Real conversations so you know what to expect. What I Expected is a podcast for women in their 30s, 40s, and 50s about what to really expect—before you experience it.
So much about life has changed since your grandmother's day, and the advice she passed 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 purchases, the changes, and the moments you wish someone had prepped you for. What to ask and what to plan for before you spend your money, your time, or your peace of mind.
Host Holly Bohn Pittman, a former CMO and CEO who knows marketing spin when she hears it, talks with experts and women who've been there. It's not a lecture. It's the advice you'd get from your closest girlfriends, minus 47 unread messages: honest, no-nonsense answers and zero pressure to keep up.
New episodes every Tuesday, from buying guides and first-time experiences to perimenopause, menopause, and the harder moments no one prepares you for. For women who'd rather hear it straight from a friend than find out the hard way.
Before You Get Cosmetic Dentistry: Whitening, Bonding & the Truth About Veneers
Send us Fan Mail Cosmetic dentistry can mean anything from whitening strips to veneers—and the difference in cost, maintenance, and commitment can be significant. In Part 2 of my conversation with Dr. Michelle DeFelice Hucke, owner of Jax Beaches Family Dentistry, we talk about what to know before you change your smile. We cover what actually works for whitening, the difference between at-home and professional treatments, when bonding may be a better option than veneers, and what really happe...
20 Oct 2026
Facing a Breast Cancer Diagnosis: What a Survivor Wishes She'd Known
Send us Fan Mail What happens after you hear the words “You have breast cancer”? And how can the people who love you actually help? In honor of Breast Cancer Awareness Month, I'm welcoming back Amy Ulmer. Last time, we talked about Pilates. This time, we're having a much more serious conversation. Amy is a breast cancer survivor, and she's sharing what her experience was really like, from discovering something was wrong and receiving her diagnosis to chemotherapy, losing her hair, navigating ...
13 Oct 2026
Dental Health After 40: Teeth, Gums & Menopause
Send us Fan Mail As we get older, our teeth and gums change too, but most of us know far less about what to expect from our mouths than we do about our skin, hair, or hormones. In Part 1 of my conversation with Dr. Michelle DeFelice Hucke, owner of Jax Beaches Family Dentistry, we cover the basics of oral health after 40: what changes with age, the oral-health issues she sees most often in perimenopausal and menopausal women, and why things may suddenly seem to stick to your teeth more than t...
6 Oct 2026
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 shopp...
29 Sept 2026
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 t...
21 Sept 2026
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 ev...
15 Sept 2026
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. nat...
1 Sept 2026
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 f...
25 Aug 2026
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...
18 Aug 2026
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 ...
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