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Hi, this is Free Thinking through the Fourth Turning. I'm Sasha Stone. How do you measure the happiness of a dog? I could not let go of my perfect, slightly annoying Jack. I stood in the corner of our tiny shack atop a mountain in Topanga and waited for my brother to come home. He would be there any minute and would see his beloved black Lab mix, Cinder, dead under his sheet in the front yard. We'd been out riding that afternoon. My mom was on our quarter horse, Teddy Bear. My younger sister and I rode the twin stallion ponies, Pumpkin mine and Fireball hers. It was summer, and we were riding to Topanga elementary to play in an empty schoolyard. Cinder came along. It was always hot, but that day it was baking and we were not prepared. And all of a sudden, Cinder collapsed. My mother, in a panic, ordered my sister and me to ride our ponies to the school and bring back water. Maybe we could save her, we thought. And when we finally got to the school, we scoured the trash cans and found empty milk cartons. We rinsed them, filled them, and then galloped back pony express style to where my mom was waiting. But it was too late. Cinder was gone. I don't remember much else of that day except what happened to my brother later when he came home. I'd never seen my tough, strong older brother cry. And that was my first lesson in the unique grief of losing a dog. They call them soul dogs or heart dogs on Reddit. It's that connection you have with a special dog that will never be matched by any other. And I have always hated how the Internet flattens things into group ideas. But in this case, they were right. I had to let go of my soul dog. Jack and I will never be the same. Mind you, I didn't want to. I rationalized it many times. I even almost took him to the hospital and asked them to cut him open, remove the large cancerous mass inside of him, give him kidney dialysis and chemo, something, anything to keep him alive. Needles, hospital rooms, strangers, bright lights. That would not have been for Jack. That was for me. And I couldn't do that to him. People have said you gave him such a happy life. And I tried. But how do you measure the happiness of a dog? To me, Jack wanted more than anything to be free. Free of the leash, free of doing only what I wanted him to do. Free to have maybe found a mate one time instead of having that possibility taken off the table. Free to roam, most of all, through the hills and the fields. I could not give that to him. The best I could do was make a situation for a dog with the urge to roam slightly less terrible. Oh, I suppose I could never have gotten him in the first place. Waited for the ideal owner, like a rancher to pick him up. I don't know if I was Jack's ideal owner or not. I just know that he was my sole dog. For better or worse. You don't choose dogs, they choose you. I'd pulled into a gas station near the four corners of Utah, Colorado, Arizona and New Mexico on route to the Telluride film festival in 2014. But I looked down and there was a furry little Wolfen creature, red headed, with bright green eyes, staring up at me. And was that a smile? He already knew how to ask for food and I was happy to oblige. Only I didn't just want to feed the dog, I wanted to rescue him. I don't know why exactly, it felt like a calling. He was red headed like my pony, Pumpkin. He had green eyes like mine. But it was his sweet disposition that meant it was love at first sight, even if I didn't know it yet. I told my daughter and her friend, both named Emma, to go get some dog food because we were taking this dog. And when I turned around, he'd crawled away and hidden under a trailer. But a woman pulled him out and handed him to me. That sealed Jack's fate to be rescued by city girls. Jack wasn't going to be my dog at first. My daughter's friend wanted him, but her parents said no. And that night, as the girls hung out in their basement room and I was cooking roast chicken, I heard little feet tap, tap, tapping up the stairs. And there he was again, smiling at me, wanting food. Okay, little pup, I thought. I guess I'm a dog person now. Don't take him if you can't keep him, my younger sister warned. I knew what she meant. She thought I'd abandoned Jack if some guy wanted me to, as I'd done once before when I was too stupid to know better. The dog went to my mom, who doted on her. But still it sent the message that I couldn't be trusted with a dog. We had three cats already, but dogs weren't allowed in our apartment in North Hollywood. When they found out, I was ordered to get rid of Jack. So we split to Burbank. I also broke up with a boyfriend over my dog. Sorry. I made my choice and there was no going back. Four years later, we finally adopted a friend for him because he hated being alone and my daughter Emma was leaving for college. We had a hard time choosing and were about to leave the shelter when a volunteer came out holding a tiny, terrified terrier poodle mix. She'd been there two weeks and no one wanted her. How could we say no? It felt like another kind of calling. Her name was Pippa, but we changed it to Luna. And though she looks desperately sad in that photo, she bloomed. And Jack and Luna became a happy, bonded pair. And the three of us were inseparable until the day Jack died. Thursday, March 19, 2026. Would you take a baby? You could, boy. That's not to say Jack was easy. He wasn't. I didn't train him properly because I never wanted to change his personality. I didn't want an obedient dog. I wanted this dog. And that meant he could be quite obstinate when. When he wanted to go in a different direction from me. It got worse as he got older. When he became a grumpy old dog, he would pull just to pull. And much of the time I'd give in. Except when I couldn't. And sometimes I couldn't. He also could not eat his food in a bowl like other dogs. It had to be on a flat surface, and he would scatter the kibble across the floor before lying down to eat it. Yes, I spoiled him, and responsible dog owners would not approve. Could have been worse. He could have been a growler or a biter. But this dog did not have an aggressive bone in his body. He was sweet and gentle, the nicest dog I've ever met. And he made friends with everyone, dogs, cats and people. I don't think it really occurred to him what his life would be like until he got older. But I think, once he figured it out, that this was really it. A life on a leash, walking through neighborhoods, occasionally running free. I think he got grumpier, more obstinate, and he pulled on his leash harder. And it became a battle of wills. And sometimes I was angry and annoyed at him. And now those moments come flooding back with an enormous sense of guilt. How could I have ever thought of being annoyed at him for even one second? Maybe I'm projecting. Maybe he never figured it out. Maybe he never thought about it. He just knew. He was frustrated with how much pain he was in and how limited his life had become. And there was nothing I could do to change that for him or fix it. I always wished he could speak. I wanted to talk to him. Remember when I found you at the Four Corners? Remember how much you loved running in the sand at the beach. Remember rolling in the snow? Remember the motels, the road trips? Remember how you liked to chase the ball? Remember driving into a blizzard? Remember getting stranded in the sand after I took a wrong turn and how we had to be towed out? Remember how you would whimper when we drove down to the airport to pick up my daughter, Emma, because you were so happy to see her? Remember how you herded us and we all had to leave the apartment at the same time or you would keep looking for the one that was missing? Remember all the friends you made in the neighborhood we live in? Remember the horse we used to feed that wanted to be friends with you? Because everyone wanted to be friends with you? Where would you like to go today? The park? The field? The hills? And I know what his answer would be. He would wag his tail and be ready to go. And when he could no longer jump into the car, I got him stairs. When the stairs became too hard, I got him a ramp. Where does it hurt, Jack? Tell me where the pain is. Tell me where to check. Tell me when you need to go to the vet. Talk to me. But all he could do was signal to me with his body, his behavior and his eyes, and I was not paying close enough attention. There's the guilt again. Could I have helped him if we caught it sooner? I don't know. Our long walks through town and our hikes began to slow down last year, and he could only make it around the block. Then, just this past week, he could barely make it down the street. Come on, buddy. We can do it. Come on. Come on, let's go. Come on. Come on. And then, barely, from the car to the front door. It was one of the hardest things I've ever had to do. Making the call to end his life. It was time for him to go, and I knew I had to grim up and face the music. He'd gone off his food for two weeks. He threw up even baby food. And then he couldn't keep down his water. He could barely breathe. I love you so much, but I always will. I would hear him retching in the middle of the night and find him stuck under the table, his body completely cold. And I kept thinking any minute he would take his last breath. But he somehow held on. Jack turned into a different dog in the last moments of his life. And for some reason, this breaks my heart the most. Gone was the willful, obstinate, slightly annoying dog who sometimes made our daily walks frustrating. And in his weakened state, he went wherever I wanted him to go. He came when I called him, and every night, almost, he disappeared into the backyard because he knew he was dying. And every night I went outside with a flashlight to call him back in. And he would come, just like a normal dog. He was doing it for me, I realize now, even at his own expense. Everywhere I look, there is Jack. The green grass I know he would want to roll in, the rib bones. I know he would want to chew the drives I know he would want to take the dog beds I bought that sit untouched in a pile on the patio, and the gravel that he could never pass without lying down in. This is grief. This is what it means to lose a soul, dog. I know I loved him too much. I was prepared for almost everything except saying goodbye. I want to tell you everything about him, to remember everywhere we went and every cute thing he ever did. Like how when he signaled to me that he couldn't get off the couch to get a drink of water, I would lift the bowl for him, and when the droplets hit his paw, he had to gently clean them off. I don't know why, but that one thing he's always done crushes my heart. I can't possibly tell you of our adventures together, how close we were, and how hard it is now for Luna to walk alone. She lies down near Jack's spot because she still senses his presence, as do I. I keep smelling his fur, which might sound weird, but I loved how Jack smelled. It was like the smell of a baby. You recognize it? I did not want to let him go. I wanted to be selfish and keep him around until he died on his own. But my younger sister, who once warned me not to take him if I could not keep him, told me that he's shown up for me and now it's time for me to show up for him. He's a happy guy now, holding him, petting him, brushing him, because I'd been doing that every day for a week. And then saying goodbye to him as the poison was injected into his beautiful tiny spotted paw. Then waiting for his heart to stop felt like falling into a deep well, into a world without color, without joy. My soul dog was my constant companion for 12 too short years. Now I try to see his soul, which was never mine, as finally free. Jack. Here he comes. I still think I hear him, especially at night. I hear his panting or his breathing, how he would sigh, letting out all of his air before settling into sleep. I would hear him pacing and circling before he lay down. I always knew where he was, and he was never far I pray that he visits me in my dreams. I pray that he's the first thing I see when I get to heaven. The first thing I hope I see when I get to heaven. My little puppy. Jedi. Run. My beautiful dog. My precious heart. My happy Jack. My buddy. Be obstinate and annoying. Be your perfect, wonderful self. Because now you are finally free. That's right, buddy. He likes this place. He likes the smell of the grass. Wet grass. It's really nice, huh? Jack, this is your favorite spot. Thank you for listening to my podcast, Sashastone.com and this post will be in video form on my substack. And here in the last minutes with this song is a montage of memories of Jack. I hope you enjoy and I hope you have a great weekend. And remember to thine own self be true.
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When I first saw you I knew I had to take you home? My friends, they argued I couldn't raise you on my own? But I was sure that you were meant to be with me? You are my angel set from above to set me free. Let's get in my car and I won't take you for a ride? Go to the bar and greet all the customers inside. I won't forget all, all that you've done for my life. My only hope is you're up there chasing butterflies. Oh,
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oh.
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Through all the hard times you were right there by my side. And when I needed answers well, I just looked into your eyes. Now I don't know all of the love you felt inside. My only hope is you're up there chasing butterflies. I know we'll be together another day, another time. But until then just keep on chasing butterflies. But until then just keep on chasing butterflies. Lo.
Podcast: Free Thinking Through the Fourth Turning with Sasha Stone
Episode: How Do You Measure the Happiness of a Dog?
Date: March 21, 2026
Host: Sasha Stone
This deeply personal and reflective episode explores the themes of love, grief, and the special connection between a person and their “soul dog.” Sasha Stone recounts her life-long bond with Jack, her beloved rescue dog, weaving together stories from their adventures, the challenges of owning a strong-willed companion, and the heartbreak of letting go. The episode poses a central question: "How do you measure the happiness of a dog?" and invites listeners to reflect on the responsibility and privilege of loving – and losing – a cherished pet.
The episode is tender, raw, and unguarded—Sasha’s voice blends nostalgia, gentle humor, and heartbreak. The storytelling is intimate, with vivid sensory details and emotional honesty. Listeners are given permission to grieve their own losses and to celebrate the imperfect but profound love we share with our animal companions.
“How Do You Measure the Happiness of a Dog?” is a cathartic meditation on love, responsibility, guilt, and letting go. For Sasha, the answer is not found in perfection, but in the willingness to love, to show up, and to finally set your companion free.