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What I Expected
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.
What I Expected
Behind What I Expected, Part 1: From Entrepreneur to CEO & Back Again
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
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.
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 choose. Others are about the things we never expected to face.
More reviews, guides & recommendations: WhatIExpected.co
Shopping Links: Shop My or Amazon.
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Intro: Why I'm answering the questions this time
Holly Bohn Pittman (Host)Welcome to What I Expected, the show that sets expectations before you buy. My website and social channels compare real life experience to marketing promises. But think of this podcast as your decision-making toolkit: what to ask before you spend your money, or your time, which is your most precious profession. Think of it like advice from a close circle of girlfriends, minus the 47 unread messages. At what I expected, you'll find friendly standards, sensible expectations, and feel zero pressure to keep up. Today's episode is a little different because instead of me asking the questions, I'm answering them. A few people have asked me to share more about who I am, how I got here, and frankly, why anyone should care what I think about shampoo or jeans or anything else that I'm advising you on. So I recruited my friend Kristie to interview me. You know her as petite and powerful. As we started putting this together, we realized my career makes very little sense if you read it on paper. I've been an entrepreneur, designed products, built brands, lost almost everything, worked in corporate America, became a CMO, eventually a CEO, and then left to start something new again at 52. But when you talk it through, there is actually a common thread, curiosity. So that's where we're starting.
Petite & Powerful (Kristie)Kristie, take it away.
Curiosity, Entrepreneurship & Where It Started
Petite & Powerful (Kristie)Sure. Well, before we jump into your career, you're a native-born Cali girl and you're the middle of three sisters. So when you were growing up, what did you think your life was gonna look like?
Holly Bohn Pittman (Host)I don't think I had anything specific in mind, like a specific career. Two things stand out from my childhood. One, I was insanely curious. Um, so curious and asking questions constantly that my parents bought me the tell me why books, so I wouldn't ask them quite so many questions. Uh and then the second part is my sisters were convinced I would become an FBI agent because I could ask so many questions. They would say, I'm I'm not bringing my boyfriend over because you ask him so many questions. You'll interrogate him. Yes. And I always think of that that Uncle Buck episode where he's like, How many consecutive questions can you ask? And I think, oh, I can ask a lot. So, but I was always so I had that curiosity, but then the other part of it was I was always creating businesses. Um we weren't allowed to watch a lot of TV. So we were very creative, and I had two sisters, and we were we were always up to something. And they would do No good. Yeah, yeah, actually, a lot of times no good. But I always had a desk that was a card table that I set up to be a desk. I always had these business ideas. So I guess entrepreneurship was in my blood. Um, but curiosity probably is a better explanation for my career. I like learning, I like entering new spaces and figuring out how they work. So that eventually explains why I wanted both entrepreneurship and corporate experience. Uh, but when you look at my career trajectory on paper, it makes zero sense. But when you talk it through the commonality is learning, I guess, or curiosity.
Petite & Powerful (Kristie)Yeah, so you didn't really start with any particular career in mind. But you started a business and became an entrepreneur
How See Jane Work Began
Petite & Powerful (Kristie)really young. Like, how did that all come together?
Holly Bohn Pittman (Host)Well, there's a couple things there that I think are important to know is one, I'm a very fearful person by nature. So, because of that, I never really could trust my fear. If you're afraid of everything, you just get used to pushing past fear. So that take that away, right? And that's something that stops people. But my first business, I really fell into it. I had put myself through school working in bookkeeping. A boyfriend's mom had trained me, and then I worked in accounting departments, and I got my degree in finance. Uh so after my second child, I wanted to take a brief break just to kind of catch my breath. And someone I knew in banking asked me to help one of their clients set up an accounting system. That was my first business. Then, because I was in offices and watching how people worked and watching how women worked, I noticed that women personalized their workspaces, but with a lot of like decor instead of being able to choose office supplies that reflected their personality. So I saw that gap there. I saw the problem. And I thought, would women pay more for office supplies that reflected their personal style? Everyone thought I was crazy. And I listened at first, but I just kept doing the research. And I finally said, you know what? The research says that women make the majority of buying decisions for office supplies. So if I only market to women, you know, that that niche approach, I think it would work. And I didn't need to beat the superstores at being a superstore. I just needed to reach a very specific customer. So I created See Jane Work that took off rapidly.
Petite & Powerful (Kristie)I mean, just faster than I could ever expect, really. Well, the products were so amazing at the time because it went from your black and beige and vanilla like notebooks to all this gorgeous stuff that really attracted women to it.
Holly Bohn Pittman (Host)Exactly. And that was like in 2004, and I don't know if you remember this, but that was a time where women were starting to feel like they could embrace their femininity in the office. Because when we first started, you're wearing the blue suits, you're trying to be a man in the workplace. And I think that was shifting where our the unique skill set and things we bring to the table was starting to be valued. And and with that, I think women could start branching out and say, you know what? I want a pink stapler. Things that make us happy at work. Exactly. So that lasted more than a decade. Um, I had the brand was later acquired by a larger, larger manufacturing company when I had some financial problems. Uh, and then we had dedicated C Jane work sections at every Office Depot nationwide, and that lasted more than a decade. Uh, I also had the opportunity to design for major mass market retailers, including Target and Walmart, under different brands.
Petite & Powerful (Kristie)Yeah, and the products, I mean, I've seen them all. They were the patterns were incredible. I also love the marketing because you really put yourself out there. You were the face of seeing Jane work, and the marketing was fantastic. So that was incredible
Failing Fast & Knowing Who to Ask for Help
Petite & Powerful (Kristie)at such a young age. Like, do you really at that time did you feel like you were qualified for any of that? Absolutely not.
Holly Bohn Pittman (Host)So it's interesting, but no, I had zero, I had finance accounting background, but I had zero training in product design, manufacturing, packaging, labeling, merchandising, signage, uh, mass market retail, which is its own thing. So I learned by doing, I failed fast. And then I think the other thing is I've always been, because of my curiosity, I've surrounded myself with a lot of interesting people. So I would say that knowing who to go to to know, you know, who was good at it and it could have advise me was another key aspect.
Petite & Powerful (Kristie)So networking's a huge piece of success.
Holly Bohn Pittman (Host)Yes. And I think a lot of times we approach networking, we think of it as that's how we're going to grow ourselves. And people are at these networking events and they want to tell you their elevator pitch. That's not how I see networking. I see networking as what can I learn from other people. And if you approach it like that, I think that's when you really develop those valuable relationships.
Petite & Powerful (Kristie)Yeah, I've heard in in many kind of leadership forums now, instead of networking, they say develop your own advisory board, like people that you respect that can challenge your ideas, help fine tune and tweak your ideas to make them more successful. And it seems like you've learned that at a really early age and were able to kind of capitalize on some of that.
Holly Bohn Pittman (Host)That's true. And I I think I do call I I've called it my board of directors. So it is, but it is like my advisory board.
Petite & Powerful (Kristie)That's great. So the other interesting thing I've heard you talk about when we've, you know, discussed in the past is you didn't really learn all of the stuff in the classroom. You're an observer and you really pay attention to like what people actually want and need. Can you tell me a little bit more of how you use that to build See Jane work?
What Watching People Shop Taught Me
Holly Bohn Pittman (Host)I think that's one of the things that made me good about it is being curious and watching people and wanting to know why. You can do surveys and ask people what their buying behavior is going to be. And they've found that sometimes it's not always accurate for what that person will actually do. We're not all self-aware. We don't know how we'll actually behave in any given situation. So for me, it was sitting and watching how are women working? What are they putting on their desks? And then later, as I developed relationships with stores, you know, if I'm doing a program with Target, for example, I'm gonna go sit in the Target and I'm gonna watch how the Target shoppers behave because it's gonna be different depending on the demographic. So what we actually choose when money is involved, it can be often different than what we say that we're gonna do because of that emotional aspect of it. It's not always reasonable. But observing taught me how people react to packaging, how quickly they make decisions in different categories. Uh, you know, somebody buying mayonnaise is gonna be a different situation than somebody buying office supplies. So I think that is one of the reasons why some of the major retailers did end up coming to me for trend advice. And it wasn't that I think that I had this amazing taste. I hope that I have good taste, but I think it was more that I just could see patterns emerging very quickly.
Petite & Powerful (Kristie)So you weren't that crazy stalker at Target. You were actually there for like a legitimate reason.
Holly Bohn Pittman (Host)I they never asked me to leave, but they might have wanted to.
Petite & Powerful (Kristie)Uh, the other thing I love about you is you're so willing to say, I don't know, when you're not sure on something. And I think it's one of your leadership skills that really come through. And so what do you think about like what would you tell future entrepreneurs and other people kind of going down this or even any leadership path of you don't always have to have the answer, right? It's okay to say I don't know from time to time.
Holly Bohn Pittman (Host)Yes, I like to know what to expect. Shocker. So I need to know the person that's gonna be able to tell me uh and and eliminate some of that uncertainty for me, I guess. So my own neurotic personality drives me to ask questions. I also recognize expertise in other people that sometimes they don't see in themselves. So just in general, and I I have a very positive mom. She thought we could do anything. And so um, well, except remember she told me I couldn't be a model. But she is amazing.
Petite & Powerful (Kristie)Um but she could, she could, she would always convince us. Wait, she told you you couldn't be a model. So is that why you did the branding for See Jane work where you modeled?
Holly Bohn Pittman (Host)You just had to prove her wrong. Yeah, but it was actually a draw. Well, that's true. I did do a lot of media stuff. So there, mom.
Petite & Powerful (Kristie)We love you, mom. It's still okay. So you had such a successful career with See Jane work, but then sometimes, you know, life throws you curveballs.
Losing Almost Everything
Petite & Powerful (Kristie)And at one point you almost lost everything. Can you tell us a little bit about that journey and what happened?
Holly Bohn Pittman (Host)Yeah, you probably should ask my kids because they get really annoyed. They're like, could you just be a normal mom and stop having these ideas? Because we'd like to, you know, go on vacations and do stuff. It was a really bad time, the banking crisis. You think of it just as a banking crisis, but there was a domino effect at that time, and it was really a it it impacted the world, not just the US. So I'm gonna just give you a couple examples, but the bank that I used went under, so I lost my credit line. Then it became harder to apply for credit lines. So then, you know, if you're in a manufacturing situation, you have to finance inventory, it's really hard. Um, so I got a manufacturing partner, then they were foreclosed on. It was just like a series of domino effects, and I could go through like 10 of those things that happened, and I just couldn't recover. So at one point I I had to sell everything my house, my car, everything. And it would be so scary at the time. It was, it was scary. I I think because of my parents kind of forcing me to work from an early age and and having to really make my own way, that I wasn't afraid of the work aspect. But once you're a mom and you have kids, you know, being afraid, can I support my family? You know, yes, yeah is a very real fear. So, but uh, you know, all these years later, I can honestly say it made me a better person, made my kids better people. They don't, they may not know that yet.
Petite & Powerful (Kristie)Yeah. And how do you think,
What Failure Taught Me About Success
Petite & Powerful (Kristie)like, what were those skill sets that you took away from that probably scary and um really difficult time in your life?
Holly Bohn Pittman (Host)Another good analogy is I think to this is is having kids, kind of being an entrepreneur and having kids. There's an analogy I can draw. When I had my first son, I patted myself on the back because I did that sleep training and it worked, and he was on a schedule. And look at me.
Petite & Powerful (Kristie)You first always do the bait and switch menu. They're always the good sleepers.
Holly Bohn Pittman (Host)Yeah, if God gave you the second one first, you'd be like, nope, we're done. Yep. So then my second one came out, basically, just from the moment he entered, it was my easiest pregnancy, but from the moment he entered the earth, he has been my most challenging human being in my life. I I like to say every single gray hair on my head is a result of him, if if I didn't color it. So I think there is a lot that you can control. And this might be an unpopular opinion for entrepreneurs. There is a lot you can control in life. So that's the whole point of what I expected, right? There is things that you can make good decisions, good educated decisions about. There are also things that you really are just gonna have to know who to go to, where to go when things go wrong, because there is gonna be stuff that you cannot control. I think having a business crisis taught me that. It taught me not to be, it also taught me not to be so full of myself. Like, oh, I didn't make all of this happen. Sometimes timing is there, you know, and and things just come together. It humbled me, it strengthened my relationship and my reliance on God. So, and and that lesson I think prepared me years later when I took this leap of faith in December when I left my corporate job. I always say, think to myself, now, well, what's the worst thing that can happen?
Petite & Powerful (Kristie)So, going through some of those difficult times, do you think it shaped how you view success? Like, do you have different criteria now of what success looks like when you enter into, you know, a new endeavor, a new business?
Holly Bohn Pittman (Host)Um I really get interested in people's stories because I think I'm a lot less judgmental. I realize, and you know, and I don't want to say that like I was a judgy person, but I think we all are to some extent, right? We see the world through our own experiences and and then we pass judgment. We say, oh, you know, that person could should be doing better, or you know, it's just like it's human nature. But some things that I know is failure isn't always evidence that you did something wrong, wrong, and success is not always evidence that you did everything right.
Petite & Powerful (Kristie)Oh, I love how you said that because so many people don't have that perspective, and it's so true. I mean, there's so many dynamics that happen in life and in the environment and business and so forth, and you can risk mitigate as much as possible, but sometimes you just get a curveball. You know, it could be you're you're building a new resort and a hurricane hits. You can't you can't plan those types of things. But, you know, I think you've done an amazing job kind of building a company, going through a difficult time, and then having the resilience to still be successful. And I would love to talk about how you went from that time and then converting from being your own Boss, your own entrepreneur, into a very, I would say, stifled
Entrepreneurship vs. Corporate Life
Petite & Powerful (Kristie)corporate world, which is very different. And we had lots of conversations when you entered corporate about culture and politics and etiquette and different ways of working. So I'd love to hear your perspective of going from an entrepreneur into corporate.
Holly Bohn Pittman (Host)It is funny. That's a loaded question. Yes, you did have to advise me because I had forgotten the corporate lingo. I don't know if I ever knew it, but when you're an entrepreneur, you you can get away with a lot, right? There people are expecting you to be creative and have these really brilliant ideas. You can say ridiculous things and people are gonna listen. And that's not to say that that happened. I mean, there were many a times when I was working with Office Depot where I had to really beg someone to listen to my idea even after I'd had a lot of success. So it's not to say you get instant clout, but definitely when you're going into a new field, and then there's all of these different things at play, right? As an entrepreneur, you're you're concerned about your problem that you're trying to solve. As you go into corporate, there's people jockeying for roles, jockey for attention. And for me, that you know, that part of it was challenging. But getting, and I'm I think I'm a little bit neurotypical too. So, yes, you gave me a lot of uh a lot of advice there. But I remember this executive at Office Depot once telling me, she was a great mentor to me. And she had said to me, I wish I had, I always wished I had been an entrepreneur. You know, what's it like? And I said, Oh, it's so funny. This actually, this day that you're asking me this, I'm thinking, God, I would have liked to have the stability of corporate. And so I guess it's important to know that the the grass isn't greener. Um, both things taught me, you know, it's a different vocabulary. I got to experience a public offering uh and going through an IPO and all of that part. And I don't, you know, understanding investors and enterprise value and governance and things that I would not have otherwise experienced. So, from a learning perspective, I think there's been value in doing both.
Petite & Powerful (Kristie)Yeah, and and I think you've been extremely successful in both of them. And and that's a hard shift. And, you know, I remember when you entered corporate, like you opened new markets for them that they hadn't even like explored because it was just it was kind of like a a step too far from their normal, and you were able to kind of open those additional channels, which is really impressive. So given
What Each Career Path Taught Me
Petite & Powerful (Kristie)that you've had success in both, I guess what what are the key takeaways like you would take away from each of those different career paths? Like what did you learn as an entrepreneur? And then what did you learn as in in the corporate world? And then how did they blend together to make you what you are today?
Holly Bohn Pittman (Host)I mean, we could talk about this for for like for hours. Forever. Yes, forever. Um, each version gave me strength or highlighted things I needed to work on, really, in myself. When I think about preparing me for what I'm doing right now, I would say that it was helpful to understand, although I did get that aspect working with the major retailers, even as an entrepreneur, but understanding limitations. So when when I'm actually right now, when I'm talking about what to expect, or I'm talking about the buying experience, or I'm setting expectations there, understand both sides of it. So I understand what's possible on a on a large scale, and I also understand why something is possible when your business is smaller and more agile. So I have seen both of those. And I and I think for me, the corporate aspect of it, I don't know that I would be happy in a in a super mature business that wasn't looking at at new opportunities because I am always thinking, how can we do this better? But I I did learn something in in both.
Petite & Powerful (Kristie)So through all of that, so you've built the business, converted it, went to corporate, and now you've decided to kind of walk away. So,
Leaving Corporate & Starting Over at 52
Petite & Powerful (Kristie)what was that decision and and why? Us through that journey.
Holly Bohn Pittman (Host)So in December recent recently, I mean, right now, just for in case somebody's listened later, we are in September 26. So December 25, uh, or maybe it was November, I made the decision because there was a long phase out that I was going to stop working. I just needed a break. I was having some health issues in my 50s. And I think it's important to know that I'm not financially able to retire. So I don't want to give people the impression that this decision was easy. Yeah. Or that I, and and I am um the I I'm remarried now, but he's not the father of my children. So I do support my kids. And it was not an easy decision. So it wasn't something that I took lightly. But I felt called to take another leap of faith. I felt that pushing of, you know, I know that there's something more for me, and I'm not living in my purpose. So, you know, the previous experiences, they gave me the perspective. Titles are temporary, controls limited, uh, you know, and and then also knowing the times when I have had things mapped out, like I clearly I like to control as much as possible, right? I'm gonna do all the research if I'm buying a new sofa. But there's all this other stuff you can't control. So the funny thing is, I don't really in any of my jobs, I don't really miss the work. Well, I think except See Jane work, I you know, I love the creative aspect. But I always miss the people. So I think that speaks volumes about if you're thinking about your career or or what's next. A lot of times it doesn't really matter what you're doing, it matters who you're doing it with.
Petite & Powerful (Kristie)Yes, for
Why I Created What I Expected
Petite & Powerful (Kristie)sure.
Holly Bohn Pittman (Host)But that's that's sort of how what I expected came up came about, because I just thought I missed that aspect of See Jane work, that aspect of connecting with consumers and learning about what people are buying and what's important to them and advising people. And I also noticed that just with all my friends, I was kind of that person that people come to.
Petite & Powerful (Kristie)Oh, yeah, I can't tell you how many times I've sent you a picture, an article, a product, and say, like, is this good? Does this look good? Is this a good product? Like, what's the research? And you always, always had an answer for it. You were always on top of it.
Holly Bohn Pittman (Host)They say buying is emotional, and I've seen a lot of studies, even because I was a CMO. So it, you know, the marketing studies, and they tell you it it's always emotional. But to me, it's not. I think there is a big part of it that is rational. Consumer reports wouldn't have done as well as it has done. You know, the it's just different personality types, right? There are some people that make emotional buying decisions, and then there's some categories where it's really more emotional. But a lot of people like to be an educated consumer, and we have so much information coming at us.
Petite & Powerful (Kristie)So many influencers just pushing products and and so forth. And so it's it's hard to cut through the noise sometimes.
Holly Bohn Pittman (Host)It is. I would even say for me, there are times like when I'm gonna post a review that I I know is gonna be amiss, I'm not selling anything. I'm really, and and there's no way to monetize that. Absolutely no way. But I'm solving a problem, and that's what I always have to keep my eyes focused on. I had thought briefly, and and I still may create products again because I loved creating, you know, I love that problem solving. But I don't know right now, I think I can offer more value by filtering all the data that's out there than I can by actually creating more stuff. Does that make sense?
Petite & Powerful (Kristie)Yes. And so that's one of the things I think myself and everyone in your network loves about you is you'll tell us the honest truth. Like, nope, that's not for you, that's not your color, that's not the right product, that quality is cheap. No. Like, but you then will say what is better and guide us in the right direction. And I believe that's what kind of brought you to what I expected.
Holly Bohn Pittman (Host)Yeah, it did. And it's funny that you say that because I was just thinking, I was driving with my sister the other day, and my life was flashing before my eyes because her driving is awful. I was reminding her of when we were in high school and she would ask me what I thought of her outfits. And if I didn't like it, she would get really mad. And I remember finally saying, Don't ask me if you don't want the honest opinion. I'm gonna say it nicely because I just think in general I'm nice and I care about people's feelings, but I'm gonna be honest. Yes.
Petite & Powerful (Kristie)Which is a great, I mean, it's it's such a great quality because you do always say it in the nicest possible way, but you do get your message across. And so I think it's great. Um, we all need that person in our corner to kind of guide us in the right direction because if you just have yes people around you, you can go down some really bad fashion like trends, and you could also go through some really bad decisions in in business and other things. So you need those real people around you.
Holly Bohn Pittman (Host)And well, that's actually a good point. That's gonna be something in corporate. It's really hard to get people that don't tell you the truth. Uh so I think there may be products down the road. I'm not ruling that out. I've certainly been approached by retailers to come back, but right now it just feels like there's so much stuff. And my skill set, I can better serve the marketplace by peeling through all of that information and and sort of making women's lives easier.
Petite & Powerful (Kristie)I'm excited for it. I mean, I feel like we've taken what we've done in private, and now you're making it available to the masses, which I think is fantastic. And I hope people really appreciate because it's it's hard to give a product a miss, especially you know, great products that might just not live up to their hype. Um, and I think you're doing a really great job of being able to provide the details behind your assessments and and really help shape because at this age in our lives, like we're overwhelmed and there's so much information coming at us. And if we're guided in the wrong direction, we'll just waste our money. And at this point, when gravity's pulling everything down, you know, chemicals are in all of our products, we need as much positive guidance to help us live a healthy, wonderful life moving forward as possible.
What’s Coming in Part 2
Holly Bohn Pittman (Host)So that's it for part one of what I expected, the podcast. In part two, Kristie and I are going to get into how decades spent designing products, watching people shop, working with retailers, and sitting inside marketing teams completely changed the way I look at what we buy. We'll talk about why a $10 product and a $300 product create different expectations, why marketing misinformation isn't always intentional, why I started writing things miss meet and exceed, and why I believe women need more honest information, not more people making us feel inadequate so they can sell us the solution.
