One Month In: What Goes Into Building a Season at Side Plot?

One Month In: What Goes Into Building a Season at Side Plot?

First of all, thank you.

One month ago, Side Plot officially opened its (virtual) doors!

Launching a business has been equal parts exciting, rewarding, and humbling. Over the past month, we've made both small refinements and significant pivots, with every conversation, question, and new perspective helping shape Side Plot into the community we envisioned.

Whether you've been here since day one or just recently discovered us, thank you. Your encouragement, feedback, and enthusiasm have become part of Side Plot's story, and we're grateful you're here as we continue building it together.

To celebrate our first month in business and the launch of Season #1, we thought we'd pull back the curtain and share what goes into creating a Season. From the first brainstorming session to the final reading list, and a few of the books that almost made the cut, this is what it looks like behind the scenes.

Stick around until the end for a list of books that didn't make the final cut this Season, but absolutely deserve a spot on your TBR!

It Starts With a Big Question

Every Season begins with brainstorming a question that's broad enough to invite many perspectives, but focused enough to create a meaningful conversation.

For Season #1, that question became Change & Pivoting.

We asked ourselves:

  • How do individuals adapt to change?
  • What inspires transformation?
  • What resists it?
  • How do institutions shape the way we change?
  • When should we embrace change, and when should we challenge it?

Then Comes the Book Hunt

Once we've settled on the central question, the search begins!

We research widely across genres, time periods, and perspectives, looking for books that don't just stand well on their own, but that speak to one another.

With every book in the "maybe" pile, we ask ourselves:

  • Does it meaningfully contribute to the Season's central question?
  • Can it be paired with another book to create an interesting conversation?
  • Is it enjoyable to read?
  • Does it add diversity in authorship, lived experience, or perspective?
  • Does it balance the overall reading list in genre and style?
  • Is it reasonably accessible in cost and available in multiple formats like print, ebook, audiobook, or through libraries?
  • Is the page count approachable alongside the rest of the Season?

Finally, the Nitty-Gritty

Behind every Season is a surprising amount of behind-the-scenes work...

Once the reading list is finalized, we begin chipping away at: 

  • creating reading outlines
  • writing discussion and guided reading questions
  • designing graphics
  • scheduling social media
  • preparing newsletters
  • updating the website
  • moderating our community
  • coordinating virtual meetups
  • and, of course, searching for the perfect speaker to bring the Season's theme to life at our Final Lecture. 

Every detail, from the first Instagram post to the final discussion prompt, is built with the same goal in mind: creating a thoughtful, welcoming experience that makes it easy for people to jump into the conversation, whether they're reading every book or just discovering Side Plot for the first time.

Despite the workload, we are actually having a whole lotta fun! Law school demanded SO much of our individual time and attention, so getting to build something with each other has been such a wonderful time.

Why "Seasons" and "Views"?

When we first started imagining Side Plot, we knew we wanted more than a never-ending book list or a traditional book club setting. We wanted something that felt fresh, gave people something to look forward to, and encouraged us to explore new ideas throughout the year.

That's how "Seasons" were born.

We borrowed inspiration from the semester system you might find at a university, not because we wanted to recreate school, but because we liked the rhythm of it. Every three months, we start over with a brand-new theme, a brand-new reading list, and a brand-new conversation. It keeps things moving and gives us a chance to explore different questions without feeling like we're stuck reading the same kinds of books all year.

We also knew that everyone has a different reading style. Some people want to curl up with a novel and get swept away by the story. Others love picking apart themes and symbolism. And some are happiest reading nonfiction that helps explain why people and the world work the way they do.

That's where our "Views" come in.

Cozy View is for readers who just want to enjoy a good story. These books lean into storytelling, memorable characters, and that feeling of not wanting to put the book down.

Critical View is for readers who enjoy digging a little deeper. If you've ever loved talking about symbolism, themes, unreliable narrators, or all those "English class" discussions (without the homework), this is probably your vibe.

Contextual View is for readers who naturally reach for nonfiction. These books explore the history, psychology, philosophy, or social forces behind the Season's big question and ask, "Why does this happen?"

No matter which View you choose, everyone comes together in the same discussions because the goal is for everyone to bring a different perspective to the conversation.

"But... Where's the Bookstore?"

Fair question.

The honest answer? Behind the scenes, we're still recovering from the financial adventure otherwise known as law school.

That's one of the reasons we launched Side Plot as an online community first. It gives us the opportunity to build a reputation, grow a community, and create the financial foundation we'll need when it's time to take the leap into a brick-and-mortar space. (Turns out commercial real estate appreciates things like steady revenue and a sexy business plan.)

Our goal is ambitious: we'd love to open our first bookstore in Winooski next year!

Until then, we're building the next best thing.

Alongside our community, we're developing an online bookstore centered on independent authors, local creators, and books we genuinely believe are worth sharing. It's our way of supporting the kinds of voices we want to see on more shelves while taking one intentional step at a time toward our long-term vision.

Will there be more bookstores after that? We certainly hope so, but for now, we're focused on building the first one well.

Bonus: The Books That Almost Made Season #1

Choosing six books turned out to be one of the hardest parts of building our first Season.

For every book that made the final reading list, there were several others that stayed in the running until the very end. Some overlapped too much with another selection, some deserved an entire Season built around their ideas, and others simply didn't fit the balance we were trying to create.

If you've already finished your Season reading (or you're looking to add a few more books to your TBR), here are some of our favorites that almost made the cut:

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