Square Peg Round Hole

Square Peg Round Hole

Ever feel like you don't fit? Like you can't be real? In other words, you have to fake it because you're not accepted as your true self. Yeah, that seems about right. And ridiculous. Every day people from every background—not just you—put on masks to make it through life. Talk about exhausting. But we keep doing it because no one wants to talk about the insanity of it even though it keeps us from being our best. Well, that's about to change. Welcome to Square Peg Round Hole with Timothy Eldred, writer, speaker, and friendly disrupter of the status quo on a mission to end aloneness and help people live and lead with authenticity in an artificial world.


March 9, 2023 26 mins

You don’t want to miss this episode. In my opinion anyway (but I’m biased).

Clearly, I’ve been away from the microphone for a few weeks—much longer than even I expected for sure. But I’ve had good reason. And the lessons I’ve been learning during this hiatus have only helped to strengthen what I’ve been wanting to say to my loyal listeners as I talk openly about my recent experiences. 

As you can ascertain from the title, my emphasis...

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Sometimes life feels insurmountable. Those are the moments when you don't believe you have the strength or stamina to overcome the obstacles in your path—the seasons when you seriously consider giving up.

You're not alone. We all face seasons in life when molehills feel like mountains. But there's always hope if we will learn to pause long enough to catch our breath and recalibrate to do the climb that lies ...

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October 27, 2022 27 mins

"If it doesn't bring you peace, profit, or purpose, then don't give it your time, energy, or attention." —Unknown

I posted that quote on social media over the last few days. As you might suppose, the response was affirming. Because it just makes sense, right? 

So why does such simple wisdom appear to be so difficult to implement in our lives? Why do we give our time, energy, and attention away ...

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October 13, 2022 25 mins

No one likes to admit the possibility they might create the majority of their own problems or that they are the source of their own pain. Even considering the idea is slightly embarrassing. Or shameful.

But is it true?

I hate to be the one to tell you, but it’s true. Most of our pain is self-inflicted.

Deliberately? Not usually. Inadvertently? Most likely.

Until we even ponder that possibility,...

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September 30, 2022 21 mins
Does that title sound a bit harsh? Well, it is certainly abrupt. Why? Because sometimes there's no sugarcoating the truth. And the truth can hurt. But there are times we need someone to speak boldly and get our attention. That's what I hope to do for us in this episode. 

My goal is to both challenge and encourage us all to remember the power we possess—the power of choice. We can choose what we listen to. An...

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September 8, 2022 26 mins

We overthink.

And the thoughts bouncing around in our brains shape our world and become our reality. We also take life too seriously. Is it any wonder we are so emotionally stressed and uptight? 

What would happen if we chose to relax, care less, and see life as a beautiful gift? Because it is precisely that, my friends. That truth is available for everyone to experience every single day.

You don't ...

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August 22, 2022 21 mins

Most of the time, many people who are trying to make significant and lasting changes in their life do one major thing wrong—they go too far too fast. It's like quitting a habit cold turkey. You are either going to fail now or relapse later because you bit off more than you can chew.

Well, breaking free from the acceptance of others is even harder because of the emotional addictions we suffer from in life that keep us ...

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August 4, 2022 25 mins

Have you heard the phrase (or used the phrase) I need to put on my face? It’s an idiom about putting on makeup; however, the concept can be applied in much broader terms. Because we all put on a “face” of sorts. Our face (or public persona) is the outward identity we reveal to others which may or may not portray the true, authentic you. 

In this episode, I talk about the idea of not only taking off your mask but actually c...

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July 7, 2022 24 mins

Have you noticed that it's nobody's fault anymore? No one is responsible. For anything. Personal responsibility is becoming ancient history. It's no longer a virtue we value.

Everyone wants to fight for their rights. But few want to be held accountable for their behavior. For their personal choices. Does life actually work that way? Has it ever? 

I'm wading into that idea today with a point o...

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What is love anyway? Has it been so exploited or so poorly explained that we really have no idea anymore? Maybe our ideas about love are the very reason we don't understand it in a healthy way. Or perhaps it's only my perspective on the whole subject that is wrong. Who knows? But either way, that's my focus on this episode for your consideration. My goal is to be encouraging, but I'm fine with challenging our th...

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June 9, 2022 21 mins

The ‘middle ground’ of compromise is becoming scarcer and scarcer. Tolerance—once a cherished concept in our world—has disappeared from our human vernacular. 

We are a harshly divided world. Is that the way it has always been? Or is it getting increasingly worse? Are we broken beyond repair? Is there a bridge from the chasm of conflict to one of decency and dignity? We’d better start answering these questions.

In this episo...

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May 19, 2022 25 mins

Life is change. And change is hard. That about sums it up, right. Every time we turn around we have to adjust to some occurrence in the world—or in our personal world at least. Obviously, that's not a newsflash. But how do you make good decisions when it comes to inevitable change? How do you discern where to invest your time, energy, and emotions and pivot to experience the greatest benefit? That's the heart of the quest...

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Here are two truths: 1) Everyone has a story. 2) Change is hard. On this episode, my guest, Dai Manuel, discusses both of these realities from his life.  Our conversation is honest and practical for anyone seeking any kind of holistic transformation: body, mind, and spirit. If you’re looking to make changes to your life, please listen and also check out his simple but effective programs and training. I am on day 10 of his 28-day ch...

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April 17, 2022 18 mins

There's no one alive who doesn't carry baggage. Yes, even you. It might be the pain of the past that has followed you around for years—even decades. It could be current problems looming over you that seem impossible to shake. Baggage comes in all shapes, sizes, and colors. Baggage has different names and labels. Regardless, it's heavy. And it's a drag to drag around. The question we all have to answer is how lon...

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Conversations don’t have to be confrontations. They can simply be honest, transparent, and vulnerable dialogue. But how do you create conditions for productive discussions? Simple. You come to the table ready to listen and learn something new about the other person. And you come without the need to prove a point.

This week on Episode 10 of Square Peg Round Hole, I invite you into an authentic conversation I had recently wi...

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March 10, 2022 25 mins

There are only two areas of life—two—what you can control and what you can’t. You know the saying: 10% of life is what happens to you and 90% is how you respond to it.

When you focus on what you can control, you become strong. When you ignore what you can’t control, you become free. So that means you must give 100% to the 10%. 

And while all of that sounds cliché and trite, it’s remains absolutely true; nonetheless, we seldom adjust ...

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February 24, 2022 24 mins

You know that story you keep telling yourself? Yeah, the one you keeping playing over and over again on a constant loop. The one that keeps you stuck in the status quo of life. Isn't it time to knock that off? Of course, the answer is yes. But how exactly? How do you stop self-sabotaging? Well, it's not terribly difficult. But that doesn't make it easy either. So here's the big idea: You start by telling yoursel...

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February 17, 2022 74 mins

Is there a relevant connection between the life of an NFL player and the average person? It might not seem like it at first glance because of the glitz and glamour that comes from being a professional athlete, but you'd be wrong to make that assumption. Real people have real pain and real problems. Regardless of our role, position, or profession, life has challenges. On today's episode, I have a conversation with my frien...

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February 10, 2022 74 mins

I love conversations that challenge my thinking because that's the beginning of learning. Well, on today's episode, my guest, Jeff Goins, didn't disappoint. I never even got to the questions I wanted to ask because Jeff just jumped to warp speed and took me on a journey I'm still processing. What made this conversation so powerful was the authenticity (even though it wasn't about authenticity). This discuss...

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February 3, 2022 44 mins

Today,  I continue my conversation with Monty Hipp about trust as we discuss 10 contributions to building trustworthiness in your life. These nuggets of truth are valuable whether you've broken trust like we talked about in part one of our conversation or not. Before we dive into the issue of trust, we lay some essential groundwork of what it means to not only have a mission but to live in mission in life. Regardless of your r...

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