I Quit My Job, Went Back To School, And Started A New Career In My 40s. I Learned 3 Lessons About Starting Again.

• Kate Portillo ended her 13-year career in retail to go to school.
• She retrained as an urban planner, but found it challenging to establish credibility in a new field.
• Portillo's advice for anyone making a midlife career pivot include finding a mentor.

This as-told-to essay is based on a conversation with Kate Portillo, 51, an urban planner who lives in Chicago. Her employment and education have been verified by Business Insider. This piece has been edited for length and clarity.

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

Although I felt great about making the pivot, I was surprised by how difficult it was to establish credibility in a new field. I assumed that my years of management experience in retail would carry weight with most employers. In reality, I didn't feel that was the case.

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

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Being a manager in retail was fun, and I was trusted with significant responsibilities

After college, I worked with non-profits for a few years, then fell into a 13-year career in retail. My sister worked at Crate & Barrel and I saw the fun she had furnishing her home using her employee discount. She suggested I apply for a job.

Within a few weeks of being hired in 2002, at around age 25, I was put on the management track.

On a typical day, I'd work both back-of-house and front-of-house: managing teams and inventory, and tracking sales. I was trusted with significant responsibilities, from delivering bad news to customers to helping open new stores.

It was high-energy, fun, and I felt energized by how much the company cared about the customer experience.

I started a new career in my 40s when my kids were in elementary school

Around 2011, seven years into my retail career, I started thinking about what was next. There was a ceiling on earning potential as a store manager, and I wasn't sure how much longer the work would feel fulfilling.

I considered getting a master's degree in business and attended a few university information sessions. The courses didn't resonate with me.

At the time, I volunteered on the board of the self-managed condominium where I lived. As part of major improvement projects, I navigated permitting processes and worked with contractors, designers, and architects. I really enjoyed it.

I realized there was a career built around that kind of work. I attended an information session at the University of Illinois Chicago about the urban planning master's degree. I left fully confident that it was a good fit.

After I was accepted on to the course and understood the level of commitment involved, I resigned from Crate & Barrel and began the program in 2016. I was 42, and both my kids were in elementary school.

My parents went back to school later in life — my father earned a master's degree in public health, and my mom earned one in education — and I think that inspired me. I was happy my own children would see that life is not static and that our callings can evolve over time.

In graduate school, I felt energized by the change. The courses stretched me outside my comfort zone, and I was learning new things.

Establishing myself in a new field was hard

When I graduated in 2018, at 44, it stung that establishing myself in a new field was harder than expected. I didn't secure full-time employment for about a year after graduating, and filled my downtime with training, workshops, and internships.

In 2019, I got a job at a consulting firm, which involved staff augmentation. I'd sit at a desk in various municipalities, acting as their in-house staff. It made me realize that I really had a lot to offer.

I loved the framework of municipal government work and, in 2022, I became an urban planner for a small community. I loved how hands-on it was and the feeling of seeing the fruits of my labor.

In 2024, I became a planning manager in Skokie, Illinois. In this role, my experience of managing teams and motivating people has come in handy. I work independently, make projects happen, but also need to mobilize people to get behind initiatives.

My 3 pieces of advice for a mid-career pivot: keep going, network, and get a mentor

First, don't get discouraged. Changing careers takes time and energy, but keep going.

Secondly, prioritize networking. I'm involved with a professional development organization for women in planning and development. Networking doesn't have to be transactional; it can be about putting yourself out there and continuing to meet people until you establish some chemistry.

Finally, seek out mentors. In past roles, more established women taught me, invited me to things, and folded me into their professional networks. That kind of organic network is really meaningful.

When I first decided to pivot, it was pretty scary not knowing where I would ultimately land, but I have no regrets about where I have ended up.