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Forging a Career Path Unique to You

By Clare Becker

October 8, 2018

CEO Stephanie Pugliese speaks against a backdrop of the Duluth Trading Company logo
Don’t compare yourself to others, Duluth Trading Company CEO Stephanie Pugliese tells the WSB audience during the M. Keith Weikel MBA Leadership Speaker Series. “Your path is going to be totally different.” Photo by Paul L. Newby II

In the age of social media, sites like Facebook and LinkedIn make it nearly impossible not to compare ourselves with others, particularly when it comes to careers. For many of us, our job histories and experiences don’t follow a linear path or even look like anyone else’s.

That’s not a bad thing—and we’re far from alone.

“What I’m going to share with you is that no matter what you hear tonight, no matter what you hear from your bosses or your professors, your path is going to be totally different,” said Stephanie Pugliese, president and CEO of Duluth Trading Company, before an audience of Wisconsin MBA students and alumni taking part in the Wisconsin School of Business’ M. Keith Weikel MBA Leadership Speaker Series.

Pugliese told the audience how she Googled “career path” prior to her talk. The resulting image showed a man in a suit carrying a briefcase, moving in a straight skyward direction. It didn’t resonate.

This is a career path,” Pugliese said as she shared a graphic that looked more like a horizontal family tree, with branches crossing and extending in different directions. “A career path and a path to leadership is going to take curves. Sometimes it might take a backwards loop or a side path. The reality is, the more experiences you have in your life, the more your path might look just like that.”

A career path and a path to leadership is going to take curves. Sometimes it might take a backwards loop or a side path. The reality is, the more experiences you have in your life, the more your path might look just like that.

Stephanie Pugliese, president and CEO, Duluth Trading Company

Intrigued by business since the age of 18, Pugliese received her bachelor’s degree in marketing from New York University’s Stern School of Business. After graduation, she worked in retail merchandising with Ann Inc. for nearly 11 years. In a decision made in the aftermath of September 11, 2001, Pugliese and her husband moved to Italy—his native country—to raise their three young children and run a bookstore. Returning to the U.S. in 2005, Pugliese held several executive positions with Lands’ End before landing at Duluth Trading Company in 2008. At Duluth, she rose from vice president of product development to senior vice president and chief merchandising officer to chief operating officer to president, and in 2015, to CEO.

Stephanie Pugliese speaks underneath the UW crest.
Pugliese encourages Wisconsin MBA students to embrace each experience along their career path. Photo by Paul L. Newby II

Regardless of where you are on your professional journey, Pugliese shared three tips that can help you make your career path your own:

  • Get your hands dirty. Dig in, create, be productive. Being hands-on lets you understand your job from the inside out. Pugliese was inspired by family members whose occupations included baker, truck driver, and house painter. “What I saw around me as I was growing up was an interest in working with your hands, and the pride and accomplishment that could come with that sort of passion,” Pugliese said. It was an early lesson and one that would later prove to be a natural fit with Duluth. Duluth customers “like to do,” Pugliese said. “They like to roll up their sleeves; they like a job well done—they expect a job well done.”
  • Learn from each stage. Looking back, Pugliese said, each of her experiences built on the one before it. Even when there didn’t seem to be a direct application at the time, she drew something valuable from each one. When Pugliese and her husband moved to Italy, she envisioned herself as a stay-at-home mom, which lasted “about 63 days.” After one of her daughters asked if they could visit Barnes & Noble—which wasn’t anywhere near their vicinity—it sparked the idea of creating a children’s bookstore, recreating the reading and browsing experience in their new small town of 4,000 residents. Pugliese and her husband added activities like arts and crafts days, reading days, and book fairs with local schools. “I went from executive to hands-on,” she said, using the opportunity to apply her business acumen and creativity in a vastly different environment.
  • Step outside your comfort zone. Don’t rest on your laurels. Keep growing, evolving, and challenging yourself—even when it’s scary. “Constantly look for what’s next, for ways to do better,” Pugliese advised. Duluth is known for its witty, innovative ads that push the envelope, and this fearless attitude extends to the company’s overall philosophy. The brand ventured into new territory in late 2015 by going public via an IPO. Pugliese said the transition meant new skills and new experiences, including gaining an investor perspective. “It’s been an incredible journey for us.”

Forging your own career path is less about knowing all of the answers and more about fostering your entrepreneurial spirit and the courage to find out. It’s also what employers look at, too. As part of the Duluth hiring process, Pugliese meets personally with prospective talent, searching beyond just an individual’s skill set.

“What I’m looking at is: Are you going to thrive in our culture? Are you curious? Are you learning? Are you open? Do you want to take one of those curvy career paths? That’s what I’m talking to them about, and that’s what we try to reinforce consistently at Duluth. We don’t always get it right, but the fact that we’re looking at it and the fact that we want to do it better reinforces the culture and grows our team.”

Speaker Stephanie Pugliese shares her life and work experience on stage in WSB's plenary room
Having a curious mindset and looking for ways to continually learn and grow are just as important as the skill set you bring to the table, Pugliese tells Wisconsin MBA students. Photo by Paul L. Newby II

The M. Keith Weikel MBA Leadership Speaker Series enables Wisconsin MBA students and alumni to interact with and learn from accomplished business leaders. Students deepen their leadership skills by hearing the distinct perspectives of these visiting business leaders.

The series was established in 2004 with a gift by John J. Oros (BBA ‘71) and his wife, Anne Wackman. Today, the series continues as the M. Keith Weikel MBA Leadership Speaker Series thanks to a gift by M. Keith Weikel (Ph.D., Marketing and Economics, ‘66) and his wife Barbara.