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What do entrepreneurs and world explorers have in common?


The Leadership Insider network is an online community where the most thoughtful and influential people in business contribute answers to timely questions about careers and leadership. Today’s answer to the question “What advice would you give someone looking to start their own business?” is by Bryan Johnson, founder of OS Fund.

Over 100 years ago, Sir Ernest Shackleton was in a world of trouble. The veteran polar explorer had sailed off for Antarctica, on a daring mission to cross the continent on foot. But before he ever got there, in early 1915, his ship–the Endurance–became trapped in ice.

the EnduranceThe Endurance beset, full sail.Photograph by Frank Hurley

I’ve always been in awe of Shackleton’s expedition. But it wasn’t until growing my own business that I began to appreciate the parallels between being an entrepreneur and an explorer. Here are a few lessons entrepreneurs can draw from the disastrous (and miraculous) Imperial Trans-Antarctic expedition:

The Shackleton “sniff test”
What Shackleton originally proposed doing–traversing Antarctica on foot via the South Pole, 1,800 miles from coast to coast–wasn’t just bold at the time, it nearly defied imagination. It was the most daring undertaking he could conceive, and he went all in from the start. For entrepreneurs, it can be worth considering a sort of “Shackleton sniff test,” whatever the venture. Ask yourself, within the parameters of your business, “Is this the most audacious goal I could be working toward?” Reassessing and pivoting will all–inevitably–come later. At first, do yourself the credit of thinking big.

Absolutely nothing will go as planned
Throughout Shackleton’s expedition, when it seemed nothing else could possibly go wrong, something always did. After 10 months inside the icebound Endurance, for instance, the crew discovered they were sinking. They abandoned ship and set up camp on nearby ice floes, drifting for months. Finally, Shackleton piled his men into three lifeboats and paddled off into the open ocean. Entrepreneurship is like treading water, and then repeatedly getting dunked. You’re forced to learn to live (and thrive) in continuous chaos–somehow planning for the future even while struggling just to make it through the day. Shackleton’s adaptability–in the face of bafflingly bad luck–is an example all entrepreneurs can take to heart.

Trust trickles down
After five days at sea, Shackleton and his exhausted crew dragged themselves onto Elephant Island, their first time on dry ground in 497 days. But it was barren, with no hope of rescue. He made a fateful decision to set out with a small group on a suicide mission–another odyssey by open boat, this time to a distant whaling station some 720 nautical miles away. Team building is tricky under the best of conditions. So how did Shackleton keep his crew together and their faith alive–for years–while trapped in the Antarctic? He was a commanding presence, to be sure. But he also put himself in the line of fire, time and time again. Without getting too dramatic, there’s a lesson here for entrepreneurs. Your team, no matter its makeup, will be tested. But sacrifice and genuine care from the top speaks volumes.

Imperial Trans-Antarctic ExpeditionImperial Trans-Antarctic Expedition on Elephant Island.Photograph by Frank Hurley

Desperation drives creativity
After leaving most of the crew behind on Elephant Island, Shackleton and a few men crossed the ocean for 15 straight days–in pretty much a glorified rowboat. Forced to improvise, they had raised the sides, built a makeshift deck of canvas, and sealed the seams with seal blood. It held up–even through hurricane-force winds–and they reached their target. For entrepreneurs, constraints of money, time and expertise go with the territory, but they’re also a beautiful thing because they force creativity and precision. A personal example: For nearly five years, I bootstrapped Braintree, the payments provider behind Uber and Airbnb. Time and time again we had to innovate, rather than spend, our way around problems. Looking back, it only made us a stronger company.

Failure is in the eye of the beholder
Incredibly, the Shackleton saga doesn’t end quite yet. After landing on the island, he proceeded to climb across 32 miles of icy ridges and chasms, finally reaching a manned whaling station–a feat even by today’s standards. A rescue was organized for his remaining crew. Despite spending almost two years marooned in the Antarctic, not a single man under Shackleton’s watch on the Endurance died. I think this is probably the most valuable lesson for entrepreneurs. Shackleton’s expedition may have failed, but he didn’t. History remembers the mission not for falling short of its target, but for the human spirit that shined through as it unfolded.

I’ve started multiple companies: some folded; some grew more than I dreamed. (Now I run a fund that invests in entrepreneurs working on global challenges, projects that definitely pass the Shackleton “sniff test.”) Markets may shift; problems may arise that no amount of planning can anticipate; and businesses may founder, but in the end, success is more than a balance sheet. The “how” of it all–the ingenuity and grit shown along the way–can be just as important.

Frank Hurley and Ernest Shackleton at Ocean Camp.Photograph by Frank Hurley

Read all answers to the Leadership Insider question: What advice would you give someone looking to start their own business?

When starting a business, it’s you vs. the world by Ryan Smith, CEO and founder of Qualtrics.

6 things every new entrepreneur should know by Erin (Mack) McKelvey, CEO of SalientMG.

Why this CEO believes an MBA is worthless by Tien Tzuo, CEO of Zuora.

How much would you sacrifice to start your own business? by Clara Shih, founder and CEO of Hearsay Social.

4 secrets behind a successful startup by Veenu Aishwarya, CEO of AUM LifeTech.

How this startup failed (twice) and still found success by Kevin Chou, co-founder and CEO of Kabam.

Are you resilient enough to start your own business? by Ryan Harwood, CEO of PureWow.

The most important lesson I learned as a tech CEO by Kyle Wong, CEO of Pixlee.

How to avoid a startup failure by Jim Yu, CEO and co-founder of BrightEdge.

3 things to consider before starting your own business by Sunil Rajaraman, co-founder of

4 ways to persuade people to join your startup by Nir Polak, CEO and co-founder of Exabeam.

GoDaddy CEO’s 5 tips for aspiring entrepreneurs by Blake Irving, CEO of GoDaddy.