The Five Traps Keeping You Stuck

#1 Obsessing about Regret and "What Ifs"

Chapters in this Guide

1. Man Down - Introduction

2. Why I’m Writing this No-BS Guide to Grief for Men

3. What the Hell is Grief Anyway?

4. How and Why Men Grieve Differently

5. What Grief Looks Like for Men in the Real World

6. The Traps Keeping You Stuck

   1. Shoulding All Over Yourself

   2. Trap #2 - Destroying Yourself by Avoiding the Pain

   3. Trap #3 - Locking Everything Away to Survive Another Day

   4. Trap #4 - Trying to Outwork the Pain

   5. Trap #5 - Playing the Victim

7. From Traps to Tools

8. The Tools

   1. How to Focus on What’s In Your Control

Sometimes, the best move a grieving man can make is not screwing things up even more. The problem is, there are a million ways to do just that. And in the moment, they can all look so damn tempting. They seem much less awful than facing the shit you’re already dealing with.

The pressure is so intense you can't take it anymore. You know you shouldn't give in. It didn't help last time. But you're so, so sick of fighting it. You're done feeling like garbage. All you want is a moment of relief. So you say, "Fuck it."

You take the drink. You smoke the joint. You watch the porn. You stay late at work again. You lock yourself in the dark basement alone. You lose your shit on people who love you. You'll do anything to escape.

But there is no escape. The drinks wear off, the high fades, the screen goes dark—and the pain is still there, waiting. Only now, you’ve added another layer of guilt, shame, and regret to the pile.

The very thing you turned to for relief drags you deeper into the hole. That’s the trap, brother. It feels like you’re taking control, but all you’re doing is giving the pain more room to own you.

I'm writing this as a guy who's tried them all, countless times. I've continued to try them even when I know they won't work. I've told myself, "Just do it dude. You've suffered enough for now." I still struggle with smoking pot to cope with the pain. And when I do, it messes with my head.

I'm writing this for me, as much as I'm writing it for you.

There are a hell of a lot more than five traps grieving men fall into. If I tried to cover them all, this guide would be a thousand pages long. So in the interest of keeping this brief, I'll talk about the ones I see most often. In myself and in the other guys I've spoken to.

Obsessing about Regret and "What Ifs"

Grief makes the past feel like a crime scene you're forced to keep revisiting. You pick apart every detail, looking for where you screwed up. And when you do that, you'll always find something. Always.

· I should have called them that night—it could’ve changed everything.

· Why didn’t I push harder to get them help sooner?

· If I had said 'I’m sorry' one more time, things would’ve been different.

· Why didn’t I notice the signs? How could I have missed it?

· Why did I spend all that time at work? Now they're gone and I'll never be able to make things right.

· Why did I say some of the stupid shit I said when I was mad? I didn't mean it and now I can never take it back.

I'm grateful that I understood this trap and how to avoid it after Chloe's death. And still, a few weeks after she died, I found myself in a horrible doom loop.

I remember sitting in my car, bawling my head off. "I wasn't up to the job of being the dad she needed," played like Hell's broken record in my head. I couldn't make it stop.

Chloe was dealing with very serious mental health issues as a result of her mother's suicide. The loss of her mother shattered her soul in a way she was never able to recover from. Her young life had become completely unmanageable.

Hindsight can be a wonderful teacher or a total curse. As I look back, I see many times I could have said or done something different. I could have listened to my wife when she told me what she was seeing. I could have pushed harder when I suspected Chloe was lying to me. I could have tried harder to force her to get treatment.

A few weeks before Chloe died, I sat in a dear friend’s office—a counselor I trust. I was worried sick and needed to know what I was missing. What else could I do to help my daughter before it was too late?

After Chloe passed, she sent me a message that changed something in me. She reminded me that Chloe’s struggle was deeper than anything love alone could fix. She said, “Some people need more than it’s humanly possible to give.” She reassured me that I had done everything I could with what I knew, but Chloe wasn’t ready to let anyone in—not me, not anyone.

She told me, “The dad she needed was the one who sat in my office, trying to help her.”

That hit me like a freight train. I hadn’t failed her—I’d shown up the best I knew how. But Chloe was fighting battles I couldn’t see, and she wasn’t ready to be saved. That realization hurt like hell, but it was also the start of some kind of peace.

I was not a perfect dad or person. No one is. But I did my damn best and I'm OK with that. Most days.

Why Do We Torture Ourselves Like This?

Let’s be real. Whatever loss you’re grieving, you messed things up before the loss. It might have been a colossal screw-up. Or it was a bunch of small things that didn’t seem like a big deal at the time. We’re human—we say and do shit that doesn’t turn out how we want.

I talked to a man a few months after Chloe died who’d lost his daughter a few days before. Their family situation was complicated and difficult. He hadn’t been present in her life. And on the day she died, her last online post was about how her dad had let her down.

Absolutely brutal. Listening to devastated dad tear himself to shreds broke my heart.

The trap snaps shut when your mind convinces you it’s better to blame yourself than accept how powerless you were. Your mind goes to war with itself.

Self-blame feels like action, like you’re taking responsibility—but it’s a lie. It's your mind’s way of pretending you had control when you didn’t.

Let's be real here. Sometimes (most times), you really did make some huge mistakes — and it tortures you. You know that if you’d done something differently, things might have turned out another way.

Maybe you delayed fixing the brakes. Maybe you brushed off a red flag because you were too tired or distracted. Maybe you let your anger get the better of you and said something horrible or hurtful. The pain from that kind of regret isn’t imaginary—it’s real. And it’s a special kind of hell.

Regret might explain the past, but it doesn’t have to define your future. It tells you your mistake is a life sentence, but it’s not. Owning your part, as brutal as it feels, isn’t about beating yourself to a pulp. It's about facing the truth, learning from it, and not letting it destroy what’s left of your life.

I’ve lived this. I’ve screwed up in ways that still haunt me. Some regrets I live with. But that doesn’t mean they get to live rent-free in my head forever. And some of those regrets? I own them. But owning them doesn’t mean they get to own me.

Regret can either bury you or teach you. And the difference comes down to this: will you carry that regret like a boulder that crushes you? Or will you put it down, face it, and figure out how to live better because of it?

A few months after losing Chloe, I read a powerful book called Finding Meaning: The Sixth Stage of Grief. A guy named David Kessler is the author and he's one of the world's foremost experts on grief.

He explains that replaying the "what ifs" and guilt-tripping yourself is your mind's way of creating the illusion of control. You convince yourself that the right move could’ve saved everything. But sometimes, no matter what you do, the wheels still come off. The chaos wins. And guilt becomes your brain’s way of pretending you had power when you didn't.

Kessler’s point? Guilt isn’t proof you failed—it’s proof you cared so much that you're willing to put the blame on yourself, even when it's undeserved. The way out isn’t pretending you were perfect. It’s learning to see that blaming yourself doesn’t change the past

Here’s the truth—sometimes, you can do everything right, and life still falls apart. Guilt becomes your brain's way of pretending you had power over the storm when you didn’t.

And that's the trap—guilt pretends to be noble, like you're owning your mistakes. Instead, it chains you to something you can’t change. It tricks you into seeing yourself as the villain—the one who ruined everything—even when no hero could have saved the day.

It’s not that your best wasn’t "good enough"—some fights can’t be won, no matter how hard you try. Your best wasn’t the problem—you’re human. And sometimes, being human means facing things that are too damn big to fix, no matter how much you care or how hard you push.

You can’t rewrite the past, but you can choose how to carry it. The goal isn’t to forget—it’s to live in a way that honors them without destroying yourself. Moving forward starts when you put down the blame and start living again.

The goal isn’t to forget them. It's to put down the blame. And it's to live in a way that honours their memory and lets you move forward without destroying yourself.

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YOUR NEXT STEPS: Learn The Most Important Relationship Skill You Were Never Taught

Ever been in a conversation where someone was grieving, upset, or overwhelmed—and you had no idea what to say?

Maybe you tried to cheer them up, offered advice they didn’t want, or just froze, unsure of how to help. And afterward, you couldn’t shake the feeling that you could’ve shown up better.

💡 You’re not alone. Most people struggle with this—not because they don’t care, but because no one ever taught them how.

That’s why I created The LEAD Model Training—so you can stop second-guessing yourself and start being the person people turn to in their hardest moments.

Here’s What You’ll Walk Away With:

✅ A simple, repeatable framework (Label, Explore, Acknowledge, Decide) that works in any emotional conversation.
✅ Confidence in what to say (and what NOT to say) so you never feel awkward or unsure again.
✅ Proven techniques that make people feel deeply heard—without forcing them to open up.
✅ Real-world role-play scenarios so you’re not just learning, you’re practicing.

Most people:
🚫 Jump to fixing before someone is ready.
🚫 Say things that make people shut down without realizing it.
🚫 Avoid tough conversations altogether out of fear of saying the wrong thing.

But the people who get this right? They build deeper relationships, gain unshakable trust, and become the person others turn to when it truly matters.

🔥 If you’re ready to stop feeling helpless in emotional conversations, join the LEAD Model Training today.