You’ve worked hard. Followed through. Been the person other people could count on. Maybe you’ve even built a life that looks pretty impressive from the outside.

But does it feel like yours?

Lori Montry joined me on Penny for your Shots to talk about the uncomfortable moment when achievement stops answering that question. Her story takes us from Harvard Law to a very different kind of work, with some honest conversation about people-pleasing, self-worth, and learning to choose what you want.

When following the rules doesn’t bring the feeling you expected

Lori had learned to look outside herself for the instructions. Achieve enough. Be who someone else needs you to be. Follow the rules, and eventually you’ll feel worthy.

She describes taking that approach into her education, her relationships, and the life she built. Then came the realization that she’d done so much of what she thought she should do, and still wasn’t happy.

That’s a hard place to find yourself. Especially when being capable and getting things done have been such a big part of how you see yourself.

Lori began looking more closely at the expectations and coping patterns she’d carried forward. That search eventually led her away from law and into the work she does today.

Getting curious about the patterns

Lori’s approach starts with understanding how a pattern developed and what purpose it served. She shares her own experiences with emotional eating, shutting down, and feeling driven to prove her worth.

She also talks about the support she still turns to when something is hard to see for herself. There’s room in this conversation for being capable and needing help. For knowing quite a bit about yourself and still having something new to learn.

You don’t have to have every answer before you ask a better question.

Two exercises, and a noticeable change in my shoulders

During our conversation, Lori demonstrates a breathing-and-sound exercise she calls “voo,” followed by a movement exercise she calls “creating space” or “push away.”

When we spoke, I was getting ready for our seasonal move from Iowa to Florida. There was plenty going on, and I was feeling it. After the second exercise, I noticed that my shoulders felt lower and more relaxed. I could feel the difference.

That was my experience in that moment. Lori also makes the point that the same exercise won’t feel the same for everyone, or even for you on every occasion. Her invitation is to notice your response.

If you choose to follow along, save the exercises for a safe place where you can give them your attention, not while driving. Stop if you feel uncomfortable.

Yes, the Barolo belongs in this conversation

When I asked Lori about her favorite wine, she chose Barolo. Then she told me about a meal with her daughter and a wine list that offered both her favorite and a less expensive option.

She caught herself considering the cheaper glass simply because she felt she should. This time, she chose the one she really wanted.

The meaningful part was that she noticed the old conversation in her head and made her own choice. She was enjoying time with someone she loved, and she let herself enjoy the wine she loved, too.

It’s such a familiar little moment. How often do you talk yourself out of a preference before you’ve even given it a chance?

Connect with Lori

Lori Montry is a former attorney, Harvard Law graduate, somatic practitioner, and author of You’re Not the Problem. Her work explores learned patterns, self-understanding, and creating a life that feels more like your own.

You can find her free resource, Your Nervous System Is Talking: Learning to Listen, and learn more at LoriMontry.com.

This week, notice one place where “I should” answers the question before you do. Then give yourself a moment to ask, “What would I actually choose?”

Content note: The episode 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.