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Where I Should’ve Been Book Review: Starting Over When the Life You Built Disappears

I found this book on a Tuesday night when I should have been sleeping. Instead I was scrolling, bleary-eyed, and something about the cover caught me. A sheep farmer. A city woman. I thought I knew exactly what I was getting into. I was wrong.

Here is the question that haunted me through every page: what happens to a person who loses everything they built, not through failure, but through someone else’s decision?

That question landed hard because I have asked it myself. Maybe you have too.

The Distraction That Became Real

Breezy Bishop is almost forty. She spent twenty years building her family’s art galleries into something real. Then her father died and left everything to her younger brother, the one who never showed up. She walked out the same day. No plan. No backup. Just a car pointed toward Vermont and her brother’s spare bedroom.

I liked her immediately. Not because she was perfect. She was prickly and defensive and kept saying she was fine when she clearly wasn’t. She reminded me of every woman I know who has learned to hold herself together by pretending nothing is wrong.

Tad Hanson is the sheep farmer everyone in Red Bridge loves. He smiles. He jokes. He cannot control his flock to save his life. But underneath that easy charm is something darker. Something that happened ten years ago that he has been running from ever since. His brother Randy followed him to Vermont to make sure he didn’t completely disappear.

Where I Should've Been Book Review: Starting Over When the Life You Built Disappears

The chemistry between them started as a joke. Breezy needed a distraction. Tad was good at distractions. But somewhere between the sheep escaping and the snowstorms and the nights spent sneaking across the field, something real snuck in. I found myself holding my breath during their conversations, waiting for one of them to ruin it.

I won’t tell you what happened. But I will say this: when Tad’s past finally came out, I had to stop and stare at the wall for a minute. It was not dramatic. It was worse. It was quiet and believable and it made me think about all the people I have known who were smiling when they should not have been.

The Grief That Lived in a House

The core of this book is not romance. It is grief. Specifically, it is about what happens when grief becomes a house you live in instead of a storm you pass through.

Max Monroe uses the sheep as a running joke, and they are genuinely funny. But the deeper imagery is about control. Tad cannot control his sheep. He cannot control his past. He cannot control the way Breezy makes him feel. Every time he tries to keep things simple, life complicates them. The sheep break through fences. Breezy stays longer than planned. His carefully constructed walls start cracking.

There is a moment when Tad thinks about “where he should have been” ten years ago, and I realized the title was not about regret in the way I assumed. It was about the impossibility of living in a present that feels like a betrayal of the past. He was alive. He was not sure he deserved to be.

Breezy had her own version of this. She kept measuring her life against what she thought she would have by now. A career. A family. A sense of purpose. Instead she was starting over at nearly forty in a town where the biggest excitement was whether the sheep would get out again.

I kept thinking about my own version of this. The plans I made at twenty-two that feel laughable now. The things I thought I needed that turned out to be weights I was carrying.

The Honest Middle Ground

Let me be honest about the problems. The writing has moments where characters think the same thoughts too many times. Some of the side characters feel like they exist only to set up future books. And there is a pregnancy plotline that I usually hate, but somehow it worked here because it was treated with care rather than convenience.

What worked for me was the pacing. The balance between humor and heartbreak felt natural. I laughed at the sheep disasters. I cried at the quiet conversations between Tad and his brother. I felt the weight of Breezy’s anger at having to start over when she had done everything right.

The book is not for you if you need constant action or high stakes drama. It is for you if you want to sit with two people who are trying to figure out how to want to live again. It is for you if you have ever felt like your life was supposed to look different by now.

The Peace I Didn’t Expect

I finished this book at 4 AM with a wet tissue in my hand and a strange sense of peace. It did not fix anything. It did not give me easy answers. But it made me feel slightly less alone in the questions I carry.

This book will not solve your life. It will not tell you that everything works out perfectly. But it might make you feel like it is okay to not have everything figured out. Like starting over at any age is not a failure. Like the people who stay when you are messy and broken and unsure are the ones worth keeping.

Have you ever had a book that made you rethink what you thought you wanted out of life?

Isabella Viora
Written by Isabella Viora

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