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Holly Bohn Pittman

What I Expected

A How To , Education and Arts podcast

#152 in How To · 🇵🇭
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About the show

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.

Newest episodes

Before You Quit Your Job and Travel the World at 40

31 min

Send us Fan Mail Most early retirement advice is about spreadsheets and savings rates. This episode is about the part no one puts in a spreadsheet: what happens when the life you planned doesn’t happen, and you build a different one. On this episode of What I Expected, host Holly Bohn Pittman talks with a friend she calls World Traveler Friend, who retired at 38 and now travels the world full-time, living off dividend income from her investments. Her life didn’t turn out the way she pictured in her 20s. But she was great at saving, and that gave her a choice most people don’t have. Questions we answer in this episode: How is life different from what she pictured in her 20s?When did she decide to stop working, and how long did the plan take?How did she build a savings habit early, and what did she give up?How does living off dividends actually work, in plain terms?What surprised her most in the first year of not working?What does a normal month look like, financially and day-to-day?What do people assume about early retirement that isn’t true?What would she tell a woman in her 30s or 40s whose life isn’t going as planned?Because sometimes the life you didn’t expect turns out to be one worth living. Why a nickname? So many podcasts are on video now, and I think that keeps a lot of important stories from ever being told. Some of the women with the most useful experiences have no interest in being on social media or having their face and name online. That shouldn’t mean we don’t get to learn from them. So when a guest would rather stay private, I give her a nickname. You get her honest story, and she keeps her privacy. This episode reflects one person’s experience and is for general educational purposes only. It is not financial advice. Talk with a qualified financial professional about what makes sense for you. What I Expected is about knowing what to expect before you buy it, try it, book it, or live through it. Some conversations are about the things we choose. Others...

Before You Get Cosmetic Dentistry: Whitening, Bonding & the Truth About Veneers

22 min

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 happens when you get veneers—including how much natural tooth structure may be changed, how long they last, what maintenance is involved, and what future replacement can look like. We also cover cost, how to know if you’re a good candidate, alternatives to consider before altering healthy teeth, and what to look for in a cosmetic dentist. Because the before-and-after photo is only part of the story. You also need to know what happens after the “after.” This episode is for general educational purposes and is not a substitute for individualized dental or medical advice. What I Expected is about knowing what to expect before you buy it, try it, book it, or live through it. Some conversations are about the things we choose. Others are about the things we never expected to face. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

Facing a Breast Cancer Diagnosis: What a Survivor Wishes She'd Known

38 min

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 relationships, and learning to live with the uncertainty that can remain long after treatment ends. We talk about what surprised her, what she wishes she'd known, and what friends and family did that genuinely helped (and what didn't). We also discuss something that doesn't always get enough attention: the emotional side of surviving cancer when everyone else assumes life has gone back to normal. I hope you never need this episode because you've received a breast cancer diagnosis. But if you do, hearing from someone who's been through it may make the unknown a little less frightening. And if someone you love is facing cancer, Amy's experience may help you better understand how to support them. A few things we cover: How Amy's breast cancer was discovered and what happened after her diagnosisWhat chemotherapy and treatment were actually likeHair loss, physical changes, and the emotional impact of cancerWhat friends and family did that helped—and what didn'tLife after treatment, follow-up appointments, and fear of recurrenceWhether there's an Amy before breast cancer and an Amy afterA note: This episode shares one woman's personal experience, not medical advice. Every diagnosis, treatment, and recovery is different. So is what each person finds comforting. If someone you love is going through cancer, ask what they need rather than assuming. For questions about your own breast health, screening, or treatment, consult your healthcare provider. What I Expected is about knowing what...

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All episodes

Before You Quit Your Job and Travel the World at 40

31 min

Send us Fan Mail Most early retirement advice is about spreadsheets and savings rates. This episode is about the part no one puts in a spreadsheet: what happens when the life you planned doesn’t happen, and you build a different one. On this episode of What I Expected, host Holly Bohn Pittman talks with a friend she calls World Traveler Friend, who retired at 38 and now travels the world full-time, living off dividend income from her investments. Her life didn’t turn out the way she pictured in her 20s. But she was great at saving, and that gave her a choice most people don’t have. Questions we answer in this episode: How is life different from what she pictured in her 20s?When did she decide to stop working, and how long did the plan take?How did she build a savings habit early, and what did she give up?How does living off dividends actually work, in plain terms?What surprised her most in the first year of not working?What does a normal month look like, financially and day-to-day?What do people assume about early retirement that isn’t true?What would she tell a woman in her 30s or 40s whose life isn’t going as planned?Because sometimes the life you didn’t expect turns out to be one worth living. Why a nickname? So many podcasts are on video now, and I think that keeps a lot of important stories from ever being told. Some of the women with the most useful experiences have no interest in being on social media or having their face and name online. That shouldn’t mean we don’t get to learn from them. So when a guest would rather stay private, I give her a nickname. You get her honest story, and she keeps her privacy. This episode reflects one person’s experience and is for general educational purposes only. It is not financial advice. Talk with a qualified financial professional about what makes sense for you. What I Expected is about knowing what to expect before you buy it, try it, book it, or live through it. Some conversations are about the things we choose. Others...

Before You Get Cosmetic Dentistry: Whitening, Bonding & the Truth About Veneers

22 min

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 happens when you get veneers—including how much natural tooth structure may be changed, how long they last, what maintenance is involved, and what future replacement can look like. We also cover cost, how to know if you’re a good candidate, alternatives to consider before altering healthy teeth, and what to look for in a cosmetic dentist. Because the before-and-after photo is only part of the story. You also need to know what happens after the “after.” This episode is for general educational purposes and is not a substitute for individualized dental or medical advice. What I Expected is about knowing what to expect before you buy it, try it, book it, or live through it. Some conversations are about the things we choose. Others are about the things we never expected to face. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

Facing a Breast Cancer Diagnosis: What a Survivor Wishes She'd Known

38 min

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 relationships, and learning to live with the uncertainty that can remain long after treatment ends. We talk about what surprised her, what she wishes she'd known, and what friends and family did that genuinely helped (and what didn't). We also discuss something that doesn't always get enough attention: the emotional side of surviving cancer when everyone else assumes life has gone back to normal. I hope you never need this episode because you've received a breast cancer diagnosis. But if you do, hearing from someone who's been through it may make the unknown a little less frightening. And if someone you love is facing cancer, Amy's experience may help you better understand how to support them. A few things we cover: How Amy's breast cancer was discovered and what happened after her diagnosisWhat chemotherapy and treatment were actually likeHair loss, physical changes, and the emotional impact of cancerWhat friends and family did that helped—and what didn'tLife after treatment, follow-up appointments, and fear of recurrenceWhether there's an Amy before breast cancer and an Amy afterA note: This episode shares one woman's personal experience, not medical advice. Every diagnosis, treatment, and recovery is different. So is what each person finds comforting. If someone you love is going through cancer, ask what they need rather than assuming. For questions about your own breast health, screening, or treatment, consult your healthcare provider. What I Expected is about knowing what...

Dental Health After 40: Teeth, Gums & Menopause

40 min

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 they used to. We also cover fluoride versus hydroxyapatite, “clean” toothpaste, whitening and abrasivity, manual versus electric toothbrushes, and flossing and mouthwash. Because dental products and technology are changing so quickly, we cover how to find a good dentist, what red flags to watch for, when a second opinion makes sense, and which advances in dental technology actually matter. If you’ve ever stood in the toothpaste aisle wondering when brushing your teeth became this complicated, this episode is for you. This episode is for general educational purposes and is not a substitute for individualized dental or medical advice. What I Expected is about knowing what to expect before you buy it, try it, book it, or live through it. Some conversations are about the things we choose. Others are about the things we never expected to face. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

Why I Started What I Expected, Part 2: How I Rate Brands & Products

39 min

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...

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

22 min

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. What I Expected is about knowing what to expect before you buy it, try it, book it, or live through it. Some conversations are about the things we choose. Others are about the things we never expected to face. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

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

29 min

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. What I Expected is about knowing what to expect before you buy it, try it, book it, or live through it. Some conversations are about the things we...

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

26 min

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. What I Expected is about knowing what to expect before you buy it, try it, book it, or live through it. Some conversations are about the things we choose. Others are about the things we never expected to face. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

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

35 min

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. What I Expected is about knowing what to expect before you buy it, try it, book it, or live through it. Some conversations are about the things we choose. Others are about the things we never expected to face. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

Before You Buy a Luxury Watch: Brands, Budget, and What to Know First

39 min

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. What I Expected is about knowing what to expect before you buy it, try it, book it, or live through it. Some conversations are about the things we choose. Others are about the things we never expected to face. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

Before You Start Pilates: What Your First Lesson is Really Like

24 min

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. What I Expected is about knowing what to expect before you buy it, try it, book it, or live through it. Some conversations are about the things we choose. Others are about the things we never expected to face. More reviews, guides & recommendations: WhatIExpected.co Shopping Links: Shop My or Amazon. Have a topic you want me to unpack? Send it my way.

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