Why Pessimists (and Realists) Are Hard to Follow as Leaders

So…if you had to describe yourself, would you say you’re an optimist, a pessimist, or as pessimists like to say in social settings to be polite, a realist?

For the record…my current theory is that realists are pessimists who don’t want to call themselves pessimists.

Most leaders (not all, but most) are optimists when they start out. I was. I’m an idealist.

But as you may have discovered, your optimism gets tested—really tested—in leadership.

Leadership not only throws you curve balls, it throws you hardballs. As in a 103 mile an hour fastball aimed right at you.

Which is why so many leaders find themselves in a place where they hardly recognize themselves anymore.

The budding idealist feels his heart go flat.

The eternal optimist finds herself rolling her eyes the next time someone says “Hey, I have a great idea.”

And the guys who used to roll out of bed in the morning excited about the future now thinks about the grind and winces at the thought of yet another meeting where nothing will get accomplished.

Recognize that person?

For so many reasons, I found my pessimism growing exponentially in my first decade of leadership.

Then, after a tough battle with burnout, came out on the other side to reclaim my optimism, which is, fortunately, absolutely possible. (I outline the journey and the principles on how to do it here.)

Here’s what I’ve learned. Pessimism and cynicism go hand in hand. Scratch the surface of a pessimist, and you’ll almost always find a cynic.

Sure, it’s hard not to grow cynical in the world we live in. In fact, a lot of people think cynicism is inevitable in life and leadership. That once a cynic, always a cynic.

But here’s the truth. Life doesn’t make you cynical. Leadership doesn’t make you cynical. You make you cynical.

Cynicism and pessimism aren’t inevitable and they are reversible.

If you’re interested in some help with that, I just released a free 5-day devotional plan on YouVersion that can help you wrestle down cynicism. (The surprise for many people is that their cynicism is also a spiritual issue.)

And if you want deeper motivation to change, how about this, leaders? It’s harder to follow a cynic than it is to follow an optimist in leadership.

Cynics think they’re better leaders because they have it all figured out.

But what they miss is that it’s actually really hard to follow a cynic for at least three reasons.

Here they are (and there’s some big help at the end of this post too…so keep reading.)

Life doesn't make you cynical. Leadership doesn't make you cynical. You make you cynical. Share on X

1. A Negative View of the Future Inspires No One

Has a pessimist ever inspired you?

Didn’t think so.

What unites cynics, pessimists and realists? A negative view of the future.

The financial forecast is bleak.

The trends are negative.

People have tried this before, and it hasn’t worked. And while it may be a great idea, pessimists can tell you 100 reasons you’re probably going to fail.

Guess what?

A negative view of the future inspires no one.

Cynics never change the world. They just tell you why the world won’t change.

Cynics never change the world. They just tell you why the world won't change. Share on X

Even in the throes of one of the darkest moments of the 20th century as Hitler swept over Europe, Winston Churchill saw how bleak the future looked and–against all odds—cast a vision for hope and freedom.

People thought Churchill was naive and stupid. Fortunately for millions, his stubborn vision for a better world won the day.

There’s a fine line between discernment and negativism.

The discerning see the obstacles, plan for them, and then forge ahead with hope. And they inspire dozens, thousands or millions to follow.

There’s enough darkness in the world. What the world needs are brokers of hope.

A negative view of the future inspires no one. Share on X

2. Pessimism Has No Vision For The Future

One of the challenges of having a consistently pessimistic view of life is that you end up with no vision for the future.

Pessimists know what’s wrong. They just can’t figure out what’s right. Similarly, pessimists don’t know what they’re for. They only know what they’re against.

How can you build a vision for the future around that?

Exactly, you can’t.

When cynicism and pessimism infect the senior leadership of any organization, vision becomes a serious challenge.

Instead of focusing on what they can accomplish, pessimistic leaders focus on what they can’t accomplish. As a result, nothing gets accomplished.

This is why, when a negative mindset takes over the senior leadership of any organization, you see a shift from leadership to management.

Instead of leading into a better future you create, you manage the current reality you have.

Sure, leadership without management produces chaos.

But management without leadership produces a constantly shrinking organization.

If you have no vision for the future, you end up with no future.

Pessimists know what's wrong. They just can't figure out what's right. Similarly, pessimists don't know what they're for. They only know what they're against. Share on X

3. Encouragement Will Die…Fast

I recently heard Frank Blake, former CEO of the Home Depot, drop this line in an interview he was giving:

We’re all pretty disappointed in ourselves.

Then he dropped the mic. No, he didn’t, but okay, he could have.

You know what most of us need every day?

Encouragement. Massive encouragement.

I have never met a single person I encouraged who said Carey, can you please stop? I’ve had my lifetime dose of encouragement. I’ve had enough.

Anyone who has sat down with a board of bean counters or cynics knows how frustrating it can be to share ideas knowing that they’ll be shut down or spun in the most negative light.

I agree with Jim Collins, reality is your friend. So is sober thought.

But fundamentally leaders are dealers in hope. You have to find the gold in people (thank you Brian Houston). Your job is to find the one thing that might work in a sea of things that won’t work.

Encouragement is the fuel people run on.

If you want to motivate your team, encourage them, deeply, honestly and constantly call out the best of them.

If you want to discourage your team, point out why everything they’re doing won’t work.

If pessimism infects your culture, encouragement is one of the first casualties. And when encouragement dies, so does hope.

If pessimism infects your culture, encouragement is one of the first casualties. And when encouragement dies, so does hope. Share on X

Motivated? 3 Things That Will Help You Reclaim Your Optimism

If you need some encouragement and some concrete help to overcome cynicism, pessimism and negativism, here are three things that can help.

A Short Cynicism Quiz

How badly infected has your mindset become? It’s a good question, and it can be hard to tell.

I developed a short, free cynicism quiz that might help you assess where you’re at.

You can take it for free here

A New 5 Day You Version Plan on Beating Cynicism 

I really believe cynicism and pessimism are spiritual problems.

At least my journey back to optimism was a spiritual problem for me.

I created a five-day devotional plan on YouVersion that you can do for free here.

This might even make a great team devotional or congregational devotional if you’re a church leader.