Trap #4: Trying to Outwork the Pain

Trying to outrun grief is like sprinting faster to escape your shadow.

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

I was sitting in my backyard on a perfect summer afternoon. I'd finished work for the day. The sun was shining, and I had a book in my hands from one of my favorite authors. I cracked it open, ready to get lost in the story. It should have been perfect.

Two minutes in, the voice showed up. The one that always did. He can be a real bastard.

"This is a waste of time. Shouldn’t you be doing something productive, you fucking idiot? You only get one shot at life, and you’re pissing it away. Like always. You’re not living up to your potential, jackass."

This wasn’t new. It was a loop I’d been stuck in for quite a few years. I’d already told myself I needed to stop this constant grind, this compulsion to do more, to chase some imaginary finish line I’d never cross. Knowing it was a problem, though, wasn’t the same as solving it.

I stared at the pages, fighting the urge to close the book and “be productive.” But either way, I was losing. If I gave in, I’d lose. If I stayed, I’d still lose—because I couldn’t focus on the book. I was too busy beating the hell out of myself.

Every day, I set ridiculous goals for myself—and every day, I fell short. I’d decide to fast all day, and last twenty-one hours instead of twenty-two. I'd commit to walking forty thousand steps and beat the shit out myself for only walking thirty-eight. I’d knock out ten big tasks and rip into myself for not doing twenty-five.

From the outside, I was living a dream. Nice house. Six-pack abs. Career firing on all cylinders. A new business taking off. I was an engaged dad, showing up for my kids.

On the inside? I was going nuts. Like trying to scratch an itch I could never quite reach.

As I was sitting there, staring at the book, my wife sat down beside me. I turned to her and said, “I need to see a therapist. I’ve got to figure out why I do this to myself. I wasn’t always like this. I don’t know what the hell happened.” True to form, I booked the appointment that day. If nothing else, I knew how to take action.

I dove right in during our first session. I tried to convince him that three hours of intense exercise every day was totally normal. I'd throw on a 50-pound rucksack to walk back and forth to work. I'd stop and do pushups on the sidewalk all the way there and back. I'd hit the gym for a weight workout at lunch. Then we'd walk the dog in the evenings.

When he suggested what I was doing was excessive, I shut him down. “What are you talking about, dude? I’m super fit, and I feel great. That’s what high achievers do. Let’s talk about something else.”

Then, in another session, I told him about one of my most painful moments since Cindy's death.

We’d found a letter Chloe wrote to Cindy, her dead mom. Chloe was sixteen. She wrote about how she’d never felt good enough, like she wasn’t worth Cindy staying alive for. She told her how much she loved her, how much she missed her, and how much she hated her for leaving.

My wife texted me a picture of that letter while I was at work. Reading it took my breath away. I felt like my heart had been ripped out of my chest. I sat in an empty office, reading it over and over, and cried for half an hour. Seeing my daughter’s pain in her own words crushed me.

I hardly ever felt anger toward Cindy for killing herself. I knew how hard she fought and how much she suffered. I used to think I’d have given up long before she did. But that day, reading Chloe’s words, I felt a deep, burning anger. I was furious at Cindy for the pain she’d caused our girls, for the wreckage she left behind.

I told the therapist this, and he hit me with a question that changed how I looked at the world. “Anger is almost always a secondary emotion. What do you think you were really feeling?”

I thought about it for a moment. “Helpless,” I said. Then it all came pouring out.

My daughters had been through hell after Cindy’s suicide. Their pain was so raw, so deep, and I couldn’t fix it. There was nothing for me to fix. I could love them, support them, be there for them—but their healing was their own. I was helpless to take their pain away. That’s a tough pill for a dad to swallow.

Then I thought about the five years leading up to Cindy’s death. Watching mental illness destroy her while I stood by, unable to stop it. Her mental health struggles determined what our days looked like, not me. I wasn’t in charge of my life. I was a passenger on a train wreck, powerless to stop it or get off.

Helplessness.

And then there was the booze. Drowning the pain, numbing the anger. Before I knew it, I was an addict, enslaved to the very thing that was killing me. I tried to quit a million times and failed every time. And the emotion that defined those moments?

Helplessness.

In that moment, it finally clicked. My obsession with overachieving wasn’t ambition. It was fear. I was terrified of ever being helpless again. So I pushed harder. Achieved more. Learned more skills. Controlled more variables. Anything to prevent me from being powerless again.

It blew my mind to realize fear had been running my life for years. Without me even knowing it.

I knew I had to break the cycle because nothing would ever be enough. It was a fool’s errand—a race with no finish line. There would always be more to do, bigger challenges to take on, higher targets to hit, and more to control. The answer wasn’t doing more. It was facing the fear and healing the pain.

And then, a few years later, my daughter was gone too. I tried to save her, but I couldn’t. It was as if God was driving the point home—showing me just how powerless I really am.

I thought hustling harder would save me—from helplessness, from grief, from failure. But the harder I worked, the more I realized: you can’t outwork the things that you have to face. That’s not strength; it’s avoidance. And I’m not the only one who’s fallen into that trap.

Your job as a man is to protect and provide for your family. Grinding feels right—productive, even noble. Especially when the people you love are drowning in grief. Staying busy gives you purpose, even when the pain is so deep you’re just going through the motions.

It’s comfortable to stack your schedule with calls, tasks, meetings, and errands. It makes you feel indispensable. It makes you feel in control. But there’s a dark side to all that motion. When you’re trapped in the cycle of constant hustle, you’re not running your life—it’s running you.

For a lot of guys, the grind isn’t about ambition—it’s about escape. The endless to-do list keeps you too distracted to ask hard questions: Why am I doing this? What am I running from?

But pain doesn’t disappear just because you’re busy. It’s like a sniper, hidden and patient, waiting for the perfect moment to take you down.

Sometimes, you’re not working hard because it’s essential.

You’re working so hard because it keeps you distracted. Distracted from the weight of loss, from your fears, or from the stuff you’re too uncomfortable to face. The to-do list becomes armor—a shield from asking hard questions: Why am I doing this? What am I running from?

You can’t outrun grief, regret, or emptiness by staying in motion. That’s like trying to escape a shadow by sprinting faster.

The Lie of More

We’re taught to believe that doing more is the path to success. Society sells us this endless loop of hustle: wake up earlier, stay later, push harder, and for what? Validation? A sense of purpose? Approval from people who aren’t living your life?

The constant hustle feels like strength, but it’s not. True strength is knowing when to stop. When to pause. When to be honest about what’s actually driving you.

The Weight of Grief

Chloe's death shattered the foundation of my self-identity. I'm a guy who gets shit done. I outwork people. I make an impact in the world. No matter what. But after she died, that version of me was unrecognizable. It took me a month to start functioning again. And even then, my capacity was so low that everything felt overwhelming. Basic tasks—getting out of bed, returning a phone call, answering an email—felt impossible.

At one point, about a month after she died, I tried to start writing this book. I was determined to work hard and win at grief, like it was just another challenge to conquer. It was nuts, but defaulting to work was all I knew. And despite how broken I felt, I kept trying. I was still running the same old program, convincing myself that if I pushed through, I’d somehow be okay.

It’s taken me two years to claw my way back to some level of capacity that feels familiar. And even now, I know I’m not the same. Maybe I never will be.

Grief isn’t just about sadness. It’s a weight—a heavy, invisible anchor that drags behind you, slowing you down. The things that used to be simple—getting up on time, making a decision, knocking out tasks—suddenly feel like trying to run through mud.

For guys who pride themselves on getting shit done, this is terrifying. When grief saps your capacity to perform, the instinct is to double down. Push harder. Grind more. It’s like running faster on a treadmill, convinced that if you push enough, you’ll break through. But you won’t. That treadmill doesn’t lead anywhere—it’s a treadmill to hell.

We cling to constant hustle because it gives us the illusion of control. But the harder you push while carrying that anchor, the more exhausted you get. The grind becomes your cage.

What Are You Building?

Imagine your life as a house you’re building brick by brick. Constant motion is like hauling bricks all day without checking the blueprint. You might wake up and realize you’ve been building a prison instead of a home.

Stopping doesn’t mean you’re weak—it takes guts. It means facing what you’ve been running from and making the hard choice to rebuild, not just survive. Stopping is recalibrating. It’s confronting the fear you’ve been trying to outrun.

The Fear Beneath the Grind

For a lot of guys, slowing down feels terrifying. When you stop moving, all the feelings you’ve been avoiding show up. The loss you never fully grieved. The mistakes you never made peace with. The moments where you felt small, powerless, or out of control. So you keep grinding because it’s easier to run a race than sit alone in the silence.

But here’s the kicker: you can’t heal what you refuse to face. And no amount of movement will fill the hole inside you. That hole only gets filled when you stop pretending motion is progress.

You’re not here to burn out. You’re here to heal. To find meaning in the life and death of the person you’ve lost. So ask yourself: What are you building? A life that matters? Or a prison where the grind owns you?

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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.