Ep187: [Hollywood On the Record] How to Create Your Dream Job by Setting Healthy Boundaries | with Jerilynn Stephens & Kimi Messina


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“If you get to a point where you’re not happy doing what you’re doing, you need to find something different. We all should be doing what we love to do.”
- Jerilynn Stephens

Jerilynn Stephens and Kimi Messina are both award-winning Hollywood hair stylists with over 60 years experience between the two of them. Jerilynn’s recent credits include Legendary, The Voice, and Shark Tank. And Kimi has worked on films such as Almost Famous, Pirates of the Caribbean, Master and Commander, and The Last Samurai. She’s also been the key hairstylist on Dancing with the Stars for 27 seasons and Legendary Seasons 2 and 3.

Building a fulfilling career path in the entertainment industry is no easy feat (and often requires constant sacrifices). If you truly want to excel in a career you ENJOY (while also‌ having quality time & energy to enjoy your life outside of work), these two women demystify how to make this your reality. In this candid conversation Jerilynn and Kimi share their personal experiences of climbing the ladder in Hollywood and talk openly about how they have learned to place healthy boundaries around their work so that they can continue to love their jobs without sacrificing their lives in the process. We also discuss the importance of saying yes vs saying no to the right opportunities, and most importantly how the quality of your life is dictated by the quality of the problems you get to solve every single day.

This conversation continues our Hollywood On the Record series where I speak to other guild members to learn what they do in various departments & crafts, understand the challenges they face, and how they’ve achieved high levels of success despite the exploitative nature of the entertainment industry. If you love what you do but you don’t want your career to destroy you, Jerilynn and Kimi can definitely guide you in the right direction!

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Here's What You'll Learn:

  • Jerilyn and Kimi’s two different pathways into becoming award winning Hollywood hairstylists
  • KEY TAKEAWAY: Loving your job comes down to knowing when to say yes and when to say no
  • KEY TAKEAWAY: You know you’ve found the right job when you enjoy the problems you are required to solve every day
  • The hidden job requirements of a hair stylist HINT: people skills are not optional
  • Who really sets the mood for the day on film and tv sets
  • How to do the job while still having energy for life outside of work
  • A day in the life of a hair and make up stylist
  • The vast differences in hours and expectations between working in hair and makeup for Scripted and Unscripted shows
  • How IATSE’s latest contract has not improved the hours on set and the workarounds studios have
  • Why staying physically fit will make you better at your job
  • KEY TAKEAWAY: Hard work is always behind every success story
  • Advice from Kimi and Jerilynn to up-and-coming hair stylists that is good advice for anyone in trying to find a fulfilling career
  • The one thing you can’t ever stop doing no matter how long you’ve been at your job
  • The key element people miss when hearing about manifesting your dreams

Useful Resources Mentioned:

Album - Wikipedia


The Five "F" Words To Manifesting Your Life: Stephens, Jerilynn

Hollywood Hairstylist ✂️ (@jerilynnstephens) • Instagram photos and videos

Kimi Messina (@cutdrytease) • Instagram photos and videos

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Guest Bio:

jerilynn-stephens-bio Jerilynn Stephens

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Jerilynn Stephens is a two-time Guild Award-Winning and ten-time Emmy nominated hairstylist. She is the head hairstylist on Legendary, The Voice, Shark Tank & other top rated shows.

She has worked as a hairstylist and or makeup artist for the past 27 years. She has attracted a personal client list that includes both celebrities and non-celebrities alike.

Jerilynn's motto is “Dream Big or Don’t Bother." She loves sharing her experience of how five simple "F" Words transformed her world and helped her manifest the life of her dreams. She is the author of The Five "F" Words To Manifesting Your Life. Her mission is helping others to dream bigger than they ever thought possible and manifest the life of their dreams through The Five “F” Words.

kimi-messina-bio Kimi Messina

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Kimi Messina is a two-time Emmy and eight-time Makeup and Hair Guild Award winning hairstylist. She has worked as a hairstylist for 40 years and in the industry for 35 years.

She has worked on films such as Almost Famous, Pirates of the Caribbean, Master and Commander, The Last Samurai, He’s All That and Anglyne in Peacock Streaming Service.

She has been the key on Dancing with the Stars for 27 seasons, Legendary Seasons 2 and 3, and numerous TV sitcoms, single camera, and Nickelodeon shows throughout her career.

Kimi’s motto is “Quality through continuous improvement”.

Show Credits:

This episode was edited by Curtis Fritsch, and the show notes were prepared by Debby Germino and published by Glen McNiel.

The original music in the opening and closing of the show is courtesy of Joe Trapanese (who is quite possibly one of the most talented composers on the face of the planet).

284 episodes