills you need to do something really useful or impactful.

After two years in college, you start to think about how you will actually find a job. You start to hear horror stories of upperclassmen stuck without a clear direction, or success stories of former students turned Google engineers. You wonder which you will become.

You begin to stress.

Instead of advising you to take action by making meaningful contributions to <profession>, or offering your services directly to employers of <profession>, you’re advised “not to quit now”, to “focus on your studies”, to “just power through”. (As an aside: this is the point where I decided to follow my own path, but I’ll continue the typical story of people my age)

You thought this was where the classes would hit a turning point, but they don’t. As you get closer and closer to graduation you wonder why you feel so desperately unprepared — why all you had were 6 week internships and classes on theory in a world of soft skills, trade offs, and gray areas.

Even still, you trust the system and spend the rest of college devoted to school. During your final year, you frantically apply to jobs, hoping to be among the successful graduates, despite doing little other than clubs and internships to distinguish yourself from the herd.

How many people live a nearly identical story? Is it any wonder that young adults feel stressed, disenfranchised, unneeded? They’ve been collectively offered one path.

It’s in the best interest of society to make people fungible — to have a set number of “templates” that our lives fit into. It makes the market operate more efficiently, it makes finding replacements easier, it simplifies standard education, it makes systems scale. People become cogs to the market that you can exchange for others with the “same skillset”.

People are encouraged to walk the same, traditional path, because it’s “what’s best”. But notice how on the traditional path, there isn’t much questioning or understanding that there are other paths. The traditional path is greedy and possessive, it pretends that it’s the only way you can achieve your goals in a world of near infinite possibility.

It pretends that there are some set of rules you must follow before you’re allowed into the club of professional life. The traditional path is built for entrenched interest groups, and often followed out of fear (fear of failure, and of non-conformity). We’re sold the lie that people who “drop out” of the traditional path in pursuit of their own path are the lazy ones, that they couldn’t handle the “rigor” of the path.

In reality, the traditional path is simply a way to postpone the need to confront a complex and difficult world. You still confront it, just later, after years spent learning in a relatively slow, unproductive environment. Oh, and did I mention that the traditional path tends to put you tens of thousands of dollars in debt? That too.

But Robert Frost knew the truth — he knew that there are obscure, winding roads in the undergrowth. The wisdom in his famous poem isn’t that these paths are always better, just that they exist in the first place.

To be clear, there is nothing wrong with following the traditional path. It’s important to have a path: it gives you a place to take the next step, to move forward in an endless, dark forest. But don’t just follow blindly where others walked before; if you know you can succeed on your own, do it! A path that few take is still a path.

Things are changing; the traditional path often isn’t enough to differentiate yourself in an increasingly competitive environment. So do what it takes to achieve your goals, and start doing it now. Follow whatever road will get you there, regardless of whether or not that road has signage.

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