Skip to main content

Have the Hard Conversations Before It’s Too Late

Strategy Series
Jen Estill and Karen Stefl
This week, we’re getting personal. The phrase “sandwich generation” refers to people in their 40s and 50s who are juggling raising children and caring for aging parents, and that’s exactly where we’re finding ourselves. Many people find themselves unexpectedly needing to make major life decisions on behalf of an elderly parent, and there’s no how-to guide on navigating how to find the right care for a parent in their final chapter. This week, we talk about our experience with aging parents and all the things we wished we knew before finding ourselves in our current positions.

Navigating the complexities of caregiving for aging parents is an endeavor fraught with uncertainty and emotion. It's a journey that often catches us off guard, forcing us to confront the profound responsibility of guiding our parents through end-of-life care.

In this episode, we delve into our personal experiences with aging parents, reflecting on the hurdles faced and lessons learned. From grappling with difficult medical decisions to finding the right support systems, we discuss the steps we wish we’d taken to prepare and share the candid realities of being members of the sandwich generation.

Old Pal

Old Pal

Old Pal
The Old Pal cocktail is characterized by its bold and complex flavor profile, with the spicy notes of rye whiskey complementing the bitter and herbal flavors of Campari and dry vermouth. It's a versatile drink that can be enjoyed as an aperitif or as a nightcap, perfect for those who appreciate the timeless allure of classic cocktails.


  • 1½ oz Rittenhouse 100 Rye
  • ¾ oz Campari
  • ¾ oz Dolin dry vermouth
  • Garnish: 1 lemon twist


  1. Stir all the ingredients over ice, then strain into a Nick & Nora glass.
  2. Garnish with the lemon twist.

More on

In our last half of this episode, we were taking stock. In part two, we are letting go. No shame. No guilt. No excuses.
The thing about being a leader—sometimes it feels pretty lonely. Heavy decisions and indecision can weigh on you. Who do you turn to when your baggage is starting to feel heavy?
Today we reveal five simple steps to finally achieving life balance! // Look in the mirror and repeat these words: Life Balance is a Fucking Lie. // Feel better?
Listen on apple Podcasts
Get it on Google Play
Listen on spotify
Listen on stitcher