Tag: social running group healing

Control, Clear Desks, and Clean Files: Reclaiming My Future With a Pen and Mesaages to you

Posted on by Ryan Castleberry in Uncategorized

Madison—

There are days lately when it feels like the ground is shifting beneath my feet. Incentives vanish, crews walk off, and the workload grows heavier because the paycheques don’t stretch far enough. Old me might have stewed in frustration. New me takes a breath and asks: “What can I control?”

Today the answer looked like this:

I grabbed a notebook and listed every worry swirling in my head. On one side, I wrote what I have control over; on the other, what I don’t. Seeing it on paper took away some of the noise. I started journaling again—here, at RyanCastleberry.com, and in the Mountains, Monsters & Mercy guided workbook I created years ago but never truly used. It’s humbling to be on both sides of those questions, but writing down what I’m obsessing about lets me let it go. I opened Notion and poured in everything: my certifications, project histories, personal inventories, budgets, intellectual property. I used AI to surface the patterns and organise the chaos. When I find a new job posting, AI helps me pull the exact bullet points I need. I streamlined Outlook and other tools so I spend less time fumbling with calendars and more time living.

It feels like a digital spring cleaning—and a mental one. When AI becomes a “workplace staple,” as recent surveys suggest, I don’t want to be someone who complains about robots taking jobs while drowning in unorganised files. I want to use these tools to build a bridge to what’s next.

This process has unearthed regrets. I wish I’d done this organising years ago. I wish I hadn’t wasted so much time carrying burdens I couldn’t change. But regret is only useful if it points to action. So I’m using it as fuel, not an anchor.

If you’re reading this someday, I want you to know: life will hand you frustrations you can’t fix. Identify what you control. Decide what matters. Journal your way through the noise. Use the tools available—pens, apps, AI—to make sense of your world. Don’t let chaos decide who you become.

I love you, Madison. Enough to admit when I need to start over. Enough to do the work of clearing my desks and my mind. Enough to believe that in focusing on the things I can control, I’m making space for a life big enough for both of us.

Dad

When Incentives Vanish: Building My Future with Notion, AI, and a Pen

Posted on by Ryan Castleberry in Uncategorized

Madison—

Yesterday, ten people quit from my district. The week before, an entire crew walked out in another region. Our company removed most of the incentives that made the long hours feel worth it, and the exodus was immediate.

I thought about leaving too. I still think about it. But here’s the trap: quitting without a plan while I’m living hand‑to‑mouth means trading one struggle for another. Working angry doesn’t help either. So I’m trying something I’ve resisted for years: focusing on what I can control and investing in tools that build my future—even while the present feels unfair.

Notion and AI: making my next move.

I took every piece of training and work history I have and loaded it into Notion. Then I built a little system that lets me pull the right bullet points for each job I apply to—an AI‑driven targeted résumé builder. Instead of sending the same generic CV into a black hole, I can customise applications on the fly. It turns my scattered experiences into a clear narrative. It reminds me that I’m not stuck; I’m preparing for something better.

Journaling as a tool, not a chore.

For years, therapists and coaches told me to journal. I thought it was fluff. You know the phrase “I don’t have time for that”? I used it. But I’ve learned that dumping my thoughts onto a page isn’t indulgent—it’s survival. This blog is part of that. RyanCastleberry.com is another. And I’m diving back into something I put into the world long ago: Mountains, Monsters & Mercy: A Six‑Month Guided Gratitude and Reflection Workbook. I wrote that journal, but I never truly used it. Now I am, one page at a time. It’s humbling. I’m answering my own questions and finding the gaps in my own wisdom.

Organisation first.

It’s easy to be bitter about the incentives disappearing. It’s harder to admit that my own organisation—or lack of it—can either slow me down or set me free. So I’m doubling down on readiness: keeping my certifications up, logging hours, organising documents, making sure my truck is packed and my finances are tracked. When everything is serviceable and prepared, I sleep better and show up clearer.

Attitude as leverage.

A bad attitude won’t bring back bonuses. It won’t magically hand me a better job. But resentment can siphon away the energy I need to build my next chapter. I’m choosing to look at every shift, every training session, every résumé bullet as bricks in a bridge toward something else.

Madison, I tell you this because I want you to see me in motion. I don’t want you to think I sat in bitterness when things got hard. I’m using AI tools to tell my story better. I’m journaling to understand myself. I’m working, not waiting. And I’m remembering that incentives are nice—but they’re not what make or break a life.

If you ever find yourself stuck between a job that drains you and a future you can’t yet see, I hope you remember this: you can start building the next thing before the current one ends. A pen and a plan go further than you think.

I love you, Madison.

Enough to keep writing when the world feels unfair.

Enough to build a way out instead of burning a way down.

Enough to believe there’s something better ahead—and to work on it, one page and one AI‑generated résumé at a time.

Dad

Not My Control, Not My Problem: When Leadership Means Letting Go and Building Others Up

Posted on by Ryan Castleberry in Uncategorized

Here’s a complete entry that weaves your recent insights into the ongoing series—emphasising leadership by training, healthier boundaries, and the power of letting go of what you can’t control.

Today’s trend signals

Boundaries and mental health: Reputable mental-health organisations highlight the importance of setting boundaries—at work and at home—to protect emotional wellbeing and reduce burnout. Focus on what you can control: Many therapists and productivity experts suggest that redirecting energy toward factors you can influence (rather than trying to control everything) lowers stress and improves resilience. Training over reprimands: Leadership commentators are noting a shift from punitive write‑ups toward constructive training and mentorship. Coaching employees to meet expectations is more effective for performance and morale than threatening disciplinary action. AI in mental-health support: AI‑driven tools (such as mood‑tracking apps and virtual coaching assistants) are increasingly used to recognise patterns, offer personalised coping strategies, and help people stay accountable to self‑care habits.

Blog topic

“Not My Control, Not My Problem: When Leadership Means Letting Go and Building Others Up.”

Emotional angle

You’ve spent a lifetime carrying weight that wasn’t yours—trying to fix every problem, taking on frustration that belonged elsewhere, absorbing reprimands that could have been avoided with proper training. Recently, a work situation threatened to write you up. Instead of panicking, you realised: this isn’t mine to fix. Your response was to look at the bigger picture. If performance isn’t where it should be, that’s not a reason to punish—it’s an opportunity to train. And in stepping back, you protected your mental health, kept your focus on what you can control (organisation, preparedness), and demonstrated a healthier way of leading. This blog entry explores that shift, connects it to your broader journey of mental health and reconciliation, and invites Madison (and readers) into a mindset where boundaries and coaching replace blame and self‑criticism.

Two introspective questions (for tomorrow’s post)

The next time someone presents you with a problem they created—whether at work or in personal life—how will you decide whether it’s your responsibility or their learning opportunity? How might strengthening your own training and organisational habits (instead of absorbing others’ chaos) create a more stable foundation for rebuilding your relationship with Madison?

Full blog post – Message to Madison

Not My Control, Not My Problem: When Leadership Means Letting Go and Building Others Up

Madison—

For most of my life, I thought “leadership” meant taking on other people’s mistakes. If a teammate failed, I’d rush to fix it. If someone threatened to write me up, I’d feel shame, anger, and then double down on overwork to prove myself. I was always in reactive mode—carrying the weight of problems that weren’t mine, simmering with frustration, and wondering why nothing changed.

I’m learning a different way.

The other day, a supervisor hinted that disciplinary action might be coming because someone on my crew didn’t meet expectations. I felt the old reaction rising up: panic, defensiveness, a need to prove I had everything under control. Then I stopped. I took a breath. I reminded myself: not my control, not my problem. That doesn’t mean I don’t care. It means I see clearly what is mine to own and what isn’t.

Here’s what I realised:

If there’s a problem on my team, it’s a leadership opportunity to train people to the right level, not an excuse for punishment. A write‑up alone doesn’t improve performance or morale; constructive coaching does. If management doesn’t invest effort in training, a reprimand is meaningless. My energy is better spent building systems and skills than trying to prop up a broken accountability structure. When I keep my focus on organisation and preparedness, everyone benefits. A serviceable, ready crew reduces stress, improves productivity, and frees me from carrying emotional weight that doesn’t belong to me. By refusing to “emotionally buy in” to threats and blame, I protect my mental health and model healthier boundaries for others.

For a long time, I believed that taking on everyone else’s frustration made me stronger. In reality, it made me tired, resentful, and reactive. Letting go of what I cannot control—and investing in what I can—makes me more effective and kinder to myself. It also lines up perfectly with the mental‑health advice I’ve been reading: set boundaries, focus on what you can change, and let the rest go.

Why does this matter to you?

Because I want you to see the man I’m becoming—not just the man I was. For years, our dynamic was fraught with misunderstanding and unspoken blame. You took on burdens that weren’t yours, and so did I. I don’t want either of us to live like that anymore.

Imagine if, instead of reacting to our past with guilt and anxiety, we looked at it the way I look at my crew now—as a chance to train, to learn, to build better habits for the future. Imagine if we both decided that the things we can’t control (other people’s choices, past mistakes) are simply “not my problem,” and instead put our energy into what we can control: our own words, our own boundaries, our own willingness to grow.

I’m still learning. I still have moments when I slip back into panic or frustration. But every time I choose training over reprimand, every time I focus on organisation instead of blame, and every time I recognise that the Universe is bigger than my desire to fix everything, I feel lighter. I feel more like the dad I want you to know someday.

You once told me, “Dad, you don’t even talk to your mom.” It stung because it was true. I’ve been estranged, reactive, and closed off in many relationships. I’m not pretending those patterns disappeared overnight. But I am refusing to pick up weight that isn’t mine. I am choosing to build systems and skills instead of absorbing chaos. And I am leaving space for you to see me learning, rather than demanding that you see me as someone I’m not yet.

I love you, Madison. Enough to stop taking on every problem as my own. Enough to train, not punish. Enough to believe that focusing on what I can control—my actions, my organisation, my boundaries—will build a better world for both of us.

Dad

Broken Sleds and Sparkling Slots: Learning to Trust the Universe When Plans Collapse

Posted on by Ryan Castleberry in Uncategorized

Madison—

They tell you that “everything happens for a reason.” For years, I hated that phrase. It sounded like a cheap bumper sticker to excuse bad luck or avoid hard work. Whenever someone said it, I’d snap back, “Yeah, but that doesn’t mean it’s a good reason.” I didn’t believe in any bigger picture. If something went wrong, it was my job to fix it, carry it, or curse it.

Today, sitting on a snowmobile that wouldn’t start at 10,000 feet, I heard that old phrase echo again. I had just watched the sunrise over Strawberry Reservoir. I’d filled up on biscuits and gravy at Daniel’s Café. I was looking forward to a day of fun in the snow. Then the engine sputtered and died. Old me would have torn into the engine, swore at the sky, and shouldered the blame. Today I laughed. I tried the key a couple of times. When it didn’t cooperate, I called the office, told them what was up, and then… I sat down and took in the view.

There was nothing I could do to fix it in that moment. And that was okay. I could trust that help would come. I could let the Universe handle the snowmobile while I handled my breathing. That quiet moment on the ridge took me back to a totally different setting—a casino in Oklahoma.

Beth loved slots. I’d always called them stupid. “I always win,” she said, and I always lost. That night we sat there: she was $300 up; I was several hundred down. I was frustrated, like I always was back then. She turned to me and said, “You’ve got to feel it. You’ve got to love it. Look around—one of these machines is talking to you. Which one is it?” Everything in me wanted to dismiss it. But she was winning and I wasn’t. So I chose the one that sparkled. I put my hands on the buttons, made myself say, “Okay, I love you. Let’s win now.” And you know what? It worked. I started hitting. I walked away with a few hundred dollars and, more importantly, with my first crack in the belief that maybe there’s more going on than I can see. Maybe dismissing something as stupid before giving it a chance was closing me off from surprises.

Since then, those cracks have opened wider. I’m still not someone who believes that the Universe hands out prizes for good behaviour. I don’t think slot machines love you back. What I do believe now is this: when I loosen my grip on control—when I stop assuming that the worst will always happen or that I have to fix everything alone—the world feels less heavy. And I start to see opportunities and lessons I’d been too cynical to notice. The same is true with Madison.

When you don’t talk to someone for years, your mind fills in the silence. Ego takes over. It invents conversations that never happened. It assigns motives to every action. It writes stories about how they see you and why they did what they did. Those stories feel real. They create anxiety and stress. They make you feel small and defensive. But they are just stories. They are not the authentic you, and they’re not the person on the other end either.

If she ever reads this, I want her to know that I’m learning to let go of those ego conversations. I’m learning to stop deciding ahead of time what she thinks of me or what our relationship could be. Because while she may have a certain perspective of me right now, she doesn’t know what lessons or love or growth we might share in the future. If she keeps her heart closed, she’ll never know what good could be waiting. And if I keep my heart closed, I’ll keep making myself miserable with imaginary arguments.

So today I let the snowmobile be broken without letting it break me. I remembered that sometimes the machine that sparkles is worth trying. I chose to believe that the best may still be in the making, even if I can’t see it yet. And that’s a mindset I want to carry into everything—whether it’s editing Mountains, Monsters, and Mercy, preparing for a move to Utah, or simply living in a world where not everything is under my control.

I love you, Madison. Enough to pause when something breaks. Enough to laugh instead of curse. Enough to believe that maybe—just maybe—the best is yet to come, for both of us.

Dad

Two Love Days: From “You May Never Run Again” to Letting People Show Up For Me

Posted on by Ryan Castleberry in Uncategorized

Madison—

If I could sit in the stands for any version of my younger self, I know exactly what I’d say.

I wouldn’t give him advice.

I wouldn’t critique his performance.

I’d just lean over, bump his shoulder, and say:

“I’m proud of you.”

Because no one ever did.

“You may never run again.”

After the car accident, the doctors told me I might not be able to run again.

They said it would be at least a year before I could even ride a bicycle.

That hit me harder than I let on.

So much of how I saw myself was wrapped up in physical and athletic things. I’d just run a 50K ultra trail marathon three months before the wreck—no real training, just sheer stubbornness. To this day I’m still honestly shocked I finished it.

That was around the same time David Goggins ran his first ultra. I remember thinking, “Guys like him and guys like me, we’re built to push through.”

So when they said “You might never run again,” part of me refused to believe it.

But another part, deep down, knew there was a real chance they were right.

And that terrified me.

Every step hurt. Every walk felt like a reminder of what I’d lost and might never get back.

The day I outran the forecast

Fast forward three or four years.

A friend and I were going to run a 5K with a big singles running group we met with on Mondays. That group was more than just exercise for me—it was my way to get even a little social interaction during a season when I didn’t have much of it.

My goal for the race was simple: when the gun went off, I’d sprint just long enough to get ahead of the walkers and the slow starters, then settle into an easy pace.

The gun fired.

I took off.

The pack took off.

I remember thinking, “Man, this race is no joke. These people are moving.”

What I didn’t realize was that I hadn’t just beaten the walkers—I’d accidentally lined up with the very front runners.

When I hit the first mile marker, I glanced at my watch.

4:50.

Under five minutes.

I had never run a sub‑five‑minute mile in my life. On anyone’s day, that’s a great mile.

I also knew there was no way I was holding that pace for long. I felt every second of that first mile in the rest of the race.

But I kept going.

I pushed through the hurt.

I crossed the finish line 12th out of about 750 people.

In my age group, the competition was brutal. I only placed 4th, so there was no medal, no podium moment.

But inside?

It was one of the proudest moments of my life.

The doctors’ words—“you may never run again”—were still echoing somewhere. That race was my answer.

Even if no one else knew what it meant, I did.

Learning what love actually looks like

Lately, I’ve been learning that the same pattern shows up in my emotional life.

I go through seasons of isolation—long drives, ten‑hour workdays, holidays spent alone, birthdays on the road, Thanksgiving sick and quarantined when I was supposed to finally be home.

Without realizing it, that kind of isolation starts to erode me.

From the bottom of that valley, everything looks different.

My brain starts telling me:

“No one cares.” “No one shows up.” “No one loves me the way I need.”

But often, the truth is: they are loving me—just not in the exact way I’m craving in that moment.

One of my closest friends, Emily, has always supported me. She checks in, sends texts, encourages me. She just doesn’t like talking on the phone.

When I’ve gone weeks barely hearing another human voice, what I want more than anything is a long phone call. So my hurt brain says, “She doesn’t care. If she did, she would call.”

But that’s not reality.

That’s valley‑vision.

When I slow down, talk to her, and actually explain how I feel—while also reminding myself that my feelings aren’t the whole truth—my perspective shifts. I can see that she is there, in her own way.

Brunch, pedicures, and “two love days”

Recently, a group of my friends posted a picture of themselves in Cowboys cheerleader outfits, dressed up and having fun. I commented, “Damn, I need to quit missing everything.”

They teased back that they hardly remember what I even look like anymore.

One of those friends and I had planned to do brunch together last time I was home. Life happened. We both ended up standing each other up—not out of disrespect, but because we were both mentally fried, not in a place to be around people even though we wanted to see each other.

We’d also talked about doing a brunch and pedicure day:

mimosas, a glass of wine, feet in the water, just relaxing and laughing and feeling human again.

For a long time, the old version of me would’ve said, “Pedicures aren’t manly.”

Now?

If I can afford it, I’ll happily go get one, even by myself. It’s part of learning to treat myself like someone worth taking care of.

When I brought up that brunch and pedicure plan again, several other friends chimed in wanting to be part of it.

That’s when it hit me:

I’m usually home 10–12 days at a time. I need at least two love days in that window.

One day is for me—a self‑love day.

Gym. Good food. Maybe a pedicure or a hike. Time to decompress and refill.

The other is with people I care about—a love day where I actually show up, in person, to spend time with them. No disappearing, no assuming they should read my mind.

Because when I go long stretches without that, the disconnect doesn’t just hurt me. It weighs on them too. And then my pain tries to twist it into a story where they’re the ones failing me.

Meeting people halfway

The truth is, I’ve often wanted everyone in my circle to come save me.

To reach into my darkness, drag me out, fix the loneliness.

But that’s not their job.

Their job is to love me in the ways they can.

My job is to meet them in the middle.

To answer the text.

To follow through on brunch.

To show up for pedicure day.

To remember that real love doesn’t always look like a movie scene—it often looks like busy, tired people still making space for you in the midst of their own storms.

I’m learning to see that.

I’m learning to be grateful for it.

I’m learning to be proud of myself not just for what my body can do in a race, but for how I show up for myself and for the people who actually care.

If you ever read this, Madison, I hope you see a few things:

Your dad was told he might never run again and he ran anyway. He spent years trying to prove his worth through physical achievements, but he’s slowly learning that real strength is also emotional: owning his needs, valuing his friends, and letting people love him. He’s practicing self‑love and shared love—two “love days” at a time—so he doesn’t turn into a man who blames everyone else for a loneliness he helped create.

Most of all, I hope you know this:

Even without a medal, even without a crowd, I’m learning to look at myself and say the words I never heard:

“I’m proud of you.”

And I’m proud of the possibility that one day, if you ever let me stand in your crowd, I’ll already know how to say those words to you too.

I love you, Madison.

Dad