Woman Pivots from Retail to Urban Planning in Midlife

Kate Portillo shares her 3 tips for making a successful career change in her 40s

Published on Feb. 21, 2026

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Kate Portillo, 51, worked as a manager in retail for over a decade before deciding to retrain as an urban planner at age 41. Though the transition was challenging, Portillo has found success in her new career, now working as a planning manager in Skokie, Illinois. She shares three key pieces of advice for others considering a midlife career pivot: don't get discouraged, prioritize networking, and seek out mentors.

Why it matters

Portillo's story highlights the growing trend of professionals making unconventional career changes later in life. As the workforce continues to evolve, more people are finding fulfillment in pivoting to new fields, even after establishing themselves in one career. Portillo's experience provides valuable insights for others considering a similar transition.

The details

After college, Portillo worked in non-profits for a few years before falling into a 13-year career in retail management at Crate & Barrel. Around 2011, she started thinking about what was next, considering a master's in business before attending an information session on urban planning at the University of Illinois Chicago. Portillo was accepted into the program and resigned from Crate & Barrel in 2016 to begin her studies at age 42. Though establishing herself in the new field was challenging at first, Portillo eventually secured a job at a consulting firm in 2019 and then became an urban planner for a small community in 2022 before taking on her current role as a planning manager in Skokie in 2024.

  • Portillo worked in retail management at Crate & Barrel for 13 years, starting around 2002 at age 25.
  • Around 2011, Portillo began considering a career change and exploring master's degree programs.
  • Portillo was accepted into the urban planning program at the University of Illinois Chicago in 2016 and resigned from Crate & Barrel to begin her studies at age 42.
  • Portillo graduated from the urban planning program in 2018 at age 44.
  • Portillo secured a job at a consulting firm in 2019, then became an urban planner for a small community in 2022, and took on her current role as a planning manager in Skokie in 2024.

The players

Kate Portillo

A 51-year-old urban planner who lives in Chicago. She previously worked in retail management for over a decade before pivoting to a new career in urban planning in her 40s.

Crate & Barrel

The retail company where Portillo worked in management for 13 years before leaving to pursue a master's degree in urban planning.

University of Illinois Chicago

The university where Portillo attended an information session about the urban planning master's degree program and was later accepted into in 2016.

Skokie, Illinois

The community where Portillo currently works as a planning manager, a role she took on in 2024.

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What they’re saying

“When I decided to retrain as an urban planner at 41, I knew I was taking a leap of faith.”

— Kate Portillo (businessinsider.com)

“In the end, changing careers in my 40s taught me a lot about starting again.”

— Kate Portillo (businessinsider.com)

What’s next

Portillo plans to continue growing in her role as a planning manager in Skokie, leveraging her retail management experience to help drive initiatives and mobilize people within the municipal government.

The takeaway

Portillo's story demonstrates that it's never too late to make a career change, even in midlife. Her successful pivot from retail to urban planning shows that with determination, networking, and the right mentorship, professionals can establish credibility in a new field and find fulfillment in an unconventional career path.