Walking Before Knowing the Path

Often when thinking of what’s next, personally or at work, we tend to delay an actual step forward and instead labor over mapping the path we should take. A collection of well-worn avenues that others – bosses, parents, heroes – have taken before us forge this potential path, the details of which we agonize over.

This is one part human nature and one part a damning effect of expecting results from a practiced action which secondary education engrains in us — we seek proven endeavors with demonstrable security that we can attain step by known step. Manifest in this time spent strategizing over each step or planning a path that mimics that of others is a stasis in two forms. We either don’t take a step at all or, if we do, the footprint we press into is already so predetermined that no new paths are created.

Over-planning may be analysis paralysis in its most painful sense, as it dampens the tremendous power that independent experience, creativity, and serendipity can have on our minds, choices, opportunities, and interactions in the chaos of finding our own way. In the startup community, it’s easy to claim that everyone just jumps in, but it’s not always the case and is much easier said then done. Taking a first step into something completely new is hard in large part because it’s fucking terrifying not to know where your foot is going to land.

When asked how they got where they are, many successful entrepreneurs – Tony Haile, Tony Hsieh, and James Altucher are examples – have more or less responded with: ¯\_(ツ)_/¯

But that can be a frustrating answer for someone who’s giving up a comfortable job to join a three-person company or another who has decided to start something themselves without a clear thought about where to begin.

But I guess the ubiquity of that shrug response proves that a golden formula does not exist for successfully starting out on our own. There is no one right path for anything. So we do a disservice to the time we have and the minds we possess, waiting for that path to emerge.

From the myriad conversations I’ve had with people about their own paths — and speaking for mine such that it is — it seems that choosing immediate experiences over a predetermined, strategic path is an answer to the inertia of planning. As a creative writing major with eyes set on venture, my intervening eight years between then and NextView went: South American nonprofit, link-shortening service, long-form nonfiction media, equity crowdfunding for local businesses. So ¯\_(ツ)_/¯ … except everything was really interesting, allowed me to support myself, and at least didn’t disqualify me from venture.

So to the question of but what will happen which is either voiced or in the back of the head of many early startup employees, founders, and operators: There’s simply no way to know. But I’ve never heard someone say they regretted taking a chance on something new or otherwise unknown. As long as the direction feels good and you’re excited about each day, then the idea, the new gig, or the return to an old passion is probably the right thing to do.