Return to the Open Road

Scott Amenta
4 min readDec 5, 2018

Allons! whoever you are come travel with me! Traveling with me you find what never tires.

— Walt Whitman, Song of the Open Road

Photo by Anna-Laura Kummer

Profile update.

I’ve sat on the question of what a profile update might look like on LinkedIn for weeks now.

Having left my role at Spring in October following its acquisition, I’m traveling with no career step planned and no real return date in mind.

LinkedIn doesn’t offer any sort of category describing a purposeful break from work. In fact posting something on this platform about traveling seems to contradict all the other industry and career centered articles I see everyday.

We’re a country built on exploration and travel through the great frontier and beyond, yet culturally we’ve condemned the idea of taking more than an allotted 14 days of holiday. For the few that have figured out a way to travel for weeks or months, the vast majority of us (even with the means to do so) still do not.

The resume gap.

Americans particularly seem to share the belief that travel is either a.) too expensive b.) reserved only for when we retire or c.) will create the dreaded resume gap. Family obligations, health, children, student loans etc. are certainly preventative. However, the extra effort, planning and saving to do so is what holds most back. Even more perplexing is the fear of having to explain months of no work on a resume. Socially, we have mixed perceptions of people taking long periods away to travel as if the skills they had before and the skills they gained away are no longer as relevant had they applied for a role while still employed.

The time spent away from work, your own culture and daily routine is the most important time you can take for personal and professional growth. Rushing from one stage of a career to the next doesn’t allow for self-reflection, doesn’t provide ample time for self-improvement and shuts out opportunities that otherwise may have been life-altering.

I’m not advocating for doing nothing during time off, but promoting a different style of “work” that is just as important as a paying day-job.

Travel isn’t simply about visiting sites and counting countries. It’s about people and places impressing experiences that alter your way of thinking. It’s about spending time letting those experiences shape the things you know are important but never dedicated real time to. It’s about giving deep thought to real-world problems — issues that tech communities all over the globe seem to bypass.

Personal progress.

I recently read a Medium article from Michael Phillips Moskowitz about mental health with some frightening statistics. In particular that “more than 300 million people, including nearly one in five Americans, suffer from clinical depression.” Travel is not the sole answer to this growing issue but it is a helpful solution in focusing attention on the five fundamental pillars experts believe to combat poor mental health: “diet, exercise, sleep hygiene, vocation, and interpersonal relationships.”

These are just a few things I’ve learned long-term travel enables -

  • Deep thinking about your purpose and goals — when do you ever get time to just reflect on this alone?
  • Writing — for yourself as a diary or publish in online blogs, forums, LinkedIn, etc.
  • Reading — non-fiction primarily, read to learn but don’t count out fiction books that can be just as inspirational.
  • Reducing alcohol consumption — away from normal social routines it’s easy to fill time with the other things mentioned.
  • Practicing yoga and meditation — learn how other cultures utilize these practices in their everyday lives.
  • Volunteering — teach english, work at animal sanctuaries/reserves, help build homes and communities.
  • Lowering social media usage — posting a photo, catching up with friends and family is okay. Being abroad makes you eager to put your phone down to experience the things and people you came to see vs. what’s on the tiny screen in front of you. + you’re limited to wifi areas only.
  • Changing diet — Trying new cuisines is also a great time to change your diet (e.g. become more plant-based)
  • Refining the art of communication, negotiation, character assessment and building relationships with near strangers navigating cultures unlike your own.
  • Building relationships and sharing experiences with family or friends you’re traveling with or while meeting new people on the road.

Many of these things can be accomplished without ever leaving your own house. The amount of time isn’t as important as the quality of that time spent. All too often at home we get caught up in someone else’s priorities before we have a chance to focus on ourselves.

Purposeful time away.

Michael Karnjanaprakorn from Skillshare has promoted the Bill Gates style Think Weeks — getting away from work and setting purposeful time to think through big questions. Whether for a current job, exploring other industries or simply for self-discovery this exercise ensures we spend time and energy over the long run doing the things that matter most.

This is not vacation. This is not escapism. This is a part of your evolution, your story and your well-being. Without a day job to keep our thoughts busy, coming to terms with yourself is not only hard, it can be downright terrifying. This is exactly the kind of thing that I’d love to see more of my peers take the time to do.

Of the progress of the souls of men and women along the grand roads of the universe, all other progress is the needed emblem and sustenance.

Walt Whitman, Song of the Open Road

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Scott Amenta

founder of Chief of Staff Network, co-founder of Propel, co-founder of Sylva, former CoS at Spring, producer @WatchRoomMovie