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Are You Suited to Entrepreneurship

5 Truths Of Ancient Wisdom That Will Make You A Better Entrepreneur

Take pride in your work. But it is not all there is.




Very few ancient philosophies can be traced back to an entrepreneur, but one can: Stoicism. Around 304 BC, a merchant named Zeno was shipwrecked on a trading voyage. He lost nearly everything.

Making his way to Athens, he was introduced to philosophy by Crates of Thebes, a famous Cynic, which changed his life. Within a few years, Stoic philosophy would be born. As Zeno later joked, “I made a prosperous voyage when I suffered shipwreck.”

Since then, Stoicism has been a source of guidance, wisdom and practical advice for millions. It’s been used by everyone from Marcus Aurelius and Seneca (one of the richest men in Rome), to Theodore Roosevelt, Frederick the Great and Michel de Montaigne. More recently, Stoicism has been cited by investors like Tim Ferriss and executives like Jonathan Newhouse, the CEO of Condé Nast International. Even football coaches like Pete Carroll of the Seattle Seahawks and baseball managers like Jeff Banister of the Texas Rangers have recommended Stoicism to their players.

Related: The Most Powerful Advice Entrepreneurs Ignore

Below are five Stoic exercises and strategies, pulled from the new book The Daily Stoic, that will help you run your business, and find clarity, effectiveness and serenity.

Find The Right Scene


“Above all, keep a close watch on this — that you are never so tied to your former acquaintances and friends that you are pulled down to their level. If you don’t, you’ll be ruined. . . . You must choose whether to be loved by these friends and remain the same person, or to become a better person at the cost of those friends . . . if you try to have it both ways you will neither make progress nor keep what you once had.” — Epictetus, Discourses, 4.2.1; 4–5

Jim Rohn’s widely quoted line is: “You are the average of the five people you spend the most time with.” James Altucher advises young writers and entrepreneurs to find their “scene”— a group of peers who push them to be better. Your father might have given you a warning when he saw you spending time with some bad kids: “Remember, you become like your friends.” One of Goethe’s maxims captures it better: “Tell me with whom you consort and I will tell you who you are.”

Consciously consider whom you allow into your life – not like some snobby elitist but like someone who is trying to cultivate the best life possible. Ask yourself about the people you meet and spend time with:

  • Are they making me better?
  • Do they encourage me to push forward and hold me accountable?
  • Or do they drag me down to their level?
  • Now, with this in mind, ask the most important question: Should I spend more or less time with these folks?

The second part of Goethe’s quote tells us the stakes of this choice: “If I know how you spend your time,” he said, “then I know what might become of you.”

Related: 10 Entrepreneurs On Advice That’s Helped Them Build Their Business

The Art of Negative Visualisation

“We say that nothing happens to a wise man against his expectation. . . nor do all things turn out for him as he wished but as he reckoned — and above all he reckoned that something could block his plans.” — Seneca, On Tranquillity of Mind 13.2–3

We often learn the hard way that our world is ruled by external factors. We don’t always get what is rightfully ours, even if we’ve earned it. Not everything is as clean and straightforward as the games they play in business school. Psychologically, we must prepare ourselves for this to happen.

If it comes as a constant surprise each and every time something unexpected occurs, you’re not only going to be miserable whenever you attempt something big, you’re going to have a much harder time accepting it and moving on to attempts two, three, and four. The only guarantee, ever, is that things could go wrong. The only thing we can use to mitigate this is anticipation, because the only variable we control completely is ourselves.

The world might call you a pessimist. Who cares? It’s far better to seem like a downer than to be blindsided or caught off guard.

You know what’s better than building things up in your imagination? Building things up in real life. Of course, it’s a lot more fun to build things up in your imagination than it is to tear them down. But what purpose does that serve? It only sets you up for disappointment. Chimeras are like bandages – they hurt when torn away.

With anticipation, we have time to raise defenses, or even avoid them entirely. We’re ready to be driven off course because we’ve plotted a way back. We can resist going to pieces if things didn’t go as planned. With anticipation, we can endure.

We are prepared for failure and ready for success.

Never Do Anything Out of Habit

“So in the majority of other things, we address circumstances not in accordance with the right assumptions, but mostly by following wretched habit. Since all that I’ve said is the case, the person in training must seek to rise above, so as to stop seeking out pleasure and steering away from pain; to stop clinging to living and abhorring death; and in the case of property and money, to stop valuing receiving over giving.” – Musonius Rufus, Lectures, 6.25.5–11

A worker is asked: “Why did you do it this way?” The answer, “Because that’s the way we’ve always done things.” The answer frustrates every good boss and sets the mouth of every entrepreneur watering. The worker has stopped thinking and is mindlessly operating out of habit. The business is ripe for disruption by a competitor, and the worker will probably get fired by any thinking boss.

We should apply the same ruthlessness to our own habits. In fact, we are studying philosophy precisely to break ourselves of rote behaviour. Find what you do out of rote memory or routine. Ask yourself: Is this really the best way to do it? Know why you do what you do.

The Start-up of You


“But what does Socrates say? ‘Just as one person delights in improving his farm, and another his horse, so I delight in attending to my own improvement day by day.’” – Epictetus, Discourses, 3.5.14

The rage these days is to start your own company – to be an entrepreneur. There is no question, building a business from scratch can be an immensely rewarding pursuit. It’s why people put their whole lives into doing it, working countless hours and taking countless risks.

But shouldn’t we be just as invested in building ourselves as we would be to any company?

Like a startup, we begin as just an idea: we’re incubated, put out into the world where we develop slowly, and then, over time, we accumulate partners, employees, customers, investors, and wealth. Is it really so strange to treat your own life as seriously as you might treat an idea for a business? Which one really is the matter of life and death?

Related: Successful SA Entreps Share Their Most Valuable Business Advice Ever Received

Don’t read the news today

Today you will be tempted – pressured even – to stay abreast of current events. To watch the news, to read a few articles, to check the stream of real-time events on Twitter. Resist this impulse.

Remember what Thoreau said: “To a philosopher, all news, as it is called, is gossip, and they who edit and read it are old women over tea.” Remember what Epictetus said, “If you wish to improve, be content to appear clueless or stupid in extraneous matters.”

Unless you’re a hedge-fund manager or a journalist, most of the breaking news out there is utterly irrelevant to your life (to say nothing of it being endlessly manipulative, exploitative and often incorrect). And considering all the things you could have been thinking about and doing instead, following it comes at a cost. A cost which is paid by you and your family and the world around you.

Don’t watch the news today. Focus on what’s in front of you. Exist solely in the present moment.

Your career is not a life sentence

“How disgraceful is the lawyer whose dying breath passes while at court, at an advanced age, pleading for unknown litigants and still seeking the approval of ignorant spectators.” – Seneca, On the Brevity of Life, 20.2

Every few years, a sad spectacle is played out in the news. An old millionaire, still lord of his business empire, is taken to court. Shareholders and family members go to court to argue that he is no longer mentally competent to make decisions – that the patriarch is not fit to run his own company and legal affairs.

Related: The Best Advice You’ll Ever Get

Because this powerful person refused to ever relinquish control or develop a succession plan, he is subjected to one of life’s worst humiliations: The public exposure of his most private vulnerabilities.

We must not get so wrapped up in our work that we think we’re immune from the reality of aging and life. Who wants to be the person who can never let go? Is there so little meaning in your life that your only pursuit is work until you’re eventually carted off in a coffin?

Take pride in your work. But it is not all there is.

This article was originally posted here on

Ryan Holiday is the bestselling author of The Obstacle Is the Way and Ego is the Enemy, whose forthcoming book, The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living, was October 18. For more, visit the Daily Stoic website and sign up for the free 7-Day Stoic Starter Pack.


Are You Suited to Entrepreneurship

Why Optimism Isn’t Enough – You Need To Also Accept The Brutal Facts

Entrepreneurs tend to depend on optimism in the same way that fish depend on water. It’s absolutely crucial for survival. In fact, it’s arguably the single most important character trait that a successful entrepreneur can have, but it also has a dark side…

GG van Rooyen




A realistic path to success

  • Lead with questions, not answers
  • Engage in dialogue and debate, not coercion
  • Conduct autopsies without blame
  • Build red flag mechanisms.

No matter how bad your day’s going, it’s probably nothing compared to your average day at the ‘Hanoi Hilton’. This was the euphemistically-named prisoner-of-war camp (actually called Hoa Lo Prison) where American soldiers were interned during the Vietnam War. Pilot Jim Stockdale was shot down on 9 September 1965 and sent to the prison. While there, he was tortured, denied medical attention, kept in a windowless cell and locked in leg irons at night. Stockdale spent almost eight years in the prison, and while many other American soldiers died there, he survived.

This brings us to the topic of optimism. You don’t survive eight years in a prison camp by giving up hope. Despite almost impossible conditions (and odds), you need to stay optimistic. Stockdale never lost hope.

“I never lost faith in the end of the story. I never doubted not only that I would get out, but also that I would prevail in the end and turn the experience into the defining event of my life, which, in retrospect, I would not trade,” Stockdale later said about his time in the prison.

Related: Shark Tank Funded Start-up Native Decor’s Founder on Investment, Mentorship And Dreaming Big

The Stockdale paradox

So, Stockdale was an optimist right? Yes, but it’s a bit more complicated than that. Jim Collins interviewed him while writing his seminal book Good to Great: Why Some Companies Make the Leap… and Others Don’t. After hearing how Stockdale refused to give up hope and stayed optimistic throughout his internment, Collins asked him who didn’t make it out alive.

“Oh, that’s easy,” he replied. “The optimists. They were the ones who said: ‘We’re going to be out by Christmas.’ And Christmas would come, and Christmas would go. Then they’d say: ’We’re going to be out by Easter.’ And Easter would come, and Easter would go. And then Thanksgiving, and then it would be Christmas again. And they died of a broken heart.

“This is a very important lesson. You must never confuse faith that you will prevail in the end — which you can never afford to lose — with the discipline to confront the most brutal facts of your current reality, whatever they might be.”

From this, Collins identified one of the key things that differentiated great companies from others: The ability to accept brutal facts. Greatness demands optimism, but not in the face of obvious disaster. Collins called this the Stockdale Paradox.

Too much optimism

What happens when a bunch of executives enter a boardroom with their charismatic founder? The founder is optimistic, inspiring… and demanding. He has absurd expectations. He wants the impossible. (Steve Jobs was a good example, who employees said had a ‘reality distortion field’ around him). The executives are eager to seem equally gung-ho, of course, even those who know that a crucial deadline won’t be met, so the brutal facts are ignored.

“We’re going to be shipping product by Christmas,” they all say. And Christmas comes, and Christmas goes. Then they say: “We’re going to ship by Easter. And Easter comes, and Easter goes. And then Thanksgiving, and then it’s Christmas again…

Related: 10 SA Entrepreneurs Who Built Their Businesses From Nothing

An overdose of optimism is a dangerous thing. While optimism is a crucial tool in the entrepreneurial kit (especially when it comes to motivating employees), it can lead to disaster if administered too liberally. Like morphine, a sensible amount can take the edge off a scary reality, but too much will distort reality to such an extent that you become oblivious to existential threats.

And how do you keep your company off the morphine? Collins suggests four things: Lead with questions, not answers. Engage in dialogue and debate, not coercion. Conduct autopsies without blame. Build red flag mechanisms. If you do this, optimism becomes a powerful tool, and not a ticking time-bomb.

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Are You Suited to Entrepreneurship

Alan Knott-Craig Weigh In On Living Your Entrepreneurial Dream

From raising capital to getting the most from your employees, business ownership is all about living your dream.

Alan Knott-Craig




How do I chase my dream? — Sam

First, you need money. Moola. Cash. Capital.

Chasing your dream without enough capital is akin to having a premature baby. All the baby’s energy goes into survival rather than growth. Start-ups are not about survival (paying the bills). They’re about growth (getting rich).

Before you chase your dream, make sure you have enough capital. Keep your lifestyle simple and living costs down. Save up enough to last two years. Or marry rich.

I’m considering selling my business. I need help. — Clark

Before you enter M&A conversations, first decide: “Am I a seller?”

You won’t find it easy backing out during negotiations. Don’t start a process you can’t finish. Don’t look for buyers if you don’t want to sell.

Most people I know that sold their business regret it, unless they had a very specific reason: i.e. the business was about to die, or the business can’t grow without a big brother, or they want to leave the country. If that’s your reason, go ahead and sell. If it’s simply to have a pile of cash, reconsider.

Related: Your Questions Answered With Alan Knott-Craig

What are you going to do with the money? Put it in your bathtub and wash yourself with notes? Buy fancy cars? Buy a fancy spouse?

Lots of money in your pocket can only tempt you to the dark side. Eventually you’ll get bored and you’ll want to start a business again, and you’ll start all over. If you don’t need to, don’t sell.

How do you instil an ownership mindset in your staff? — Johan

It’s hard to work with people that have no drive. Some people just come to work and go home with no planning or vision or energy. Start with getting rid of the bad apples, then start fine-tuning recruitment to only let in the folks with a good attitude.

Use some of these methods to motivate and encourage buy-in from staff:

  • Ask staff for feedback.
  • Do not tolerate mediocrity.
  • Make sure everyone knows their job.
  • Share information. Keep everyone in the loop.
  • Look after your staff and they’ll look after you.
  • Lead by example. Pick up litter. Be first to office. Be last to leave.

How do I determine what venture to dedicate my energy to and when do I know when to stop pursuing one of the opportunities? — Mike

Go with whatever gets traction first. Ruthlessly scratch everything else off your to-do list. Generally speaking, go with the business with the most tried-and-tested business model. 

I left my former employer to move away from the legal side of things. I know that I have the technical skills in this area and I have used that in completely running the legal side of the micro lending venture, but the ultimate aim is to be an entrepreneur/businessman rather than constantly seen as the ‘lawyer’. Do I discontinue the legal consulting or slowly taper off? — Mike

If you can live without the sideline income, do so. Focus 100% on business. If you need the money, keep selling hours on the side.

Related: Alan Knott-Craig’s Answers On Selling Internationally And Researching Your Idea

I have a very successful farm store. I’m considering expanding countrywide. Any advice? — Elo

Ask yourself “why?”

If the answer is to get rich, that doesn’t necessarily mean you need to scale your successful farm store.

Maybe a better option is to take the free cashflow of your farm store and invest it in a different business. An annuity revenue business. A business that will make money while you sleep, rather than only when you’re behind the till. Cash cows are hard to come by. If you don’t want to lose your cow, don’t try to scale it unless you’re 100% sure you never have to sell it.

Can you help me flesh out the detail of a pitch to investors? — Mamkhele

There’s only so much you can rely on others for. At some point, you need to man up and do the work yourself. You need to answer the questions yourself. The answers for all pitch-related questions are on the Internet. Google it. No one will save you, only you will save you.

Listen to this

Alan’s audible book Be a Hero: Make Life an Adventure is now available on and

Read by Alan himself, Be a Hero is a collection of stories on how to make your life an adventure by changing your mindset and tackling adversity.

Go to or to download your copy. Be a Hero is also available in Kindle and paperback through

Read ‘Be A Hero’ today


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Are You Suited to Entrepreneurship

What Real Entrepreneurs Do When They Hear The Word ‘No’

Are you strong enough to push through early struggles?

Jason Saltzman




In this video, Entrepreneur Network partner Jason Saltzman sits down with two founders to hear their stories of perseverence and resilience.

Raul Tovar is the co-founder of WindowsWear, a fashion tech company based in New York City that archives display windows. He moved from Mexico to New York determined to make something of himself and resolved that he would not go home empty-handed.

Jordan Wan is the founder and CEO of CloserIQ, which builds sales teams for startups. He started his business through tragedy – losing his mother and his marriage in the early stages.

You might think these difficulties – whether moving, or being told their ideas weren’t good enough, or working through tragedy – would be enough to make them give up. But they didn’t. They only spurred them to greater success.

Related: How To Start A Business With (Almost) No Money

Click play to learn more.

This article was originally posted here on

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