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Leadership Pain: The Classroom for Change

Compiled by Chuck Olson

Leadership PainTitle: Leadership Pain: The Classroom for Growth

Author: Samuel Chan

Copyright Date: 2015

I became a fan of Sam Chand, who describes himself as a leadership architect and consultant, author, change strategist, speaker, and dream releaser, after reading Cracking Your Church’s Culture Code. Just a few weeks ago, I finished reading his most recent book, Leadership Pain: The Classroom for Growth, and have found myself referencing it on multiple occasions. While decidedly written to and for those in ministry-related leadership, its value can be easily transferred to any sphere of leadership endeavor.

Candidly, for my part, Chand’s take on leadership at times seems extreme. But at the end of the day, I buy his premise, mainly because I have lived his premise. Leadership IS painful. True. Very true. But equally true, as Chand convincingly argues, is this hard-core reality: the crucible of leadership will do a work. A deep work. A good work. A transforming work. It will grow you. It will humble you. And it will break you—in every good sense of the word.

I recommend this book strongly to those who are looking to make sense and ultimately leverage the pain of leadership


Book Description:

Do you want to be a better leader? Raise the threshold of your pain. Do you want your church to grow or your business to reach higher goals? Reluctance to face pain is your greatest limitation. There is no growth without change, no change without loss, and no loss without pain. Bottom line: if you’re not hurting, you’re not leading.

But this book is not a theological treatise on pain. Rather in Leadership PainSamuel Chand—best-selling author recognized as “the leader’s leader”—provides a concrete, practical understanding of the pain we experience to help us interpret pain more accurately and learn the lessons God has in it for us.

Chand is ruthlessly honest and highly practical as he examines the principles and practices that make our pain a means of fulfilling God’s divine purposes for our churches, communities, and us.

Book Quotes:

It’s inevitable, inescapable. By its very nature, leadership produces change, and change—even wonderful growth and progress—always involves at least a measure of confusion, loss, and resistance. To put it the other way: leadership that doesn’t produce pain is either in a short season of unusual blessing or it isn’t really making a difference. So, Growth = Change Change = Loss Loss = Pain Thus, Growth = Pain.

Organizational guru Peter Drucker observed that the four most difficult jobs in America are, in no particular order: president of the United States, university president, hospital CEO, and pastor. (I’ve been in two of these roles: pastor and university president.) If you’re a church leader and struggling in your role, you’re in good company!

In fact, leadership—all leadership—is a magnet for pain, which comes in many forms. We catch flak for bad decisions because people blame us, and we get criticism even for good decisions because we’ve changed the beloved status quo.

In her book On Death and Dying, Elisabeth Kübler-Ross observed the progression of dying patients as they faced the ravages of their disease. She noted they went through definable stages of grief: denial, anger, bargaining, grief (or sadness), and acceptance. Others observed that people pass through these stages in any kind of significant loss. Leaders experience them too.

For pastors and all other leaders, ignoring pain is leadership leprosy. It may promise the short-term gain of avoiding discomfort, but it has devastating long-term consequences.

For church leaders, pain is pervasive and persistent. People who are involved in any form of church leadership, and especially pastors, see more of the underbelly of life than members of any other profession. Insurance agents see those who come to them for protection against loss; bankers and mortgage brokers see people who have financial needs; doctors treat physical problems; and mechanics look under the car hood—none of them look into people’s heart like a pastor does. None of these people see people at the apogee and perigee of their lives—times of greatest celebrations, like weddings and births, and times of deepest loss, like divorce, disease, and death. Pastors are exposed to the highest hopes and the deepest wounds of those in their care. And it’s not temporary; it’s from the womb to the tomb.

Pastors are exposed to the dreams and dreads of people at every stage of life. In the span of an hour, a pastor may receive several glowing reports and as many messages about tragedies. This role in the lives of families is an incredible honor, but it produces tremendous pressure and often excruciating vicarious pain. If they aren’t careful, the cumulative pain can crush the life out of them—figuratively and literally.

Making friends with your pain is part of leadership. Our pains tell us we’re moving in the right direction. New pains will always be a part of your life as you continue climbing the ladder to your destiny.

Pain isn’t an intrusion into the lives of spiritual leaders; it’s an essential element in shaping the leader’s life. LOCATION: 461

Do you want to be a better leader? Raise the threshold of your pain. Do you want your church to grow? Do you want your business to reach higher goals? Reluctance to face pain is your greatest limitation. There is no growth without change, no change without loss, and no loss without pain.

You’ll grow only to the threshold of your pain.

If you’re not hurting, you’re not leading. Your vision for the future has to be big enough to propel you to face the heartaches and struggles you’ll find along the way.

If we see pain as only an unwelcome intruder, we’ll fail to ask the right questions, and our heartache will be wasted.

Let me give you a taste of the principles I want to impart to you. When you’re bleeding:

  • Understand and interpret your pain.
  • Clarify the lesson you’re learning.
  • Spend time with leaders who have high pain thresholds.
  • Take care of yourself—mentally, physically, spiritually, relationally.
  • Always be aware of your internal temperature.
  • Listen to your spouse (or best friend).
  • Don’t ask God to raise your pain threshold. He might just answer that prayer!


In the principles and stories in this book I hope you’ll find the courage to do three things:

  1. See pain as your greatest teacher. Don’t avoid it. Don’t minimize it. And don’t numb yourself to it. Pain never just goes away. When it’s not resolved, it sinks deep into our minds, creates anxiety in our hearts, causes resentment and depression, and creates tension in our relationships. As the old motor oil ad said, “Pay me now or pay me later.” Face pain sooner and you’ll learn important lessons about God, about yourself, and how to help others grow as they encounter difficulties. Face it later with devastating results.
  2. Let your vision drive you. Keep the vision fresh and strong. Don’t let your mind be consumed by your immediate pain and obvious limitations. When you interpret your pain as bigger—more important, more threatening, more comprehensive—than your vision, you’ll redefine your vision down to the threshold of your pain. Focus on the big picture and let your anticipated legacy give you the courage you need to face each day’s troubles. Your vision will continually renew your hope, restore your courage, and refresh your perspective. It will enable you to pay the price to face the pain and take the next step forward.
  3. Have a rigorous personal development plan. If you have a plan to grow spiritually, relationally, and professionally, you’ll incorporate difficulties into the learning process. Don’t coast. Read the best authors, spend time with courageous leaders, and craft a plan to sharpen your skills. At many points you’ll bump up against various obstacles—internally and externally, real and perceived. As you face each of them with courage, you’ll raise your pain threshold and you’ll become a better leader. In the process, you’ll see pain as your friend, not your enemy.


To be a better leader, raise the pain threshold in your life. To accomplish this, you first need a firm grasp on the three kinds of difficulties you will encounter: external challenges, internal stresses, and growing pains. LOCATION: 581

As we lead organizations—businesses, nonprofits, and churches—size doesn’t matter as much as another crucial factor. The biggest difference between leaders of large organizations and small organizations isn’t their location, the size of their building, the scope of the vision, the number of staff members, or their talent. In fact, some of the best leaders I’ve ever met have small organizations. But in all my consulting and conferences, I’ve seen a single factor: leaders of larger organizations have proven they can handle more pain.

There are many different external challenges for pastors, but resistance and personal animosity rank at the top. I was raised in a pastor’s home, I’ve been a pastor, and I talk with pastors every day. The greatest heartache I hear from them is the pain inflicted by their friends.

I then tell them, “Remember: growth equals change; change equals loss; loss equals pain; so inevitably, growth equals pain. That’s why leadership is both brutal and beautiful. It’s bleedership! It’s brutiful!” If you’re leading, you’re bleeding.

It’s human nature for people to try to build themselves up by putting others down, and ministry leaders are very visible, accessible, vulnerable targets.

It’s a paradox of leadership: our efforts to help people experience the love and power of Christ create envy in the hearts of some who are watching (and receiving our love). Most people are grateful, but a few—and it only takes a few—undermine us with open opposition, lies, and gossip.

Many pastors have wonderful visions of how God can use the church to accomplish great things, but they haven’t selected the right people to hold their ladder. They may have found someone who could hold it if they went up to twenty feet, but no farther. If they’re unwilling to make changes in the people holding the ladder, they’ll never climb higher. Never. Leaders can do one of three things with those who hold their ladders: retain them because they’re effective, release them because they aren’t, or reassign and retrain them to hold someone else’s ladder.

Most ministry leaders are more committed to keep from hurting anyone’s feelings than accomplishing the vision God has given them. I’ve never been to a church where someone didn’t need to be fired.

Contrary to the thinking of many people, stress isn’t the problem. Too much unrelieved stress is the culprit. A little stress brings out the best in us. Our adrenaline flows, and we become more creative, more energetic, and more determined to reach higher than before. But many leaders live without safety valves. They are like pressure cookers with a blocked valve. Every difficult conversation, every hard decision, every failure, every challenging question, and every self-doubt adds to all the ones that have already filled the pot. With each new strain, the addition seems imperceptible, so the person doesn’t do anything about it. As stress rises to the point of explosion or implosion, it seems completely, absolutely normal.

The signs of stress include:

  • Emotional symptoms: feeling overwhelmed, hopeless, isolated, irritable, or moody
  • Behavioral symptoms: eating too much or too little, sleeping too much or too little, using medications or alcohol to relax, neglecting normal responsibilities, compulsive behaviors, low resistance to temptation, and not enjoying things that used to bring pleasure
  • Cognitive symptoms: anxiety, scattered or racing thoughts, inability to concentrate, and lack of judgment
  • Physical symptoms: stomach problems, tension headaches, odd aches and pains, or the loss of interest in sex


In the vast majority of cases, burnout is the result of a long series of disappointments, setbacks, and heartaches. Any one of them cannot cause irreparable damage on their own, but the cumulative effect of unrelieved tension, ungrieved losses, and unresolved conflict ultimately exacts a heavy toll.

The exhaustion caused by constantly loving, giving, serving, and sacrificing—especially coupled with feeling alone, resentful, and hurt—erodes a Christian leader’s ability to cope with life. Some call it compassion fatigue and compare it with combat fatigue.

For pastors and church staff, caring for needy people is standard operating procedure—it’s their calling, their responsibility, their privilege—but the unusual intensity of specific events or prolonged seasons of care can significantly downgrade a person’s ability to function effectively.

Perfectionism creates unrealistic expectations, which inevitably produce either nagging self-condemnation or crushing self-doubt. But this isn’t the only thing that can overwhelm leaders. A strained marriage, kids out of control, debt, health problems, unresolved tension, taking care of elderly parents, moral failure, secretiveness, and a hundred other problems can take them beyond discouragement into depression.

Most cases of depression, however, are caused by circumstances outside the body; in other words, unrelieved stress and unresolved anger. One of the classic ways to describe this kind of depression is anger turned inward. This common depression can range from mild to severe.

In an article on the silent suffering of pastors, Fred Smoot, executive director of Emory Clergy Care in Duluth, Georgia, reported that when pastors can’t live up to the excessive demands placed on them by their own perfectionism and the expectations of others, they often “turn their frustration back on themselves,” which produces a downward spiral of self-condemnation and hopelessness.

When numbed leaders flatline their feelings, they try to go through all the motions, but their hearts are far, far away. They may not feel the crushing pain of the stress as much as before, but neither do they feel love, joy, and celebrations of God’s blessings. It’s easy to slip from taking responsibility to assigning blame when things don’t go well. Numbed leaders become sour, crabby, impatient, and selfish.

A church leader who trains hundreds of pastors each year told an audience that the pain we experience in the first forty years of our lives gives us the wisdom and experience for a far more profound ministry for the rest of our lives.

Virtually all leaders in every field of business or ministry assume that growth will relieve stress, but growth actually increases stress. This misunderstanding adds a large measure of confusion to the considerable pains of leadership.

Again and again, I talk with pastors who haven’t yet grasped this fundamental principle of organizational leadership: if you want to grow, you have to learn the lessons of pain and suffering.

Difficulties are God’s curriculum for those who want to excel.

Leading a growing, changing, dynamic organization requires tremendous courage, wisdom, and tenacity. LOCATION: 1703

Value diversity and welcome different perspectives, but be sure to recruit, hire, and train people for at least one level higher than your church is today.

When the well is running dry, we need to drill deeper. As a leader, your most valuable resource is your own heart. The greatest risk is becoming so tired, so discouraged, or so angry that your soul begins to shrivel. Then you’re running on empty and running blind. When we’re not replenishing our hearts with inspiration, encouragement, and insight, we have to strain just to make it through the next sermon or meeting. And if we’re straining to make it through, we can be sure the people in our meetings are struggling, too, as they try to listen to us. When we remain dry for a long season, the desert often expands to our staff, key volunteers, and eventually the whole church.

When you chart the course of your church toward growth, start with one basic assumption: your efforts to grow are going to create many, many problems. Expect them, anticipate them, and welcome them as God’s instructors.

People and organizations grow with the fertilizer of pain. We may not like it. We may resist it. But it’s a principle of the kingdom. To live, something has to die. In order to give birth, a mother has to endure the suffering of the birth process. Before the resurrection was the pain of the cross. And Jesus said, “Whoever wants to be my disciple must deny themselves and take up their cross and follow me. For whoever wants to save their life will lose it, but whoever loses their life for me will find it” (Matthew 16:24–25). Before God promotes us, he takes us through pain to purify our hearts, deepen our dependence on him, and impart spiritual wisdom.

Your happiness is inversely proportionate to the shoulds in your life.

Exaggerated expectations inevitably lead to disillusionment: a common form of leadership pain.

When pastors try to be experts at everything, they lose their sense of reality and sense of identity. As pressure mounts and frustration (from all sides) multiplies, they feel even less secure. They try to stay idealistic and upbeat, but the foundation underneath is cracking. Some leaders lose sight of pleasing God and, instead, live to please the next person who walks into their office.

In the twelve-step world, people know you’re only as sick as your secrets. As long as we try to hide our insecurities, sins, and limitations, we’ll suffer far more leadership pain than is necessary. Instead, we need to be completely honest with ourselves, with God, and with at least one other person. If you don’t have a friend who is supremely trustworthy, find a therapist. They’re paid to understand and stay quiet.

Insecure, threatened, stressed-out leaders give, but they don’t know how to receive. Secure leaders receive with humble, thankful hearts, and the grace multiplies in glad giving and sharing.

Throughout the Bible and church history, we see a clear pattern in how God works with people. No matter how gifted they were, God humbled them before he used them. A. W. Tozer believed that the experience of pain is essential for any leader to become pliable in the hands of God. In one of his most famous books he wrote, “It is doubtful whether God can bless a man greatly until He has hurt him deeply.” God’s methods may vary, but he always manages to get a person’s undistracted attention to teach the most fundamental lessons of trust.

Pain isn’t an accident in God’s world. Even when it’s self-inflicted through doubt and sin, God graciously weaves the strands of these experiences into something beautiful—if we’ll let him.

Sooner or later, the God who has transported us out of the kingdom of darkness into his marvelous light takes us out of the light and into a dark night of the soul. It’s part of the way of the cross—to some degree for every believer, but especially for those of us who have been called to lead God’s people. We find true spiritual strength when we trust God when we’re weak. Similarly, our leadership is far more attractive and authentic when we’ve been broken and then lead out of humility instead of pride.

When people suffer in any way, it is human nature to ask, “Why did this happen?” “Why did this happen to me?” These questions are part of our DNA. The goal, then, is to make a searching and fearless assessment to assign appropriate responsibility. The problem is that most people lack at least one and perhaps both of two essential elements: insight and courage. Instead, they tend to become either blame sponges or blame throwers to affix blame quickly and get the conflict over as soon as possible.

Not all pain is personal. Sometimes the pain is the direct result of the organization’s stage of development. I’ve consulted with leaders in churches and businesses for many years, and I’ve noticed predictable stages as they take steps to implement their vision for growth. In each of these stages the leaders and the organization suffer particular pains. Let me outline the five stages I’ve noticed and describe the pain in each one:

  1. The entrepreneurial stage: At the beginning, a new vision captures the leader’s heart and mind. All things seem possible, and a bright future looks very promising.
  2. The emerging stage: As the new plans are implemented, the leader and the organization are squarely in no-man’s-land—in between the certainty of the past and the hopes of the future.
  3. The established stage: In businesses, churches, and other organizations that have functioning systems, leaders who press for change often feel like they’re pushing a huge mass of jelly. Organizational inertia is very difficult to overcome, even for the most passionate leader.
  4. The erosion stage: I’ve talked to many leaders who woke up to realize their organizations had stopped growing and were actually declining. When they took a closer look, however, they realized the acid of erosion had been introduced years before.
  5. The enterprising stage: Leaders can’t afford to stand still and watch their organization continue to grow. It won’t happen. To stay in touch with the people they must stay sharp and continually reinvent the product and their services.

LOCATION: 2400-2440

From the divine perspective we can draw a number of important conclusions that help us endure:

  • God never abandons us, even when we can’t sense his presence.
  • Our faith and character are developed most powerfully in times of adversity.
  • God sometimes delivers us from pain, but more often he delivers us through it.
  • When we trust God in difficult times, our stumbling blocks become stepping-stones of growth.
  • When we face our deepest fears, our faith grows because we find God to be faithful.
  • When doubts cloud our minds, it’s time to refocus on God’s grace, greatness, and wisdom.
  • We may not like the path God has chosen for us, but we need to humbly accept pain as part of his plan.


At some point, we actually welcome pain because the effects are so positive. Those who have embraced pain as a way of life are seldom surprised by suffering, seldom devastated by difficulties, and seldom reactionary when things aren’t what they hoped.

Pain is a surprising substitute teacher in our lives. We’ve gotten used to the way things are in our leadership strategy, thoughts, perceptions, and practice. Pain is the new teacher we want to avoid or get rid of as soon as possible, but in reality it’s the best instructor we could ever have.

Pain teaches us five crucial lessons (among many others):

  1. We Are Weaker, More Self-Absorbed, and More Fragile Than We Ever Imagined
  2. Actually, We Don’t Have a Clue What God Is Up To
  3. We Become More Grateful
  4. We Find God to Be Beautiful Instead of Just Useful
  5. We Become More Tender, More Understanding, and More Compassionate

LOCATION: 2707-2738

Change is hard, but sometimes it’s absolutely essential. No more excuses, no more delays. It’s time to make the necessary adjustments in our intentional planning and our responses to people and situations. Superficial change may not take much effort, but changing how we think and how we instinctively respond requires discipline, determination, and accountability.

Today, a lot of communication is done through email and texting, but the intent of the heart often doesn’t come through to us digitally. A good principle is to move up at least one medium. If you’d normally send a short text, send a longer email. If you’d regularly email, make a phone call. If you’d usually call, ask for a face-to-face meeting. Relationships are forged on trust, and trust can’t be built when hearts fail to connect.

Work hard to build or rebuild trust. With it, you can fulfill the greatest dreams. Without it, you’ll crush people’s spirits. It’s much easier to change staff members and programs than to change the culture of an organization. Ask the right questions and keep on asking them. At every level of growth, work hard, communicate well, and pray like crazy that God will produce a healthy culture. And remember, it begins with you. If you aren’t healthy, your organization’s culture doesn’t stand a chance.

The kingdom of God is all about taking risks. The heroes in Hebrews 11 laid it all on the line. And the point Groeschel makes that is most pertinent to our study of leadership, which I also call bleedership, is that the way of the cross always involves pain. The amount of pain we’re willing to endure sets the limit of our effectiveness. If we avoid it or numb it, we’ll risk nothing, sacrifice nothing, feel nothing, and accomplish nothing.
Pride shows itself in two very different forms. Superiority is the assumption that we know better than God how life should work and we’re making it happen. Inferiority is based on the same initial assumption, but with the opposite conclusion: we can’t make it work, so we’re colossal failures. We instantly know that superiority isn’t humility, but sometimes we mistake inferiority for a humble heart. It’s not. A truly humble person doesn’t feel compelled to put himself down. He knows he’s deeply flawed—in fact, he’s brutally honest about his sins and limitations—but he’s also convinced that the grace of God is more wonderful than anything he can imagine. He’s free from the bondage of defending himself or proving himself. He’s beyond the temptations of praise and the ravages of blame.

When we’re in pain, it may not seem like much of a privilege to represent God at that moment and at that place, but God himself has appointed us, empowered us, and placed us “for such a time as this.” He trusts us to endure with grace. The moment of pain, then, is a point of high honor earned by faithfulness, effectiveness, reputation, and proven character. It’s an honor and a challenge to be God’s representative in a time of heartache. People are watching us. It’s an incredible opportunity. We dare not miss it.

Our secrets will kill us. They will haunt our dreams, cloud our plans, and distort our relationships. We may harbor secrets because the truth about a single evil past act or a continuing bad habit is too shameful to tell, or we may keep our secrets hidden because we don’t have any real friends who will genuinely listen. Either way, we remain alone, isolated, and desperate to stay hidden.

Pain can only be effectively managed in a trusting, affirming, honest community—not necessarily a large community, but at least a few people who genuinely understand. Most leaders have to endure seasonal storms that last for a while and then subside. For pastors, however, the storms never stop. The torrents keep coming. Without a strong, supportive community, pastors wither away under the pressure.

A spouse can be a wonderful encourager and a leader’s number-one fan, but church leaders need a peer or two who are shouldering similar loads and who understand the complexities of the role.

The way we interpret and respond to pain throws us into a gear that propels us forward or backward. While pain itself is indifferent, it never has an indifferent effect. Pain will shift you one way or the other. We all have a default mode of dealing with pain: fight, flight, or freeze. It’s the way we’ve dealt with conflicts, threats, fears, and loss all our lives, but our default mode may not be a productive, healthy way to handle pain any longer. Now it’s time to change.

Change only happens when our level of desire (or actually desperation) rises above the level of our fears. Pain is a watershed: it can cause us to shrink back into a hole and hope it goes away, or it can galvanize new hopes, new plans, and new passions to learn the lessons it can teach us.

Hopefully, the principles and perceptions in this book have helped you to understand the power of pain to destroy and build up, but even more, I hope you’ve gotten some insights about your responses to different types of pain. You have choices. And all choices are consequential. At some point, you’ll stop seeing pain as the enemy and make peace with it. Like Paul, you’ll see pain as a surprising source of strength. God’s power, Paul learned, “is made perfect in weakness” (2 Corinthians 12:9).

Do you want to be strong in God’s grace and power? Make peace with the pain God sends your way. Recognize it as a springboard for growth and a platform for greater effectiveness. You’ll need it. God has much more in store for you.

Self-pity isn’t humility. It’s the opposite of humility. It screams for people to look at us and notice how much we’ve suffered. Humility is the bedrock security that doesn’t demand or expect applause or recognition. The essence of genuine humility isn’t thinking less of ourselves but thinking of ourselves less. Pain has the power to crush us, but what’s left in the bottom of the crucible? Is it someone who is angry, resentful, and self-absorbed, or is it someone who has met Christ there, experienced his grace in a new way, and been transformed and freed by the encounter with pain?

Don’t run from your pain. Don’t deny it exists. It’s the most effective leadership development tool the world has ever known. You’ll grow only to the threshold of your pain, so raise it!

Note: should you wish to find any quote in its original context, the Kindle “location” is provided after each entry.

Chuck Olson

As founder and president of Lead With Your Life, Dr. Chuck Olson is passionate about inspiring, resourcing and equipping Kingdom leaders to lead from the inside out.  To lead, not with the external shell of positions, achievements or titles, but from an internal commitment to a deep, abiding and transparent relationship with Jesus. Serving as a pastor and leadership coach for over forty years, Chuck has a track record of building these truths deep into the lives of both ministry and marketplace leaders.

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