Pack Light: How To Turn Vacation Clarity Into Vocation Clarity

There’s very little that a two-week trip to Bali can’t cure.

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My wife and I went last August, and it was every bit as refreshing and centering as it

sounds. We split our time between the ocean and the jungle, and did everything from

snorkeling to surfing to meditating by forest rivers. But most of all, we both separated

ourselves from hustle culture—and felt its pressures lift.

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Now, fast forward to today. I am back in the day-to-day of running a growing startup

in a less than ideal economic climate. The pressures have returned, and the clarity

I felt when out of the grind has retreated.

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The question becomes: How does one carry that clarity from vacation to vocation?

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I’m sure you’ve felt that same clarity after a trip, day off, or even a relaxing walk

around the block, but leaving work each time you feel stressed is not an option.

Neither is immersing yourself in the grind to the exclusion of all else—a grind is

only useful insofar as it serves your life. The balance, especially for founders,

is elusive. But there are some tangible ways to bring it forward.

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How to turn vacation clarity into vocation clarity

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1. Put your objective in perspective. When I reflect on my career—and the life

of my company—I realize that there have been about six major decisions that

have kept us going past many of the stages at which startups tend to fail.

There was the moment we chose to raise money through a Roll-Up Vehicle (RUV)

instead of following the conventional fundraising route. There have been

several key hires who have altered the trajectory of the company. It works

out to one or two major decisions per year. You don’t realize it in the moment,

but the fate of your company—and everyone who relies on you—hangs on

those decisions. Your goal: Be as mentally clear as possible when making

those decisions. They could arise at any moment, and so it’s your job as a

founder to be mentally ready for them when they do.

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2. Identify and remove barriers from your decision-making process.

Living and working in our kind of culture fills us with barriers to sound

decision-making. Our news cycle is skewed and sensationalized; our social

networks are image-obsessed and disingenuous; professional decorum

often demands that we suppress our anxiety. All of this adds up to a cultural

mindset in which ego is everything. How you seem—not how you are—is

what matters in social and professional spheres. You can’t always wear

your anxiety on your sleeve. But you can find methods of checking your

ego (or of deconstructing your manufactured self) that let you make

decisions without its interference. This could mean meditation or

mindfulness practice. Or regular immersions in nature to shake off the

artifice of the office. In general, it means putting yourself through

something that has the opposite qualities of your day-to-day

work—something without deadlines, without financial ROI,

without a parade of notifications.

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3. “Be formless, shapeless, like water.” That’s a Bruce Lee quote. He goes on

to describe water’s infinite capacity for shapeshifting—it adapts to its container;

it can seep, flow, or crash. It has few intrinsic properties but adapts to all

dynamics.Founders get pulled in innumerable directions, often at once. The

ideal founder mentality is one that can adapt to whatever the circumstance

demands. And that includes stepping away when necessary/possible to avoid

flowing away into oblivion.

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When I think back on the Bali trip, and on the musing I’ve done as a result,

I can summarize it in a single metaphor: Pack light. Pack light physically, only

bringing with you what you absolutely need for the trip. Pack light mentally,

considering only the topics that are relevant to your decisions. And pack light

emotionally—don’t overwork your heart when serenity is what’s called for.

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