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Didn’t See It Coming

Compiled by Chuck Olson

Title: Didn’t See It Coming: Overcoming the 7 Greatest Challenges That No One Expects and Everyone Experiences


Author: Carey Nieuwhof

Copyright Date: 2019

Early in the pages of his every-leader-must-read book, pastor, podcaster, and thought leader Carey Nieuwhof in Didn’t See It Coming: Overcoming the 7 Challenges That No One Expects and Everyone Experiences, writes these sobering words: But a few years into my adult life, I began to notice highly competent people who became disqualified from leadership. These were smart, skilled people with great educations, incredible minds, and finely tuned skill sets who were at the top of their fields. One after another, they resigned or were forced out. From there, Nieuwhof unpacks seven realities of leadership that every leader needs to place on high-alert status: cynicism, compromise, disconnectedness, irrelevance, pride, burnout, and emptiness. For each challenge, he provides insightful and field-tested counsel on how to steer clear of these potholes and how to navigate back to wholeness.

This book needs to find itself on to every leader’s REQUIRED READING list. Here are a set of Book Notes that will more than whet your appetite for the benefits that await.

Signature Chuck

Book Description:

Founding Pastor of one of North America’s most influential churches, Carey Nieuwhof wants to help you avoid and overcome life’s seven hardest and most crippling challenges: cynicism, compromise, disconnectedness, irrelevance, pride, burnout, and emptiness. These are challenges that few of us expect but that we all experience at some point. If you have yet to confront these obstacles, Carey provides clear tools and guidelines for anticipation and avoidance. On the other hand, if you already feel stuck in a painful experience or are wrestling with one of these challenges, he provides the steps you need to find a way out and a way forward into a more powerful and vibrant future.

Book Quotes:

The way most people get into these unintended places is simple: They miss the warning signs. They don’t see it coming. The good news is that you can see it coming. This book is for people who want to see the signs that there’s a major life challenge ahead before it’s too late. LOCATION: 192

These warning signs, if recognized and heeded, are gifts from God to spare us from the self-inflicted sadness and heartbreak that mark too many lives these days. LOCATION: 199

Cynicism, compromise, disconnection, irrelevance, pride, burnout, emptiness—none of these need to be your final story. You can see them coming. You can identify them when they arrive. And when you name them, when you see them, they lose some of their allure as well as their power. LOCATION: 237

Cynicism isn’t just something other people experience; it’s something you sense growing within you. LOCATION: 284

Cynicism begins not because you don’t care but because you do care. LOCATION: 348

Most cynics are former optimists. You’d never know it now, but there was a time when they were hopeful, enthusiastic, and even cheerful. There’s something inside the human spirit that wants to hope, wants to think things will get better. Nearly everyone starts life with a positive outlook. LOCATION: 353

At least three things happen to the human heart as it grows cynical.

  1. You Know Too Much
    But now you know too much. You’ve experienced the heartbreak, betrayals, and backstabbing. You understand that people let you down. You’ve seen that some people can’t be trusted. You know love hurts. You realize that people are fickle and selfish. You recognize that not everyone succeeds, despite good intentions and best efforts. The longer you live, the more you know. Which is why cynicism and age are frequent companions.
  2. You Project the Past onto the Future
    Cynicism grows beyond its infancy when you start to protect yourself from future hurt. Having been burned once or twice, you tell yourself only fools get burned three times. So you start to guard your heart. You shelter your soul.
  3. You Decide to Stop Trusting, Hoping, and Believing
    Perhaps most disturbingly, cynicism begins to infect your relationship with God. When you close your heart to people, you close your heart to God.  LOCATION 355-418

What I needed to understand is what you need to understand: cynicism is actually a choice. Cynics aren’t born; they’re made. Life doesn’t make you a cynic; you make you a cynic. LOCATION: 441

Cynicism is so cruel. When I was at my most cynical, the thing that died within me was hope—hope that the future would be better than the past, hope that the next time could be different, hope that my heart would feel again. LOCATION: 463

Cynics find hope hard because hope is one of cynicism’s first casualties. LOCATION: 466

The remarkable part of Christianity is not that we have a Savior who came to deliver us but that we have a Savior who sees us for who we really are and loves us anyway. Jesus stared hate in the face and met it with love. He confronted despair and made it abundantly clear it wouldn’t win. LOCATION: 485

How do you battle cynicism on the days when discouragement and despair are once again knocking at your door? That brings me to the little hack I’ve picked up to help me in the times I struggle to battle my creeping cynicism. An incredibly effective antidote to cynicism is curiosity. Yes, simple curiosity. LOCATION: 502

One thing I’ve noticed again and again is this reality: curious people are never cynical, and cynical people are never curious. LOCATION: 504

Here are five keys I’ve discovered to help anyone become more curious and stay curious throughout life.

  1. Schedule Thinking Time
    Busyness is the enemy of wonder, and many people feel frantically busy these days.
  2. Ask Open-Ended Questions
    At the heart of conversation’s demise is a lack of question asking.
    If you listen longer than most people listen, you’ll hear things most people never hear.
  3. Give Fewer Answers
  4. Dream More
    When your life becomes focused on what you know and what you can control, dreams die.
  5. Ask Two Pivotal Questions
    Finally, the curious come back to two questions again and again: “Why?” and “Why not?” LOCATION: 515-552

But a few years into my adult life, I began to notice highly competent people who became disqualified from leadership. These were smart, skilled people with great educations, incredible minds, and finely tuned skill sets who were at the top of their fields. One after another, they resigned or were forced out…These people usually left their esteemed positions because of an addiction, an affair, abuse, embezzlement, greed, internal fighting, ego, or sometimes just being a jerk. Athletes, politicians, business leaders, actors, industry moguls, and pastors alike fall to issues like these month after month, year after year, decade after decade. And those are only the ones we hear about. Start looking for the stories that never make the news, and the onslaught seems endless. LOCATION: 652

So if competency doesn’t determine capacity, what does? Character does. All the competency in the world can’t compensate for a lack of character. Ultimately, your character is your lid. Even in a workplace that wouldn’t espouse any religious affiliation at all, character is the great leveler. You may be smart, but if people don’t like you, they won’t want to work with you. You may be the best software developer in your field, but if you lie, people won’t trust you. You may be able to bring reams of cash into the company, but if you mistreat the people who work with you, they’ll leave or they’ll make sure you do. LOCATION: 659

Lack of character kills careers, shatters families, ruins friendships, and destroys influence. And even if you never get fired or divorced over the compromises you make, your lack of character will limit the intimacy, joy, and depth you experience with God and with people. Like it or not, character, not competency, determines capacity. LOCATION: 663

Character determines so much more than you think. Ultimately, it not only dictates your capacity in work and in life but also becomes your legacy. Your competency leaves the first impression, but your character leaves the lasting one. The crowd is intrigued by your competency, but your family and close friends are influenced by your character. LOCATION: 669

When you’re no longer breathing, the legacy you’ll leave will center on your character. People will remember if you loved well, if you forgave easily, if you cared enough to be there for them. They’ll remember if you served or preferred to be served. They’ll know whether you thought life revolved around you or whether you really tried to honor God and others. They’ll remember whether you were generous or miserly, arrogant or humble, compassionate or indifferent. They’ll remember your temper or whether you learned the rhythms of grace. LOCATION: 682

Developing your character is never easy, which is why so many people abandon the pursuit. But it’s so worth it. Character matters more than anything because you bring who you are into everything you do. Your character determines the kind of spouse, parent, friend, employee, and leader you are. No matter how hard you try, you can’t escape you. LOCATION: 708

So what are some telltale signs you’re drifting, that you’re not becoming who you intend to be? Here are five.

  1. There’s a Growing Gap Between Your Public Life and Private Life
    Your character is compromised when you can no longer tell the world the truth. You project an image of yourself that isn’t accurate.
  2. You’re Hiding Things
    As the gap grows between your real self and the projection of your false self, you won’t want anyone to discover the truth about you. Compromise eventually leads to cover-up.
  3. You Fail to Follow Through on What You’ve Said
  4. You Justify Your Bad Actions and Decisions
  5. Your Life Has Become All About You LOCATION: 736-777

When you keep compromising, eventually you craft a life that is almost entirely self-centered. And that’s the opposite of who you know you should be. LOCATION: 777

And let’s be honest: character development is far more painful than skill development. Working on your character forces you to go into the crags and crevices of your heart. It encourages you to look at your past to forge a better future. It makes you look in the mirror. LOCATION: 796

The antidote to compromise is simply this: work twice as hard on your character as you do on your competency. It could be that you need to work five times harder. Or ten times harder. I don’t know. Twice as hard feels doable, and it’s a reminder that I’m likely going to resist it, so I’d better pay attention. According to Jesus, very few people ever manage to do it. LOCATION: 827

If you do go through the deep journey Jesus invites you to take, you’ll stop compromising. Your outside will begin to look like your inside. You won’t need to hide because there will be nothing left to hide. You’ll be so consistent that there will be no distinction between who you are publicly and who you are privately. Keeping your word will be easy because your yes will mean yes and your no will mean no. LOCATION: 863

The process of changing your character from the inside out could fill this entire book, but here are three ways to get started.

  1. Take Responsibility
    Every time you blame others, invent justifications, or craft a fresh excuse, you evade responsibility.
  2. Make Your Talk Match Your Walk
    Let me tell you what happens when you are relentlessly committed to making sure your talk matches your walk: you change your walk. Every time I line up my public talk to match my private walk, it makes my private walk better. Words have that kind of power if they’re honest. The shame and humiliation of admitting who you really are to people you respect and admire will motivate a big shift in behavior…One of the best things you can do to overcome your hypocrisy is to humble your talk and accelerate your walk.
  3. Put Yourself First When It Comes to Personal Growth
    Jesus had a very different end in mind for the spiritually mature. He didn’t define maturity by how much you know. He defined it by how much you love. Working on your character twice as hard as you do on your competency will lead you into the place where God’s love regenerates everything about you. LOCATION: 873-96

Competency gets you in the room. Character keeps you in the room. For all of us, it’s our character that determines how we’ll be remembered. More important, it’s our character that God is most interested in. Reverse the compromise that’s happening in your life, and you will finally close the gap between who you are and who you want to be. Your interior life will finally begin to sync with your exterior life. Not only will you experience a newfound peace and even deepened humility and self-respect, but you will change your legacy. The people closest to you will become the people most grateful for you. LOCATION: 977

As a culture, the more connected we’ve become, the more isolated we’ve grown. This is our strange twenty-first-century paradox: we’re connected to more people than ever before and we’ve never felt more alone. LOCATION: 1017

Technology does a good job of revealing what’s already inside you. If you’re narcissistic by nature, social media gives you a new platform to express your self-centeredness. If you lean toward workaholism, you’ll always have access to your office as you carry your devices with you everywhere. LOCATION: 1034

In essence, technology is like money: it makes a terrible master but a wonderful servant. Technology can be used for tremendous good, and it can bring out the worst inclinations in us all. LOCATION: 1042

In my lifetime, I’ve noticed the decline—perhaps the near death—of two vital things I see sliding further into the abyss with each passing year. Their demise may be part of the reason people feel so distant from others.

  1. The Demise of Genuine Conversation
    Great conversation is a beautiful art. It involves the exchange of ideas between two or more people who care enough about one another to listen as well as speak. Sadly, conversations seem to be devolving into an exchange of monologues among people who don’t seem terribly interested in one another. People today appear to be talking at one another more than they’re talking with one another.
  2. The Death of Confession
    Beyond the death of genuine conversation, there’s an even deeper loss happening: confession seems to be disappearing. LOCATION: 1113-1139

Confession is the part of prayer and life where we come before God and one another to admit all that we aren’t: our shortcomings, our intentional sins, and myriad unintentional sins. When we confess our brokenness, we admit that we are not all we pretend to be, hope to be, or could be. We own up to the fact that we are a mess. LOCATION: 1144

Here’s what I’ve realized in my life: confession and progress are inexorably linked. You won’t address what you don’t confess. If you think about this more deeply, it’s the things that you refuse to confess that grate on the relationships that matter to you. LOCATION: 1161

When you stop using your past as a justification, you’ll also begin to realize that maybe, just maybe, you have problems for which you are responsible. LOCATION: 1204

When you take an interest in others more than in yourself, it’s a very small form of dying to yourself, something very close to the heart of Christ. When you give your life away, something greater rises. LOCATION: 1225

We hear a lot about our accelerated pace of life and for good reason. The speed at which we travel is exciting but also problematic. I have discovered that a hurried life leads to an unexamined and disconnected life. Hurry kills intimacy with God, with family, and with friends. LOCATION: 1272

Love has a speed. And it’s slower than I am. There’s a good chance it’s slower than you are. Love pauses. Love lingers. Love offers full focus and gives far more than it takes. When I run too fast, I outrun love, and the people I love pay a price. LOCATION: 1277

Irrelevance can be cruel as it silently squanders your influence. Most of us spend considerable energy and effort in our younger years trying to influence the people we care about and advance the causes that matter to us. Irrelevance sabotages that influence. Without ever telling you why, people quietly dismiss you as someone who doesn’t quite get it. They write you off as quaint, outdated, and even insignificant. LOCATION: 1338

Rick Warren said it well: “When the speed of change around an organization is faster than the speed of change inside the organization, the organization becomes irrelevant.” That’s also true for people. The gap between how quickly you change and how quickly things change is called irrelevance. The bigger the gap, the more irrelevant you become. LOCATION: 1344

The goal is not to chase culture, morphing into a different person every season. No, the goal is to understand the culture well enough that you are able to speak into it. And that, of course, requires change and adaptation. LOCATION: 1350

You’re ready to change because the pain associated with the status quo just became greater than the pain associated with change. That’s the moment most of us change. LOCATION: 1451

The brain has a bias toward what it already knows. LOCATION: 1511

Surprisingly, success makes you conservative. The more successful you are, the less likely you are to change. LOCATION: 1516

In addition to being aware of why you’re biased against change (which we’ve just seen), here are four insights and strategies to make sure you stay current.

  1. Love the Mission More Than the Methods
  2. Get Radical
  3. Become a Student of Culture
    Why should you become a student of culture? Simple. People who don’t understand today’s culture will never be able to speak into it. Whether you agree with the culture or not, understanding it is a prerequisite to being able to influence it.
  4. Surround Yourself with Younger People LOCATION: 1531-1570

The best years for leaders who are able to communicate with the culture often seem to happen somewhere between age forty-five and seventy-five. If you don’t navigate these years well, these are also the years where irrelevance accelerates. But if you pay attention to the things we’ve discussed, these can be not only your peak earning years but also your peak contributing years. LOCATION: 1588

The difference between change and transformation is powerful. On the outside, they look similar. Looking at a person who’s changed versus one who’s been transformed, you won’t see a big external difference. But inside, the transformed person is significantly different. What’s happened? The transformed person no longer wants to go back to the way things were. Unlike the story of Moses and the Israelites, the slaves no longer want to go back to Egypt. When true transformation occurs, the person embraces the future more than the past. LOCATION: 1608

Change is hard, but the right kind ushers in so much good. You may prefer to do things your way and keep everything the same. But for the sake of the next generation, for the sake of contributing meaningfully throughout your entire life, don’t just intend to change. Actually do it. Because unimplemented change will become regret. LOCATION: 1622

The most obvious form of pride is narcissism, which is an issue for some people but not most. How do you know if you’re in that category? Narcissists really do think they’re God’s gift to humanity. They demand to be the center of attention; they dominate conversations, interrupt people, think they’re better, have to stay on top at all costs, can’t celebrate the success of others, and always have an excuse if they’re not first. They’re obsessed with themselves because they think they’re oh so awesome. LOCATION: 1681

Pride at its heart is an obsession with self. It generates the desire you feel to protect, project, manipulate, jockey, advance, pretend, inflate, and brag. LOCATION: 1689

Pride will snuff out your empathy, stifle your compassion, create division, suffocate love, foster jealousy, deaden your soul, and make you think all this is normal. LOCATION: 1699

Pride will lead to cynicism and accelerate burnout. It will leave you feeling disconnected and can cause you to become irrelevant. And by the time it has run its course, pride will leave you feeling empty, despite everything you’ve accomplished. Pride will cost you friendships, intimacy, respect, lost opportunities, rest, peace of mind, wisdom, and even money. It’s hard to imagine the stakes being much higher. LOCATION: 1703

Pride sneaks in even among the insecure and drives a wedge between who we think we are and who God thinks we are. LOCATION: 1721

One sure sign of insecurity is that your opinion of yourself rises and falls with how you perform or what others say about you. Your identity should be more secure than your latest results, but for many of us, it’s not. LOCATION: 1742

Proud people end up being controlling people. If insecurity drives you, you’ll always want to add your little bit of knowledge, insight, or even an anecdote to everyone else’s story. It won’t feel complete if the other person gets the spotlight and you get overlooked. LOCATION: 1768

Let pride run its course, and it will deaden your heart. Pride inoculates you from the counsel of others and the stirrings of your conscience. It makes you think that the rules don’t apply to you or that you can violate them without repercussion. LOCATION: 1784

Which begs the question, What exactly does a hard heart look like? Glad you asked. There are at least four characteristics to watch for.

  1. Superior
    A proud and hardened heart makes you feel superior to others (notice this crops up all over the place when you’re proud?)
  2. Judgmental
    A judgmental attitude springs directly from the noxious well of superiority because to stay ahead, you have to invent reasons why others are behind. To bolster your sense of success, tenuous as it is, you concoct explanations for why you’re better than everyone else.
  3. Unaccountable
    A hardened heart will also help you justify avoiding real accountability.
  4. Isolated
    You may spend your entire life building your kingdom, but just know this: a life devoted to self ultimately leaves you alone. That’s exactly where pride leaves you: isolated. LOCATION: 1812-1841

The problem with success (even a small bit of it) is that you get addicted to all the trappings. And pride will convince you that you are entitled to it all. LOCATION: 1889

How do you tame the raging beast of pride in all its forms? Through humility. Nothing kills pride like humility does. Only humility can get you out of what pride got you into. LOCATION: 1890

The more you have, the easier it is to lose your gratitude. Scarcity creates gratitude, and most of us live in relative abundance, globally speaking. LOCATION: 1929

Gratitude fosters humility because it moves you out of the role of the star in your story. LOCATION: 1945

Helping others succeed and sharing the stage with them doesn’t make you less valuable; it makes you more valuable. When you’re humble, you realize the overall mission is more important than you are. LOCATION: 1990

Just know this: Of all the lies we tell, the ones we tell ourselves are the deadliest. Unconfessed and unaddressed, they will continue to damage the people around us (and us) indefinitely. Level with yourself and with God. Everyone else knows your weakness. So does God. Why not admit it? LOCATION: 2025

I’ll describe eleven signs and symptoms I personally experienced as I burned out. If you recognize one or two of them, you’re likely not burned out. Consider them warning signs. If you show six to eight, you may be in low-grade burnout or heading for the cliff. If you resonate with most or all of them, you’re likely in full-fledged burnout. I hope these signs can help you see the edge before you careen past it.

  1. Your Passion Fades
  2. You No Longer Feel the Highs or Lows
  3. Little Things Make You Disproportionately Emotional
  4. Everybody Drains You
  5. You’re Becoming Cynica
    Cynicism never finds a home in a healthy heart.
  6. Nothing Satisfies You
  7. You Can’t Think Straight
  8. Your Productivity Is Dropping
  9. You’re Self-Medicating
    People who are burning out almost always choose self-medication over self-care.
  10. You Don’t Laugh Anymore
  11. Sleep and Time Off No Longer Refuel LOCATION: 2148-2205

The truth is that we all struggle with unresolved problems. And the sooner you deal with them, the better off you and everyone around you will be. Your unresolved past will sink your future unless you deal with it. LOCATION: 2219

So how do you recover from burnout?

  1. Tell Someone
  2. Develop a Circle Around You
    Why do friendships matter? Because you need people who believe in you when you’ve stopped believing in yourself.
  3. Keep Leaning into God
    First, if your emotions aren’t working and you feel mostly numbness, you likely won’t feel like God is there for you. But just because God seems silent doesn’t mean he’s absent. I did not feel God for months.
    What I’ve learned is that obedience is greater than my emotions. Eventually your emotions catch up to your obedience.
  4. Rest
  5. Find Something to Take Your Attention Away from Your Pain
  6. Do What You Can
  7. Don’t Make Any Big Decisions
  8. Grieve Your Losses
  9. Reopen Your Heart
    Trusting again after your trust has been breached keeps your heart fresh and alive and—ultimately—hopeful again.
  10. Live Today in a Way That Will Help You Thrive Tomorrow LOCATION: 2247-2346

Pride and fear are villains in the burnout story. They keep you first from admitting and then from telling. Both will tell you there’s still too much of a stigma attached to burnout, anxiety, and even depression for many people to feel comfortable talking about them. LOCATION: 2375

Workaholism is the most rewarded addiction in America today. You may get fired for drinking too much, but working too much usually gets you promoted. LOCATION: 2612

Overeating is another crippling form of self-medication our culture has embraced wholeheartedly. And when I use the word crippling, it’s not in the metaphorical sense. Globally, obesity now kills three times more people than malnutrition does. And even if it doesn’t kill you, it can significantly affect the quality of your life. LOCATION: 2624

Ready? If you want to beat emptiness, find a mission that’s bigger than you. As long as you keep making your life all about you, you’ll experience one round of emptiness after another. LOCATION: 2696

One of the reasons 70 percent of employees are disengaged at work is because people don’t understand the greater purpose or mission behind what they do, and most managers and leaders never try to move people toward something greater. LOCATION: 2708

Selfishness looks good only to the selfish in the same way that pride is attractive only to the proud. Humility will win you what pride never will: the affection of others. And that’s exactly what selflessness will do. Other people naturally gravitate toward people who live for a cause beyond themselves. LOCATION: 2760

Self-aware people have a conscious knowledge of their motives, desires, feelings, and character. They are also in tune with how their actions affect others. The more self-aware you are, the more likely you are to see it coming. LOCATION: 2808

One way to test your level of self-awareness is to figure out what self-aware people know that others don’t. In my experience, there are four things.

  1. Their Impact on Others
    Self-aware people understand not only what their own emotions and actions are but also how their emotions and actions affect others.
  2. Their Weaknesses
    Self-aware people understand their weaknesses and limit their activities in areas where they are not gifted.
  3. Their Strengths
    If you use your gifts as part of a larger mission and for the benefit of others, you’ll actually avoid the emptiness so many people feel otherwise.
  4. Their Limits
    Self-aware people have a realistic sense of what they can do and what they can’t do, where they end and where others need to begin. When they need a break, they take one. When they’re tired, they acknowledge it and take responsibility for getting some rest. When they’re running on all cylinders, they give whatever they’ve got to whatever they do. LOCATION: 2818-2852

And so it comes full circle. Without knowledge of self, there’s no knowledge of God. And without knowledge of God, there’s no knowledge of self. LOCATION: 2875

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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