What happens when you’ve done everything you thought you were supposed to do, and still don’t feel at home in your own life?

Lori Montry knows that feeling. A Harvard Law graduate, former attorney, and now a somatic practitioner and author, she shares how a life built around achievement and other people’s expectations led her to ask what she actually wanted.

We talk about those familiar “good girl” patterns, trying to prove we’re enough, and learning to notice our own needs. Lori shares her perspective on the coping patterns we carry forward and demonstrates two exercises. I try them with her and describe the change I feel in my shoulders.

And, of course, there’s wine! Lori’s memory of sharing a meal with her daughter and choosing a favorite Barolo brings this conversation about self-worth into a wonderfully everyday moment.

In this episode:
- Questioning a life built around everyone else’s expectations
- Recognizing people-pleasing and the pressure to achieve
- Exploring Lori’s approach to old coping patterns
- Trying the “voo” and “creating space” exercises
- Asking for support and allowing change to take time
- Choosing something you love without talking yourself out of it

Connect with Lori:
- Website
- Free guide: Your Nervous System Is Talking: Learning to Listen
- Book: You’re Not the Problem
- Instagram
- YouTube
- Facebook community

Find more conversations and ways to connect at Penny for your Shots, or explore Wine Camp. Follow the show for a new conversation every Thirsty Thursday, and share this one with a girlfriend who might recognize herself in it.

Content note: This conversation includes discussion of childhood sexual abuse and emotional eating.

Lori shares her personal experience and approach. This conversation is for education and reflection, not medical or mental health advice. If you choose to try the exercises, do so somewhere safe, not while driving, and stop if you feel uncomfortable.

Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.

Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call

Wine Camp 2027 - Join the list or save your spot:
https://www.pennyforyourshots.com/winecamp

Become an Insider for weekly updates, tips, inspiration, and episode extras:
https://www.pennyforyourshots.com/insider

Love cocktails + community? Join the Sipper Club:
https://www.pennyforyourshots.com/sip

Explore all things Penny: coaching, podcast, events, & more:
https://www.pennyforyourshots.com

Follow Penny on Instagram: @penny4yourshots
Or on Facebook: Penny (Kuhlers) Fitzgerald

After years of taking care of everyone else, what do you want for yourself?

Jen Mentesana knows how easily that question can get buried beneath family responsibilities, work, and being the person who keeps everything going. Her path took her from corporate America to coaching, then into the restaurant business with her husband. Eventually, she realized she had lost touch with the work and interests that made her feel like herself.

Jen joins me for a conversation about finding your way back, making room for joy, and choosing where your time and energy go.

In this episode:

• The moment Jen realized she needed to change direction
• How women’s roles and responsibilities can crowd out their own interests
• Remembering how to play and have fun
• Making space for quiet, reflection, and intuition
• Practical language for saying no
• Recognizing the cost of always saying yes
• Honoring your own version of a fulfilling life

We also talk French rosé, vodka sodas with lemon, and the girlfriends who’ve known us through all our different chapters.

Connect with Jen:
Website: https://jenmentesana.com/
Instagram: https://www.instagram.com/jen_mentesana/
Podcast: Where Passion Meets Purpose, available through her website

Follow Penny for your Shots: Conversations (and Cocktails) with Brilliant Women and join me every Thirsty Thursday.

Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.

Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call

Wine Camp 2027 - Join the list or save your spot:
https://www.pennyforyourshots.com/winecamp

Become an Insider for weekly updates, tips, inspiration, and episode extras:
https://www.pennyforyourshots.com/insider

Love cocktails + community? Join the Sipper Club:
https://www.pennyforyourshots.com/sip

Explore all things Penny: coaching, podcast, events, & more:
https://www.pennyforyourshots.com

Follow Penny on Instagram: @penny4yourshots
Or on Facebook: Penny (Kuhlers) Fitzgerald

What does it take to build a business when your family’s needs have to come first?

For Kymbirley “Kym” Brake, it began in a hospital room. While caring for her daughter, she started helping other parents with taxes and insurance paperwork. That work grew into a business that allowed her to support them both while remaining available for her daughter’s care.

Kym joins me to talk about financial independence, finding confidence in your own abilities, and making business decisions that reflect the life you actually need. We also discuss taxes, asking for professional guidance, and the challenge of knowing when to keep going and when to change direction.

In this episode:
• How helping other families became the beginning of Kym’s business
• A teacher who saw her gift for numbers
• Building a career around caregiving
• Asking better questions about your business and taxes
• Perseverance, pivoting, and the pressure to keep your word
• Choosing your clients and protecting your energy
• Making room for travel, connection, and a little fun

Connect with Kym:
Website: https://www.octaxbrake.com/
Instagram: https://www.instagram.com/octaxbrake/

Visit her website to explore her services, courses, and membership.

Know a woman who is building a business around a complicated life? Share this conversation with her.

This conversation is for general information and is not individualized tax or legal advice. Consult a qualified professional about your circumstances before acting on any tax strategy discussed.

Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.

Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call

Wine Camp 2027 - Join the list or save your spot:
https://www.pennyforyourshots.com/winecamp

Become an Insider for weekly updates, tips, inspiration, and episode extras:
https://www.pennyforyourshots.com/insider

Love cocktails + community? Join the Sipper Club:
https://www.pennyforyourshots.com/sip

Explore all things Penny: coaching, podcast, events, & more:
https://www.pennyforyourshots.com

Follow Penny on Instagram: @penny4yourshots
Or on Facebook: Penny (Kuhlers) Fitzgerald