Last Saturday, April 23, marked 400 years since the death of William Shakespeare the man. The words of William Shakespeare The Bard live on; and those words, written hundreds of years ago, are still amazingly relevant to the lives we live today. That may be a testament to Shakespeare’s gift; it may also simply be proof that however much society transforms and evolves, people remain fundamentally the same.

England embarked on a day-long celebration that included President Obama visiting a replica of Shakespeare’s Globe theatre, and a star-studded gala at the playwright’s birthplace of Stratford-upon-Avon (streamed live all over the UK and Europe) which included noted Shakespearian actors performing his work, as well as a recitation of the “To Be Or Not To Be” speech from Hamlet by none other than Prince Charles.

As a proud English Major, I couldn’t let the anniversary go unmarked in this Tip column, especially because Shakespeare’s words have so much to offer small business owners—and I’m not just talking about Merchant of Venice, though that’s a good place to start.



I’ll have my bond; speak not against my bond:
I have sworn an oath that I will have my bond.
Thou call’dst me dog before thou hadst a cause;
But, since I am a dog, beware my fangs
–Shylock, Merchant of Venice [III,3]

According to the Shakespeare Concordance, the word “Contract” appears 26 times across 12 Shakespeare plays, the word “Contracted” in 9 plays and 2 Sonnets, but not once in Merchant of Venice—a play in which a distasteful contract has a central role. That is likely because in Shakespeare “Contract” more typically refers to a marriage contract, than a business one. In Merchant of Venice the contract is a “bond” by which Antonio agrees to forfeit a pound of his flesh if he defaults on the interest-free loan he took from Shylock. Portia (disguised as Balthasar a “Doctor of Laws”), agrees that by strict textual interpretation of the “bond’s” language, Shylock is indeed owed his pound of flesh, yet implores him to show “mercy” and accept late payment instead slicing into Antonio. When Shylock refuses mercy, she directs him to extract his pound of flesh without removing any “blood” which the terms of the contract do not permit. Being unable to do so, and having refused to act equitably, Shylock is stripped of all his possessions, and his religion. (An ending applauded in Shakespeare’s day, but found deeply unequitable and merciless by many today.)

The court scene in Act VI, Scene 1, has been dissected in many a law school class as a classic example of the conflict between law and equity—or the problems that arise when strict reading of contract language conflicts with fairness to both parties. (Read a great discussion on this topic here.)

Merchant of Venice also highlights key things to consider when entering into contracts for your small business:

  • Read the fine print, and always completely understand exactly what a contract says and what it doesn’t. Sometimes the most important, and most potentially costly, mistakes stem not from the language in the contract, but in the language omitted from it. In short, never demand only flesh, always go for “flesh and blood” since the two are inextricably linked.
  • The best contracts are those that benefit both parties. If you approach all your contracts with the goal of extracting a pound of flesh, then you may end up on the wrong end of the knife in the end.
  • Don’t agree to terms or penalties that you can’t live with, even if you think the likelihood of the contingencies that will trigger them are remote. You simply can’t bet your life (or the life of your small business) on your ship coming in, or coming in on schedule. Sh** happens, schedules go awry, and market forces intervene unpredictably.



Good Paulina,
Lead us from hence, where we may leisurely
Each one demand an answer to his part
Perform’d in this wide gap of time since first
We were dissever’d: hastily lead away.
— Leontes, Winter’s Tale [V,3 final lines]

Using the lessons of Shakespeare’s plays to teach entrepreneurial leadership is a common theme. From triumphs of ascending Kings to tragedies of fallen ones, the plays contrast the public performance of The Monarch to the insecure frailty of the man. The Histories and the Tragedies (King Lear, Macbeth, Hamlet, Richard II, Richard III) examine leadership, and its downfall, from the top down. These often larger-than-life characters exemplify the perils of hubris, inattentiveness, corruption, and unquenchable thirst for power. There is no dearth of “experts” plucking these obvious examples for modern leadership lessons. (For example, in this article from The International Journal of Management Research and Business Strategy.)

Far more interesting is a look at Shakespeare’s Comedies, where lessons in leadership emerge more subtly. Rather than looking at a character’s ability to “move the masses,” leaders in Shakespearian comedies are more likely to be those who can move the plot to engineer the outcomes they desire. And in many cases, these leaders are women (who often disguise themselves as men).

Case in point is Portia, who as noted above, is not only responsible for the key arguments that bring Merchant of Venice to its conclusion, but also for arranging all of the proper character couplings in the end. In Twelfth Night, Viola begins the play shipwrecked, penniless, and separated from her brother. She disguises herself as a male, and surreptitiously maneuvers events such that at the end of the play she marries the Duke, ensures a bright prosperous future for herself, and is reunited with her brother.

Perhaps the best example of a woman leading the action is Rosalind in As You Like It. Widely acknowledged as one of Shakespeare’s strongest female characters, (having more lines than any other), Rosalind takes control of her life, and the rest of the play, after being banished by the power-hungry current Duke who overthrew her father, the old Duke. Though in a seemingly powerless position, Rosalind uses her wit, guile, and humor to transform the reality in which she finds herself into the reality she wants—not only for her own benefit, but for the benefit of all the worthy people around her (may the unworthy get what they deserve).

These Shakespearian women teach valuable lessons to any budding entrepreneur:

  • Even if you appear to be in a powerless position, if you act intelligently you can maneuver those with power (a large customer, a giant competitor, etc.) to affect the outcome you desire.
  • It is not necessary to be a larger-than-life figurehead in order to be an effective leader. Working in the background and directing the action can be just as effective.
  • Truly successful leaders not only work to achieve their own goals, but the goals of all stakeholders. Shared success is a far more powerful tool than a singular triumph.
  • A little deception can be a useful tool. For example, you may need to make your startup appear larger than it is to land your first big contract and live up to the image.



Go and tell him,
We come to speak with him; and you shall not sin,
If you do say we think him over-proud
And under-honest, in self-assumption greater
Than in the note of judgment; and worthier
than himself
–Agamemnon, Troilus and Cressida [II, 3]

The examples in the previous section show how easily gender is assumed based on dress. While clearly a necessary plot deceit, had all those male characters looked just bit closer they may not have been undone by those women masquerading as boys and young men.

Shakespeare plays are full of characters who find themselves undone by faulty assumptions. King Lear’s downfall begins when he assumes that the only daughter who truly loves him, loves him not because she refuses to say so in the manner he requires. Othello accepts Iago’s lies and assumes Desdemona’s infidelity leading him to strangle her. Romeo assumes that Juliet is really dead and kills himself out of despair, mere minutes before she awakes from a drug-induced coma.

Perhaps the greatest tragedy of faulty assumptions is Macbeth. Macbeth assumes that he can operate with impunity when told by the Weird Sisters that, “Macbeth shall never vanquish’d be until Great Birnam wood to high Dunsinane hill Shall come against him” and that “none of woman born Shall harm Macbeth.” After all he reasons, everyone is of woman born and, “That will never be Who can impress the forest, bid the tree Unfix his earth-bound root?” In the end, Macduff (who was born by what we would now call a c-section, and not technically of woman—another Shakespearian literal language construction trap) instructs his army to cut pieces of Burnam Wood trees to use as camouflage as they approach Dunsinane, and goes on to defeat Macbeth in a sword fight. So much for self-deluding assumptions.

As a small business owner it is important to be aware of the assumptions underlying your decisions, so that you can make the most informed decisions possible. Remember the following lessons from Shakespeare:

  • People lie. It may be a casual acquaintance, a competitor with ulterior motives, or a trusted advisor who shouldn’t be so trusted. When making important decisions, don’t assume facts you can’t substantiate.
  • Everything is not always as it appears. It is easy to assume the worst, when in fact you are more likely to be successful if you keep your options open and work towards the result you want. For example, a prospect may appear as dead as Juliette on a slab, but don’t give up if there is even a slight opening in which you can still make the sale.
  • Don’t blind yourself with wishful thinking. Even when encouraged by positive market research, glowing product reviews, or enthusiastic capital support, it is still possible for things to go wrong and for forecasts not to match reality. You may think you have considered every possible scenario, but sometimes the highly unlikely turns into sad actuality. And, sometimes your trusted advisors (even if far more well-meaning than those Weird Sisters), will tell you what they think you want to hear. As a small business owner, you owe it to yourself and to your company to listen to many different points of view, and to spend at least some time contemplating—if not actually planning for—even seemingly impossible contingencies.


Delving Further into Small Business Lessons from Shakespeare

If you’re interested in delving further into business lessons from Shakespeare, check out the following books:

If you’re in the NYC area, consider attending Heroes and Heroines: Women in Shakespeare and Lessons for Today’s Leaders, a talk sponsored by The New-York Historical Society on June 26th, 2016. (You’ll also get a chance to see the 1623 First Folio in person.)

And, if you’d like to try your hand at identifying whether popular English phrases came from Shakespeare or the King James Bible (noteworthy sources both), take the BBC’s Bard or Bible quiz.

Get Small Business Tips like this one by signing up for our Small Business Smarts newsletter.

Lisa Hephner

Lisa Hephner

My name is Lisa, and I'm the Vice President of Knowledge, responsible for the management of corporate, product, competitor, marketplace, legal, and regulatory knowledge, and creation and dissemination of knowledge tools using these assets to PaySimple prospects, customers, employees, and partners.

More Posts - Website - Google Plus