Meet Madison - Overcoming High Pressure And People Pleasing

Meet Madison. It’s dinner time, and her family is taken aback by her sudden outburst. Her daughters fall silent, and her husband, with a concerned look, gently asks, “Honey, are you okay?” Forcing a smile, Madison replies, “Yeah, I’m fine,” and excuses herself to the bathroom. Alone, she gazes into the mirror as tears flow uncontrollably. Madison is the general manager of a luxury hotel in downtown Chicago, overseeing a team of 25. At home, she has a supportive husband and three young children—two daughters and an 18-month-old son. Her days start at 6 a.m., balancing family responsibilities with an increasingly demanding job. Tomorrow, her hotel will host a major event for a Fortune 500 company, and last-minute changes have thrown her meticulously planned schedule into chaos. She feels torn between being present for her family and addressing the mounting work requests piling up on her phone. As the pressure mounts, Madison feels like she’s losing control. Jay sits down with Rebecca O'Brien to explore the challenges of balancing work and personal life through Madison’s story. Rebecca, who has 15 years of experience in international sales and marketing, has faced burnout herself. Now a certified stress management instructor, she offers keynotes, workshops, and one-on-one coaching to help leaders prioritize their health and well-being. Tune in to hear Rebecca’s advice for Madison on how to overcome the tendency to put others first at the expense of her own well-being, while still being an effective leader and a great parent. In This Episode: (00:01) Madison's story (03:32) Introduction to Rebecca (04:35) Rebecca's burnout experience (07:00) Recognizing burnout signs (10:47) Mindful workday concept (15:29) Ineffective strategies for Madison (18:33) People-pleasing patterns (22:21) Overcoming people-pleasing (24:35) Understanding inner work (25:52) Unbreakable boundaries (31:12) Befriending your stress (34:37) Managing stressful situations (35:34) Leaving work stress at home (39:15) Creating mindful associations (40:49) Supporting emotional release (42:13)The importance of connection with others and seeking help (47:20) Mindful physical symptoms (48:32) People-pleasing dynamics (49:00) Befriending your stress (49:43) Mindful workday strategy Notable Quotes “You are not broken. It’s about doing the inner work, and sometimes that means revisiting your past with a therapist.” — Rebecca O'Brien, 00:24:35 “I see you. I hear you. I am here. Take your time and let whatever is coming up right now come up.” — Rebecca O'Brien, 00:40:49 “Listen to your body and notice if there are symptoms such as fatigue or feelings of lacking motivation. This could very well be a symptom of burnout or anxiety.” — Jay Abbasi, 00:47:20 “There are holes in one's own self-worth if they need other people to like them in order to feel safe.” — Jay Abbasi, 00:48:32 “Simplify your workday down to one, two, or maybe three main focuses for today, and have a very clear start time and end time.” — Jay Abbasi, 00:49:43 Resources and Links Rebecca O'Brien Website: http://www.wellnessbyrebecca.com/ LinkedIn: https://www.linkedin.com/in/wellnessbyrebecca/ Instagram: https://www.instagram.com/wellnessbyrebecca X: https://x.com/wellnessbyr Jay Abbasi Website: https://jayabbasi.me/ LinkedIn: https://www.linkedin.com/in/jayabbasi/ Instagram: https://www.instagram.com/jayabbasi_/ Facebook: https://www.facebook.com/thejayabbasi/ YouTube: https://www.youtube.com/@jayabbasipodcast