What Diocletian’s Retirement Teaches Modern Business Owners
I’m writing this from the ancient stones of Diocletian’s Palace in Split, Croatia, where the only Roman Emperor smart enough to retire successfully built his dream exit plan in stone…
As I sit in an apartment within the walls of what was once the private quarters of a Roman Emperor, I’m struck by something remarkable: I’m sitting inside one of history’s most successful exit strategies.
Diocletian didn’t just retire from being Emperor (something no Roman leader had ever done voluntarily), he planned it, executed it, and lived to enjoy 8 peaceful years in this stunning palace he’d built on the Adriatic coast. While his successors fought civil wars and met violent ends, Diocletian was tending his vegetable gardens in what is now Croatia’s second-largest city.
For modern business owners struggling with succession planning, there’s no better case study than a man who successfully “exited” the most powerful position in the ancient world.
The Ultimate Succession Challenge
Imagine the succession planning challenge Diocletian faced in 305 AD:
- The “business”: The Roman Empire – spanning three continents, 50 million people, dozens of provinces
- The problem: Too large and complex for one person to manage effectively
- The precedent: Every previous “CEO” had died in office (often violently)
- The stakes: Chaos, civil war, and collapse if the transition failed
- The family: How to manage the many interests
Sound familiar? While your family business might not span continents, the core challenges remain the same: complexity, control, and ensuring continuity after your departure.
Diocletian’s Masterstroke: The Tetrarchy System
Rather than do what every emperor before him had done – cling to power until death – Diocletian created something revolutionary: the Tetrarchy, or “rule of four.”
His succession strategy had three brilliant elements:
1. Systematic Division of Responsibility
Instead of keeping all power centralised, Diocletian split the empire into manageable parts:
- Two senior emperors (Augusti)
- Two junior emperors (Caesares)
- Clear geographical boundaries and responsibilities
- Built-in succession pathway from Caesar to Augustus
Modern lesson: Many family businesses fail because founders refuse to delegate meaningful authority. Diocletian proved that dividing responsibility doesn’t mean losing control – it means creating sustainable systems.
2. Planned Leadership Development
The Caesares weren’t just waiting in the wings – they were actively governing their territories, learning the role, and being evaluated. When promotion time came, they were ready.
Modern lesson: Too many business owners assume their children will naturally be ready to take over. Diocletian’s system required proven competence before promotion. As he allegedly said when pressured to return to power: “If you could see at Salona the cabbages I raise with my own hand, you would never urge me to give up the happiness of this place for the storms of a never-resting ambition.”
3. Exit Plan on His Own Terms
Most remarkably, Diocletian stepped down at the height of his power, on May 1, 305 AD. He didn’t wait for health problems, palace coups, or external pressures. He planned his exit and executed it.
Modern lesson: The best time to plan your succession is when you don’t need to.
The Split Exit Strategy: Planning Your Post-Exit Life
Here in Split, surrounded by the limestone walls of Diocletian’s Palace, you can see another crucial element of his exit strategy: he knew exactly what he wanted his post-exit life to look like.
This wasn’t just a retirement home – it was a carefully planned lifestyle transition:
- Strategic location: Close enough to stay informed about imperial affairs, far enough away to avoid daily interference
- Architectural statement: The palace demonstrated his continued status and legacy
- Personal fulfilment: His famous gardens and peaceful pursuits
- Legacy preservation: The palace still stands 1,700 years later, how’s that for lasting impact?
Modern application: How many business owners spend decades building their companies but no time planning what they’ll do after they exit? Diocletian shows us that a successful exit requires as much planning for the “what’s next” as the “how to leave.”
Where Diocletian’s Plan Ultimately Failed (The Family Feuds)While Diocletian’s personal exit was flawless, the Tetrarchy system collapsed within a generation in a spectacular display of what we’d recognize today as classic family-business warfare.
The “next generation” turned on each other:
- Constantine (son of one of the Caesars) and Maxentius (son of Diocletian’s co-Augustus Maximian) became bitter rivals, literally going to war for control of the “family business”
- Maximian – Diocletian’s own partner – came out of retirement to try to regain power, undermining the entire succession plan
- Multiple “heirs” claimed legitimacy simultaneously, fragmenting the empire
The parallels to modern family business feuds are uncanny:
- Siblings fighting over who should really be in charge
- The “founding generation” (Maximian) unable to stay retired and let the plan work
- Each family branch believing they deserved the top role
- Cooperative agreements breaking down the moment the founder stepped back
The Game of Thrones:
Interestingly many scenes for Game of Thrones were filmed in the palace, but there are deeper parallels:
- Caracalla murdered his brother Geta rather than share power – making Joffrey look reasonable
- The Year of the Four Emperors (69 AD) saw competing family claims tear the empire apart – the original “War of the Five Kings”
- Commodus fought constantly with the Senate (think: family business vs. advisory board conflicts)
The Romans arguably wrote the playbook that George R.R. Martin borrowed from – succession crises, family betrayals, and the brutal cost of unclear inheritance rules.
The brutal irony: Diocletian executed a perfect personal exit, but the “family business” couldn’t maintain the collaborative culture he’d established. His successors turned cooperative governance into competitive warfare – exactly what happens when family business siblings can’t agree on roles, authority, and succession timing.
This wasn’t about external threats or market conditions. This was about family dynamics destroying a perfectly designed system.
Modern Lesson: Even brilliant succession plans need continuous management, clear conflict resolution mechanisms, and sometimes external governance to prevent family relationships from destroying the business.
Five Diocletian-Inspired Principles for Modern Succession Planning
Standing in the Emperor’s former throne room (now a bustling café), here are the timeless principles every business owner should adopt:
1. Plan Your Exit at Peak Performance
Don’t wait for crisis, illness, or decline. Diocletian stepped down when he was most successful – giving him maximum leverage and options.
2. Divide to Multiply
Consider whether your business is “too big” for one person to manage effectively. Could operational divisions, regional splits, or functional leadership teams create stronger management?
3. Create Apprenticeships, Not Inheritances
The Caesar-to-Augustus pathway required proven competence. Your succession plan should include real responsibility, measurable results, and earned advancement.
4. Design Your Post-Exit Life First
Before you plan how to leave, plan the what, where and why of your exit. What’s your equivalent of Diocletian’s Split gardens?
5. Build Systems That Survive You
The palace still stands because it was built to last. Is your business structured to thrive without your daily involvement?
The View from the Palace
As I write this, tourists from around the world are walking through Diocletian’s former private apartments, now home to shops, restaurants, and hotels. His “retirement home” has become a living, breathing city centre – perhaps the ultimate measure of a successful legacy.
The emperor who voluntarily gave up absolute power created something more lasting than those who clung to it until death.
For modern business owners, Diocletian’s example is both inspiring and instructive. He proves that stepping back doesn’t mean stepping down – it means stepping into a new phase of life that you’ve designed intentionally.
His palace walls have witnessed the fall of Rome, the rise of medieval kingdoms, Venetian rule, Austrian empire, Yugoslav federation, and now Croatian independence. Through it all, the stones of his exit strategy endure.
The question for every business owner is simple: Are you building something that will outlast you, or something that depends entirely on your presence?
Whether or not you plan for it, an exit will happen, will you and your business be ready?
At Exitologists, we help business owners design succession strategies that protect both their legacy and their lifestyle – just as Diocletian did 1,700 years ago here in Split. Because the best exit strategies aren’t about leaving – they’re about transitioning to what comes next.
