Neverending Grief
- Alisha (Kara’s Sis)

- Sep 3
- 6 min read
Updated: Sep 5
Note: This space has been a home for sharing Kara’s journey but today I need to place another piece of my heart here. Grief does not separate itself neatly. It touches everything and writing is the only way I know to carry it.
I didn’t know what to do, so I just started to write. What is with this neverending grief that God keeps calling me to carry?
This morning I found out that my friend Will passed away. I’m not sure my heart could take any more aches, but here we are.
I met Will while I was in college. I was home for the summer and my dad was pretty insistent that I needed a job that paid better than teaching tennis lessons. So I applied to be a camp counselor at the YMCA.
My first morning on the job, a kid started throwing chairs at the other children for reasons I still don’t know. Then he whipped one at me. With no real training, my instincts kicked in: I chased him, wrestled him to the ground, put him in a hold and then he spit in my face. I’d like to say things calmed down as the summer went on but those kids kept us on our toes every single day.
I quickly realized that being a camp counselor was not going to be a walk in the park. Every day brought some new kind of chaos and if you didn’t laugh, you would cry. Will’s humor is what kept me sane that summer. And even with the challenges, it was still the most rewarding job. Connecting with the kids, witnessing their growth and knowing I had made an impact still sticks with me.
Most of the camp counselors were around my age. They were studying education, teaching, or already working in school settings. Will was older, going back to school to become a teacher. One day I jumped into his car and found a muumuu and a wig buried in the backseat. I immediately put them on and we broke into character. That was the moment I knew we were going to be friends. I had finally met someone who not only embraced my goofiness but matched it. Reminiscing on that moment now makes me realize how that version of me has become a long distant memory.
I’ve always been drawn to weirdness and Will will know I mean that in the very best way. Growing up in small-town Iowa, it often felt like your destiny was already written: go to school, play sports, get a job, get married, raise kids, and repeat the cycle. For many people, that is a beautiful life. For me, it never felt quite enough.
I’ve always craved diversity in thought and lifestyle. People often accused me of thinking I was “better than everyone” simply because I wanted something different. Then I met Will. He was the first adult I knew who was unapologetically doing life in his own way, no matter what anyone thought. I loved his story, his realness and our friendship. It was sacred, it was comforting and it was everything I needed at a pivotal point in my life.
Will had already lived a whole life and traveled before settling down here. Changing his career path to teaching didn’t necessarily make sense, at least not in a traditional way or financially. But he followed his heart and knew what he wanted. I loved that about him. It showed me that no matter where life was about to take me, I could always change my mind. He was proof of that.
When I decided to leave Chicago and had no idea what to do next, Will was the one who convinced me to pick up shifts at Wide River Winery. Before long I was helping with marketing, booking bands and beginning to establish a life here. That nudge changed the course of everything for me.
Will was a single dad by choice. He planned it that way and he was the most incredible father. Watching the way he loved his daughter Piper and the experiences he wanted to give her was so inspiring. We went out to dinner and ate all the cultural foods that none of my family or friends wanted to try. He had a zest for life that was hard to match and he lived so fully. He was always up for anything.
We went on all kinds of adventures and even vacationed together: zoos, waterparks, go-kart tracks and museums. Many times little Madalyn would be in tow too. Often we were mistaken for husband and wife. I would roll my eyes, frustrated at how society is conditioned to see a man, a woman and children only through that lens. But sometimes we would lean into it. One night he proposed to me in the parking lot of the school with a Ring Pop, with Andy Green there to witness.
We'd joke about how marriage wasn't a goal for either of us but maybe we could make it work, platonically of course. We quickly became like family. He actually made one of my all-time dreams come true when he drove me out to a farm to play with and feed a baby cow.
Will was the kind of person you could share anything with and never feel judged. There were no strings attached to the friendship. It did not matter if months went by without talking. The love stayed the same. He loved hearing about my crazy life, was endlessly supportive and could always make me laugh no matter how heavy the topic was. He never balked at my hopes and dreams. He was encouraging all the time. Whether I was in Dubuque, Chicago, back home, chasing a boy band on tour or ready to jump on a plane to Europe, he would have supported.
We did not stay in touch as often as I would have liked but whenever we reconnected, he always told me how proud he was of me. And I think the hardest part of my grief right now is losing someone who genuinely cared.
The strangest part is that before I heard the news today, I thought of him last night and again this morning. I was supposed to get my cholesterol checked and wanted to put it off. Then I told myself, don’t be stupid. Heart problems are rare at my age but not unheard of. Look at Will. I remind myself, you have to take care of yourself. So I sucked it up and went to the lab this morning. On my way home, Roger called and struggled to give me the news.
I recognize the gift it was to know him. Alongside the sadness, I hope I can still find ways to be inspired by his beautiful spirit. We could all use a lesson in friendship from him. This is an emptiness that will last a lifetime for many but I already know he would not want us to sit in grief forever. He would want us to laugh, to live fully and to love people without reservation.
That is part of why I am placing these words here. This blog has been my home for Kara’s story but grief does not stay in neat boxes. It weaves itself through everything: loss, love, fear and hope. As Kara continues her own fight, maybe that is why Will’s story feels even closer to me right now. Life and loss, love and laughter, they all sit together in the same space. Writing is the only way I can attempt to hold it all. Please send your extra prayers to Piper and the rest of Will's friends and family <3.
If You're New Here
Hi, I’m Alisha, Kara’s sister and biggest advocate. Kara was diagnosed with Stage 4 Triple-Negative Invasive Ductal Carcinoma (TNBC) in December 2024. Her cancer has spread to her bones, liver, and other areas, making this an incredibly difficult and uncertain journey.
Despite it all, Kara’s light still shines so brightly—she’s full of love, giggles, and endless positivity. This blog is where I share updates on her fight, the highs and lows, and the incredible community rallying around her.
Thank you for being here, for your love, support, and prayers. We need them more than ever. 💛 And of course, Go Hawks!
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