Chapter 11: Generosity You Can Keep Up

The Person Who Always Says Yes to a Shift

Marisa is thirty-six and works as a care assistant in a home for elderly people. She is kind, reliable and much loved by the residents. She is also the person the managers call first whenever someone is ill or a shift needs covering. Marisa almost always says yes. She knows how hard it is for the residents when the home is short-staffed, and she does not want to let her colleagues down.

Over the past year, Marisa has worked many extra shifts. Her colleagues have come to rely on her. When someone wants to swap a shift or take a day off at short notice, they ask Marisa, because she never refuses. The managers have come to expect it too. When she once said she could not cover a weekend because of her daughter's birthday, the manager sounded surprised and a little disappointed, as if Marisa had broken a promise.

Marisa is now exhausted. She has had a cold that will not go away. She snaps at her daughter in the evenings. She has started to feel resentful toward her colleagues, who seem to take her generosity for granted. And she has noticed something that worries her: at work, she is less patient with the residents than she used to be. Her generosity with her time is beginning to cost the very people she wanted to help.

Last month, Marisa reached a breaking point. After three extra shifts in one week, she called in sick for two days, simply because she could not face going in. She felt guilty and ashamed. The managers were frustrated, because they had come to depend on her. Some colleagues muttered that she had let them down. Marisa felt that she had given everything, and that the moment she stopped, people resented her for it.

Machiavelli wrote about this pattern in a chapter about generosity. He was writing about rulers who spent money lavishly to gain a reputation for generosity, but his observations apply just as well to anyone who gives their time, energy or resources at work in a way they cannot sustain.

Generosity That Consumes Itself

In chapter 16 of The Prince, Machiavelli considers whether a ruler should be generous. It would be good, he says, to be thought generous. But generosity practised in a way that is designed to win a reputation for it can harm the person who practises it. To keep a reputation for generosity among people, he explains, a ruler must keep spending lavishly, and so he soon uses up all his resources. Then, to continue, he must burden his people with heavy taxes, which makes him hated. And when he finally tries to stop, he is immediately called mean (The Prince, chapter 16).

Machiavelli puts this in a memorable way. Nothing, he says, uses itself up as quickly as generosity: while you practise it, you lose the means of practising it (The Prince, chapter 16). Generosity that is not sustainable eventually destroys itself, and often leaves resentment behind.

His advice to rulers is surprising. A wise ruler, he says, should not worry about being called careful with money. In time, he will be considered more generous than the lavish ruler, because his resources will be enough to defend himself and to undertake useful projects without burdening his people. He will be generous, Machiavelli says, to all the many people from whom he takes nothing, and careful only with the few to whom he does not give (The Prince, chapter 16).

Machiavelli's main concern was money and taxes, and his tone, as usual, is calculating. But the pattern he describes is very human, and it appears in working life all the time. A person gives generously, perhaps to be liked, perhaps out of genuine kindness, perhaps because they find it hard to refuse. Others come to expect it. The giver's resources, whether time, energy or money, run down. Eventually, the giver cannot continue. And when they stop, they are resented rather than thanked, because the generosity had become an expectation.

This is exactly what happened to Marisa. Her extra shifts were genuine generosity, born of real care. But they were not sustainable. She used up her energy, as Machiavelli's ruler used up his treasury. And when she finally had to stop, the people who had come to rely on her felt let down. Her generosity had consumed itself.

Steady Generosity

Machiavelli's analysis suggests a different kind of generosity: one that is steady and sustainable rather than lavish and exhausting. The steady giver gives what they can keep giving, over a long time, without running down their own resources. They may give less in any single moment than the lavish giver. But over months and years, they give more, and they do not leave resentment behind when they reach their limits, because they have never pretended that their limits did not exist.

In working life, steady generosity might mean helping colleagues regularly but within limits, covering a shift sometimes but not always, answering messages promptly during working hours but not at midnight, or offering a reasonable amount of extra effort rather than unlimited amounts. It means making sure that what we give today does not prevent us from giving tomorrow.

A simple image may help. Think of a well in a village. If everyone draws as much water as they want, as fast as they want, the well runs dry in the hot season, and then nobody has water. If people draw steadily, within what the well can refill, it serves the village all year round. Our energy and time at work are like that well. Drawing on them steadily keeps them available for the long run. Drawing on them without limit leaves us, and the people who depend on us, with nothing when it matters most.

Steady generosity also protects the people who receive it. When a colleague relies on someone who always says yes, they may never develop other solutions. When that person finally collapses, the colleague is left without help and without alternatives. When generosity is steady and limited, others learn to share the load and to find other sources of support, which makes the whole team more resilient.

There is also a question of expectations. Machiavelli noted that a ruler who has been lavish is called mean the moment he becomes careful. In the same way, a worker who has always said yes is resented the moment they say no, because the yes had become expected. A worker who has been steady from the beginning does not create this expectation. Their occasional extra help is received as a gift, not as a duty.

Finally, steady generosity is often more truly generous than lavish generosity. Lavish generosity is sometimes, though not always, driven by a wish to be seen as generous, or by difficulty in saying no. Steady generosity is more likely to be driven by genuine care, because it takes into account the long-term well-being of both the giver and the receiver. In this sense, Machiavelli's cold-sounding advice points toward a warmer and wiser kind of kindness.

Marisa Finds a Sustainable Pace

After her two days off sick, Marisa sat down with her manager. She was nervous, but she explained honestly that she had been working too many extra shifts, that she was exhausted and that she could not continue at that pace. She said that she still cared deeply about the residents and her colleagues, and that she wanted to keep helping when she could. But she needed a limit.

Her manager, to Marisa's relief, was understanding. She admitted that the home had come to rely too heavily on Marisa, and that this was not fair. Together, they agreed that Marisa would cover a maximum of two extra shifts a month, and only when she offered, not when she was pressed. The manager also agreed to build a list of other staff willing to cover shifts, so that the burden was shared.

At first, some of Marisa's colleagues were unhappy. They were used to asking her for swaps at short notice, and now she sometimes said no. But over a few months, they adjusted. They began to plan further ahead and to ask different colleagues. The shared list of cover staff grew. The home became less dependent on any single person.

Marisa's energy slowly returned. Her cold finally cleared. She was more patient with the residents and with her daughter. When she did offer to cover a shift, her colleagues thanked her warmly, because it was now a gift rather than an expectation. "I thought I was being generous by always saying yes," Marisa says. "But I was really using myself up, and in the end I helped nobody. Now I give less at once, and more over the whole year."

Marisa's situation was also partly caused by a staffing problem that was not hers to solve. When a workplace relies on one person's unlimited goodwill to fill gaps, the problem lies with the organization, not only with that person. Marisa's conversation with her manager helped to make this visible, and the shared cover list was a step toward fixing it. If you find yourself in a similar position, it may help to raise the underlying problem as well as your own limits.

Obi and the Credit at the Shop

Obi is thirty-nine and runs a small grocery shop in a busy neighbourhood. He is popular because he is generous. He gives discounts to regular customers, lets elderly neighbours pay at the end of the month and often adds a free piece of fruit for children. Over the years, more and more customers have come to expect these kindnesses. Some now ask for credit as a matter of course, and a few take weeks or months to pay.

Last year, Obi realized that his shop was in trouble. His costs had risen, but he had not raised his prices, because he did not want to seem greedy. The money owed to him by customers had grown large. He was struggling to pay his suppliers. He was working longer hours to make up the difference, and he was exhausted and worried.

Obi's situation was a clear example of Machiavelli's generosity that consumes itself. His kindness had been genuine, and it had made him well loved. But it had not been sustainable. If he continued, he would lose the shop altogether, and then he could not be generous to anyone. Yet if he stopped suddenly, he feared, his customers would see him as mean, as Machiavelli predicted.

Obi decided to make changes gradually and openly. He put a small, friendly sign by the till explaining that, because of rising costs, he would need to raise some prices a little and limit credit to one week, except for a few elderly customers he knew well. He spoke personally to the customers who owed him the most, kindly explaining that he needed them to pay what they owed over the next two months. He kept the free fruit for children, because it cost little and meant a lot.

Most customers understood. A few grumbled, and one or two stopped coming. But the shop survived, and Obi's finances slowly recovered. He found that he could still be generous in small, sustainable ways, and that his customers valued these more because they were not taken for granted. "I thought being kind meant giving everything," Obi says. "But if the shop closes, my kindness closes with it. Now I try to be kind in ways that will still be possible next year." His story shows a principle: generosity that destroys its own source cannot last.

Liv and the Midnight Messages

Liv is twenty-eight and works as a junior designer in a small company that makes websites for local businesses. She is enthusiastic and eager to please. From her first week, she answered messages from clients and colleagues at any hour, often within minutes, even late at night and at weekends. Clients loved her responsiveness, and her manager praised her dedication.

After a year, Liv was finding it very hard to rest. Clients had come to expect instant answers from her at any hour. If she took a few hours to reply on a Sunday, they sent follow-up messages asking whether something was wrong. Her colleagues had started sending her non-urgent questions late at night, because they knew she would reply. Liv felt that she could never switch off, and her sleep had become poor.

Liv realized that she had set an expectation she could not sustain. Her responsiveness had been generous, but it had trained everyone around her to expect something no person could keep giving forever. Like Machiavelli's lavish ruler, she now faced a choice: continue until she collapsed, or pull back and risk being seen as less dedicated.

Liv chose to pull back, but carefully and openly. She talked with her manager, who agreed that the company should not expect staff to answer messages outside working hours, except in real emergencies. Liv then sent a short, friendly note to her regular clients, explaining her working hours and when they could expect replies. She set her phone to silence work messages in the evenings and at weekends. For genuine emergencies, she and her manager agreed on a simple system: clients could call the company's out-of-hours phone line, which the team answered in turns.

Some clients were briefly surprised, but none left. Most said they understood completely. Liv's sleep improved, and she found that she did better work during her working hours because she was rested. "I was so proud of being always available," she says. "But always available is not a promise anyone can keep. Now I am reliably available, which is better for everyone, including me."

Augusto and the Promises He Could Not Keep

Augusto is fifty and manages a team of fifteen in a company that maintains lifts in office buildings. He is a warm and generous manager who wants his team to be happy. When team members asked for things, he tended to promise them: a raise at the next review, extra days off at the busy time of year, a place on a training course, a new van. He meant every promise sincerely. But many of them depended on decisions made by his own managers, which he could not control.

Over time, many of Augusto's promises were not kept. The raises were smaller than he had suggested. The extra days off were cancelled because of a large contract. The training places went to another team. Augusto felt terrible each time, and he apologized sincerely. But his team began to lose trust in him. They liked him personally, but they stopped believing what he said. Some began to feel that he was not being honest with them.

Augusto's situation shows a different side of Machiavelli's warning. His generosity was in promises rather than money or time. But the pattern was the same. By promising lavishly, he created expectations that he could not meet. When the promises failed, the disappointment was greater than if he had promised nothing, and he gained a reputation not for generosity but for unreliability.

Augusto decided to change his approach. He began to promise only what was within his own power to deliver. When team members asked for things that depended on others, he said honestly, "I will ask for this, and I will tell you what they say. I cannot promise the answer." He kept careful notes of what he had said he would do, and made sure he did it. When he could deliver more than he had promised, he did, which delighted his team.

Within a year, trust in Augusto had recovered. His team knew that when he said he would do something, he would do it. "I used to promise everything because I wanted them to be happy," Augusto says. "But broken promises made them unhappier than no promises. Now I promise less and keep everything, and they are much happier." This is a modern version of Machiavelli's advice: a ruler who is careful with what he gives will, in time, be considered more generous than one who gives lavishly and then cannot continue.

Practical Steps: Sustainable Generosity

The first step is to look at what you give at work. Your time, your energy, your extra effort, your availability, your promises, your help to colleagues. Write down where you give the most. For each, ask: can I keep giving this at this level for the next year? If the honest answer is no, you may be practising generosity that will consume itself.

The second step is to notice the expectations you have created. Have people come to expect your generosity as a matter of course? Would they be surprised or upset if you stopped? If so, your generosity may have become an expectation, which makes it harder to sustain and harder to adjust.

The third step is to set a sustainable level and communicate it. Decide what you can give steadily, without running down your resources. Then, like Marisa, Liv and Augusto, explain your limits openly and kindly to the people affected. A clear limit, explained in advance, is much easier for others to accept than a sudden collapse.

The fourth step is to promise only what is yours to deliver. When you make promises at work, make sure they depend on your own actions. When something depends on others, say so honestly. Then keep every promise you make. Reliability is a more valuable form of generosity than lavish promises.

The fifth step is to protect your resources. Your energy, your health and your rest are the sources of your generosity. Like Machiavelli's careful ruler, who kept enough resources to defend himself and undertake useful projects, protect the things that make it possible for you to give.

The sixth step is to raise systemic problems. If your generosity has been filling a gap that your workplace should fill, such as staffing shortages, unrealistic workloads or unclear responsibilities, raise the underlying problem with the people who can solve it. Personal limits are important, but they work best when the system is also fair.

Careful Is Not Mean, and Your Limits Are Not a Failure

It is important not to misread this chapter as advice to stop helping people. Machiavelli's careful ruler was not mean. He was, in the long run, more generous than the lavish one, because his generosity lasted. The aim is not to give less in general, but to give in a way that can continue. Marisa still covers shifts. Obi still gives fruit to children. Liv still answers clients promptly. Augusto still fights for his team. They simply do so in a way they can sustain.

It is also important to say that having limits is not a personal failure. Everyone has limits of time, energy and resources. Marisa felt ashamed when she reached hers, as if her exhaustion were a weakness. But it was simply the natural result of giving more than any person can give for long. Recognizing our limits early, before we collapse, is a sign of wisdom, not of weakness.

Finally, if you have been giving beyond your limits for a long time and feel exhausted, unwell or unable to cope, please take this seriously. Talk to someone you trust, and consider speaking with a doctor or another qualified professional. If your workload or working hours seem unfair, or if you are unsure about your rights, it is wise to find out where you stand from a trusted official source or qualified adviser.

A Short Exercise: A Generosity Budget

This exercise helps you plan a level of generosity at work that you can sustain. It takes about twenty minutes.

Take a page and write three headings: "What I give now", "What I can keep giving" and "What I will say". Under the first heading, list the main ways you give beyond your basic job: extra hours, covering for colleagues, availability outside working hours, promises, favours, emotional support. Be honest and specific. "About eight extra hours a week." "Answering messages until eleven at night." "Covering every shift swap I am asked for."

Under the second heading, for each item, write the level you could sustain for a whole year without harming your health, your family life or your work. "Two extra shifts a month." "Messages answered during working hours, emergencies by phone." "Swaps when I offer, not when I am pressed."

Under the third heading, write a short, kind sentence you could use to explain the new level to the people affected. "I want to keep helping, so I am limiting extra shifts to two a month, so that I do not burn out." "I will reply to messages during working hours. For emergencies, please call our out-of-hours line." Keep the sentences warm and clear.

Finally, choose one item to change in the coming month, and decide when and to whom you will say your sentence. After a month, write a few lines about how it went and how you feel. Marisa did this exercise before her conversation with her manager. Her sentence was: "I care about the residents and the team, and I want to keep helping for years, not burn out in months. So I will cover up to two extra shifts a month, when I can." She said it almost word for word, and it worked.

Chapter Summary

In chapter 16 of The Prince, Machiavelli warned that generosity practised lavishly uses up its own means: while you practise it, you lose the ability to practise it. A ruler who spends lavishly to be thought generous soon exhausts his resources, burdens his people and is called mean the moment he stops. A careful ruler, Machiavelli said, will in time be considered more generous, because his resources last. In working life, the same pattern applies to time, energy, availability and promises.

Marisa and her extra shifts, Obi and the credit at his shop, Liv and her midnight messages and Augusto and his broken promises all found that generosity which cannot be sustained ends in exhaustion and resentment, while steady, honest generosity lasts and is valued more. Being careful is not being mean, having limits is not a failure and when one person's goodwill fills a gap that the workplace should fill, the underlying problem deserves to be raised.

In the next chapter, we will look at another surprising idea from Machiavelli: that disagreement and conflict, handled well, can make a group stronger rather than weaker.