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Curating a Career Pivot and a Life That Fits | Jennifer Conrad, Founder & President Twigs, Ep. 11

From Wall Street trader to fashion entrepreneur, Jennifer Conrad moved from New York to Madison, WI, on September 11, 2001. While coping with the events of that day, Jennifer identified a need in her new city — and a vision for what to do next. So she did what a former day trader would do: she trusted her gut, moved quickly, and built it herself.

Jennifer, Founder & President of Twigs, an elevated, fashion boutique, will discuss how she built this career pivot on instinct and discipline, how she’s kept the business strong through pandemics and recessions for two decades, the importance of prioritizing your people, and what she’s learned about building both a career and a life that fit.

ABOUT THE GUEST:

Twigs is an independent women’s fashion boutique with locations in Madison and Brookfield, WI, with a nationwide online presence at shoptwigs.com. Jennifer opened Twigs on January 2002, drawing on the economics degree she earned at Columbia and a career as a money market trader at Citigroup. In 2012, Elle Magazine recognized Twigs as one of the best boutiques in America.

What make’s Twigs stand the test of time is Jennifer’s approach to curation: a thoughtful mix of contemporary clothing, jewelry, and accessories for three generations of women — carefully pulling together pieces that are worth your time and attention. What keeps customers coming back is the Twigs team’s ability to cultivate a community while providing exceptional customer service and attention to the little details.

WHAT YOU WILL LEARN:

  • 08:49 —Spotting a need in a field you didn’t come from — and deciding to act on it
  • 11:52 —How Jennifer uses her background as a trader to assess risk and make fast decisions when the business needs to pivot
  • 13:32 —The “big enough and small enough” philosophy that has shaped how she’s grown — staying nimble while building real durability through a pandemic and a recession
  • 24:04 —When to take the leap to expansion — and how a candid conversation with another retailer helped her say yes to a second store
  • 34:25 —Jennifer’s leadership style and why appreciating her team is the foundation of everything
  • 39:13 —The art and joy of curating — how Jennifer finds designers, edits a collection, and curates for three generations of women
  • 49:08 —What it takes to keep a business healthy over the long haul, including the team and the benefits that have kept her people with her
  • 50:55 —Jennifer’s honest advice for any woman thinking about a real industry jump
  • 56:11 —Learning to take care of yourself in order to be there for others

GUEST LINKS:

ADDITIONAL RESOURCES:

  • “The Artist’s Way” by Julia Cameron,Amazon link here.
  • Note, by using the link HIR will receive a small affiliate link compensation.

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Music from #Uppbeat (free for Creators!):

About the Show:

Her Intentional Reset is a midlife podcast for women navigating career change — honest, deep-dive conversations about career pivots, second acts, and reinvention with women who’ve actually lived it. This women’s empowerment podcast speaks to women in 30’s, 40, women over 50, Gen X women, working moms, empty nesters, and corporate women dealing with burnout — women redefining success and finding their why after a layoff, a career wall, or the moment work just stopped feeling right. Each episode traces a real transition story: the catalyst for change behind it, whether that’s a layoff story, career burnout, or hitting a wall; the steps and timeline behind how she actually made the change — quitting a corporate job, leaving corporate America, starting over professionally, and/or going from employee to entrepreneur; and an inside look at her industry along the way.

The conversations also get into the practical side most career-change content skips: transferable skills, upskilling and reskilling in midlife, starting a business with no experience, and career change without a degree. And because money is always part of the story, guests talk financial planning for a career change — paying yourself first, building a financial runway and safety net, income gaps, self-employed health insurance, saving for retirement while self-employed, and the money mindset it takes to trade a paycheck for financial freedom in midlife.

Guests share the career pivot lessons learned, the advice for career changers, and what they wish they’d known before quitting — then close out with a Rapid Round covering the real-life stuff: family recipes, book and show recommendations, a life motto, and a wellness or self-care tip for midlife women, because women are often each other’s best guides and teachers. It’s never too late to make a change, follow your intuition, and listen to that quiet voice — every episode leaves listeners feeling inspired and empowered to explore their own career pivot, second act, or next chapter, on their own terms. New episodes of this career change podcast and midlife podcast for women release biweekly on Apple Podcasts, Spotify, and YouTube.

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