What I Expected

Holly Bohn Pittman
  • 5.0 (5)
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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. 2d ago

    Behind What I Expected, Part 2: From Entrepreneur to CEO & Back Again

    Send us Fan Mail In Part 1, Kristie and I talked about how I went from starting See Jane Work to nearly losing everything during the financial crisis, moving into corporate America, becoming a CMO and CEO, and eventually deciding at 52 to take another leap of faith. In Part 2, we get into why I started What I Expected. After decades spent developing products and brands, working with major retailers, sitting inside marketing organizations, and watching people make buying decisions, I see shopping very differently than I did when I started. And maybe more importantly, I think differently about expectations. In this episode, we talk about: what marketing should actually do—and why I don’t believe its job is to convince you to buy something you don’t needthe disconnect that can happen between product, marketing and sales teamsexplicit expectations versus the expectations created by price, positioning, environment and brand reputationwhy an expensive product isn’t automatically a better onewhy customer service and what happens after something goes wrong are part of the product experiencehow MISS / MEET / EXCEED evolved, and why a MISS doesn’t necessarily mean something is a bad productwhy I created the Goldilocks Guides for categories where there isn’t one universal “best”why I care so much about quality over quantity, and have since long before I had the budget to support the preferencewhat happens when a brand you trust gets acquired or starts changingwhy I continue to follow products and brands even after I review themwhat it actually takes to earn an EXCEED from meand why reducing decision fatigue has become such a big goal for me at What I ExpectedWe also talk about something bigger than shopping. By your 50s, you’ve lived long enough to know that life rarely turns out exactly the way you expected. You’ve also learned that there is a lot you cannot control. But you can be more intentional about some things—particularly how you spend your time and how you spend your money. That’s really what What I Expected is about. I’m not here to tell you what you should buy or convince you that you need more stuff. I want to help you understand what you’re getting, what questions to ask, what the brand actually promised, and whether the reality lives up to it. Hopefully that means fewer bad purchases, a little less decision fatigue, and more confidence walking into everything from a skincare aisle to a jewelry store to a Rolex boutique. Because you have more important things to do. 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 29

    Buying Fine Jewelry, Part 2: Understanding Jewelry Lingo So You Know What You’re Getting

    Send us Fan Mail Have you ever looked at a piece of jewelry online and thought, “Okay…but what am I actually buying?” Waterproof. Hypoallergenic. Gold vermeil. Gold-plated. 14k. 18k. Sterling silver. Platinum. Jewelry descriptions can start to feel like their own language—and the words on the product page don’t always tell you what to expect once you actually wear the piece. In Part 2 of Buying Fine Jewelry, I’m back with Nicole Nettles and Kashmirr Elkin of Blue Water Jewelers to translate the jewelry lingo into plain English. We get into:  what “waterproof” and “anti-tarnish” claims may actually mean gold vermeil vs. gold-plated jewelry what to consider if you have sensitive skin or see “hypoallergenic” 14k vs. 18k gold, white gold and platinum  why some jewelry needs more maintenance than you might expect  what chlorine, pools and hot tubs can do to your jewelry  why the durability of the gemstone matters too—not just the metal  buying designer costume jewelry  choosing jewelry based on your actual lifestyle, not just how it looks  and why knowing who you’re buying from can matter long after the sale. Two pieces can look almost identical online but have very different prices, materials, durability, and (of course) expectations. If you missed Part 1, start there for lab-grown vs. natural diamonds, sparkle, size, settings, and what to know before making a diamond purchase. Part 2 is about understanding the language so you know what you’re getting before you spend the money. 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 21

    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.

  4. 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.

  5. 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.

  6. 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.

  7. 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.

  • 7 Episodes

5
out of 5
5 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
    7
  • Rating
    Explicit
  • Copyright
    © 2026 What I Expected
  • Show Website
    What I Expected

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