You Can Have It All, Just Not All at Once

This week on the Grow Like a Mother podcast, I’m joined by Rashi Kakkar, a global leadership expert, former management consultant, and founder of the Decks & Diapers newsletter, for a powerful conversation about what happens when the life you’ve built on paper doesn’t match the one you’re actually living.

Rashi shares how she realized that chasing traditional success left her burned out, misaligned, and disconnected from what truly mattered and how she found the courage to pivot, own her story, and lead with authenticity. We talk about ambition, motherhood, identity, and what it means to stop performing and start living.

We talk about:

• The moment she realized success ≠ happiness

• Why she turned down a major promotion to explore joy and curiosity

• The truth about working motherhood (and why she’s not hiding it anymore)

• How Decks & Diapers became a community lifeline during the pandemic

• Leading with empathy in male-dominated spaces

• The difference between glass balls and plastic ones
  

Timestamps:

3:20 – “I always confused success with achievement… which was happiness, right?”

6:10 – When she realized getting the promotion wouldn’t actually make her happy

9:45 – “You can have it all… just not all at once.”

12:00 – Rashi shares the ‘glass vs plastic balls’ metaphor that changed how she prioritizes

16:50 – The origin story of Decks & Diapers and building what she couldn’t find

22:30 – “Being a mom is a feature, not a bug”—why she proudly claims motherhood at work

About Rashi:

As a former consultant, Rashi has advised Fortune 100 clients on complex strategic, operational, and organizational challenges. She has led digital transformations, enhanced organizational effectiveness, and redesigned operating models. Outside of work, Rashi enjoys writing, she authors a bi-weekly newsletter and has published 80+ opinion pieces in leading global publications. She is an avid golfer, a former varsity tennis player, and a newly minted pickleball enthusiast. She is mom to a 5 year old daughter and resides in the Greater Toronto Area with her husband and their mini goldendoodle, Bruce!

Disclaimer: All views expressed are Rashi’s own, and do not necessarily reflect the views of any organization she may be associated with.

Connect with Rashi:

https://linktr.ee/RASHI.KAKKAR

Resources Mentioned:

Decks and Diapers Substack: https://decksanddiapers.substack.com

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Follow Jill Wright:

🌐 Website: www.jillwright.ca

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