Chapter 10: Matching Your Way to the Times

A Careful Man in a Hurrying World

Hyun-woo is forty-eight and has worked for twenty years as an accountant in a firm that provides bookkeeping services to small businesses. He is careful, thorough and patient. He checks every figure twice, considers every risk and never rushes a decision. For most of his career, these qualities have made him one of the most valued people in the firm. Clients trusted him because he never made mistakes. Managers relied on him because his advice was always sound.

In the last two years, the firm has changed. A new generation of clients, many of them young people starting businesses online, want quick answers and fast service. They send questions by message late at night and expect replies within hours. The firm has introduced new software that does much of the routine checking automatically. Younger colleagues work quickly, try new approaches and accept that they will sometimes need to correct small errors later.

Hyun-woo finds this very difficult. His careful approach, which used to be his greatest strength, now seems slow. Clients have complained that he takes too long to respond. His manager has suggested, kindly, that he could trust the new software more and check less. Hyun-woo feels that the world has changed around him, and that the qualities that made him successful are now working against him. He feels hurt, and a little frightened.

At the same time, Hyun-woo has noticed something else. When a young client's business ran into serious trouble last spring, because of a large tax mistake made in a hurry by another accountant, it was Hyun-woo who was called in to untangle it. His patience and thoroughness were exactly what was needed. So his way was not simply wrong. It suited some situations and not others.

Machiavelli understood this kind of experience very well. In The Prince and in the Discourses, he wrote about people whose way of acting suited one time and not another, and about why it is so hard for any of us to change our way when the times change. This chapter explores his ideas and what they might mean for a working life in a changing world.

Two Ways to the Same End

In the second half of chapter 25 of The Prince, after his image of fortune as a river, Machiavelli makes another observation. People, he says, pursue their goals in different ways. One acts with caution, another with boldness. One uses patience, another its opposite. And each of them, by these different methods, may reach the same goal. Yet two people who act in the same way may have different results: one succeeds, and the other fails (The Prince, chapter 25).

Why? Machiavelli's answer is that success depends on whether a person's way of acting matches the times. If someone governs with caution and patience, and the times and circumstances turn in a way that suits caution, he will succeed. But if the times change and he does not change his way of acting, he will fail. Machiavelli gives the example of a ruler of his own time who always acted boldly and impetuously. Because the times happened to suit boldness, he succeeded in everything. If times had come that required caution, Machiavelli says, he would have been ruined, because he would never have departed from the ways to which his nature inclined him (The Prince, chapter 25).

Machiavelli then explains why people find it so hard to change. There are two reasons. First, we cannot easily depart from what our nature inclines us toward. A cautious person finds boldness uncomfortable, and a bold person finds caution frustrating. Second, when we have succeeded by walking along one road, it is very hard to persuade ourselves that it is time to leave it. Our past success becomes a trap, because it convinces us that our way is simply the right way (The Prince, chapter 25).

This passage describes Hyun-woo's situation precisely. His careful nature had been rewarded for twenty years, in times that suited care. Now the times had changed, and his way no longer fitted as well. Both of Machiavelli's reasons applied to him: his nature inclined him to caution, and his long success with caution made it hard for him to believe that anything else could be right.

Machiavelli adds a striking thought. If a person could change their nature to match the times, he says, their fortune would not change. In other words, much of what we call good or bad luck is really the meeting between our fixed way of acting and the changing times. A person who could adapt perfectly would always be fortunate. Nobody can do this perfectly. But each of us can learn to adapt a little more than we do.

The Advantage of Many Ways

In the Discourses, Machiavelli returns to this theme with an example from the history of ancient Rome. During a long war against a brilliant enemy general who had invaded Roman lands, one Roman commander became famous for his caution. He avoided pitched battles, wore the enemy down slowly and refused to be drawn into risky fights. This patient approach suited the times exactly, because the Roman armies were not yet strong enough to defeat the invader directly. His caution saved Rome (Discourses, Book 3, chapter 9).

But later in the war, when the time came to take the fight to the enemy, a different kind of leader was needed: one who was bold, quick and willing to take risks. Machiavelli observes that if the cautious commander had remained in charge, he would not have changed his ways, and Rome might have missed its chance. The republic succeeded because it could choose different leaders for different times (Discourses, Book 3, chapter 9).

From this, Machiavelli draws a conclusion about why republics, with many citizens of different temperaments, can adapt better than a single ruler. A single ruler has only one nature. A republic has many, and can choose the one that fits the moment (Discourses, Book 3, chapter 9). For ordinary working life, this suggests something important about teams. A team made up of people with different ways of working, cautious and bold, patient and quick, can adapt to changing times better than a team where everyone works the same way.

This also offers comfort to people like Hyun-woo. His caution is not a flaw. It is one of the ways a team needs. The question is not whether to abandon it, but how to use it well: in the situations that suit it, alongside colleagues whose different ways suit other situations. A team that values both careful people and quick people, and knows when to rely on each, is stronger than a team that values only one kind.

So Machiavelli's ideas suggest two kinds of adaptation. The first is personal: learning to stretch our natural way a little, so that we can respond better when the times change. The second is shared: recognizing that we do not have to be good at everything, and that working with people whose ways differ from ours can help a whole team match the times.

Hyun-woo Stretches His Way

Hyun-woo thought carefully about his situation. He did not want to become someone he was not. But he recognized that the times had changed, and that some of his habits no longer fitted. He decided to stretch his way of working, without abandoning it.

First, he looked at where his caution was truly needed and where it was simply habit. He realized that checking every routine figure twice, when the new software already checked them, was habit. Checking complex tax calculations and unusual transactions carefully was genuinely valuable. So he began to trust the software for routine work and to save his careful checking for the cases that needed it.

Second, he set himself a simple rule for client messages: acknowledge every message within a few hours, even if the full answer would take longer. "Thank you for your question. I am looking into it carefully and will reply by tomorrow afternoon." Clients appreciated the quick acknowledgment, and most were happy to wait for a careful answer once they knew it was coming.

Third, he talked with his manager about how his particular strengths could be used. They agreed that Hyun-woo would become the firm's specialist for complex problems and for reviewing work in difficult cases, like the tax mistake he had untangled. Younger colleagues, who worked quickly, would handle more of the routine work. In this way, the firm had both kinds of ability, each used where it fitted best.

The hardest part for Hyun-woo was emotional rather than practical. Trusting the software for routine checks felt, at first, like lowering his standards. He worried that a mistake would slip through and that he would be blamed. To ease this worry, he and his manager agreed on a simple compromise: for the first three months, he would check a small sample of the software's routine work each week. The sample showed that the software was reliable for the kinds of tasks it was designed for. Seeing this evidence with his own eyes allowed Hyun-woo to let go of the old habit with a clear conscience.

A year later, Hyun-woo feels much more settled. "I thought I had to choose between being myself and keeping up," he says. "Actually, I needed to do both. I learned to be a little quicker where quickness was fine, and I found a place where my carefulness is exactly what is needed." His manager says that the firm is stronger for having both Hyun-woo's caution and his younger colleagues' speed, just as Machiavelli's republic was stronger for having commanders of different natures.

Amadou and the Food Van

Amadou is forty and runs a small food van that sells grilled meals at markets, festivals and office areas at lunchtime. He started the business three years ago with great boldness. He left a stable job, borrowed money from his family, bought an old van and taught himself to cook in large quantities. He took risks, tried new locations and new recipes every week and worked long hours without rest. His boldness got the business started when a more cautious person would never have begun.

But now, three years in, the business is at a different stage. Amadou has regular customers, a good reputation and a modest income. He also has debts to repay to his family and a young daughter at home. His bold way of working, which suited the beginning, is causing problems. He keeps trying new, untested locations, which sometimes lose money. He changes the menu so often that regular customers cannot find their favourite dishes. He has no time for his daughter, and he is exhausted.

Amadou's sister, who works in a bank, pointed out the pattern to him. "You were the right person to start this," she said. "You were bold when boldness was needed. But now you need to be steady. You need to keep what works and stop risking it every week." Amadou was annoyed at first. Boldness was who he was. But he recognized the truth in what she said.

Amadou made a few changes. He kept his three best locations and stopped trying new ones every week, allowing himself one new experiment a month. He fixed a core menu of his five most popular dishes and added one new dish each month as a special. He set two evenings a week as time with his daughter, no matter what. He found that the business became more stable, his income more reliable and his exhaustion less. He did not lose his boldness. He saved it for the moments that called for it.

"The bold part of me built the business," Amadou says. "The steady part keeps it alive. I had to learn to let the steady part lead for a while." Amadou's story is the mirror of Hyun-woo's. One was naturally cautious and had to stretch toward speed. The other was naturally bold and had to stretch toward steadiness. Both found that the times had changed, and that their natural way, though valuable, needed to be adapted.

Margot and the Library That Changed

Margot is thirty-three and works in a public library. She chose the job because she loves books, quiet and order. For most of her eight years there, the library was a calm place, where her main tasks were helping people find books, organizing collections and running a monthly reading group. She is gentle, careful and patient, and she dislikes sudden change.

Over the past two years, the library has changed a great deal. Many people now borrow electronic books. The library has become a community centre as much as a place for books, with computer classes, children's activities, job-seeking help and events. The pace is faster and noisier. Margot has struggled. She misses the quiet, and she feels uncomfortable with the new technology and the constant activity.

For a while, Margot resisted the changes quietly. She kept to her old tasks and avoided the new ones. But she noticed that the library's managers were giving the more interesting new projects to colleagues who embraced the changes, and that her own role was shrinking. She realized that if she did not adapt at all, she might find herself left behind.

Margot decided to look for a part of the new library that suited her nature. She noticed that many older visitors were confused and anxious about the new computers and electronic books, much as she had been. Her patience and gentleness, which had seemed out of place in the busy new library, were exactly what these visitors needed. She offered to run a quiet weekly session for older people learning to use the library's technology. To teach it, she had to learn it properly herself, which helped her own confidence.

The sessions became very popular. Older visitors trusted Margot because she understood their nervousness and never rushed them. Her managers praised her work, and the role suited her. "I could not become a loud, fast person," she says. "But I found a way to use my quietness in the new library, instead of hiding from it." Margot's story shows that adapting to the times does not always mean changing our nature. Sometimes it means finding the place within a changed world where our nature is most useful.

Keziah and the Two Colleagues

Keziah is forty-five and leads a small team that plans events for a large public museum: exhibitions, lectures and family days. Two members of her team have very different ways of working. One, a man named Felipe, is bold and full of ideas. He loves to try new things and is impatient with details. The other, a woman named Hedda, is careful and practical. She notices every risk and likes to plan everything in advance.

For a long time, Felipe and Hedda frustrated each other. Felipe thought Hedda was too slow and negative. Hedda thought Felipe was careless and unrealistic. Keziah found herself constantly trying to make them agree, and she sometimes wished that both of them worked more like her.

After reading Machiavelli's passage about the cautious and bold Roman commanders, Keziah saw her team differently. Felipe and Hedda were not a problem to be solved. They were two different abilities, each suited to different moments. Felipe's boldness was exactly what was needed at the beginning of a project, when new ideas were wanted. Hedda's caution was exactly what was needed later, when plans had to be made safe and practical.

Keziah began to organize the team's work around this insight. At the start of each project, she asked Felipe to lead the creative phase, generating ideas freely. Then she asked Hedda to lead the planning phase, examining the ideas for risks and turning the best ones into workable plans. She explained to both of them why their different ways were valuable, and she encouraged each to respect the other's phase. Felipe learned to listen to Hedda's concerns. Hedda learned to welcome Felipe's ideas before judging them.

The team's events improved noticeably. They were more creative than before, and also safer and better organized. Keziah says that the biggest change was in her own thinking. "I used to want everyone to work the same way, preferably my way," she says. "Now I see that a team with different ways is like Machiavelli's republic. It can choose the right way for the right time." This is the shared adaptation that Machiavelli described: not every person changing their nature, but a group using different natures wisely.

Practical Steps: Matching the Times

The first step is to know your natural way. Are you naturally cautious or bold, patient or quick, careful or creative, steady or adventurous? Most people lean in one direction. Knowing your natural way helps you see when it suits the times and when it does not.

The second step is to read the times. Ask yourself what your work currently requires. Is this a time for caution or for boldness? For steady maintenance or for new ideas? For speed or for thoroughness? The times can change within a single year, a single project or even a single week.

The third step is to notice when your past success is holding you back. Machiavelli warned that success on one road makes it hard to leave it. If you find yourself saying, "This has always worked for me," pause and ask whether the times have changed. Your past success is real, but it may belong to past times.

The fourth step is to stretch, not abandon, your way. You do not need to become a different person. Like Hyun-woo and Amadou, you can stretch a little toward the way the times require, while keeping your natural strengths for the situations that need them.

The fifth step is to find the place where your nature fits. Like Margot, look for the part of your changed workplace where your particular way is most useful. Every workplace needs different kinds of people, and there is often a place where your nature is exactly what is needed.

The sixth step is to value people whose ways differ from yours. Like Keziah, see colleagues with different natures not as obstacles but as resources. When the times call for a way that does not come naturally to you, there may be someone beside you for whom it does.

Adapting Is Not Abandoning Yourself

There is a risk of misunderstanding this chapter as advice to change yourself completely whenever the world changes. That is not what Machiavelli meant, and it is not wise. Machiavelli himself acknowledged that people cannot easily change their nature, and he did not suggest that they should try to become someone else entirely.

More importantly, some things should not change with the times. Our ways of working, our pace and our style can and sometimes should adapt. But our values, such as honesty, fairness, care for others and the quality of our work, should not. A person who becomes careless because the times favour speed, or dishonest because the times seem to reward it, has not adapted. They have lost something important. Hyun-woo became quicker, but he did not stop being accurate. Amadou became steadier, but he did not stop being creative.

It is also worth recognizing that adapting to change can be genuinely hard, especially later in a working life or when the change is large and sudden. If you find that changes at work are causing you serious stress or worry that affects your health, please talk with someone you trust, and consider speaking with a doctor or another qualified professional. If the changes affect your rights or your position, it is wise to find out where you stand from a trusted official source or qualified adviser.

A Short Exercise: Your Way and the Times

This exercise helps you see how well your natural way matches the times you are working in now. It takes about fifteen minutes.

Take a page and draw a line across the middle. Above the line, write "My natural way". List three to five words that describe how you naturally work: for example, "careful, patient, thorough" or "quick, bold, creative". Below the line, write "What the times need now". List three to five words that describe what your work currently requires.

Compare the two lists. Where do they match? These are the areas where your nature is a strength right now. Where do they differ? These are the areas where you may need to stretch, or where you may need help from someone whose way differs from yours.

For one area of difference, write a small way you could stretch your natural way, without abandoning your values. For example, "Acknowledge messages quickly, even if the full answer takes longer." Then write the name of a colleague whose natural way fits that area, and one way you could work with them or learn from them.

Finally, write one sentence about the place in your work where your natural way is most valuable, and how you could spend more time there. Hyun-woo did this exercise. His natural way was "careful, patient, thorough". What the times needed was "quick, responsive, comfortable with new tools". His stretch was "acknowledge every message within three hours". His colleague was a younger accountant named Sunniva, who helped him learn the new software. His most valuable place was "complex problems and difficult cases". Within a year, that was where he spent most of his time.

Chapter Summary

In chapter 25 of The Prince, Machiavelli observed that people pursue their goals in different ways, cautious or bold, and that success depends on whether their way matches the times. People find it hard to change, because their nature inclines them one way and because past success persuades them that their way is simply right. In the Discourses, he described a cautious Roman commander whose patience suited one stage of a war and argued that a republic, with citizens of many temperaments, can adapt better than a single ruler (Book 3, chapter 9).

Hyun-woo the careful accountant, Amadou with his bold food van, Margot in her changing library and Keziah with her two different colleagues all found ways to match the times: stretching their natural way a little, finding the place where their nature fits and valuing people whose ways differ from their own. Adapting our methods is not abandoning our values, which should stay steady whatever the times.

In the next chapter, we will look at Machiavelli's warning about generosity that cannot be sustained, and what it means for people who give too much at work.