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Book Summary: Necessary Endings The Employees, Businesses, and Relationships That All of Us Have to Give Up in Order to Move Forward By Dr. Henry Cloud

Endings bring about new beginnings.

Clinical psychologist Henry Cloud shares his strategies for negotiating endings in business and in life. He shows how to handle endings with skill, clarity and proper intent. Using examples from his leadership consulting experience, Cloud illuminates how businesses falter and relationships fester due to an inability to accept that a time has come when things aren’t working.

The author’s advice isn’t only for business leaders. You can learn how to navigate endings in everyday life, from breaking up with a partner to confronting a loved one who suffers from addiction.

Cloud’s lively summation of three kinds of people – The Wise, The Foolish and The Evil – is an added bonus. He explains how to recognize and deal with each one of the three. Cloud’s engaging and thoughtful advice will benefit you when you face your own inevitable endings.

Summary of Necessary Endings The Employees, Businesses, and Relationships That All of Us Have to Give Up in Order to Move Forward By Dr. Henry Cloud


Clinical psychologist Henry Cloud shares his strategies for negotiating endings, in business and in life. No one likes endings, even for positive change. Ending something that isn’t working is a wise, courageous decision. Cloud shows how to handle endings with skill, clarity and proper intent. He illuminates how businesses can falter and relationships fester due to an inability to accept that a time has come when things aren’t working. The author also covers navigating endings in everyday life. Cloud’s engaging and thoughtful advice will benefit you when you face your own inevitable endings.


  • Endings don’t have to be bad if they are done well.
  • Stop bad behaviors in order to start good ones.
  • Once you understand how pruning helps business, incorporate it into your workplace culture.
  • Change the “internal maps” that keep you stuck in bad situations.
  • Leaders must determine when to have hope and when to accept a situation as hopeless.
  • You can end a business relationship with respect and consideration.
  • When you see the need for an ending, you must overcome internal and external resistance.
  • Let go of one wish in order to pursue another.
  • You only have so much time and so many resources. Don’t deplete either.
  • Accept that grief is part of the process, and incorporate the lessons you learned from past mistakes.


Stop the Bad to Start the Good
In business and in life, people must decide whether to keep fixing something that isn’t working or to let it go. Growth demands change, and change means endings. To make room for the next good thing, often you must rid yourself of the last bad thing. Endings are difficult. People make excuses to stay with something familiar because they fear the unknown. Most people don’t know how to manage the endings that life forces on them, and that results in unnecessary pain. Failing to end things correctly dooms people to repeating their mistakes. But when good endings are done well, they bring hope.

Gardeners prune rosebushes for three reasons: to foster the best buds because the plant can only sustain a certain number of blooms; to eliminate sick branches that won’t recover, and to clear out dead branches to make space for new growth. Pruning optimizes and sustains the viability of the plant. Failing to prune means accepting mediocrity or even failure. Still, people resist cutting things out of their lives or firms because facing reality is a struggle, and cutting hurts. To be competitive, you must “choose between good and best.”

“In your business and perhaps your life, the tomorrow that you desire and envision may never come to pass if you do not end some things you are doing today.”

Know what you’re pruning and why. Prune “toward” a vision of how you want a situation to be. Define the standard and align your actions accordingly. GE CEO Jack Welch’s command to “fix, close or sell” any part of the company that isn’t running optimally is an example of how to prune with intent, even if it hurts. Pruning must be strategic, and have purpose and structure. It must be measurable.

The Natural Cycle
Endings are part of the natural cycle of life. Try to stop seeing endings as a problem and, instead, to learn to accept them. Sometimes, you will run out of solutions, and the results you want will never materialize. Accepting that endings are normal and necessary gives you the incentive to make hard decisions. To learn how to normalize endings, witness the natural world. Every season has its activities. Spring is the time to plant. Summer is a time to tend. Fall brings the harvest, and winter is a time for resting to prepare for the cycle to begin again. Businesses must spend the appropriate time “sowing” and “tending.” Leaders who mistakenly think the harvest never ends will run short of resources in lean times.

Two Kinds of Pain
If you ever suffered having a tooth pulled, you understand that sometimes pain is necessary to relieve the anguish. Beware of another, more insidious pain: the lingering misery of being stuck with no relief in sight. This kind of pain, if nurtured, becomes normal, and that’s dangerous. With help, you can make a change and be free. You can overcome “learned helplessness”: that state you fall into when your brain gets hardwired to see your situation as hopeless and unchangeable. During the financial crisis of 2008, many employees felt defeated. For some, however, the crisis provided new challenges and opportunities to help their companies or their clients. They focused on what they could control.

Internal Maps
If your brain sees something as “wrong,” it will resist or flee. When it sees something as “right,” it will mobilize to ensure its success. When you see endings as normal, your brain executes “conflict-free aggression”: an energy that engages with reality and solves problems. Internal maps that inhibit this energy include having a high threshold for pain; taking too much responsibility for others; thinking that ending equals failure; prioritizing relationships over personal growth, and practicing co-dependence – taking on others’ pain instead of letting them take responsibility for their mistakes. Having experienced a bad ending can keep you stuck and feeling helpless when you need to create a purposeful end. Leaders boldly end the misery. They don’t accept or live with unpleasantness.

When to Have Hope – and When Not To
To exercise “fearless will,” you must accept reality. Being aware of hopelessness brings you to a “pruning moment” when you realize things have to change and an ending must occur. This means letting go of delusions. Hope can get people through almost anything. They lionize hope as a heroic quality. Hope buys time but also spends it. False hope – hope that doesn’t acknowledge reality – spends even more time and can keep you from pursuing another path, one that could lead to success. Sometimes people must embrace hopelessness to motivate them to take action.

“Wise people know when to quit.”

How do you know when to hope? Unless you have a good reason to expect a significant change in outcomes, “the best predictor of the future is the past.” When it comes to people and hope, a character is essential. Too often, people look at the results they want, not at the people who must achieve those outcomes. If a loved one or an employee performs poorly and is sorry, or promises to do better “this time” but has no strategy for improvement, don’t wish for that person to suddenly excel. Character and past performance matter most. You need reasons to believe in people.

“When truth presents itself, the wise person sees the light, takes it in, and makes adjustments.”

If people are willing to structure a proven and measurable change process – such as coaching – into their routines, that can give you an indication of their commitment to change. People must acknowledge that they need skilled help and support. Change takes time, so assess each person’s progress before giving up. Remember: Hope is not a strategy.

“The Wise, The Foolish and The Evil”
Knowing how to deal with different kinds of people also can help you assess someone’s openness to change. Some people can’t change. Some people don’t want to. And some people will stand in your way just to bring you down. You might have everyone’s best interests in mind and, therefore, expect others to share your view. But some may not.

“Hopelessness can bring us closer to fearlessness, as it does not take courage to stop doing what you know is not going to work.”

Wise people listen to feedback and ask for help when they need it. They learn and grow from the experience. They don’t become defensive when others criticize them. When they make mistakes, they show remorse, make sincere pledges to improve and follow through. With a wise person, you can hope for change, but that won’t always make the wise person the best fit. He or she can try and still fail, and you can both walk away knowing you did your best. People tend to do well at what they are good at. Play to the strengths of your team members, and remove obstacles that may threaten their potential.

“Just as hope can conquer all, false hope can ruin everything.”

Foolish people are the opposite of wise people. They don’t listen to feedback and talking things through with them doesn’t help. In fact, talking creates conflict. They blame others or resort to anger or self-pity so they can look like victims and absolve themselves of responsibility. The only way to change their behavior is to allow them to suffer the consequences personally.

“Part of maturity is getting to the place where we can let go of one wish in order to have another.”

Evil people are just evil. Avoid them at all costs. If you must engage with them in your business, protect yourself. “Lawyers, guns and money” are always a good investment.

“You are not designed to cope, but to thrive.” The human brain needs two things to spur it into action: fear of a bad consequence as a result of doing nothing and the lure of a good outcome. You need to see the world as it truly is, with all its danger and opportunity, and then “play the movie” – project yourself into your desired future. Compare it to an alternative future in which you do nothing and things get progressively worse. Which do you prefer? Paint a picture of how things could be, and get support from your allies to bring it to life. You need the vision to turn your – or your organization’s – aspirations into reality. Set deadlines for endings. Establish a structure to keep the urgency alive, such as regular meetings or accountability sessions. Don’t isolate yourself from problems, a common CEO mistake. You need to feel the pain to make the change. When you face resistance, remember that sometimes leaders must make tough decisions.

Resistance: Internal
Incompatible wishes are a major obstacle to change. You might want your team to have more meetings, but you also want to work from home more often, and you can’t have both. A mature person knows when to let go of one wish to fulfill the other. To bring about the right ending, you need to know what you want. You will enjoy greater flexibility if you don’t get attached to a particular outcome. Endings always involve loss. You might even lose everything, but if the alternative is continued stagnation, making a change could still be the best course.

“The clearer and kinder you are in your communication of endings and bad news to people, the better the people you will find yourself surrounded by in life and work.”

“Medicating thoughts,” the way people lie to themselves to avoid pain, are another form of internal resistance. For instance, hoarders keep things because they “might” need them someday. Procrastinators never have to follow through on their promises. Idealists see only what they want to see. To be realistic, people need to challenge these thoughts and see the whole picture, positive and negative, so they understand their world realistically.

Resistance: External
Some people will resist your decisions because they truly believe you are in error, or they have a better solution. Those people have value, even if they are wrong. But other people will resist your decisions because they have ulterior motives or seek to protect themselves and their interests. These people will try to control you. Self-absorbed resisters can’t see the big picture or put aside their often-petty interests to serve the greater good. The threatened resister sees change as jeopardizing his or her status quo. The “NoNos” create anxiety around change because they are inflexible and incapable of processing new information. If you encounter resistance when trying to make a change, that’s usually a sign that you’re on the right track. Doing things differently is hard. Accepting the status quo is easy.

Instead of always making tough decisions, let people decide for themselves. Set a standard for the results you want and allow people to choose whether they want to meet that standard. People who are ill-suited to a goal take themselves out of the picture. Those who embrace the challenge know what to expect. Use self-selection on yourself. Set the standard for what you want to bring about, and include a deadline. Be judicious, but objective. This demonstrates your commitment to make changes and to accept endings.

The “Good” Ending
The biggest obstacle to letting someone go is having the terminating conversation. Most people tend to imagine the worst outcomes. If you prepare well, you can avoid hurting the other person. Keep the end in mind and have specific goals. As much as you care about a person, accept the truth of the situation. Remember that if you’re facing a bad situation, the other person is also. Don’t rob people of the opportunity to get better. If you take the right tone and show that you care, the person will know you empathize. Don’t make it personal. Focus on the issues. Sometimes, people react badly, regardless of their attempts to mitigate the pain. The only person you can control in this situation is yourself. Be calm but firm. You may need outside assistance. More often than not, these endings benefit everyone. You don’t have to burn bridges. Maintain friendly contact. You never know if you might need that person someday, but, generally, once a door closes, it should stay closed.

Grieving the Ending
For you to muster the energy to embrace the next new thing, you must disinvest from old ways and that requires a proper goodbye. If you don’t look forward, you may maintain false hopes or, as people often do, act irrationally “on the rebound.” Another way to grieve healthfully is to perform an “autopsy”: Examine what went wrong so you can avoid future mistakes. Share the lessons you derive from your team. You are the living result of all your past decisions, good and bad.

To be personally sustainable or to build a sustainable company, you must protect your resources from depletion. You can stay in a bad situation only so long before you do damage to yourself and others. Without resources, you have no options, and without options, you have no hope. Forcing an ending to an unsustainable situation may be difficult, but it may be necessary and vital to your well-being.

About the Author

Dr. Henry Cloud is a clinical psychologist and leadership expert. His books on business leadership include Boundaries, Integrity and The Power of the Other.

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