From Retail Manager to Urban Planner at 40: 3 Life-Changing Lessons for a Mid-Career Pivot

When Kate Portillo decided to retrain as an urban planner at 41, she knew she was taking a leap of faith. After ending her 13-year career in retail management, she embarked on a journey that taught her invaluable lessons about starting over in a new field.

Kate Portillo went back to school in her forties.

Being a Manager in Retail Was Fun and Fulfilling

After college, Kate worked with non-profits before falling into a 13-year career in retail. Within weeks of being hired at Crate & Barrel around age 25, she was put on the management track. Her days involved managing teams and inventory, tracking sales, and handling significant responsibilities—from delivering difficult news to customers to helping open new stores. The work was high-energy and fun, and she felt energized by how much the company cared about the customer experience.

Starting a New Career in Her 40s When Her Kids Were in Elementary School

Around 2011, seven years into her retail career, Kate began thinking about what was next. There was a ceiling on earning potential as a store manager, and she wasn't sure how much longer the work would feel fulfilling. She considered getting a master's degree in business but found the courses didn't resonate with her.

Her breakthrough came through volunteer work on her condominium board, where she navigated permitting processes and worked with contractors, designers, and architects. She realized there was a career built around that kind of work. After attending an information session at the University of Illinois Chicago about the urban planning master's degree, she left fully confident it was a good fit.

Kate Portillo used to work at Crate & Barrel.

After being accepted into the program, she resigned from Crate & Barrel and began her studies in 2016 at age 42, with both her kids in elementary school. Inspired by her parents—who both earned master's degrees later in life—she was happy her children would see that life isn't static and that callings can evolve over time.

Establishing Herself in a New Field Was Harder Than Expected

When Kate graduated in 2018 at age 44, she found that establishing credibility in a new field was more challenging than anticipated. She didn't secure full-time employment for about a year after graduating and filled her downtime with training, workshops, and internships.

In 2019, she landed a job at a consulting firm that involved staff augmentation, sitting at desks in various municipalities and acting as their in-house staff. This experience made her realize she had a lot to offer. She loved the framework of municipal government work and, in 2022, became an urban planner for a small community, enjoying the hands-on nature and seeing the fruits of her labor.

Kate Portillo pivoted from a career in retail to one in urban planning.

In 2024, she became a planning manager in Skokie, Illinois, where her experience managing teams and motivating people proved invaluable. She now works independently, makes projects happen, and mobilizes people to get behind initiatives.

3 Pieces of Advice for a Mid-Career Pivot

1. Don't Get Discouraged Changing careers takes time and energy, but it's crucial to keep going. The journey may be challenging, but persistence pays off.

2. Prioritize Networking Kate is involved with a professional development organization for women in planning and development. She emphasizes that networking doesn't have to be transactional—it's about putting yourself out there and continuing to meet people until you establish genuine chemistry.

3. Seek Out Mentors In past roles, more established women taught Kate, invited her to events, and folded her into their professional networks. This kind of organic support system is incredibly meaningful and can accelerate your growth in a new field.

When Kate first decided to pivot, it was scary not knowing where she would ultimately land, but she has no regrets about where she has ended up.