The “supermom” cape looks shiny until it weighs a ton. We sit down with Shaily Gupta — powerhouse HR leader, executive coach, and mom—to unpack why chasing perfection drains our energy, dims our joy, and keeps us from seeing the help already around us. Her stories cut through the noise: the bold career pivot from engineering to HR, the dinner-table debate that flipped a “strawberry generation” stereotype, and the simple family rule that transformed summers into core memories.
What stands out is how small shifts change everything. When relentless travel and meticulous planning left her burned out, a friend asked, “What if you drop the ball?” She tried it—and watched a father–daughter bond bloom without her orchestration. That insight fuels a practical framework: treat life as seasons. Sometimes you choose a stable job to protect family bandwidth; other times you lean into a career sprint. Shelly’s own courageous ask led to a flexible month-in-Singapore setup, helping her scale a company while gaining more presence at home. It’s proof that honest communication and clear proposals can unlock manager support.
We also dig into parenting without control. Kids learn in the wild: swimming, skating, confidence, and resilience often appear when we step back. Support the safety net; don’t build a cage. Shaily shares why mothers should stop grading themselves against impossible standards, how to turn guilt into choices and iterations, and why coaching family is a boundary she won’t cross—mentoring when asked and referring to independent coaches instead. Now, with her daughter grown, she’s channeling fresh ambition into teaching HR leadership, executive coaching, and exploring HR tech and AI.
If you’re tired of tightrope walking between ambition and home, this conversation gives you tools to rebalance with intention: ask for what you need, share the load, and let some balls drop so the right ones can stay in the air. Subscribe, share with a friend who’s juggling too, and leave a review to tell us the first “ball” you’re ready to drop.
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Host: Edit Kerekes, former diplomat, senior strategic advisor, mom of two.
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