EP07 The What I Expected Story: Part 2

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A few people have asked me the obvious question: Who am I, how did I get here, and why should anyone care what I think about shampoo, jeans, skincare, or anything else I’m reviewing?

So for this episode, I’m switching seats. Instead of asking the questions, I asked my friend Kristie (AKA Petite & Powerful) to interview me.

On paper, my career makes very little sense. I started as an entrepreneur, built and sold a brand, designed products for major retailers, lost almost everything during the financial crisis, moved into corporate America, became a CMO and eventually a CEO. Then, at 52, walked away to start something new again.

But when I look back, there is a thread running through all of it: curiosity.

In Part 1, we talk about:

  • how my first business became See Jane Work

  • why observing how people actually shop taught me more than surveys ever could 

  • building products and brands without formal training in either 

  • what success, and losing nearly everything, taught me about luck, control, and failure 

  • the very different lessons I learned as an entrepreneur and inside corporate America 

  • why titles and career paths matter less to me now than the people and purpose behind the work 

  • and why I ultimately left the corporate world and started What I Expected at 52. 

This isn’t really a story about having a perfectly mapped-out career. Mine certainly wasn’t.

It’s about staying curious, learning as you go, knowing when to ask for help, and realizing that sometimes the experiences that make the least sense while you’re living them are the ones that prepare you for whatever comes next.

Holly Bohn Pittman

Holly Bohn Pittman is the founder of What I Expected. She previously founded See Jane Work, sold exclusively at Office Depot, and developed products for major retailers including Target, Walmart, Staples, Costco, and Sam's Club. A former CEO and CMO, she now tests what brands promise against what women 40+ actually experience, and rates each one MISS, MEET, or EXCEED.

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EP06 Buying Fine Jewelry: Part 2