Necessary Endings

Physical Copy:


By: Dr. Henry Cloud

Rating: A

I was given this book by a friend a couple of years ago. I listened to it on audiobook several years ago and have always thought very highly of Henry Cloud. His book Boundaries is excellent! Necessary Endings is one of those books you need to read and reread in different seasons of life to examine yourself. What am I holding onto that I need to let go of? That is one of the hardest questions you can ask yourself. That is hard self-work but is, as the title implies, necessary. 

Endings: The Good Cannot Begin Until the Bad Ends

In both normal life and life gone wrong, endings are a necessity.

When we fail to end things well, we are destined to repeat the mistakes that keep us from moving on.

Learning how to do an ending well and how to metabolize the experience allows us to move beyond patterns of behavior that may have tripped us up in the past.

Endings are a part of every aspect of life. When done well, the seasons of life are negotiated, and the proper endings lead to the end of pain, greater growth, personal and business goals reached, and better lives. Endings bring hope.

When done poorly, bad outcomes happen, good opportunities are lost, and misery either remains or is repeated.

Pruning: Growth Depends on Getting Rid of the Unwanted or the Superfluous

In business and life, executing the three types of necessary endings described below is what characterizes people who get results.

  1. An initiative siphoning off resources that could go to something with more promise is pruned.
  2. An endeavor that is sick and is not going to get well is pruned.
  3. If something is already dead, it is pruned. 

Are you avoiding an ending? Gut Check. Ask these questions to yourself and your team:

  • What is your intellectual response to the idea of pruning?
  • What is your emotional response to the idea of pruning?

Pruning is not about cutting costs or reducing the head count. The kind of pruning the author describes has to do with focus, mission, purpose, structure, and strategic execution. We are talking about defining what the bush is going to look like and pruning everything that is keeping it from realizing that vision – be it good, bad, or dead.

Normalizing Necessary Endings: Welcome the Seasons of Life into Your Worldview

Three Principles to Help Make Peace With Endings

  1. Accept Life Cycles and Seasons. Nothing lasts forever.
  2. Accept The Life Produces Too Much Life. One reason pruning is needed is the fact that the bush produces more buds than it can bring to full maturity. One of the most important types of decision making is deciding what you are not going to do, what you need to eliminate in order to make room for strategic investments.
  3. Accept That Incurable Sickness and Evil Exist. Your business and your life will change when you really, really get it that some people are not going to change.

When Stuck Is the New Normal: The Difference Between Pain with a Purpose and Pain for No Good Reason

How to know the difference? Focus on what you can control. Don’t spend time and energy focusing on all of the things that are falling apart that you can do nothing about. Instead, think hard and fast about what you can do something about.

What keeps people from necessary endings? Five Internal Maps That Keep Necessary Endings from Happening:

  1. Having an abnormally high pain threshold
  2. Covering for others
  3. Believing that ending it means I failed
  4. Misunderstood Loyalty
  5. Codependent Mapping

“There is a difference between helping someone who is disabled, incapable, or otherwise infirm versus helping someone who is resisting growing up and taking care of what every adult (or child, for that matter) has to be responsible for: herself or himself. When you find yourself in any way paying for someone else’s responsibilities, not only are you stuck with a delayed ending, but you are probably harming that person.”

Getting to the Pruning Moment: Realistic, Hopeless, and Motivated

You have to get hopeless about what is not going to work.

If hope is good but false hope is not, how do we know the difference between the two? We need a good diagnostic. Let’s define “Hope”. 

Hope contains two elements. The first is “desire or expectation” for something in the future to occur. The second is usually “grounds for believing” that something in the future will occur.

The real problem is when you have a desire without any grounds.

In the absence of real, objective reasons to think that more time is going to help, it is probably time for some type of necessary ending.

The Wise, the Foolish, and the Evil: Identifying Which Kinds of People Deserve Your Trust

Not everyone on planet Earth is like you. Not all take responsibility for themselves or care about how their actions are affecting other people or the mission. Moreover, some are even worse than that. Some people are actually out to do you harm.

The Three Kinds of People:

  1. Wise People: The person who ultimately does well is the one who can learn from his own experience or the experience of others, make that learning a part of himself, and then deliver results from that experience base. When truth presents itself, the wise person sees the light, takes it in, and makes adjustments.
  2. Foolish People: Do not believe they can be the problem. They reject feedback, resist it, explain it away, and do nothing to adjust to meet the requirements. The fool adjusts the truth so he does not have to adjust to it. When you know you are dealing with a fool, quit talking with them and talk to them, place limits and consequences that will occur if they cannot change. Then keep your word.
  3. Evil People: You must go into protection mode, not helping mode, when dealing with evil people. Do not hope for the evil persons to change. It could happen, and it does, but it does not happen by giving in to them, reasoning with them, or giving them another chance to hurt you.

Creating Urgency: Stay Motivated and Energized for Change

Endings, no matter how needed, are hard. They involve change, and for many reasons that we have seen, we resist the changes that we need to make, even when they would be good for us personally or for our business.

Create Urgency: To create an ending, and getting the people around you to do the same, is going to take both: the fear of the negative and the draw of the positive.

You must create urgency.

Strategies for Creating Urgency: Make the threat to our future as real in our minds as it is in reality.

  1. Create “Ending Alliances”
  2. Create Vision of the Future
  3. Set Deadlines
  4. Create Structure
  5. Stay Close to the Misery
  6. Measure, measure, measure
  7. Use Authority and Make an Executive Decision

Having the Conversation: Strategies for Ending Things Well

One key ingredient is to be prepared for the conversation itself. That preparation can make all the difference in the world. It can provide the confidence and the skills needed to finally pull the trigger.

Preparation for the Conversation:

  1. Integrate care and truth inside yourself
  2. Practice and role-play if necessary
  3. Get the tone right
  4. Validate the person and the relationship
  5. Get agreement
  6. Deal with defensiveness and reactions
  7. You may need others present or to help
  8. Except in rare cases, don’t burn bridges


What are you holding onto that you need to let go of? What are you putting energy into that is holding back something even better? Saying yes to something means saying to no to many more. This book is a great instruction to examine yourself and your business to say yes to the truly great and no to everything else.


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