Knowing Your Capacity & Adjusting Your Expectations with Katie Kastner
Sometimes the most powerful thing you can say in business is "I don't know." Not as a cop-out, but as a declaration. A permission slip to stop forcing what doesn't fit and start building something that actually feels like yours.
Katie Kastner spent 2025 living in what she calls her "I don't know era." After running The Haven, a thriving community for business-owning moms, she hit a wall. Not because it wasn't working, but because it felt too restrictive. Too small. Not quite her anymore. So she did what most business coaches would tell you not to do: she stopped, reassessed, and completely pivoted, not out of desperation, but out of deep alignment.
This is the story of how one creative woman entrepreneur burned down her "successful" business model to build something that actually lights her up. And spoiler alert: it's working better than ever.
The "I Don't Know" Era: When Your Business Stops Feeling Like Yours
The Haven launched in fall 2024 as a community specifically for business-owning moms. Women building companies, raising kids, doing all the things. It was small but mighty, filled with founding members who got it. But as Katie moved through her own evolution, something started to feel off.
"The reason behind it changed," Katie explains. "It felt almost a little too restrictive for me. I felt like the women in there and the women that I wanted to continue to build a community with – yes, we were moms – but there was so much more to me that I wanted to put in my community."
Here's what nobody tells you about niching down: sometimes you niche yourself right into a corner. And when you're a multi-passionate, creative, evolving human, that corner can start to feel like a cage.
Katie realized The Haven needed to expand. Not just for her members, but for herself. She wanted to bring in women at different life stages – moms with grown kids, moms with school-age kids, women without kids at all. She wanted to talk about divine feminine energy, about being neurospicy, about the woo-woo stuff that lights her up. She wanted it to be hers.
So she gave herself permission to say, "I don't know what this looks like yet, but I know it needs to change." That's courage, not confusion.
The Winding Path: Why Career "Failure" Is Actually Just Exploration
If you're looking for a straight-line success story, Katie's not your girl. And honestly? That's exactly why her story matters.
She graduated with a marketing and PR degree in 2004-2005, right into one of the worst job markets imaginable. Her goal? To be Helen Hunt in What Women Want – the sharp, creative advertising exec who could read minds and crush campaigns. Instead, she worked retail. Then nonprofit business development. Then luxury cosmetic sales. Then she went back to school and got a master's degree in special education. Why? "I guess because why not?"
Katie laughs when she calls herself "a chronic career failurist," but here's the thing: none of those experiences were failures. They were her figuring out what she didn't want, which is just as valuable as knowing what you do want.
The one constant through all of it? Writing. She had a blog back in the Xanga days (if you know, you know). She kept blogging through Blogger. When her son was a year old, she started training for the Chicago Marathon and launched a WordPress blog to chronicle the journey. She taught herself SEO, long-form content creation, and content marketing – all without realizing she was building the foundation of her future business.
"Writing has always been like a through-line for me in my life," she says. Even when she couldn't see where it was leading, she kept following that thread.
Before the pandemic hit in 2020, Katie took a detour through the MLM world. "That was a horrifically bad experience," she admits. But even that misstep led her somewhere good. She found a group for women becoming freelance writers and launched her own freelance writing business in the fall of 2019. That evolved into content marketing. Then digital marketing strategy. Then coaching. Then The Haven.
None of it was planned. All of it mattered.
Motherhood as a Business Catalyst (Not a Roadblock)
Katie never planned to be a stay-at-home mom. It just kind of happened – the way it does for so many women. Her daughter turned one, circumstances shifted, and suddenly she was home full-time. And she was in her early 30s, having a full-blown identity crisis.
"I thought I was going to be Helen Hunt. That didn't work. Then I thought I was going to be a special ed teacher. Then I ended up a stay-at-home mom, which I never thought I was going to be."
Here's where it gets real: Katie started noticing that when she was "an unfulfilled, passionately bored mom," she wasn't showing up for her kids the way she wanted to. She needed something for herself – not as a luxury, but as a necessity.
"In order to be the best mom I could be, it was necessary for me to be doing something for myself. Whatever that was, it was necessary."
This realization flies in the face of everything we've been taught about "good motherhood." Katie grew up watching her boomer mom downplay her needs, turn off her desires, ignore her passions, all in service of her kids. That level of self-sacrifice was held up as the gold standard of mothering.
But Katie, like so many elder millennials who've been through enough therapy to see the cracks in that model, recognized it wasn't healthy. It wasn't the example she wanted to set for her daughter. She wanted her kids to see that being a mom doesn't erase your identity, it expands it.
"I want my daughter to understand that being a mom is not a complete identity and doesn't have to be a complete identity. It is good and healthy and important for you as a woman, not just as a mother, to know yourself deep enough that I can be a mom and I can also do this."
And here's the secret sauce: Katie's husband is her biggest cheerleader. From day one, he's treated her business as equally important as his corporate job. They're true partners – picking up each other's slack, supporting each other's ambitions, modeling real partnership for their kids.
"That's one of the reasons my business does work so well, because I do have a true partner who sees what I'm doing as just as important as what he does."
For many women entrepreneurs, having a secure partnership is the difference between thriving and burning out.
The Truth About Entrepreneurship at Different Motherhood Stages
The online business world loves talking about entrepreneurship with babies and toddlers. Nap time hustles. Building during the trenches. And that's important, necessary content. But Katie's living proof that the conversation needs to expand.
Her daughter is 12 now, in seventh grade. Her son is 10, in fourth grade. She has entire school days to work. After-school isn't as intense as it once was. On Sundays, she and her husband sleep until 8:30 because the kids can make their own breakfast without burning the house down.
"It does get easier," she says. "It really does."
But – and this is a big but – it's not easier in the way you might think. Yes, you have more actual hours on the clock. But those hours come with different challenges.
Katie's daughter is neurospicy, dealing with anxiety. One day, her daughter texted mid-day saying she was having a rough time. Katie knew that meant the afternoon hours she'd planned to wrap up work were going to disappear. Her daughter would need co-regulation when she got home. And after that emotional labor, Katie would need time to recover herself.
"Yes, I have more time. Yes, the hours on the clock are not as restrictive. But there's just a different sort of friction that I have to work through now with these older kids."
Friction. That's the perfect word. It's not a restriction, exactly. It's not a hard stop. But it's a force you have to account for, plan around, hold space for.
The mental and emotional labor of parenting pre-teens while running a business is real. And it's not talked about enough in entrepreneurial spaces that focus almost exclusively on the baby years.
Breaking Free from the "Right Way" to Do Things
Katie went to Catholic school. So did I. And if you've been there, you know: there's a plan. You follow the plan. The plan is God's plan, society's plan, your parents' plan. You don't deviate.
College. Job. Marriage. Babies. Check, check, check, check.
"I was very dedicated to following a path I thought I was supposed to be following," Katie says. "And if I somehow didn't follow that path, I was doing it wrong. I had somehow screwed it all up."
But here's what's wild: Katie realized she was deeply judgmental of people who did go off-script. "I was like, 'Well, you're not doing it right. You're doing it wrong.' When in reality, I was so deeply jealous and envious of people that were able to do it. My deepest self was desperate to do the same."
She believes millennials are the last generation raised with that hard-and-fast "you must do it this way" mentality. And honestly? The veil is thinning. The truth is coming to light. We're all starting to see that the rules are made up, the points don't matter, and you really can build your life however the hell you want, as long as you're operating from what Katie calls "highest and best."
Answering the Chaotic Questions
If you could go back and tell your 2005 self one thing, what would it be?
First of all, you're not doing it wrong. You've never been doing it wrong. And trust yourself. Start now with learning to trust yourself. Start now with reconnecting to that knowing, because you're going to spend a lot of time ignoring her, and it's going to be more work on the other end.
A new mom comes to you for advice. It could be about business, motherhood, or just life in general. What’s the first thing you tell her?
Know your capacity and adjust your expectations.What do you want your kids to remember about you and this time?
I hope they see and understand that there's the possibility to do it your own way and that it can work in whatever life you're living.
Here's What Actually Matters
Katie's story isn't about finding the perfect niche or the perfect business model. It's about giving yourself permission to evolve. To say "I don't know." To burn it down when it stops fitting and build something new that feels like you.
She's not just building a business. She's modeling a life. She's showing her daughter that motherhood doesn't erase your identity. She's showing her son what real partnership looks like. She's proving that you don't have to choose between being a present parent and a passionate entrepreneur. You can be both, messily, beautifully, imperfectly.
If there's one thing to take away from her journey, it's this: the "right way" to build your business is the way that lights you up. The way that feels sustainable. The way that lets you be the fullest version of yourself – not just for your business, but for your kids, your partner, and most importantly, for you.
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If Katie's journey resonated with you, you're going to love The Chaotic Middle podcast. Every episode features real, raw conversations with women navigating the beautiful mess of entrepreneurship, motherhood, and everything in between.
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Because honestly? We need more women with microphones. There are way too many white dudes talking about business like it's a linear path. It's not. It's chaotic. It's messy. And it's so much better when we talk about it together.
