Friday, 9:30 pm, another humiliating workday. Boss mocked your client presentation—then four-letter insulted you in front of colleagues. Come 4:30 pm, he threw you a “little weekend project,” due Monday morning.
Back home, ready to scream, you head to the kitchen: “Please oh god, let there be malt whiskey.”
Tonight, consider a less inebriating way to “get a little perspective” about your boss from hell. Banish your sorrows with Josiah Osgood’s fun and instructive How To Be A Bad Emperor: An Ancient Guide To Truly Terrible Leaders (introductory essay plus texts, translations, from the ancient Roman biographer, Suetonius).
Take a breath. Things could be worse. Imagine if you worked for some cruel and depraved emperor from Roman history.Consider Caligula (AD 12-41). This tyrant reveled in humiliating rivals (e.g. extorting sex from their wives) and brutalizing august Senate elders (forcing them to honor a horse as their consul, and to run behind the emperor’s chariot). Caligula’s nightly paranoia was to lie in bed, plotting false accusations against his countless enemies. Rome sighed in collective relief when a few of his body guards dispatched him with loving swords.
Or how about reporting to Nero (AD 37-68)? Notorious for murdering his wife, mother and hundreds of Christians, this creature also demanded that subordinates ooh and aah for his operatic songs (yes, while Rome burned).
Or imagine a boss like Emperor Tiberius (AD 14-37): a craven scoundrel who enriched himself with stolen citizen fortunes, chased carnal pleasures in Capri while ignoring repeated public crises, and proudly proclaimed that “as long as people obey me, I take joy in their hatred.”
Beyond imperial antics, Roman civilization also offers some positive wisdom. That empire endured many chaotic bosses, but still kept all the operational machinery whirring for centuries. Some workaday professionals clearly figured out how to survive the monsters in charge. I asked Professor Osgood to reflect on Roman lessons for coping and prospering if you work for a boss both loathed and feared.
“Much is just common sense,” he began. “But there are also timeless insights in the stories of well-intentioned people serving awful leaders.”
Our discussion surfaced five career-enhancing suggestions:
1. Understand the risks and rewards of your professional aspirations. Do you have the stomach for a heartless supervisor? If you’re ambitious, there will always be one or two along the way, as you climb the ladder. Osgood explained why the risk increases as your career progresses—drawing from ancient Rome. “Working for the Emperor—essentially the CEO—was the ultimate prize: like today, a route to glory, wealth, and more prestigious marriages. The competition to join imperial service was fierce—which also made the man at the top the fiercest of all. Rising in the ranks always enters you into more stressful arenas.”
Own what every ancient go-getter knew: you have to steel yourself for the professional dangers and personal costs of some horrific boss in your future. It’s just part of the career-building game.
2. Accept assignments but keep learning and performing. The most effective leadership development derives from experience in different jobs—but only if you work harder and smarter with each new post. The more you grow, the greater your value—even to future bosses from hell. Increasing skills become a protective asset.
The Georgetown professor invoked another Roman text: “Tacitus’ Agricola, a biography of a successful imperial statesman, reminds us that nothing builds your career faster—or better insulates you from reproach—than developing your capabilities and continuously improving. Agricola was first sent by Nero to help pacify the unruly British province. He turned the difficult commission into a learning opportunity. Working under experienced generals, he year by year cultivated essential knowledge about waging war and commanding soldiers. It eventually made him invaluable. He took less abuse from volatile emperors, because they needed him.”
3. Align yourself with the fundamentals of strategy and values. Beneath every bad boss lies an organization with tangible goals and its own cultural values. Anchor yourself to those, to help withstand the gales of a stormy overseer. Osgood again bridged to an ancient example: “Agricola’s success was buttressed by his steady focus on traditional Roman ways and empire-building. In Britain he resisted personal luxury and enrichment which was the norm of provincial generals. He also consolidated military victories by importing Roman institutions and schooling the locals in Latin. He shrewdly kept furthering the civilization for which his boss emperors wanted to be known.”
4. Reach for the sky—but not too high. “Never look better than your boss”— sage advice today, and no less for ambitious Romans. Jealousy is a dangerous human emotion—especially in your supervisor. Strive to contain it.
First, have some empathy for the boss himself: jealousy springs less from vanity than fear. Professor Osgood underscored that with another Roman insight: “There was no law of succession for emperors, so anyone could potentially usurp—or kill— them. They had reason to be paranoid, and not surprisingly, many lashed out when they saw rival talent rising.”
“Note, therefore, the contrarian wisdom of Agricola. Throughout his career he tip-toed with his personal reputation. Asked to organize public games for Nero—who himself loved hosting big flashy circuses—Agricola produced events that were professional but never extravagant.”
“Under Domitian, who was a poor military leader, Agricola sent campaign dispatches that were informative, but minimized his own accomplishments. He deliberately restrained friends from boasting on his behalf. Assiduous modesty propelled his rise.”
5. Dare the tyrant only when you dare. Even if you do everything right, you’ll still come to some moment of final despair with your insufferable boss. You’re fed up and want to fight back. But before you do, press “pause”—consider what you’re willing to sacrifice. Or not. And why the confrontation.
Osgood again explained: “Many Roman statesmen reached the breaking point with cruel emperors, and then died for opposing their wishes. Today, thankfully, most of us don’t have to worry about that—but of course insubordination in a job can quickly get you fired. That can be its own existential moment in a career. History again offers some instructive insights.”
“First, know your bosses and your true worth to them, before you decide to push back. Consider the story of Marcus Agrippa. The emperor Augustus heavily depended upon this all-competent lieutenant. So occasionally, if Agrippa was unhappy with some imperial demand, he would subtly hint about retiring from service. Then, as now: if you think you’re on solid ground, be willing to walk. But weigh the risks and rewards—if you miscalculate, there’s no turning back.”
“Second, confronting a boss will be different in different moments of your career. Some Roman statesmen, in their later years, simply became more philosophical about their lives (literally “Stoic,” following the then popular school). They were not afraid to take the consequences of challenging a corrupt leader — for the greater good of the institution.”
“One famous Senator, Thrasea Paetus, rebuffed the disgraceful subservience demanded by Nero. In visible dissent, Paetus spurned both applauding the Emperor in public games, and praising him in the Senate. The emperor had him killed. But Paetus took comfort in a noble death. His bravery echoes that of whistleblowers and others who act courageously in service to someone in power—at great personal cost, for the betterment of something more important than just flattering a self-absorbed leader.”
P.S. For a more lighthearted but still historical Roman tale—with contemporary lessons about leadership, imperial power, art and romance—check out Esme von Hoffman’s charming new film, Ovid and the Art of Love (streaming on multiple platforms).
Originally published on Forbes.com