The 7 Deadly Leadership Challenges

Pay attention to these seven insidious issues that can quietly sabotage your ability to lead.

You didn’t start out in leadership to give up early or never realize your potential, but admit it: You’ve seen it happen to leaders around you all the time.

The question is: Is it happening to you?

It’s a great question to ask … and not enough leaders ask it.

There are challenges that almost everyone experiences but no one expects in life and leadership. And they’re the most deadly.

At age 18, no one says “I hope by the time I’m 35, I’m cynical, jaded and burned out,” but it happens all the time.

The questions is why.

Surprisingly, it’s rarely issues of skill, talent or ability that take down leaders and entrepreneurs or cap their growth. Often, it’s the soft issues that can sideline even the best leaders; things like cynicism, disconnectedness or even pride that just turn you into someone you never wanted to be.

And those are the issues almost no one ever sees coming. When you understand how they start, you can spot them before they take you out.

I tackle all seven issues in depth in my book, Didn’t See It Coming: Overcoming the 7 Greatest Challenges That No One Expects and Everyone Experiences, but to give you an overview, here are seven issues almost everyone experiences and none of us expect:

1. CYNICISM

You probably didn’t start out in life and leadership as a cynic. But if you’re like most people, you find yourself growing a little more cynical with every passing year.

Cynicism begins, not because you don’t care, but because you do care. It starts because you poured your heart into something and got little in return.

Or maybe you got something in return, but it was the opposite of what you desired. You fell in love, only to have that relationship dissolve. You threw your heart into your job, only to be told you were being let go. Or you were completely there for your mom, only to have her tell you you’re such a disappointment.

And you can’t help but think to yourself, What gives?

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.

As much as you may not want to admit it, cynicism is a choice. Life doesn’t make you cynical. You make you cynical.

Once-a-cynic doesn’t mean always-a-cynic. Not if you get Jesus involved.

Curious as to how cynical you’ve grown? Take this short quiz and find out.

2. COMPROMISE

Most of us know people who have sold out, who’ve given in to the dark forces of greed, self-absorption, blind ambition, moral trade-offs or ruthlessness. In the process, they threw integrity out the window.

And even if you don’t personally know someone who’s done this, a quick scan of the headlines on any given day will usually yield an athlete, a politician or a business leader who has.

So how does a person get there? Even if your family hasn’t forsaken you and it hasn’t cost you your job, you may sometimes look in the mirror with the sinking feeling that you didn’t do what you should have done, and you’re not who you thought you’d be.

You know how compromise starts? Subtly.

There was that time when you weren’t 100 percent honest with a client, or maybe many clients. You could have kept the promise, but you didn’t. You haven’t told your wife about your porn problem, but you tell yourself it’s no big deal when you know deep down it’s ruining your intimacy with her.

Maybe you know you should be more present for your kids, but you hide behind your laptop because you just can’t handle the chaos of bedtime and don’t want yet another fight with your wife. Work is just easier. At least people respect you there.

The subtle compromises we make day after day—the half-truths, the rationalizations, the excuses—create a gap between who we are and who we want to be. You’re not a terrible person, but you’re certainly not at your best either.

And if you got dead honest with yourself, you’d say that although you haven’t sold your soul to the Devil, you’ve rented it.

A thousand little compromises leave you … compromised.

3. DISCONNECTION

In the end, life and leadership are relational. It’s about your relationship with God and your relationship with people.

And since leadership is influence, it really depends on your ability to motivate people to a calling and cause beyond themselves, which again, depends on connection and relationship.

But something weird is happening in our culture. Technology is changing rapidly, and it seems to be changing us rapidly.

We live in a world where you can have five hundred friends and still feel isolated and abandoned. 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.

What it means for most of us is that a devious disconnect is underway. You and I are connecting with people, just not the people who are in the room with us. We’re having conversations, just not with the people we need to most. As a result, we’re sacrificing prime time to people we can’t hug or touch or see face to face. We might find ourselves paying more attention to someone we knew in college than the people closest to us right now.

And it’s making us feel very isolated. Nothing good happens in isolation. Solitude is a gift from God, but isolation is not—isolation is a tool of the Enemy.

If you wonder what can cap your leadership or take you out—being disconnected from the people you need to be connected to is a subtle but very real contender.

4. IRRELEVANCE

Irrelevance has a sting to it that catches many people off guard. The once-sharp leader is out of work at fifty and almost unemployable.

The preacher everybody listened to a decade ago speaks to a congregation that grows smaller and older with every passing year.

The entrepreneur who had several thriving businesses in his thirties now peddles ideas that just get blank stares—or, worse, looks of pity. The dad who coached Little League and whom kids adored now just sits at home anesthetized by the TV.

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.

Why is irrelevance a natural drift in almost all our lives? Here’s the problem: Culture never asks permission to change. It just changes.

And why is your ability to understand current culture so critical?

Simple. Relevance gains you permission to speak into the current culture.

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.

5. PRIDE

It’s so easy to spot pride. Okay, let me try that again. It’s so easy to spot pride in other people. There, that’s far more accurate.

You’re probably not a raging egomaniac or a diagnosed narcissist, but does that mean pride hasn’t snagged you?

Strangely, most of us don’t see ourselves as proud, yet many of us are. It should be no surprise that pride runs deep, because pride is, in many ways, the master sin. It’s the root of our rebellion against God, against others and even against what’s best for us.

Here’s why pride is so universal: 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.

It’s so pervasive that, as Benjamin Franklin observed, if you ever reached the point of becoming humble, you might find yourself wanting to boast about how meek you are.

What’s so surprising is that pride most often shows up in the form of insecurity.

Insecurity makes people just as obsessed with themselves as narcissism does. All you can think about is you.

Insecure people are afraid to have smarter people in the room. They want to hog the spotlight because they’re afraid other people might be better than them. The insecure constantly compare themselves to others.

Why does it stunt your leadership? Because you’re so preoccupied with yourself that you’ll never truly be able to advance others or even the mission. If you’re insecure, it’s all about you.

6. BURNOUT

Burnout is almost an epidemic among church leaders today, and it’s increasingly common among business leaders as well.

Even young leaders are burning out. No longer is burnout an “I’ve been at this too long” kind of phenomenon.

The more people I meet and the more I look around our culture, the more I think there may be many people suffering from burnout or what I might call “low-grade burnout.”

By that I mean the joy of life is gone, but the functions of life continue. You’re not dead, but you’re certainly not feeling fully alive.

The symptoms are not enough to stop people in their tracks, but they’re present enough to sap the meaning and wonder out of everyday life.

If you think you’re immune from burnout (I did … until I burned out), just remember that denial is an accelerator. Maybe you’re thinking you’re stronger than burnout. Chances are you’re not. Remember, you’ve got control until you fall off the cliff. Then all control is gone.

Or maybe you think you’re just tired or that the rules don’t apply to you. Well, good luck with that. Every day you remain in denial, you make burnout more likely, not less likely. Rather than care for yourself and deal with your issues, you push on, closer to the edge than ever.

Burnout isn’t inevitable, and it’s not final.

You don’t need to live this way, but too many leaders do.

7. EMPTINESS

Of all the challenges that take out leaders and stunt their potential, emptiness seems like a weird one.

After all, the other six obviously impact your ability to live and lead well.

But what’s the deal with emptiness?

Empty is a feeling I’ve had more than once in my life, most particularly after a peak. It happened after I graduated from law school, after our church became one of the largest in our denomination and after we finished a few multimillion-dollar building projects.

Don’t get me wrong. I’m grateful. Very grateful. But feeling grateful doesn’t leave you feeling full.

Feeling empty is something I’ve seen afflict a surprising number of successful people. It’s what causes lawyers making mountains of money to buy a lottery ticket and shout to their staff, “If I win this thing, you’ll never see my face again.”

In fact, the emptiness so many people experience in life is more intense in success than it is in failure. When you fail, you have nowhere to go but up. But when you’re up, when you’ve done what others have only dreamed of doing and you still don’t feel great … well, then what?

Most of us have this notion that Once I get to a certain place or achieve a certain thing, life will truly start in full, and I’ll finally be happy and whole. It just doesn’t work out that way. You graduate, but you find there’s still something inside you that says there has to be more.

You find the one, get married and have kids. And it’s great, but still, what’s that thing inside that says there must be more? You land a job and then a career job and then your dream position, but still, there’s a quiet-but-real gnawing inside that says it’s not all you imagined it would be. You pick different markers—time off, vacations and savings goals—but still the high continues to be short-lived. Keep going, and before you know it, you’ve convinced yourself retirement will fill the hole nothing else has been able to fill.

It’s quite the game.

It’s also a game you lose.

You’ve done everything you know to do, everything that was supposed to bring you satisfaction, and you still can’t help but feel a bit empty. What gives?

Well, for starters, you need a mission that’s far bigger than you.

You aren’t the mission. Your job is to point people to the mission—a mission worth spending a major chunk of their lives working toward.

Give people a cause, a mission to make a difference in the world, a way to help others, and they will rally. Let them know their efforts have made a difference in someone else’s life, and they’ll look forward to getting themselves out of bed.

There is no end to the sad discontent of making you the mission of your life.

Every time you make you the mission of your life, you feel empty.

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Carey Nieuwhof is a former lawyer and founding pastor of Connexus Church in Toronto, Canada. He’s the author of several best-selling books, including Didn’t See It Coming: Overcoming the Seven Greatest Challenges That No One Expects But Everyone Experiences. This article originally appeared on CareyNieuwhof.com.