If you’re wondering how to advance your career in retail, Lesley Timpe’s path offers a compelling case study. 

As the owner and designer of Chicago’s Squasht Boutique, Lesley built her business from the ground up. What began as a side hustle soon evolved into a full-fledged retail brand known for funky dresses, reversible hats, tunics, headbands, and more. 

Squasht showcases Lesley’s original designs alongside pieces from other independent designers, with a focus on local, handmade, ethically produced fashion and a strong commitment to community impact.

As Lesley built her business, she acquired critical skills, made bold choices, and remained true to her values. 

If you’re figuring out how to get a job in retail or thinking long-term about entrepreneurship, follow along to learn seven actionable insights from Lesley’s journey.

1. Start by Getting Your Foot in the Door

Your first retail job doesn’t have to be the perfect fit. Lesley’s first experience wasn’t even in fashion. She worked in a retail-adjacent job at a homeopathic pharmacy. To her, it wasn’t the job title that mattered most, but the exposure to people, products, and the ability to learn problem-solving skills. 

She learned how to:

• Use basic inventory systems like QuickBooks
• Understand customer needs
• Observe what made a small business succeed (and fail)

If you’re wondering how to get a job in retail, don’t limit yourself to a particular niche. Remember that any customer-facing or small business experience can serve as your launchpad to future success.

2. Use Side Projects to Build a Portfolio and Gain Confidence

Before Squasht became a brand, it was Lesley’s side hustle. She began designing hats while working full-time and gradually built her way into the fashion industry by testing products and gathering feedback.

Rather than jumping all in, she scaled her time by doing the following:

• She started with a full-time day job, dedicating her nights and weekends to her business.
• She gradually scaled back her full-time job hours from four days to three, then down to one as demand grew.
• Finally, she committed to the business full-time because of her confidence in her customer base, revenue, and readiness to go all in.

If you’re looking to start a retail career, start small. Begin your passion project as your side hustle. It’s a good idea to test interest in specific products or work part-time in a store, as this will give you real insight into what people buy and why, without having to take on a big risk. 

3. Turn Every Job into a Retail Skills Training Ground

Retail jobs are often dismissed as “entry-level,” but Lesley’s story proves they can be the foundation of leadership. She utilized each job she had to develop core retail skills, particularly those not taught in design school.

These skills included:

• Retail sales associate communication skills
• Basic bookkeeping and operations
• Time management under pressure
• Customer relationship-building

What she learned prepared her to manage her own store, team, and supply chain. Recognize that every job is an opportunity to practice the fundamentals, bringing you one step closer to becoming a successful store owner.

4. Let Your Values Define Your Brand and Drive Growth

Ethical sourcing and local production aren’t just buzzwords for Lesley; they’re the reason Squasht exists. She built her store around a mission: to showcase independent designers and avoid fashion made in sweatshops.

“Even when I just started my business of Squasht, my entire mission statement was to have everything be handmade, and I wanted to avoid having anything made overseas,” she shares.

This value-driven model helped her stand out from big retailers. It also attracted customers who were committed to supporting small businesses with a positive mission. 

Being mission-focused is a crucial point in your journey. As you consider how to advance your career in retail, don’t chase roles. Chase causes or products you actually believe in.

5. Hire (and Be Hired) Based on Alignment

Eventually, Lesley had to grow her team. When she did, she was intentional about creating a hiring process that reflected the values and instincts needed to succeed in fashion retail.

Instead of only focusing on resumes, she asked potential hires the following questions: 

• What’s your personal style?
• Where do you like to shop?
• What kind of experience would you want as a customer?

This approach highlighted what really matters in retail roles: attitude, empathy, and customer connection. If you’re applying to a retailer, tailor your pitch around these themes to land your ideal role.

6. Create Experiences That Make Customers and You Want to Stay

You can enjoy your retail job more when you shift the focus from selling products to creating an environment that inspires and connects people. Lesley views her store as a space designed to spark creativity, foster meaningful interactions, and leave customers feeling uplifted.

From curated window displays to seasonal layouts, her boutique offers shoppers a memorable experience. This is key for anyone working in retail, especially if you want to grow into a manager or visual merchandiser.

If you’re planning to move up in retail, look for ways to make the customer journey personal, warm, and brand-aligned. That’s what turns jobs into careers.

7. Think of Retail as a Platform for Entrepreneurship

Many people treat retail jobs as short-term, but Lesley proves they can be an empowering step into entrepreneurship. She originally moved to Spain to teach English, but her passion for fashion led her to enroll in a local design school, where she completed a two-year program.

Through hands-on experience in retail that included managing inventory, serving customers, and working the sales floor, Lesley gained the exact skills she needed to build her brand. She eventually opened her boutique, expanded her product line, and began growing a team.

If you’re wondering how to start your retail career, Lesley’s story is a reminder that it might just be the first step toward something much bigger.

Conclusion

Lesley Timpe’s story shows that advancing your career in retail doesn’t follow a straight line. It’s built through curiosity, values, and persistence.

Use your early jobs to build fundamental retail skills. Remember to stay open to where each role leads, and let your passions shape your path. Whether you’re applying for your first job or thinking of owning your own store, the next step in your retail career is yours to design.

Want to hear more powerful retail stories? Learn from retail owners across Illinois who are making a difference.

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