#351 | Inside A Difficult Breastfeeding Journey: Flat Nipples, Tongue Tie and Slow Weight Gain

January 21, 2026

In this episode, Jessica shares the breastfeeding journey she never expected. After a smooth birth at a birth center, feeding quickly became complicated: flat nipples, an early nipple shield, a missed first feeding window, a significant tongue tie, and a baby who grew increasingly sleepy and underweight. What followed was weeks of pumping, weighted feeds, donor milk, tongue-tie revision, and the ongoing effort to understand why breastfeeding wasn’t working despite doing everything “right.”

Jessica describes the emotional strain of those early weeks, from feeling inadequate to questioning her own anatomy, and the constant fear she was letting her daughter down. This conversation brings needed attention to the realities behind many breastfeeding challenges and the gaps that leave mothers without the support they need. 

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About Cynthia Overgard

Cynthia is a published writer, advocate, childbirth educator and postpartum support specialist in prenatal/postpartum healthcare and has served thousands of clients since 2007. 

About Trisha Ludwig

Trisha is a Yale-educated Certified Nurse Midwife and International Board Certified Lactation Counselor. She has worked in women's health for more than 15 years.

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