What I Expected

Holly Bohn Pittman
  • 5.0 (4)
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Welcome to What I Expected—a podcast for women in their 30s, 40s, and 50s about what to really expect, before you experience it. So much about getting older has changed since your grandmother's day, and the advice she used to pass down doesn't always fit the world you're actually living in. Think of this as that same wisdom, updated for modern life—your toolkit for the changes, the purchases, and the moments you wish someone had prepped you for. What to ask, what to plan for, before you spend your money, your time, or your peace of mind. Except it's not a lecture. Think of it like the advice you'd get from your closest girlfriends—minus 47 unread messages. We break through the hype with honest, no-nonsense answers, sensible standards, and zero pressure to keep up. New episodes every Tuesday—covering everything from Pilates to jewelry to the changes your body springs on you—for women who'd rather hear it straight from a friend than find out the hard way.

Episodes

  1. 5d ago

    Behind What I Expected, Part 1: From Entrepreneur to CEO & Back Again

    Send us Fan Mail 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 Workwhy 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. In Part 2, we’ll get into how decades spent designing products, watching people shop, working with major retailers and sitting inside marketing teams changed the way I evaluate what we buy, and ultimately became the foundation for What I Expected. Know what to expect before you buy it, try it, book it, or live through it. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

  2. Sep 15

    Buying Fine Jewelry, Part 1: Diamonds, Lab vs. Natural & What to Know Before You Buy

    Send us Fan Mail Have you ever wanted to buy a diamond or another piece of fine jewelry, but felt like you should already know what you’re doing before you walk into the store? This episode is for you. I sit down with Nicole Nettles, owner of Blue Water Jewelers, and Kashmir Elkin, an engagement ring specialist, to talk through the questions people actually have before making a significant jewelry purchase. We’re keeping it practical: no gemology degree required. We get into lab-grown vs. natural diamonds, what really affects sparkle, why cut matters, how carat weight can be misleading, what to know about resale and upgrade policies, choosing a setting that fits your lifestyle, and why seeing a diamond in person can matter more than the grading report alone. We also talk about self-purchasing, traveling with valuable jewelry, and a few expensive mistakes buyers make when they don’t know what questions to ask.  This is Part 1 of Buying Fine Jewelry, because as with watches, there was far too much to fit into one conversation. In Part 2, we’ll get into buying jewelry online, metals, and why having a relationship with a jeweler can matter more than you might think. Know what to expect before you buy it, try it, book it, or live through it. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

  3. Sep 1

    Hair After 40: Thinning, Gray, Frizz, and What You Can Do About It

    Send us Fan Mail Your ponytail's suspiciously thinner, your texture's changed, the grays multiplied, and suddenly your hair requires a negotiation. I sit down with Sherry Diedrich—my stylist for more than a decade, and someone who's guided women through this exact shift for 40 years (and lived it herself). This is basically what you'd hear in a salon chair from someone who isn't trying to go viral. We cover thinning vs. breakage, what actually helps thinning hair, gray strategy, dryness and frizz, heat and color damage, why DIY color is a bad idea if you want salon results, how to find a great stylist, and what's actually worth paying for. A note: this episode is for general education, not medical advice. If you're dealing with sudden shedding, bald spots, pain, sores, or inflammation, please check in with a dermatologist or healthcare professional. Know what to expect before you buy it, try it, book it, or live through it. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

  4. Aug 25

    Watches 101: The "No-Stupid-Questions" Guide to Buying a Nice Watch

    Send us Fan Mail Have you wanted to buy a "nice" watch but were too embarrassed to ask the basic questions at the counter? This one's for you. I sit down with Sara Seifert, Publisher of WatchTime Magazine, to answer all the questions people are afraid to ask when buying a fancy watch. Fair warning: this topic is a lot — watches are the kind of hobby that starts with "I just want one nice watch" and ends with spreadsheets. We're covering the essentials here, but you can already tell we'll need a Part 2. Here's what we get into: how to buy your first nice watch, what's actually worth the money, whether a smartwatch counts, how to avoid fakes, how to buy used without getting burned, and the maintenance realities nobody mentions at the counter. Know what to expect before you buy it, try it, book it, or live through it. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

  5. Aug 18

    Pilates: What to Expect Before Your First Lesson

    Send us Fan Mail Pilates has been having a moment online lately, especially reformer Pilates — and I remember exactly how overwhelming that felt when I was starting out. In this episode, I sit down with Amy Ulmer, a certified Pilates instructor I personally train with and trust, to break it all down in plain English. I've been practicing Pilates for about 25 years, and I can't imagine my life without it — it transformed my body and put an end to the muscle strains and random spasms that used to leave me flat on my back for days. Whether you're Pilates-curious or ready to book your first class, we're covering how to get started, what it typically costs, who it's great for, what to watch out for, and why it might be worth it — so you can decide if it's right for you. Know what to expect before you buy it, try it, book it, or live through it. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

  • 5 Episodes

5
out of 5
4 Ratings

About

Welcome to What I Expected—a podcast for women in their 30s, 40s, and 50s about what to really expect, before you experience it. So much about getting older has changed since your grandmother's day, and the advice she used to pass down doesn't always fit the world you're actually living in. Think of this as that same wisdom, updated for modern life—your toolkit for the changes, the purchases, and the moments you wish someone had prepped you for. What to ask, what to plan for, before you spend your money, your time, or your peace of mind. Except it's not a lecture. Think of it like the advice you'd get from your closest girlfriends—minus 47 unread messages. We break through the hype with honest, no-nonsense answers, sensible standards, and zero pressure to keep up. New episodes every Tuesday—covering everything from Pilates to jewelry to the changes your body springs on you—for women who'd rather hear it straight from a friend than find out the hard way.

Information

  • Creator
    Holly Bohn Pittman
  • Years Active
    2026
  • Episodes
    5
  • Rating
    Explicit
  • Copyright
    © 2026 What I Expected
  • Show Website
    What I Expected