Jay Shetty & Claudia Oshry ON Overcoming Body Shame

Have you ever wondered how someone known for humor and spontaneity manages serious life transitions like marriage, significant weight changes, or major career decisions?

In this On Purpose episode, Jay Shetty interviews popular digital creator Claudia Oshry, often recognized for her quick wit and influential online presence. Her open conversation reveals unexpected layers behind her confident personality, explaining how she navigates insecurities, body-image struggles, marriage at an early age, and a highly successful media platform that entertains millions.

Early Fame and an Unconventional Start

Claudia Oshry's journey to fame began when she was in her first year at college. She gained a following on Tumblr, which eventually led her to become popular on Instagram, before content creation was considered a valid job. She was already pitching herself to brands at seventeen and eighteen and negotiating fees without the help of any manager. The comedian told Jay Shetty how surreal it felt making more money than in an entry-level media position by working from home and having no formal schedule.

Yet, although successful, Oshry still needed to learn the ropes of being an entrepreneur. She felt anxious in the absence of a sense of structure or accountability. Moreover, people around her struggled to understand her work, because it didn't follow the conventional path after graduation. The comedian jokes telling Jay Shetty how she feared going to jail because she didn't understand how to do her taxes and miscalculated the amount she needed to pay. Oshry also priced her services lower sometimes, because she didn't have a good understanding of the industry and how brand collaborations worked. Yet, over time and with the appropriate help, she managed to turn a social media hobby into a career.

From Spontaneity to Sustained Media Success

A significant turning point in Oshry's life was when she started her podcast The Toast, together with her sister Jackie. Creating the podcast offered her some structure in her work - she needed to plan episodes, research, and record live conversations. The comedian admitted to Jay Shetty that while her previous freestyle seemed fun, it often lacked direction, and she is happy to have found professional discipline in her podcast.

Moreover, Claudia Oshry addressed the misconception that comedians and people doing a show only work for the duration of said show. She and Jay Shetty agree that sustaining a conversation in front of the camera requires extensive preparation, rehearsals, and research. Additionally, Oshy manages her marketing agreements, creates show outlines, handles post-production, and performs many other tasks that are invisible to the public. Also, being a comedian involves skill honing, timing, listening, and being willing to constantly evolve.

Marriage at Twenty-Three and Personal Growth

Claudia Oshry opened up to Jay Shetty about marrying her husband, Ben Soffer. They met when the comedian was still a college freshman and decided to wait until she finished school before fully committing to marriage. While most people tend to wait and go through numerous significant changes in their twenties, Oshry married Soffer when she was twenty-three, despite societal warnings against marrying too young.

The comedian told Jay Shetty that having a loving and supportive partner played a significant role in her success. Being still young in her twenties but having a happy, stable relationship allowed her to focus more on her career and achieve greatness. She also considers herself lucky to have a husband alongside whom she could grow, and that they both chose to grow in the same direction, not apart. Oshry attributes her personal development to her husband's patience and kindness.

Body Image Struggles and Discovering Ozempic

Claudia Oshry discussed openly her struggles with Ozempic and how she managed to lose weight by using this drug. She told Jay Shetty that she has always struggled with her body image, ever since she was young. When she was a child, she even attended a so-called “weight-loss camp,” in an attempt to become thinner and fit into the tabloid beauty standards.

Although Ozempic was initially intended as a diabetes management drug, it is often prescribed for weight loss. Oshry resorted to using it because she felt that her habits were getting in the way of her weight loss, but she felt embarrassed by it. The comedian shared with Jay Shetty that she chose to publicly admit her Ozempic usage for fear or judgment, especially during public debates, suggesting that the use of Ozempic could potentially deprive diabetics of essential medications.

Though the drug brought her the results she had expected both physically and mentally, Oshry struggled to process her guilt and shame. It was difficult for her to open up to the public about her struggles, but the comedian finds it important to discuss her perspective and how Ozempic can be a lifeline for certain people.

Self-Acceptance Versus External Pressures

Claudia Oshry claims that losing weight was not only a positive experience; she was used to her old body and learned to accept it. The comedian told Jay Shetty that stepping on a scale used to cause her mild discomfort, but also acceptance. However, after losing weight, she became obsessed with the numbers on the scale, this way trading one insecurity for another. After losing weight, Oshry felt that the numbers on the scale represented a daily reminder and assessment of her self-worth.

Moreover, the comedian became more aware of the constant presence of public commentary. Early in her career, fans and critics used to call her unhealthy because of her visible weight. However, after losing many pounds while medicating with Ozempic, people accused her of cheating and playing the system, stealing drugs from those in need. Jay Shetty explains that everyone has a reason behind their decisions and that these reasons are not openly visible to everyone, so a lot of the judgment is based on insufficient information.

Society often criticizes those who struggle with their health, but, at the same time, it is cynical when someone turns their life around and achieves their health goals. Claudia Oshry found her peace and fulfillment through medical guidance and her determination, learning that happiness shouldn't rely on the approval of social media.

The Emotional Process of Leaving Ozempic

After using Ozempic for a year, Claudia Oshry discontinued it - she managed to lose what she considered a lifelong "Roman Empire" amount of weight, and changed her routine to be more mindful of her eating habits and more disciplined with exercise. She shared with Jay Shetty that getting off the medication was like a test for her, to see if she could maintain a healthy lifestyle all by herself, without relying on a weekly injection.

The comedian proudly admits to Jay Shetty that Ozempic served as a catalyst to change rather than a crutch in keeping her healthy. She recognized how important her support system was, alongside the commitment to eating healthy meals and regular gym visits. Oshry is aware that opening up about such personal and vulnerable topics can make her a target for pity or mockery. Yet, she believes that being transparent about Ozempic might free others from unwarranted shame.

Pregnancy and Family Plans

Claudia Oshry explained to Jay Shetty that she stopped taking Ozempic because she wanted to start a family. Although she had married young, she was not yet prepared to conceive; so she decided to focus on her career and health before embarking on the motherhood journey.

The comedian told Jay Shetty that growing up in a modern Orthodox Jewish environment, it was not uncommon for people to marry and start a family young. However, she wanted to experience more of life before becoming a mother, like enjoying a fulfilling post-college life, developing her media brand, and being absolutely sure she was genuinely happy to have a child. Now pregnant, Oshry experiences a range of mixed emotions: she is overjoyed to soon welcome her first child, but at the same time sad that her late father won't be able to meet his grandchild.

On Grief and Vulnerability

Claudia Oshry opened up to Jay Shetty about grief - she had lost her father when she was a teenager. Recently, she also experienced the death of her beloved dog and companion, Theo. The comedian was taken aback by the overwhelming sadness she felt when she had to euthanize her canine family member due to terminal cancer. She describes the last weeks as being far more challenging than the moment of his death - watching him die made her weaker than she usually is.

Seeing her dog struggle for a long time, she understands that maybe it is better to have a quicker demise, even if it means being unable to have a final talk. Oshry told Jay Shetty that her father suffered an unexpected heart attack and was gone before she had the chance to say goodbye to him, but she understands that he suffered less this way. Jay Shetty explained that grief is often accompanied by feelings of guilt, sadness, and confusion, and sometimes it even leads to partial withdrawal. The comedian admitted to having temporarily vanished from the public eye for a period, to deal with her feelings in private.

Maintaining Personal Boundaries

Claudia Oshry has spent the last years as a public figure, well known by her fans. Yet, she warns against parading your entire life on social media - she told Jay Shetty that she would prefer to raise her child offline; while the decision is not yet final, the comedian strongly feels that children can't consent to public exposure. Similarly, she believes that people shouldn't share personal struggles (such as fertility or health issues) as a response to speculation. She believes that you should only speak about them openly if you decide to do so yourself, not because of external pressure.

However, Claudia Oshry is aware that her career is built and thrives on relatability and transparency, which can easily lead to oversharing or feeling that she has nothing left just for herself. Today's digital climate often pushes creators to turn every aspect of their lives into content. Yet the comedian adopted a cautious strategy that allows her to keep certain elements of her life only for close friends, such as her marriage and family growth. She believes that people sometimes overshare, and she uses this strategy to prevent any future regrets about sharing too many private memories for temporary public attention.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode on “Claudia Oshry ON How to Stop Letting Your Body Image Hold You Back & Build Lasting Confidence” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at jayshetty.me.