A Classic Poem's Timeless Lessons for Entrepreneurs

Rudyard Kipling's 'If' can be a breezy read, but if you stop to read each verse carefully, you'll find lots of nuance that applies to business.

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By Andrew Medal


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Chess -- I love the game. Early in my career, I found myself working for an angel investment team. One of the leaders of the team was a big chess fan. He was a person who I later learned to respect, but word around was that nobody had been able to beat him. When I was younger, I was overtly cocky to hide behind my lack of experience. But not with chess.

His office was dark as usual. Zen music was playing in the background, but the tension was anything but calm. I could feel him staring at me, with a squinting, piercing gaze. His leather chair reminded me of Scarface's chair, the one in the last scene when he has his face in a pile of blow. His grimace was equally as threatening. It didn't matter. He knew. I knew. It was inevitable.

In that instant, I had a flashback from two years prior. I was in the yard sitting at a makeshift table on the basketball court, with two paint buckets turned upside down used as chairs and a third for a table, in the middle of the Nevada state penitentiary. It was like 120 degrees outside, in the middle of summer, in the middle of the Las Vegas desert. It was like a scene straight out of "Prison Break." The yard was crowded. I stood up, looked Bones (the black shot caller and OG crip from Donna street) dead in the eye and somberly stated, "checkmate cuz." The yard went crazy.

I shook the memory. Queen backed by knight, with a bishop covering my flank, I looked up from the board and calmly breathed the word, "checkmate."

Respect is a funny thing.

Some people respect kindness, some strength, some intelligence -- everyone respects different things. Plato said that some men are lovers of wisdom, some religion and some money. For this man, on this day, I earned my former leader's respect by beating him at his own beloved game.

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This man and I had an interesting whirlwind of a friendship that is currently non-existent. We respected each other in different ways. We were close and then drifted apart, destined to live out our respective fates as destiny deemed fit.

He introduced me to a lot of things -- the startup game from A to Z, Panerai's fine craftsmanship and the power of the written word. He also introduced me to the poem If by Rudyard Kipling. Here, I break down what each piece of the poem means to entrepreneuers:

If you can keep your head when all about you are losing theirs and blaming it on you; if you can trust yourself when all men doubt you, but make allowance for their doubting too.

Trust in yourself.

This reminds me of one of my favorite business quotes, from former CEO of Netscape Jim Barksdale: "If we have data, let's look at data. If all we have are opinions, let's go with mine."

We will always have doubters, critics and haters in all that we do. Pay them no mind, and have confidence in yourself. On the same hand, take constructive criticism to heart, without being too self-righteous.

If you can wait and not be tired by waiting, or, being lied about, don't deal in lies, or, being hated, don't give way to hating, and yet don't look too good, nor talk too wise.

Stand firm in your values.

Kipling is urging us to not follow the crowd, be our own thinkers and stand firm in our own beliefs and values. He's gently reminding the reader there are answers we may not have, and to keep an open mind and be open to learning.

If you can dream -- and not make dreams your master; if you can think -- and not make thoughts your aim; if you can meet with triumph and disaster and treat those two impostors just the same.

Just be.

This is my favorite lesson of the poem. To treat triumph and disaster as the same imposter is to learn how to "just be." Life is a journey of ups and downs. I've learned that the person who can embrace all volatility and just "be" has the most joy, peace and contentment in life.

Ryan Holiday preaches stoicism from the rooftops, and I am a big advocate as well. He teaches that the Obstacle is the Way, and this verse has an underlying stoic theme.

If you can bear to hear the truth you've spoken twisted by knaves to make a trap for fools, or watch the things you gave your life to broken, and stoop and build 'em up with worn-out tools; If you can make one heap of all your winnings and risk it on one turn of pitch-and-toss, and lose, and start again at your beginnings and never breathe a word about your loss.

Live without regret.

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Take risks. Do what you love. You don't like your job? Quit. You want to be an entrepreneur? Be one. If school is calling your name? Go back. Want to sell your possessions and travel the world? Do it! Life is too short for dogma, and being trapped living a life you don't enjoy. Most important, life without regret.

If you can force your heart and nerve and sinew to serve your turn long after they are gone, and so hold on when there is nothing in you except the will which says to them: "Hold on.' If you can talk with crowds and keep your virtue, or walk with kings -- nor lose the common touch; If neither foes nor loving friends can hurt you; If all men count with you, but none too much.

Don't forget who you are, or where you came from.

Hate them, or love them, there are a lot of famous people who give back.

Mark Zuckerberg gave the Newark, N.J., school district $100 million to reform the education system.. Lebron James is sending 1,100 kids to college. Rapper The Game has a project dubbed The Robin Hood project, where he gives back to people on the streets. It's easy to let fame and success get to our heads, but Kipling urges us to stay grounded and to remember where we came from.

If you can fill the unforgiving minute with sixty seconds' worth of distance run -- yours is the Earth and everything that's in it, and -- which is more -- you'll be a man, my son!

Live with your eyes wide open.

Life is short. We only have a finite time here on earth -- "the unforgiving minute, with sixty seconds worth of distance run" -- and should use it as best as we can.

I love classic poems and arts of writing that contain timeless lessons that stay relevant even today. In fact, I believe these writings and lessons are not just enjoyable, but vital. It is in these classic lessons we can stay grounded.

With our infinite technological advancements, continued globalization, the true dawn of artificial intelligence and space exploration, it's nice to be reminded at the end of the day that we're all just a bunch of humans on earth for a very short time. So we must learn to enjoy life for all that it is, and remember life is just a game of chess.

Related: Ask Yourself These 3 Questions to Set Yourself on a Path to a Better Life

Andrew Medal

Entrepreneur Leadership Network VIP

Entrepreneur & Angel Investor

Andrew Medal is the founder of The Paper Chase, which is a bi-weekly newsletter. He is an entrepreneur and angel investor.

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