Claudia Oshry's Guide to Unshakeable Confidence (Before & After Weight Loss)

Here are the top 10 key takeaways from Claudia Oshry's candid conversation with Jay Shetty about body image, relationships, and finding confidence in your own journey.

1. Building confidence despite insecurities

Claudia Oshry shared that much of her confidence came from having a supportive partner who loved her unconditionally. Her husband Ben's unwavering belief in her worth helped build her self-confidence when she was struggling with her self-image. She mentions that while getting validation from a man isn't the ideal path to confidence, it worked for her.

Her confidence was something she had to deliberately work on. She describes how she didn't naturally feel confident about her body but made a conscious decision to build her confidence "brick by brick." This deliberate approach to confidence construction shows that confidence can be developed intentionally rather than waiting for it to appear naturally.

2. The transformative journey with Ozempic

Ozempic gave Claudia control over her weight for the first time since college. She described it as achieving a "lifelong dream" that she never thought would be possible. This medication changed her relationship with food and allowed her to finally feel in control of an aspect of her life that had previously felt unmanageable.

She approached her weight loss journey in two phases. First, she let the medication "do its thing" for six months while maintaining her regular eating habits. Then she actively changed her lifestyle by joining a gym, getting a trainer, and eating healthier. This two-phase approach helped her create sustainable changes beyond what the medication alone could achieve.

3. The complex relationship with sharing personal struggles

Claudia initially felt embarrassed about using Ozempic and was hesitant to share her journey publicly. She worried people would judge her for needing medication to control her eating. When she finally decided to share, she faced both support and criticism, with some accusing her of "stealing drugs from diabetics."

Despite the initial reluctance, she ultimately found value in sharing her experience. She felt that her openness could help others feel less ashamed about their own journeys. Claudia was motivated to speak out because she saw primarily negative coverage about Ozempic in the media and wanted to counter that narrative with her positive experience.

4. The evolution of self-perception after significant weight loss

After losing weight, Claudia experienced a new kind of confidence that wasn't just about appearance. She discovered she was capable of changing a significant aspect of her life that she previously thought was unchangeable. This realization transformed her mindset from "I can't change anything" to "I can do anything."

However, this transformation came with unexpected challenges. She found herself becoming more appearance-focused after losing weight, developing an obsession with how she looked that hadn't existed before. This shift illustrates how achieving a long-desired goal can sometimes create new psychological challenges to navigate.

5. The interplay between parenthood and self-image

Claudia discussed the complexity of getting pregnant shortly after significant weight loss. She expressed feeling that she was "mourning" her body, particularly after working so hard to transform it. The timing created a unique emotional challenge that isn't often discussed publicly.

She also touched on the decision to wait until her 30s to have children. She explained that she always knew she wanted to be a mother but waited until she felt truly ready. This readiness came naturally after she had lived fully in her 20s and addressed her weight concerns that had previously made her anxious about pregnancy.

6. Marriage at a young age and growing together

Claudia got married at 23 after meeting her husband Ben when she was 18. She acknowledged that marrying young is often discouraged, and with good reason, as people change significantly in their 20s. Yet she explained how she and Ben consciously chose to "grow up together," adapting to each other's changes.

She credits much of their successful marriage to Ben's patience. She described him as the "kinder, more patient one" who saw her potential even when she wasn't at her best. This balance in their relationship allowed them to navigate the challenges of growing up and changing while maintaining their connection.

7. The evolution of content creation as a career

When Claudia started her Tumblr blog in college, content creation wasn't considered a viable career path. She faced skepticism when choosing to pursue social media full-time instead of a traditional job after graduation. Despite the uncertainty, she followed the opportunities that were presenting themselves.

Over time, her approach to work evolved from an unstructured lifestyle to establishing clear boundaries. She now operates on a Monday to Friday, 9-to-5 schedule with defined work hours. This structure has brought her fulfillment and stability in a career path that can otherwise feel chaotic and unpredictable.

8. The balance between sharing and privacy online

Despite being known for her openness, Claudia has become more selective about what she shares online. She described how she used to share "a piece of content every 30 minutes" but has learned that not every thought needs to be public. This boundary-setting has helped her maintain some personal space despite having a public career.

She's particularly thoughtful about her approach to sharing her pregnancy and future child online. While she plans to share her journey as a mother, she's decided against putting her child on social media. This decision reflects a growing awareness among content creators about the potential downsides of exposing children to public scrutiny.

9. Working with family as business partners

Claudia and her sister Jackie co-host their podcast "The Toast," despite not being particularly close growing up. What makes their partnership successful is their complementary differences. Claudia is outgoing and talkative, while Jackie is more reserved, creating a dynamic balance on their show.

Their podcast's authenticity comes from their commitment to spontaneity. They deliberately avoid discussing topics before recording to ensure genuine reactions and conversations. This approach has helped them maintain the show's freshness and authentic sibling dynamic that resonates with their audience.

10. Navigating grief at different life stages

Claudia shared insights about experiencing grief as a child versus as an adult. When her father died suddenly when she was in ninth grade, she found herself able to "bounce back" relatively quickly. As a child, she was adaptable and resilient in ways that surprise her now looking back.

In contrast, losing her dog Theo as an adult was profoundly difficult. She found grief much harder to process as an adult because she had a deeper understanding of loss and its implications. This experience gave her unexpected perspective on her father's sudden passing, making her grateful he didn't suffer through a prolonged illness as her dog had.