Podcast Summary

Miss Represented - Episode 68

Guest: Sydney Shrewsbury (Miss Indiana USA)
Host: Lisa Opie
Date: October 15, 2025

Episode Overview

In this engaging episode, Lisa Opie welcomes Sydney Shrewsbury, Miss Indiana USA, for a candid, lively conversation. Lisa and Sydney unpack Sydney’s whirlwind journey into pageantry, balancing a full-time tech sales career with pageant success, redefining authenticity as a titleholder, and her entrepreneurial ideas for women’s workwear. Full of laughs, real talk, and actionable advice, Sydney’s down-to-earth take on empowerment shines throughout.

Key Discussion Points & Insights

1. Welcome to Miami & Pageant Chaos

• Lisa and Sydney share lighthearted stories about Miami, including beauty mishaps (hair disasters, new extensions gone wrong, an itchy scalp scare) that set a fun, relatable tone.
  • Quote: “There’s always a hair disaster when you’re in Miami, I feel like.” — Lisa [00:49]
  • Quote: “Anyone that knows me knows I like to say I’m a walking train wreck.” — Sydney [08:04]

2. Sydney’s Pageant Journey: Fast-Tracking a State-Level Win

• Sydney started with a high school cheer fundraiser pageant, won in her second year, and stepped away until a friend drew her into the local Miss America system.
• Feeling stagnant after a move to Indiana and driven by a desire to make friends outside work, she entered Miss Indiana USA—placing high her first year, then returning with renewed focus to win.
  • Quote: “I just changed my mindset… Everything I did was super calculated on either how this could make me grow, how this could make me better… I wanted to be memorable.” — Sydney [03:47–04:33]

3. Balancing Career and Pageantry: Breaking Stereotypes

• Initially hesitant to share her pageant pursuits at work, Sydney found unexpected support from colleagues. She highlights the importance of showing that women can have both career ambitions and vibrant lives beyond the 9-to-5.
  • Quote: “You can be successful with your career and you can also do what you want and set goals and achieve them in your personal life.” — Sydney [07:20]

4. Authenticity as a Titleholder: The ‘Cool Pageant Queen’

• Sydney’s social media persona celebrates her chaotic, unfiltered personality, which she struggled to reconcile with pageant expectations post-title.
• A mentor’s feedback helped her realize the importance of staying real online, as relatability and authenticity are key for audience engagement.
  • Quote: “If that is messy and a disaster and chaotic, then that’s what it is. And that’s what makes people care.” — Sydney [10:08–10:42]
  • Memorable Moment: The zipper malfunction at a parade—shared for laughs and relatability—went viral on TikTok [10:08].

5. Pageantry as a Platform for Building a Brand

• Sydney is clear: her identity isn’t defined by a crown. She chose the USA system for its networking opportunities, aiming to launch a women’s workwear brand—a “work leisure” line bridging the gap between comfort and professionalism for women.
  • Quote: “Win or lose, that’s my end goal… How can I be the one that they’re like, ‘Oh, whatever happened to Indiana? Where’s she at?’” — Sydney [11:55]
  • Behind the Scenes: Reference to Gold Hinge, an athleisure golf brand, as inspiration. Sydney seeks a similar success story (20:08–21:11).

6. Tech Sales Career & Advice for Women

• Sydney advocates for women in sales, highlighting natural empathy and social skills. She reveals her own journey—over 245 job rejections before landing at Salesforce—and shares modern job-hunting tips.
  • Quote: “If you’re stuck on a career choice and you’re a woman, absolutely look into sales… It goes back to being relatable and authentic.” — Sydney [14:14–14:38]
  • Advice Segment:
    • Skip job boards—search LinkedIn posts for hiring managers/recruiters directly [17:35]
    • Optimize profiles with keywords/skills relevant to target roles [18:57]
    • Persistence pays off: rejection is redirection.

7. Mentorship and the Power of Asking for Help

• Sydney has mentored 11+ students/jobs seekers, embracing both learning through failure and mutually supportive networking.
  • Quote: “If you’re too scared to try, you’re never going to learn anything. You also should always ask for help.” — Sydney [23:50]

8. Rapid-Fire 'This or That' Game

• Fun, personality-driven insights:
  • Confidence: “From the career. You have to have confidence to get the crown.” [23:31]
  • Blazer and heels or sneakers and strategy: “Sneakers and strategy.” [23:38]
  • Pop of color over neutrals, jumpsuits for long legs, maximalist, group coaching vs. one-on-one chat
  • Playful critique of “minimalist capsule wardrobe” trends.
    • Quote: “Clean girl, old money and capsule wardrobe are three trends I’m over.” — Sydney [25:09]

Notable Quotes & Memorable Moments

• “I’m not a regular pageant queen. I’m a cool pageant queen.” — Sydney [07:45]
• “You don’t want to win Miss USA. That’s not good for them. Because once you win Miss USA, that’s it. But the girls who placed are on TV and have businesses.” — Lisa relays industry wisdom [12:32]
• “When you don’t hit your goal, it’s just twice as motivating.” — Sydney [13:03]
• “Text me on your flight home if you make your flight!” — Lisa [23:11]
  • Context: Sydney’s commitment, squeezing in the interview before a flight.

Major Timestamps

• 00:28–01:23: Miami misadventures, hair stories
• 01:40–04:45: Sydney’s rapid pageant ascent and shift in mindset
• 05:12–07:43: Work-place perceptions, blending career and pageant ambitions
• 08:04–10:42: Authentic social media presence
• 10:59–13:47: Pageantry, career alignment, branding goals
• 14:01–16:54: Women in tech sales, challenges and advice
• 17:35–19:21: Job search strategies and success story (Salesforce)
• 20:04–22:49: Vision for women’s workwear brand, inspirations and planning
• 23:24–25:20: ‘This or That’ rapid-fire and fun style opinions
• 25:27–25:40: Where to follow Sydney and heartfelt goodbyes

Where to Find Sydney

• Instagram: @SidShrews
• TikTok: @SidShrews

Summary Takeaway:
Sydney Shrewsbury exemplifies the empowered, multidimensional woman—embracing chaos and authenticity, bridging corporate and creative life, and building empowerment for women in both career and pageantry. Her advice and humor make this a must-listen for anyone navigating ambitious journeys, career changes, or chasing big dreams with heart and honesty.