Hemingway’s ‘The Old Man and the Sea’: a fundamental guide to business

Ernest Hemingway’s The Old Man and the Sea is a timeless, Pulitzer Prize winning novel, both rich in symbolism and conspicuously relevant in its contemporary application. As a parable for entrepreneurs, it is practically without parallel. A simple tale that sees a man set out to achieve a goal, and tackle the challenges that befall him and his determination to realise his ambition.

The Old Man and the Sea‘s succinct, powerful grit registers as a fundamental guide to business. It’s a book I have read many times, and with each new reading I feel a stronger kinship with the book’s protagonist, Santiago. Here are the parallels I’ve drawn between his resolve and my experience as it relates to business and entrepreneurship:

On loving the playing field as well as the game

He always thought of the sea as la mar which is what people call her in Spanish when they love her. Sometimes those who love her say bad things of her but they are always said as though she were a woman. Some of the younger fishermen, those who used buoys as floats for their lines and had motorboats, bought when the shark livers had brought much money, spoke of her as el mar which is masculine. They spoke of her as a contestant or a place or even an enemy. But the old man always thought of her as feminine and as something that gave or withheld great favours, and if she did wild or wicked things it was because she could not help them. The moon affects her as it does a woman, he thought.

This should be the first rule of entrepreneurship: “Love What You Do!” If you don’t you’re going to get tired along the way, you won’t be able to fake it and you will run out of energy. Building, or running, a successful business takes passion, and that passion can’t be faked. As Bill Gates said, “Business is a good game, lots of competition and a minimum of rules.” I agree and I’ll add, “be sure you enjoy playing the game first.”

While playing the game you’ll encounter those that don’t love the platform (in my case digital), they’re only in it for the money (the mint.com replicas, the Groupon clones, the gambling and porn sites) don’t be distracted by these people they will come and they will go. They don’t love the playing field, and as a result, their success is most often short-lived.

On luck and skill

But, he thought, I keep them [his lines] with precision. Only I have no luck any more. But who knows? Maybe today. Every day is a new day. It is better to be lucky. But I would rather be exact. Then when luck comes you are ready.

In business you’ll often hear people say, “you’re so lucky” or “I’ve been very unlucky.” Yes there are people who are lucky, some extremely so. The key to being lucky is to know how to react when you are presented with opportunity. Like a fisherman who keeps his lines with precision, a good entrepreneur has the skill to strike at an opportunity. Conversely when a good entrepreneur experiences bad luck, he knows how to react and has often already mitigated the risk. Think clients that don’t pay, or clients who drop you from a project with no notice. I believe the precision to strike at an opportunity and the preparation to mitigate risk in case you find yourself behind the eight-ball are an entrepreneurs greatest assets. “It’s not safe to hope for the best, without preparing for the worst.”

On working hard

Don’t think, old man, he said to himself, rest gently now against the wood and think of nothing. He is working. Work as little as you can.

Working hard doesn’t necessarily lead to success, working smart does. Rest when you can and enjoy the rest. If possible, don’t even background process your problem — you’re still working and you won’t be fresh in the morning when you have to tackle the problem again. We have a saying at NML (a quote from our Ironman champion and NML project manager Raoul De Jongh) — “Fitness comes at 70% of your max heart rate.”

You’re going to have to put in the hours (I very much believe that 10 000 hours are required to become a specialist) but you don’t have to overexert yourself. Building a business is a marathon, not a sprint and you’re going to need a lot of time in the saddle for your ideas to come to fruition and to garner a customer base.

Time in the saddle also allows you the opportunity to make mistakes, which guaranteed you will make, and recover from them. You’ll hear the saying, “my overnight success took 10 years,” a number of times in your career — it is a classic, almost clichéd, phrase because it is so true.

On showing strength and weakness

I wish I could show him what sort of man I am. But then he would see the cramped hand. Let him think I am more man than I am and I will be so. I wish I was the fish, he thought, with everything he has against only my will and my intelligence.

This might sound like a classic scenario of fake it till you make it, I don’t read it that way. I believe there are times when it is critical that you don’t show weakness. If you’re on the ropes and desperately need a project to come in, you can’t reveal how keen you are, or how tired or weak you’re feeling. Man up! Negotiating well relies on you being able to hide your actual feelings, a poker face if you will.

The problem with this is that when you ask an entrepreneur how things are going he or she will tell you, “just fantastic,” even when things are not. There is a fine balance between being positive, hiding your feelings for strategic reasons and seeking help. I have a fantastic arrangement with some of my competitors where if a job is pulled and we have available skills, we offer them at a reduced rate, just to cover costs.

Sometimes your competitors can be your best allies. On the idea of faking it till you make it, I would warn any young entrepreneur against pretending to be something you’re not – talking about a team when you’re a one man show, or lying about the size of your team to get work – the community is small and with two phone calls you’ll be found out. Showing strength in the face of adversity? Yes! Lying? No!

On building on your successes

The thousand times that he had proved it meant nothing. Now he was proving it again. Each time was a new time and he never thought about the past when he was doing it.

We are always judged, maybe unfairly, on our last job whether we achieved success or failure. Our persistence has to transcend our previous laurels and we have to build off our successes with further successes. Conversely if we fail we have to take it on the chin, pick ourselves up and aim for success again. Don’t talk about your successes many years ago. Honestly, no one cares.

On ethics and the brutality of business

“I must save all my strength now. Christ, I did not know he was so big.”
“I’ll kill him though,” he said.
“In all his greatness and his glory. Although it is unjust,” he thought.
“But I will show him what a man can do and what a man endures.”

There are two themes here. The first is that business can be ruthless and brutal. You will have to fight for what you believe in. You will have to fight for work and you will have to fight to keep clients. If you aren’t up for the fight you aren’t up for business development. There is always someone younger and hungrier than you are. Be prepared to fight, using your experience and your wit to win the battles.

The second is ethics. There is a big difference between being ruthless and being unethical. The old man has to be ruthless to kill the big fish, but it isn’t (to my mind) unethical to kill the fish if he wants to feed himself and others with it. Hemingway mentions those that are only fishing for shark fins and livers, they’re unethical, and like most unethical people they can’t see their lack of ethics.

On mentors and heroes

But I must have confidence and I must be worthy of the great DiMaggio who does all things perfectly even with the pain of the bone spur in his heel.

Santiago often mentions his hero DiMaggio, the famous baseball player. Have a hero or mentor — you don’t know everything. There are many people who have far more experience than you, find a wise person (possibly not even in your field) who can give you impartial advice. If you don’t have a mentor, have a hero that you aspire to. Let that person be your motivation.

On Planning

If I had brains I would have splashed water on the bow all day and drying, it would have made salt, he thought. But then I did not hook the dolphin until almost sunset. Still it was a lack of preparation.

Plan, plan and plan some more, not necessarily a large wordy business plan, but have a clear strategy. A strategy for growth, a strategy for sustainability and a strategy for the worst-case scenario. Make sure you are mitigating risk all the time.

On being realistic

He could not talk to the fish anymore because the fish had been ruined too badly. Then something came into his head.

“Half fish,” he said. “Fish that you were. I am sorry that I went too far out. I ruined us both.”

Context: Santiago has landed the fish, but can’t put it in the boat. Instead he straps it to the side, but the sharks come and eat most of the fish.

This is a mistake I’ve made and observed many times. There is a fine line between naively aiming for the stars and being unrealistic. One of the last products I worked on the client often said, “Make sure it (the product) is going to be in the Gartner leading quadrant for xyz”.

Unfortunately the Gartner leading products in this space had long histories in big American banks and subsequently became standalone products in their own right. These assets had evolved into fantastic feature rich products over multiple-release version evolutions. Being in the Gartner leading quadrant was not realistic, not on the sort of budgets we had. If Santiago was honest with himself he would have quit much earlier, he aimed too high and he ruined the fish and he ruined himself.

Be honest with yourself about what you are trying to build and achieve.

Another Facebook? A competitor to Twitter? Forget about it.

An online shopping plugin for Facebook or Twitter? Now we’re talking!

On persistence

I don’t want to give a specific quote to illustrate this point as persistence is the most prevalent theme in the book, much like it is the most common attribute in any successful business person.

Estée Lauder said it best when she said, “When I thought I couldn’t go on, I forced myself to keep going. My success is based on persistence, not luck.”



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