Shifting from the corporate world to retail ownership is a bold decision. It’s one that many professionals dream of but few dare to pursue. 

For Ann Kienzle, owner of Play, a Chicago-based children’s toy and gift store known for its curated selection and neighborhood charm, that dream became a reality. After nearly three decades of working in the toy industry, she leveraged her corporate experience to create a retail business rooted in community, design, and joy.

Now operating in five locations across Chicago, Ann’s journey offers real-world advice for professionals who want to start their own business. 

These six tips will help guide your transition from working at a corporate desk to owning your own retail store.

1. Use Your Industry Experience as a Strategic Advantage

Ann didn’t start from scratch. She began from strength. After working at Brio, the wooden train company, and a career that included roles as a vendor, sales representative, and consultant across the toy industry, she brought deep knowledge of product quality, supply chains, and customer behavior to the table.

With that knowledge, she built a store that reflected everything she had learned over 29 years.

She leveraged her background to curate better products, negotiate more effectively with vendors, and avoid common mistakes that beginners often make. In her words, she took the “best of the best” and turned it into a worthy and unique retail experience.

If you’re moving from corporate to retail, consider how you can leverage your insider knowledge to give you a competitive edge.

2. Start in a Community You Understand

When deciding where to open Play, Ann didn’t rely on market analysts. She simply looked around her Logan Square neighborhood and noticed a growing community that lacked a curated, family-friendly retail store. She understood the area, its vibe, and its needs, and her first store was deeply connected to the people it served.

That local-first mindset didn’t stop with her first location. As Play expanded, Ann never tried to replicate the same store five times. Instead, each location was tailored to its neighborhood’s unique personality:

• Andersonville: Diverse and inclusive book selection
• Hyde Park: Evolving based on community input
• Lincoln Park: Broad, neighborhood-friendly product assortment
• Logan Square: Artsy, music-focused inventory
• West Loop: Foodie toys and chef-themed books

Designing each store with the community in mind not only made each one stand out but also invited people in. Whether it’s your first store or your fifth, start with what you know and let each space grow into something that feels personal, local, and loved.

3. Embrace the Creative Freedom of Retail

Ann made the move to retail because she wanted something corporate life couldn’t offer: creative control. She loved designing product displays, curating selections, and creating a store experience that reflected her personal style. 

“Retail gave me the creative freedom that I didn’t have in consulting,” Ann shares.

For Ann, a customer picking up items from a display she designed and watching them build the perfect gift from her curated selection is when she feels true fulfillment.

Think about what makes you feel fulfilled. If having more creative control is part of that, retail could be the perfect outlet to bring your vision to life.

4. Grow Slowly With Purpose

Many first-time store owners think expansion means immediate success, but Ann took a different path. She ran her first store for eight years before opening a second, and each subsequent location came naturally, leading to sustainable, value-driven growth.

Each neighborhood was carefully selected based on gaps in the local market, and each store reflected the vibe of its surroundings. This steady approach allowed Play to grow without compromising its identity or spreading itself too thin.

If you’re considering scaling your retail business, wait until your first location is both stable and well-established. That’ll make it easier to open your second location with confidence.

5. Prepare for Financial Challenges 

Despite her background, Ann faced significant financial hurdles, particularly when opening new locations. The Hyde Park location, for example, became costly before it could become profitable. 

Her Andersonville store opened just three weeks before the pandemic shut everything down, and it became a real struggle to stay afloat and optimistic. She credits her survival to a mix of landlord generosity, loyal customers, and pandemic relief.

If you’re transitioning from a corporate setting to retail ownership, create a financial buffer and be prepared for unexpected obstacles. Building a savings cushion that covers several months of operating expenses and exploring lines of credit or small business loans in advance will ensure that you’re not scrambling in a crisis. 

It also helps to build strong relationships with vendors, negotiate flexible lease terms, and closely monitor your cash flow from day one. This will provide an additional layer of security for your store in the event of unexpected challenges. 

6. Define Success on Your Terms

After decades in the corporate toy world, Ann redefined what success looked like. It wasn’t about big margins or national growth but more about joy, creativity, and community. 

For her, watching someone interact with her displays is more meaningful than any consulting contract she could have signed.

Retail offered the chance to lead with heart instead of KPIs.

If you’re making a career change, think about what success truly means to you. Is it seeing happy customers? Giving someone a great recommendation? Or creating visual experiences? Whatever it is, let that lead and drive your decisions.

Conclusion

Ann Kienzle’s journey from corporate to retail ownership shows that with the right mindset, the leap is possible and transformative. By combining her professional experience with personal passion, she created a business that’s profitable, community-centered, and deeply fulfilling.

If you’re considering how to transition from corporate to retail, follow Ann’s path: move intentionally, stay creative, know your value, and always let your community lead the way.

Want to learn more about other Illinois retail leaders? Read inspiring stories from retailers across Illinois who are making a difference.

If you loved learning about the Play’s story and know a retailer who deserves recognition, Nominate A Retailer to submit your nomination!