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St George in Retirement Syndrome: How to Know When to Quit?

Problems are precious. They challenge us, make us learn and grow, and give meaning and purpose to our lives. Especially when we’re pursuing the laudable goal of making the world a better place. Hooray for us! But what if our noble intentions become a crippling addiction? In this case, we might be affected by the so-called St George in Retirement Syndrome, a condition that keeps us from knowing when to quit. To understand what it is and what we can do about it we must first look into its origins, the legendary story of Saint George and the dragon.

The Legend of Saint George

St George in Retirement Syndrome has its roots in one of the oldest stories of mankind. George of Lydda, as he was known before his noble deeds were rewarded with sainthood, was a Roman officer of Greek descent. Presumably, his story took place in today‘s Libya where a fierce dragon was terrorising a village.

In an attempt to appease the fire-breathing creature, the villagers had already sacrificed their farm animals. When they ran out of sheep, the king gave orders to sacrifice the people‘s children instead. By way of lottery, to keep it fair. Unfortunately for the ruler, it was so fair that one day his own daughter was selected to be sacrificed.

Enter George who just happened to be in the area. He takes on the challenge and manages to tame and kill the dragon after spotting its vulnerability. The rest is legend. He rescues the princess, is hailed as brave and courageous, good wins over evil (and the whole village converts to Christianity).

I casually tell this story, but it has of course a deeper meaning. One that‘s still relevant today. There are plenty of symbolic dragons in our lives. If we want to get ahead, we must confront those problems, which are often the ones we least want to face. We can put them off temporarily by sacrificing our needs and even what we love the most. But not indefinitely. Only when we face those inner demons can we achieve our biggest goals.

With this legend in mind, what is St George in Retirement Syndrome all about?

What Is St George in Retirement Syndrome?

St George in Retirement Syndrome describes a situation in which we fail to quit a noble struggle. Instead, we keep losing ourselves in increasingly small and trivial skirmishes. The term goes back to Australian author Kenny Minogue who turned the legend around Saint George into a metaphor for the story of liberalism. In the introduction of The Liberal Mind, a 1963 book about the past, present and future of liberalism in the Western world, Minogue remarks:

The story of liberalism, as liberals tell it, is rather like the legend of St. George and the dragon. After many centuries of hopelessness and superstition, St. George, in the guise of Rationality, appeared in the world somewhere about the sixteenth century. The first dragons upon whom he turned his lance were those of despotic kingship and religious intolerance.

These battles won, he rested for a time, until such questions as slavery, or prison conditions, or the state of the poor, began to command his attention. During the nineteenth century, his lance was never still, prodding this way and that against the inert scaliness of privilege, vested interest, or patrician insolence.

But, unlike St. George, he did not know when to retire. The more he succeeded, the more he became bewitched with the thought of a world free of dragons, and the less capable he became of ever returning to private life. He needed his dragons. He could only live by fighting for causes—the people, the poor, the exploited, the colonially oppressed, the underprivileged and the underdeveloped.

As an ageing warrior, he grew breathless in his pursuit of smaller and smaller dragons—for the big dragons were now harder to come by.

Kenneth Minogue

While Minogue doesn’t seem to have used the expression himself, St George in Retirement Syndrome is a fitting term for what he describes: the pathological state an initially heroic person can wind up in. After having succeeded in a righteous battle, the winner becomes preoccupied with increasingly trivial causes. In the end, the hero is too committed and too proud to call it quits. What started out as a laudable pursuit is now indistinguishable from madness.

It echoes a common sentiment. In contrast to fictional stories, real life continues after the happy ending. It’s where the Australian philosopher’s interpretation picks up. Once the dragon is slain, George of Lydda becomes addicted to fighting for the oppressed. Initially, the knight got into the dragon-killing business by mere chance. Now he can’t get enough of it. Eventually, the once-proud knight turns into a pathetic shadow of himself.

The Dangers of Achievement

You don’t have to be an outspoken liberal to suffer from this condition, though. In fact, political convictions may not have much of an influence. Just like the broader meaning of the original legend, I think our syndrome reflects a general problem rooted in the human condition.

It all seems to imply a counter-intuitive truth: achievement can be dangerous. When it comes to its downsides, there are three things we might consider: the relationship between achievement and pleasure, the postponement of a task and the role of our ego.


Goals and Dopamine

According to neuroscientist Dr Andrew Huberman, we get our dopamine kicks from progressing towards a goal, not achieving it. This serves the function of keeping us motivated, especially when we pursue a highly ambitious cause over a long period of time. Problems seem to arise when our happiness comes solely from progressing towards a single goal and we actually achieve it. The source of our happiness dries up so to speak. No more little wins along the way, no more dopamine.

St George in Retirement Syndrome could be a response to such a dynamic. In order to avoid drifting aimlessly, we become a solution in search of new problems, no matter how trivial or unrealistic. It would also explain the downward spiral George finds himself in. As St George fights for his Daseinsberechtigung, the dragons become smaller, easier and quicker to defeat, with smaller and smaller rewards along the way. To an extent, he becomes the victim of his own effectiveness.

Yak Shaving and Procrastination

St George in Retirement Syndrome also has some striking similarities to Yak Shaving. When under the spell of Yak Shaving, we lose ourselves in increasingly trivial sidequests. On the surface, they have no obvious relationship to our larger goal. But they’re still necessary. Imagine having to attend a party because it’s the only way to track down a colleague you’ve been trying to contact for ages. Through the process of Yak Shaving, your socialising becomes part of your work.

The problem is that there’s a fine line between Yak Shaving and self-deceptive rationalisation. In this way, St George in Retirement Syndrome may be another form of procrastination. One where we put off finding a new long-term goal. Both George and the misguided Yak Shaver seem to evade true productivity. Both are undoubtedly busy. But they lack focus and perspective. They deceive themselves into thinking that completing those little trivial tasks is worthwhile. So broadly speaking, major achievements can cause us to postpone finding a new purpose.

Ego and Other Vices

There seems to be another aspect to St George in Retirement Syndrome, one that has to do with our ego. The fact that George becomes “bewitched with the thought of a world free of dragons” implies he succumbed to perfectionism, overconfidence and arrogance. Interestingly enough, we never hear from the people he’s fighting for and if they actually appreciate his breathless pursuit.

Storywise, it’s quite reminiscent of Herman Melville’s Captain Ahab, the whale hunter who becomes obsessed with hunting down Moby Dick. Ahab’s quest becomes an obsession as he projects all evil ever endured by humanity onto the white whale. In other words, both Ahab and George get corrupted in their pursuit to fight evil. Both become blind to their surroundings and the consequences of their actions.

According to best-selling author Robert Greene, we’re most vulnerable in the moment of victory. Grandiosity, arrogance and hubris can cause us to lose everything we’ve achieved. As he describes in The 48 Laws of Power, victory should be the time to pause and reflect. A time to consolidate our gains and avoid taking more risks. His advice, therefore, is to “set a goal, and when you reach it, stop.”

The Art of Slaying Dragons

That ties into the question of a potential cure and prevention for St George in Retirement Syndrome. How can we make it less likely that we succumb to the syndrome? How can we know when to quit? Six strategies come to mind:

  1. Set clear goals. That includes periodically reminding ourselves of what we’re trying to achieve and having a clear mind about when we‘ve achieved it. Depending on the goal, it may also be advisable to pre-define a deadline regardless of achievement so we can cut our losses and change goals.
  2. Premeditate. While we’re at it, we might also want to think ahead. If not retire, what are we going to do once we’ve achieved a big goal? Better yet, we come up with a system, which is a set of behaviours and habits that help us achieve a goal. Author James Clear once famously said: “You do not rise to the level of your goals. You fall to the level of your systems.”
  3. Stay flexible. Before going on our dragon-slaying mission, we may also want to give some thought to the following questions: How malleable should our goals be? Under what circumstances might we adapt them? Our initial ones could be too ambitious, in which case it pays to make a lateral move or use an exit strategy. Goals might also have been too unambitious, in which case it pays to set the bar higher.
  4. Outsource. Checking in with the people we’re trying to help seems like a good idea, too. When picking goals, we don’t want to be overbearing by stealing other people’s problems. Instead, we make sure our help is needed and wanted. If it’s not, we let someone else take over and we can find something more worthwhile to do.
  5. Avoid short-term battles. It’s also a good idea to pay attention if our actions primarily serve a long-term or a short-term goal. We want to avoid getting lost in tactical fights of no abiding significance. We may be winning them all but to the detriment of our long-term goal. Let’s assume we won’t be able to notice this ourselves, so we have people around us with whom you can check in every once and a while.
  6. Reevaluate and regroup. Finally, whenever a minor or major goal is achieved and we feel that little dopamine kick, we pause and reset. We re-evaluate the path we’re on and whether we should change course. We remind ourselves what we’re doing and why we’re doing it. If we realise we’ve achieved our goals and don’t have something equally good or more worthwhile to do, perhaps it’s time to finally retire.

Closing Thoughts

Ultimately, St George in Retirement Syndrome comes down to an inner struggle triggered by outstanding achievement. This crisis of purpose leads to a dependency on fighting smaller versions of the old battles, which makes it impossible to know when to quit. Problems can be so precious that they can become an addiction.

It’s easier to realise when we should stop doing something that’s obviously evil. The real challenge is to notice when something positive becomes pathological as any criticism can easily be drowned in claims of virtue. But no matter how seemingly virtuous, how much help is a knight with a spear for whom every problem looks like a dragon?