Do you ever feel like the career you built is the one you thought you wanted - but then you wake up one day and realize it’s no longer clicking?

That’s where Caroline Witmer found herself. Brown grad. Columbia MBA. Wealth management. Private equity. She’d ticked all the boxes, jumped from chapter to chapter with ease, externally she was ‘crushing it’… but never looking inside to ask herself, are you happy? Is this really what you want?

In this episode of Character, I sit down with Caroline—who's actually a former coaching client of mine—to talk about her journey from finance to founding Tuck Shop, a handcrafted chocolate company capturing the spirit of your happy place.

Caroline shares how she’s building something meaningful while raising three kids under four without the pressure and intensity that colored her career in finance.

In this honest conversation about career change and building a life with character, we explore:

- How do you know when it’s time to leave a career that looks good on paper?

- Letting go of other people’s opinions.

- Giving yourself permission to play.

- Building a business while raising babies.

- What it takes to let go of the pressure and hold things looser.

Connect with Caroline and Tuck Shop:

Website: https://shoptuckshop.com/

Instagram:

@shoptuckshop https://www.instagram.com/shoptuckshop/

Timestamps:

00:00 Introduction & Early Aspirations

01:33 Path into Finance

03:38 Finance Career Growth

05:15 Business School & Transitioning Roles

07:04 COVID & Life Changes Triggering Reflection

09:08 Coaching & Transitioning Mindset

12:43 Shifting from Finance to Entrepreneurship

16:25 Founding TuckShop

20:01 TuckShop Growth & Operations

24:24 Learning Operational Skills

27:14 Spirituality & Grounding Practices

29:18 Balancing Motherhood & Entrepreneurship

32:38 Impact of New York City on Career & Creativity

34:53 Advice to Younger Self & Key Takeaways

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