Fake Eventually Falls

Expose Your Flaws Before Someone Exploits Your Failures

A few days ago, I recorded a podcast with Jack Eason who has a new book coming out called, The Loneliness Solution. He contacted me to have a conversation because of my last post, It’s Time to Talk About the Real Dangers of Wearing Masks. Specifically, he was interested in one of the most difficult questions I unapologetically ask people:

“Is the loneliness of leadership self-inflicted?”

The reason I refuse to relent on this question is because it strips away all the pretensions we use to protect ourselves and gets to the heart of being human. (And yes—it is self-inflicted.)

As you already know, aloneness obviously isn’t just an issue for leaders. This timeless problem transcends every aspect of life which is why it remains the cause of most of the unhealthy behaviors we employ to cover up the residual pain feeling alone exposes.

[Jack and I share the same vocation. We’re "professional Christians”. I look forward to doing an exclusive series on the unique aspects of our pastoral occupation later where I’ll share my views on how churches are guilty of creating an artificial culture that make it almost impossible for people of faith to live and lead with authenticity. Subscribe now to make sure you don’t miss it.]

Begin with Self-Reflection

The older I get, the more I find myself looking in the mirror and wondering where the years have gone. And I’m also asking harder questions than I want to answer—at least publicly. Here’s the one confronting my conscious lately: What have I really accomplished in my career anyway?

Some days, I ask that question and honestly believe the answer is—nothing. I can really beat myself up when I feel like it (which feels slightly better than someone else doing it to me). But there’s a fine line between self-reflection and self-pity. If you want to know if you’re practicing for a pity party, here are three telltale signs from Aletheia Luna:

  1. You find it hard to laugh at life and at yourself.

  2. You tend to crave drama.

  3. You tend to crave sympathy.

Self-pity lends itself to being fake and artificial. Self-reflection leads to becoming true and authentic. Introspection is the first step in revealing enough of yourself to connect with others. Now, you do need to practice some discretion because exposure creates exposure. My CompleMentor, Monty Hipp, shared that with me recently. [BTW: If you’re looking for a new personal growth and professional development plan, you must check them out.]

I’ve worked hard to be an authentic leader for 30 years, but I admit that I’m guilty of exaggerating my successes to compensate for my shortcomings in order to feel significant. Unfortunately, that formula is how most people attempt to meet the unrealistic expectations created by our culture. Demanding perfection every day isn’t possible—it’s damaging—because it forces people to perform which only increases their aloneness.

I’ve had enough. And I’ve come to a point where I am unwilling for the “alone” to be alone any longer.

If I have to reveal my weaknesses in order to remove the aloneness of others, then I will expose myself in every post and podcast I produce regardless of the risk. Because fake eventually falls anyway—so you and I might as well expose our flaws before someone else exploits our failures. People see through charades. So today, I want to give you some strategies toward becoming more authentic that have helped me from Tina Meilleur.

Reflect on the following tactics:

  • Get real about defining your authentic self.

    • What don’t others know about you?

    • What about your personality and your life lights you up?

    • What is so crucial to who you are that you can’t describe yourself without including those values and traits?

  • Paint a picture of how your present yourself—your “public” mask.

    • How would others describe you?

    • What are the things you try to portray when interacting with others?

    • What do you think you are trying to protect by portraying yourself this way?

  • Create an inventory of behaviors critical to expressing who you really are.

    • What behaviors are a true reflection of your authentic self?

    • What happens when you show your authentic self?

    • How do you feel when you exhibit these authentic behaviors?

  • Create a list of behaviors that have served you well in the past.

    • What are the behaviors and traits that you have portrayed and have served you well?

    • Have you experienced deepened relationships and interactions as a result of these behaviors?

    • Do these behaviors reflect your authentic self?

  • Craft a plan to utilize these new behaviors to illustrate your authentic self.

    • Can you take a risk and decide to be more vulnerable in your interactions?

    • Can you decide to let go of the fear of how others might react to you acting differently?

    • Can you embrace this new way of “showing up” more authentically because it makes you feel good?

Perfection + Production + Performance = Pressure

Undue pressure is the leading cause for anxiety in life—from the boardroom to the bedroom. No wonder people feel forced to fake it just to fit in today. I’m inviting you to join me and say, “I’ve had enough.” Be your authentic self in an artificial world. Let’s end aloneness once and for all and stand #togetherforone.


Additional Reading

A couple of years ago, Forbes published an article titled, The Real Difference Between True and Fake Leadership, I’d encourage you to read it today. Review their two apposing lists and ask yourself which camp you fit in most frequently. Be honest!

If you’re willing, please take a moment to share your own struggle with authenticity in the comments below. Your vulnerability may be exactly what is needed to help somebody through their struggle. So go ahead—expose yourself—you’ll feel better.

It’s Time to Talk About

The Real Dangers of Wearing Masks

The question about wearing masks during the COVID-19 crisis might feel major at this moment. But it pales in comparison to a far greater problem consuming our culture during this critical time—leaders masking their aloneness.

Whether or not you “mask-up” when you enter a gas station or grocery story today is your decision. I’m sure you have an opinion or position on the matter. I don’t particularly care one way or another what you decide. You have the right to choose.

And no. I’m not making light of the Coronavirus at all. But long before this disease was named or deemed a global pandemic, our world was already infected by an epidemic more deadly and damaging than we want to admit. And after COVID-19 has come and gone, this issue will remain because it can’t be cured by a vaccine.

Is the loneliness of leadership self-inflicted?

The world lost another fine leader this past week. Darrin Patrick died of a self-inflicted gunshot wound. While there will remain speculation about the actual cause of his death, there’s no doubt he suffered. Like so many other leaders, this poor man struggled with the pressures of his profession until the pain was unbearable.


In the last few years, I have been saying—without apology—that the “loneliness of leadership is a self-inflicted wound”. In other words, it’s manufactured. We choose aloneness as leaders more than we’re comfortable confessing. But the problem is real. Because leaders live in a world where people prefer we hide our flaws behind a facade.

Pastors, politicians, parents—people—we all tend to pretend. And in the end, everyone pays a terrible price. Maybe that’s because since the beginning of time we’ve always preferred the lie. Always struggled with trust. And always sought to control.

A couple of weeks of ago, I did a Zoom call with a group of influencers on this topic. I asked them how they deal with the “loneliness of leadership” struggle. Almost to a person, they each admitted, “I don’t.” Why? Because the potential for criticism it too high a price to pay. Sharing your burdens has become a recipe for vocational suicide.

How ironic. Not sharing your burdens results in the same outcome far too often. And while it might not always end in literal death, the decision to disguise is still deadly. Many leaders are dying inside. Their relationships suffer. And their health does, too.

No one wants to see behind our masks and witness the weakness we all share. They’d rather we breathe in our own bacteria. But that cannot be an excuse anymore. We cannot give into the insecurities of those we serve. It’s time for a new “normal” if you will. And like the COVID-19 crisis, it will come with a cost. But the alternative is worse. Just ask Darrin Patrick’s family. And by the way, don’t think you’re immune!

I’d love to hear your thoughts on this matter. But only share if you can be honest.

  1. Do you wear a mask to protect your identity and reputation?

  2. What is your greatest fear of being authentic and vulnerable?

In my book, Alone Sucks: God’s Cure for Our Human Crises, I quote Pastor Rick Warren,

“The most exhausting activity is pretending to be what you know you aren’t.”

As I turn 50 this year, I’m getting ready to take a deep dive and distance myself from working exclusively in ministry, which has been my vocation for 30 years. After three decades of leadership, I’ve determined that the need to help people live and lead with authenticity in an artificial world is a bigger issue I must tackle. I hope you continue to join me on my journey. I’d love to help you become healthy and whole in your role.

Please subscribe to continue to read my blog and listen to my upcoming podcast, Square Peg Round Hole™, where I will talk about ideas that just don’t fit the norm.

Thanks for answering the questions above in the comments below. Or feel free to connect with me personally at: tim@timothyeldred.com. I’m happy to listen. And please, share this post with others. Let’s make sure no one feels alone in leadership.


The Secret Powers of Your Mailbox

A 21-Day Challenge to Improve Your Life and Leadership While Social Distancing

My fingers are stained with ink from my fountain pen today. But I’m not complaining. It’s a small price to pay to connect with people I’ve not seen in-person for a while.

In these days of cell phones, email, and text messages, writing is a lost art. But it’s worth bringing back. Because writing offers an experience technology can’t touch. Facebook and Twitter are terrific ways to tell others what you just ate. And email works for a quick exchange of ideas. But for sharing matters of the heart, nothing compares to handwritten words.

Because sending a letter is the next best thing to showing up at someone’s door.

Words crafted with your own hand hold significance. They display a deep connection to the reader. The thoughts you pen come from a place of intimacy that subtly communicate, “You matter.” There’s value to words etched into the fibers of fine velum.

In this time of social distancing when life-on-life is limited, handwritten communication is the best alternative to being in-person. With a push of a key or the swipe of your finger, digital communication is instantly deleted. But handwritten letters have the ability to last a lifetime.

There’s a folder in my desk of correspondence I’ve received over the last 30 years I hold dear. Most of these letters and notes were sent as words of encouragement. As I rifle through this file, I’m reminded of the impact of these thoughtfully written words. And I’m certain that when I’m gone my sons will read them and realize why I held on to these timeless treasures.

As I get older, I’m giving more consideration to my legacy. And I’m wondering, “Does anyone have my handwritten letters in their drawer?” Maybe a few people. But certainly not enough.

Words matter. My wife uses that phrase constantly. Cindy is always writing to people. She never misses an opportunity to put her thoughts on paper. Because she never wants anyone to ever wonder how much they meant to her. So today, I’m taking a lesson from her playbook.

This morning I took out a stack of personalized notecards and envelopes from my desk, filled my pen with fresh ink, and made a list of people I care about deeply. Then I lit my favorite pipe and started to write making sure to share my heart with sincere and honest words.

My desire to help people live and lead with authenticity in an artificial world requires that I continue to create healthy habits in my own life. But I want to encourage you to join me. So I’m offering a challenge to help you improve your own legacy as well.

Write at least one handwritten note or letter to someone for the next 21 days.

I still open the mailbox every day in hope of finding more than bills and credit card applications only to be disappointed with what I find. But then I remember my mom’s words when I was a kid, “If you want to get mail, you need to send mail.” That is still true today.

But perhaps we haven’t written a letter in so long we have forgotten the format. No, really? This used to be taught in school—I don’t know if it is anymore. So just in case you need a refreshed since snail mail is no longer favored, I’m going to offer some instruction below.

My hope is that you will give serious consideration to my thoughts and take me up on this simple challenge. I am confident that it will enhance your own life and leadership while it creates lasting memories and impressions on the lives of those to whom your write. If you’re up to the challenge, please click the button below and tell me!

I'm taking the challenge, Tim!

Order Empathy and Encouragement Cards from Tim

Use code ALONESUCKS2020 for a limited time BOGO offer. Shop now!

Tools and Techniques


As I mentioned earlier, writing is a lost art. And art requires tools and techniques. A couple of years ago, I designed my own notecards and envelopes (see pic at top). I chose notecards over stationary simply because it requires fewer words. This isn’t easier or a shortcut. Saying something meaningful is harder when you have less space.

If you’re interested in creating you own notecards, you can download the free design files here. I’ve included multiple formats to make it easier. If you go this route, I suggest you use GotPrint.com. I’ve never found better printing for a better price.


Again, I mentioned that my preferred utensil for writing letters and cards is a fountain pen which requires practice. There’s something unique and sophisticated about using this tool for writing. But you should use the pen that’s most comfortable in your hand.


Since I send notecards, I don’t always follow conventional rules for writing letters. But I thought I’d refresh your memory on the standard five parts of any letter:

  1. Date
    I like to add the date to my correspondence regardless of format. People may search their folders of warm fuzzies someday and wonder exactly when you sent that gem.

  2. Greeting
    I’m sure this seems like common sense, right? But in our informal society, it think it bears mentioning that it’s best to use a person’s name instead of saying, “Hey, Dude!”

  3. Body
    I don’t write lengthy messages. I’m more concerned with quality than quantity. In order to utilize the space best and keep from making mistakes, I practice on scratch paper.

  4. Closing
    I believe this element of the letter shouldn’t be taken lightly. Over the years, I have used different closings. Today, I sign 99% of every correspondence with “You’re Not Alone!

  5. Signature
    I think a person’s signature is sacred. When I receive a signed letter, it holds weight. If I get unsigned correspondence, I typically throw it in the trash. Always sign your letters.

Square Peg Round Hole™ with Timothy Eldred is created to help you live and lead with authenticity in an artificial world. Subscribe now for free for this blog and podcast below. To learn more about the mission of Square Peg Round Hole™, please go here.

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