Making Dreams a Reality

Ever since I fell in love with reading (“late” in life, I was in college!), I’ve always dreamed of owning a bookstore. It felt pretty abstract for a while. More like watching You’ve Got Mail and thinking about how wonderful it would be to own a bookstore. (Minus the whole Foxbooks taking over part.)

The more I dreamed about it, the more it seemed like something I actually wanted to do. More like a plan/goal than a dream. Especially moving to this amazing small town with a great community, I knew it was something I was going to try to do.

(Just a spoiler alert in case you’re getting excited, it’s not happening just yet for me. Sorry to disappoint, trust me I’m even more disappointed!)

I wrote a list of what I wanted to accomplish in the next 10 years on January 1. Among a short list of big goals and dreams for the decade, I wrote “bookstore.” And then less than a week later, I got word that the adorable bookstore in town was closing. I found out via a Facebook post at 11pm as I was trying to fall asleep. My heart started pounding. I was both crushed that the town could potentially be losing the bookstore and then thrilled that this could be my chance. Mike had already fallen asleep and I sat awake staring at the ceiling for thirty minutes driving myself crazy with the fact that I wasn’t ready for it, but I wanted it. Mike rolled over at one point and kind of opened his eyes, so I pounced at my opportunity, “Oh great, you’re awake. The bookstore is closing and I want it.”

Actually saying the words out loud made me realize how badly I wanted to make it happen. Over the next two weeks I realized this was absolutely a dream of mine, while I worked through some numbers and talked to various people (real estate, branding, interiors, independent booksellers, etc.). Sometimes it seems like just an abstract idea, but it was clear: this is what I wanted.


Unfortunately, the reality was that I was nowhere near prepared to do it in such a time crunch. It was going to be a nine-week turnaround before the lease would start and then it’d be crunch time from there to get things operational as to not hemorrhage money. As real as this dream felt to me, it was just as real that this was NOT the time for it to happen.

I surprised myself by how crushed and devastated I felt. It was a long shot to begin with: a handful people also wanted the space, the timeline was very tight, and I have zero experience running an independent bookstore.

However, I did walk away from this whirlwind with a LOT of new information beyond just my realization that I legitimately and strongly wanted this dream to come to fruition. I had so many amazing people reach out to me to connect me to friends and family friends who own or owned independent bookstores. I learned about organizations, retreats, and workshops that educate people on owning and operating independent bookstores. I met people in town who are just as passionate as I am about books and community and how they can come together. I created a skeleton of a business plan that I can elaborate on as time goes on.

Essentially, this lit a fire under me. I know in my heart that I didn’t have the bandwidth to focus on all those things above in my mid/late twenties. I knew when I wrote my list of goals that I wasn’t ready to start a new business in the first few years of the decade. But I will say that I was super disappointed in myself nonetheless. I felt like a failure for not being able to get it together in two weeks. (Which, rationally, is a ridiculous level of pressure to put on myself.) I also know that even if I HAD gotten it together, it could have been an epic failure because it was rushed.

Still, I had to sit with this disappointment for a while. And it was made even more challenging by people in town asking how it was going and I had to admit, out loud, that I couldn’t make the timing work.

I read listen to a lot of business podcasts and people always mention these types of “milestones” (for lack of a better word) that they faced before they got their business off the ground. But it’s usually summed up in a few sentences at best, and with the benefit of hindsight. I imagine I’ll be able to quickly summarize this very brief, in the grand scheme of things, period of time at some point down the road.

I know there will be a point in the future where I think, “thank goodness it happened this way.” And in the meantime, I have a lot of things to prioritize and get in order so that when the next opportunity presents itself (hopefully in, like, four or five years haha) I’m ready and can put things into action.

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I hate it when bookstores go out of business, it’s really rough out there, but maybe it will happen for you later on in a few years. You never know where life may lead you.


I really enjoy your blog. Honestly I think owning a bookstore would be an uphill battle. I very occasionally enter mine for a gift idea. But in terms of my own reading, I use our wonderful public library or free offerings on Amazon Prime. I’m at the age I don’t want to collect more items.


This was a rollercoaster. I know exactly what you mean. I too found myself in a positions where I went: This must be sign, it’s all there, if only I scrambled and overhauled my whole life, but where it turned out to be impossible to actually do this. It does help to clarify how much you actually want to do something, if you’re willing to take the long road and prepare.

It is so very impressive that you actually checked if you could make it happen! All of this research and the informed decision take a lot of courage.

Courtney Jenney

I am SO excited for you, whenever this “next chapter” (no pun intended) begins. It’s great you realized you didn’t want to rush the situation-when it’s meant to be, it’ll happen! And whenever it does happen, just know I’ll be at that bookstore at least once a week 🙂


This is awesome! Do you think you will tie in the Carly the Prepster brand into your bookstore- decor, other items for sale? Offer books to buy via your blog (like e-commerce)? I’m excited for you!


I assumed that having a small bookstore was doomed from the beginning these days so am surprised, but pleased, its not. Can you share some of what you’ve learned in all your research about them sometime if it comes back up?


I missed the disclaimer and had to skip to the bottom because I needed to know immediately if you actually bought a bookstore!! So true that you don’t really realize how badly you wanted something until the opportunity arises and passes though.


I’m a long time follower, but have never commented on any story but felt a connection to this one. I also had a similar opportunity, jumping in on a small
retail store in my city very quickly. The situation was right, but the location was not, and while we are still in business a few years later, the business model is much different from when we first opened. Successfully running a retail business will consume your life, unless you have a team of employees or an endless supply of cash. You were right to wait it out and plan for it, even though it’s totally disappointing in the short term. Happy to chat about it more if you ever have any questions!


While it would’ve made for a great story, you’ll always be glad you made the rational decision. I’d love to know more (without disclosing personal details of course) how you went about this decision-making process and what factors you took into account, financially and from a business perspective. Thank you for sharing this story!


What’s meant to be, will be! These are all great steps to achieving your goal when the timing is right. When you finally get there, you’ll likely look back and think “thank God that first place didn’t work out!”

Biby Chacon

Can you share some of the business podcasts you’ve been listening to. My mom and I are actually thinking about doing something similar…a dream to reality…and I would love to hear what you’ve been listening to.


I’m about 30 minutes away from Madison and would love to eventually visit your bookstore! Hope it works out down the road.

In the meantime, have you ever considered working part-time at one? Either a weekday or two or on the weekend?


This is actually exactly what I was going to suggest also. I think a part time job at a store similar to what you’d want to eventually own would be a very logical first step.


That would require her getting a job though. When this declining blog somehow is “full-time.” Idk, she seems above have a real job 🙄

Amanda Ray

As a long time reader, this is one of my favorite posts of yours! Thanks for being vulnerable and sharing!


Second and Third careers are common place in the 21st century. The workplace is changing so quickly that staying in one career can be difficult. The idea of a bookstore may be the start of a second care in one form or another. You’ll be successful in whatever you do moving forward.

Amy Hustad

I love your dream of owning a bookstore and hope it happens for you at the right time!


This article, as many of yours do, really spoke to me. Sharing your hopes and dreams, alongside the reality of the situation is so beneficial to your readers. I sincerely and warmly hope you obtain/acquire/purchase/own/work at an independent bookstore. Whatever you please, whenever you please.

It’s so cool to see women dreaming and succeeding! Good luck to you and us all!

Kate Keeper

Hey Carly! I’m an indie bookstore owner and let me tell you how wonderful this community is! If and when you decide to take the jump into entrepreneurship you will find so much support here. I’m sad to hear your town will be losing it’s store; it’s definitely not easy to stay relevant without getting really creative or as someone mentioned below having a surplus of cash to float you. I would definitely recommend getting a part-time job as a bookseller if possible to get some insight into the inner workings. Totally not absolutely necessary but it could definitely help you to have a more robust understanding of what it takes to operate one! You’ve Got Mail is a horrible depiction of the process, though a cute movie! Reach out if you ever want to chat more specifically!


Carly I’m so excited to follow you as you make this dream a reality. I’ve been a reader for years now and I’m so proud of you for putting this amazing plan in action. Can’t wait to visit your bookstore one day!

Brigid Devney-Rye

Thanks for sharing your hopes, dreams and even your disappointments with us. Timing is everything. Always rooting for you.


This was so interesting to read. In 2012, a very similar thing happened to me. A local shop was closing, and within 2 weeks, I was opening the replacement. I can’t say I regret it because I learned a ton, but within 4 years, we closed. We never were able to be sustainable. If I hadn’t acted only on emotion and excitement, I would have probably changed a few things, haha. And maybe it would have worked, maybe not! But I do think things happen for a reason. 🙂

Jules Buono - book blogger

This was such an interesting post! I never heard anyone talk about the process of opening a bookstore. I give you so much credit for diving right in and figuring things out. It sounds like you made the smart choice for right now. I wish you the best with your goal in the future!

Lauren G

I got unbelievably excited for you when I read the title of this post! As others have said, I totally think things happen for a reason. If anything this process just reaffirmed that this IS something you want to pursue at some point down the road, and for me discovering that is rewarding in itself! Maybe somebody we will all be visiting your shop!

Nicole @ Laughing My Abs Off

Good for you for having the maturity and self-awareness to know this isn’t the right time. Not everyone would handle this so gracefully. I am so excited for when it does happen for you though; it’s gonna be an epic little place <3


Looove the idea of you running a book store! I really believe it’ll happen for you. Best of luck! ❤️


Thank you for sharing this! I really loved you recent post on getting involved, and I don’t know if this fits with your vision of the bookstore I know you will own in the future 😉, but it was worth a share – there’s a bookstore/café called Manny’s in San Francisco that’s a hotspot for events and activities that help people engage in thoughtful activism and civic responsibly. They are a nonprofit themself, have a wonderfully diverse set of literature, and host candidates, non profits, etc. I don’t know if some thing like would be a fit in the town you’re in, but maybe weaving that vein into your store could be one more way of getting involved and making a difference ☺️


Omg, I can so relate to this feeling! One of my dreams is to start a coffee shop (but not just any coffee shop), but one with a personal touch; lot’s of books/magazines one can read, with focus on quality coffee and a few treats. I know that I’m in a point in life where this isn’t supposed to happen, but it feels great to hang on to the feeling that there might be an opportunity someday. Btw, this is the cutest bookstore ever! 🙂