Abandoning the Should: Why Sara Blakely Waited Until 37 to Get Married
You know the list. You should be married by 30. You should love being home with your kids, or love your job just as much as you're supposed to love them. You should meditate every morning, hit your steps, and never let anyone see you sweat. In this episode, Erica Anderson Rooney names the pattern underneath every one of those rules: most of your shoulds were never actually yours.
Erica walks through her own should: meditation. In the episode right before this one, guest Lee Wager pushed her to explain why she felt she had to meditate every day. Erica's honest answer was that everyone says you're supposed to, everyone says you'll feel better. Not because it made her calmer, not because she enjoyed it, just because it was the should. She also points to Sara Blakely, who built Spanx into an empire before getting married at 37, years after most of her friends had already walked down the aisle. Had Blakely followed the should, Spanx never happens.
Abandoning the should means running every expectation through one filter: does this come from what you actually want, or from what you think you're supposed to want. Keep the ones that pass. Let the rest go.
You're not imagining the pressure. A YouGov poll from August 2024 found 52% of women describe themselves as people-pleasers compared to 44% of men, and women are far more likely to say they were socialized into it, 38% versus 25%. Psychology Today reported in May 2025 that ambitious, high-achieving women face a distinct burnout pattern rooted in chronic self-neglect, not just workload. The shoulds aren't just background noise. They're costing you energy, identity, and sometimes the life you actually wanted. Pick one should on your list today and ask yourself honestly why it's still there.
TRANSCRIPT:
Erica: Hey, girl. By now, you know I have Her Collective, my online community for ambitious women who are done doing it alone. Her Collective is for the women who are smart, capable, and driven, but they find themselves stuck on the sticky floors like self doubt, burnout, and waiting for permission that quite honestly never comes. Inside HER, you get more than motivation. You get real support, real strategies, and real momentum.
Erica: We work on things like clarifying what you want now and what's coming next, building confidence without burning yourself out, navigating hard conversations, career moves, and leadership moments with clarity, and surrounding yourself with women who actually get it. This isn't about hustling harder. It's about moving intentionally with the right tools and the right people in your corner. If you're ready to stop spinning, start choosing yourself, and build a career in life that actually feels aligned, I'd love to welcome you inside her collective. You can learn more and join us at Collective.
Erica: Because honestly, girl, you were never meant to do this alone. Have you ever found yourself caught in the endless loop of should I be doing this or shouldn't I have achieved that by now? It's as if society has mapped out a predefined checklist for our lives, and we are expected to conform to every box. But here's the twist. Not all shoulds are created equal, and not all of them should define your path.
Erica: To kick things off, let's talk about the science behind our tendency to conform. And truly, it's simple. We want to belong. Our brains are wired to seek acceptance and belonging. It is quite literally a survival trait back from the tribal days, and our societal expectations just tap into this instinct, which makes us feel compelled to follow the crowd.
Erica: And I think you know where I'm going with this one. That doesn't always work for us. Each one of us is a unique person living a unique life with unique goals and ambitions and dreams. We have different experiences. We have different interests.
Erica: So sometimes, these societal expectations, they clash with what we really want. I mean, think about it. I remember thinking that my life would have this very clear and very linear path. I would go to high school, get good grades so I could get into a good college. I would meet a nice boy.
Erica: I would get a good job. We'd date for a year, get married, have babies, have the house, take the nice vacation, etcetera, etcetera, etcetera. But not everybody has that dream or wants that dream. And even sometimes those who want that dream, it just doesn't happen that way for them. It doesn't always follow this linear path that we are led to believe it would.
Erica: Sara Blakely, the founder of Spanx, talked about wanting to build her empire before getting married, and she struggled a bit because all of her friends were getting married. She was that always a bridesmaid, never a bride kind of girl. And then it wasn't until she was 37 before she got married. Y'all, I remember thinking 37 sounded so old, but my point is, if Sara Blakely had followed in the footsteps of everyone else and did what society told her to do, what she should be doing, she would never have founded Spanx. And she would probably be married to the wrong person, maybe divorced, who knows.
Erica: But how many of you know someone who stayed with someone, the wrong person, or even got married, even had kids, because they felt they should be moving along life's perfectly planned path? I know personally a few of those people. So let me get to my point. It is essential to recognize that not all societal norms align with individual happiness. Often, we find ourselves adopting the shoulds, and all of that just leads to stress, anxiety, heartbreak, and sometimes a sense of emptiness, depression, all of that.
Erica: It's crucial that we evaluate each should and determine if it resonates with our authentic selves. Now in the episode right before this one, with Lee Wager, she helped me uncover that I should give up my unrealistic goal of meditation. Y'all, I cannot meditate to save my life. And she helped me realize that I had this goal not because I thought it would make me happy, not because I thought it would make me feel better or feel less stressed. And she quite literally asked me, like, why do I feel like I should meditate every day?
Erica: And I was like, well, everyone says I should. Everyone says I'll feel better. All that, you know, all these things. And it was honestly complete bullshit. Ugh.
Erica: I'm just not a meditator. My mind wanders. It wasn't a good goal for me, and that's just a small example. And I'm committing to giving up feeling like I should meditate. Right?
Erica: It's not easy to go against the grain. Meditation is a goal. It's a small one, but it's just a glimpse of something that I can give up to be more of my authentic self. Now here's the thing. When you don't do all the shoulds, you stand out.
Erica: You're going against the grain. It can be uncomfortable, but no real change happens by just doing what everybody else is doing. All of the greats out there stood up to the shoulds, and they stepped out. And now look at them. We admire them.
Erica: We want to be them. Let's take entrepreneur and influencer Jenna Kutcher, for example. She was a small town mama who took her camera and her photo business and turned it into an empire. Now I am sure she had some people that said she should be happy doing her photo business, and that she shouldn't work so hard, that she should settle down with her family and her kids and just do her dang thing. But y'all, she didn't wanna do that.
Erica: You know? How many people would continue to go against that grain when they have a life that they, air quote, should be happy with, but they know they're meant for more? She did not succumb to the societal expectations of should. She followed her heart and her dream, and now she's living her best life, and with a lot of cash in her pocket too, y'all. So the massive question is, how do we break free from these unrealistic expectations that society puts on us, that we've put on ourselves?
Erica: And, guys, I've got your simple yet not so simple answer. You have to be your authentic self. Yep. Just be who you came to be. Start by really looking inward.
Erica: Question every single should that comes your way and ask yourself why. Why do I think I need to do that? And if it's because someone else says you should do it, you need to stop. If it's because you know it makes you happy, you know it keeps you stress free, you know you enjoy it, then keep on doing it. But ask yourself, does this align with my goals?
Erica: Does this align with who I want to be and what I want to do? Does this fulfill me? And go back to that podcast that I just dropped on anxiety and intuition. What does your gut say about it? And I want you to get quiet, and I want you to listen, and surround yourself with a supportive community that encourages you to be unapologetically you.
Erica: Your journey is unique, and your path to happiness, it may not always follow the path you originally thought it would. So shed the weight of all of those unrealistic expectations, all of those shoulds, and embark on a journey that is uniquely yours. Remember, y'all, not all shoulds belong in your story. Now if you were inspired by today's episode, share your thoughts with me on all the socials, LinkedIn, Facebook, and Instagram, and make sure that you rate, review, and subscribe to the podcast, as it truly helps it land in the hands of the person that needs to hear it the most.
​RESOURCES MENTIONED IN THIS EPISODE:
- Join HER Collective, Erica's community for women in corporate America ready to close their own AI gap and get more women into rooms of power.
- Spanx, founded by Sara Blakely, who built her company before getting married at 37.
- Jenna Kutcher, entrepreneur and podcaster referenced as an example of ignoring the shoulds.
- Rate, review, and subscribe to Glass Ceilings & Sticky Floors so this episode reaches the person who needs to hear it.
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FREQUENTLY ASKED QUESTIONS:
What does it mean to abandon the should in Erica Anderson Rooney's Glass Ceilings & Sticky Floors episode?
It means questioning every expectation you've inherited, whether it's about marriage, career, or motherhood, and keeping only the ones that actually align with what you want. Erica calls out her own should around daily meditation as a small example: she kept doing it because everyone said she should, not because it made her happier. Abandoning the should is about choosing on purpose instead of by default.
How do you tell the difference between a should you actually want and one society handed you?
Ask yourself why you feel obligated to do it. If the honest answer is because someone else says I should, that's a red flag it's not really yours. If it's because it makes you happy, keeps you stress free, or genuinely aligns with your goals, it's worth keeping. Erica suggests checking in with your gut and asking whether the should fulfills you or just checks a box.
Why did Sara Blakely wait until 37 to get married, and what does it teach about ignoring the shoulds?
Sara Blakely prioritized building Spanx into an empire over following the timeline her friends were on, even as she watched them get married around her. Erica uses her story to show that the shoulds around marriage and timing don't fit everyone, and following them anyway can cost you the life you were actually meant to build. Blakely's choice to go against the grain is proof that stepping out of the should can pay off.
MORE FROM ME
Follow me on Instagram @ericaandersonrooney and @joinhercollective
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Hi, I'm Erica!
In the last 15 years, I climbed to Chief People Officer, 6x'd my income, walked away from a culture that stopped matching my values, wrote two books, and built HER Collective to help thousands of women rise to power and lead in the age of AI. I've learned a thing or two about smashing ceilings and closing gaps, and Glass Ceilings & Sticky Floors is where I open the playbook, the receipts, and the real stories to share it all with you.
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