If you’re wondering how to move up 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.