Retail might look like it’s all about the cool products and eye-catching decor, but the real story happens behind the scenes.

Charlotte Walters, owner of Lost Eras in Chicago, has turned a century-old building packed with antiques, oddities, and theater props into a successful retail space. But keeping it afloat comes with challenges. 

Charlotte’s story offers real insight into what it takes to push through the toughest parts of store ownership.

If you’re facing operational hurdles in retail, here are seven tips you can use to handle and overcome them with confidence.

1. Have a Streamlined Cleaning System

At Lost Eras, nearly every item comes in needing attention. Charlotte learned early on that customers love old items, but they don’t want the dirt that comes with them. Dirt, age, and decades of neglect make cleaning one of the biggest time drains for the Lost Eras team. It’s a hurdle that’s easy to underestimate but impossible to ignore.

If you’re a retailer working with vintage or secondhand inventory, it’s important to have a dedicated cleaning workflow. Start by setting up a specific station for intake and restoration that is fully stocked with the tools and supplies your team needs to work efficiently. Then, incorporate training into the process, so staff know how to handle a range of materials safely and effectively. 

No matter if your merchandise is vintage or brand new, cleaning should be non-negotiable. Equip your team with the right supplies and routines, and you’ll move products faster, reduce returns, and create an environment shoppers want to come back to.

2. Simplify Your Inventory System 

With everything from vintage hats to massive antique furniture, Charlotte quickly realized that having a clunky SKU system brought operations to a crawl. Managing a diverse array of items like hers required a more flexible, user-friendly setup. When your team can’t easily tag or track items, things can easily fall through the cracks.

Begin by auditing your current system and then strip it down to what matters most. To improve efficiency, consider these steps:

• Use a customizable POS system that allows flexible categorization and item-specific fields.
• Incorporate visual aids like color-coded tags, QR codes, or category stickers to streamline tracking.
• Establish a simplified naming or numbering structure to reduce confusion and improve speed.
• Regularly train staff so they can navigate, update, and troubleshoot the system with confidence.

The right tools only work if everyone knows how to use them. Invest a little time in training, create quick reference guides, and you’ll reduce mistakes while freeing up hours each week.

3. Reduce Theft Risk with Strategic Store Design

Theft is a real concern for any store owner, and Charlotte openly shares that it’s one of the hardest parts of retail. Still, there are simple and effective ways to protect your space without turning it into a fortress.

Start with customer engagement; even a friendly greeting or a quick wave lets people know they’re seen. That simple moment of acknowledgment can set the tone and discourage unwanted behavior right away.

From there, ensure high-value items are placed within your team’s line of sight, allowing staff to monitor without excessive attention. Reinforce visibility with thoughtful tools like mirrors or cameras, and make a habit of regularly reviewing footage. 

If you’re a store owner, remember that technology can only go so far. An engaged, attentive staff who knows how to spot suspicious behavior and act quickly will always be your strongest safeguard against theft.

4. Get Ahead of Financial Headaches 

Charlotte didn’t learn about taxes or record-keeping before opening, and like many small business owners, she had to figure it out on her own.

“You need to have somebody to be able to show you how to do the books, how to pay your taxes, all of that, because a lot of it was never taught in school. I had to find people to accurately tell me, this is how you pay your retail tax, your rental tax. This is how you do your yearly books,” she explains. 

Here are a few practical steps you can use to stay ahead of financial stress:

• Hire a local accountant who understands the retail landscape, even if it’s just for quarterly check-ins or annual filing support.
• Use accounting software to automate invoicing, track expenses, and generate clear reports.
• Set weekly reminders to review cash flow, outstanding invoices, and upcoming tax obligations so nothing slips through the cracks.
• Keep digital and physical records organized from day one to make tax season faster and less painful.

Your business could be brand new or decades old, but proactive money management is what keeps it steady. Create simple systems for tracking revenue and expenses, and you’ll be able to plan your next move without second-guessing.

5. Master Pricing with a Scalable Approach

Lost Eras sees a constant stream of new, unusual inventory, which means pricing is a daily job. Without clear standards, it would be easy to undercharge, overprice, or fall behind. If you are a retail owner who relies on secondhand or consigned goods, having a great pricing strategy is one of the most important and time-sensitive decisions you’ll make.

Start by building a simple pricing rubric, using factors like condition, uniqueness, and comparisons to similar sold items. To make those decisions even smarter over time, keep notes in your POS or pricing app that track how long different types of inventory tend to sit on the shelves. 

The goal isn’t to get pricing perfect every time but to stay consistent and efficient. When you can price confidently and keep inventory moving, your cash flow remains strong, you feel more secure in your profit margins, and your store stays dynamic.

6. Turn Store Organization into a Daily Ritual

Charlotte opens each day with a top-to-bottom walkthrough to make sure the store is clean, functional, and presentable. In a space as eclectic as Lost Eras, this is no small task, but it’s a necessary habit that keeps the store feeling fresh and keeps operations on track.

Follow her lead and build a daily reset routine that works for your space and team. Here’s a simple structure to start with:

• Assign zones to each team member so everyone knows which area they’re responsible for tidying and checking each day.
• Restock supplies and displays at the beginning of the day, making sure high-traffic areas look full and inviting.
• Before doors open, do a full-floor walkthrough to fix out-of-place items, tidy messes, and check all lighting and displays.

If you’re a store owner, don’t overlook the power of order. A tidy, well-kept space instantly improves the customer experience while giving your staff the clarity they need to work efficiently.

7. Create a System for Handling Unscheduled Inventory Drop-Offs

People often walk into Lost Eras unexpectedly with new items to sell or consign. While Charlotte welcomes the opportunity, the unpredictability can create chaos if not handled properly. Managing the constant inflow is just as important as what you do once the items are in your hands.

For those dealing with the same issue, it’s important to build a straightforward intake process, even if it’s simple. Use a basic form to gather seller information, temporarily tag each item, and place it in a designated intake area until it can be cleaned and priced. 

To keep things manageable, consider batching intake during set hours so your team isn’t juggling new arrivals during peak customer times. This kind of structure keeps the flow steady, prevents clutter, and helps your team stay focused without getting overwhelmed.

Conclusion

Operational retail challenges are inevitable, but they’re also opportunities to grow stronger and get smarter. Charlotte’s journey with Lost Eras proves that you don’t have to be perfect. You just need systems, support, and a willingness to adapt. If you’re in the thick of running your store, these small shifts can make a huge difference.

Focus on one hurdle at a time, test your systems, and don’t be afraid to ask for help. That’s how enduring retail businesses are built.

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