It was the winter of 2008, in my senior year, and I was at a crossroads with what I wanted to do after finishing high school. Was I going to university? Should I move out with my friend and find a job? Should I continue my pursuit for a professional basketball career? By the way, a basketball career was my dream all through high school, but by the time I got to the 12th grade, I had to face reality: 1. I got a terrible knee injury that hindered me from playing to my full potential; 2. My grades were low; and 3. I had no back up plan.

As difficult as it was, I had to end my pursuit for a professional basketball career. Did I quit basketball completely? Of course not! I just had to shift my focus. Basketball went from being my number one priority to an activity I did for exercise and enjoyment. This is what Henry Cloud calls a “necessary ending” in his book Necessary Endings. In this post, I will highlight some of the main points and ideas I took away from the book.

Henry Cloud is clinical psychologist and leadership expert and uses his book to provide valuable insights and questions that you can ask yourself to determine what needs to go—whether it’s employees, businesses, or relationships that hinder you from moving forward— in order for better things to come.

Decision Blockers

So let’s get started with some reasons why many hesitate to give up certain things in their lives.

  • Fear of the unknown: What’s going to happen if I give up this relationship? My life is has been so tied to this person for so long that I can’t imagine what life will look like without them.
  • Not knowing how to approach the situation, feeling stuck: How do I tell this employee that he is not living up to our company’s standard, and even worse, that we are thinking of letting him go? I’ve never had a conversation like this before.
  • Unsure whether executing a necessary ending is the right move: How do I know for sure that this old equipment is what’s costing our company so much money? What if the employees just need some more training?

As you can see, some of these questions aren’t so easy to answer. The hardest one for me is not knowing how to approach the situation. Why? Because it often means having difficult conversations, disappointing someone, or feeling guilty after making the decision. However, this book helped me understand that discomfort is a part of the process when making important decisions; the present discomfort will be worth the future benefits.

Determining your Necessary Ending

Here’s the big question: How do we differentiate between a necessary ending and an improvement? In some situations, you may need to re-evaluate, adjust, and keep moving forward with a certain goal or intuitive. But other circumstances demand a necessary ending in order to pursue better things. Next time you are wondering whether you should stop or continue pursuing an endeavour, ask yourself these three questions for some clarity:

Question 1: Is there something that is taking up space where something else could? Something in your company could be working well or simply doing what it has always done, but is it making much of a difference? Is there something else that will reap a better return? For example, filing your documents in a cabinet might work well for the company, but by asking this question you might realize that going paperless frees up office space and makes it easier for employees to access files.

Question 2: Is something sick and not doing well? In high school, one of my friends (let’s call him Jake) got me a job at his dad’s company; because of this, I felt indebted to him and found it difficult to decline his invites to hang out. But the problem wasn’t so much about not wanting to hang out. The problem was in the nature of our friendship. In other words, Jake was a serial liar. He was manipulative, and at one point, he stole money from one of my family members. Though I tried to work it out with him, it became obvious that I needed to distance myself from the friendship. Eventually I found a job somewhere else and the friendship slowly came to an end. My friendship with Jake was sick and not doing well; it required some boundaries, and those boundaries resulted in a necessary ending.

Question 3: Is something already dead? The most obvious indicator that it’s time to execute a necessary ending is that something is already dead. It’s not producing anymore. It’s obsolete. You see this happen a lot with trends that come and go every few years or so. For example, when I was 14 years old, I owned an ancient artifact called a Walkman, where you inserted a CD inside of it to play your music. But if you were to ask the average 14 year old today what a Walkman is, chances are they wouldn’t have a clue. At some point, companies that sold Walkman’s had to execute a necessary ending because the world of Mp3 players, iPods, and cell phones would eventually dominate the way we listen to music.

Hopelessness?

In his book, Dr. Cloud also shared that a sense of hopelessness can actually help you succeed. I know…sounds strange doesn’t it? But let me elaborate. Hope is a great quality to have in most scenarios. You need resilience and patience to handle setbacks when pursuing a goal or endeavour. However, hoping can also keep you going in the wrong direction when you are faced with a false reality. You might be hanging on to something that has been dead for a while, hoping that some day it will change, when it reality, you need to let it go. That’s where a healthy sense of hopelessness can help you face the reality of your situation so you can make the necessary endings that will produce better results. This often happens in the world of professional sports.

A team may start to feel a sense of hopelessness after losing and losing and losing again. Eventually they realize that drastic changes need to be made. Maybe it’s a player that needs to be traded or a coach that needs to be fired. Take Kawhi Leonard for example: He wasn’t getting along with the San Antonio Spurs establishment nor with his head coach, Gregg Popovich. And I’m sure they tried to work it out, but it just wasn’t the best fit for Kawhi. This called for a necessary ending. The Spurs traded him to the Toronto Raptors in the fall of 2018, and Kawhi went on to lead the team to their first-ever NBA Championship!

people near buildings
Toronto Raptors fans celebrating after taking home the 2019 NBA Championship.

Let me end off by sharing a passage that I believe communicates the essence of necessary endings:

 For everything there is a season, and a time for every matter under heaven:

a time to be born, and a time to die;
a time to plant, and a time to pluck up what is planted;
a time to kill, and a time to heal;
a time to break down, and a time to build up;
a time to weep, and a time to laugh;
a time to mourn, and a time to dance;
a time to cast away stones, and a time to gather stones together;
a time to embrace, and a time to refrain from embracing;
a time to seek, and a time to lose;
a time to keep, and a time to cast away;
a time to tear, and a time to sew;
a time to keep silence, and a time to speak;
a time to love, and a time to hate;
a time for war, and a time for peace.” – Ecclesiastes 3:1-8

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