Most people build a business and let it consume their life. Monica Roccasada built one that works around hers.
A financial strategist and founder of Agile Planners with 13 years of building a business entirely on her own terms — Monica has helped hundreds of small business owners get out of the financial fog and back to the vision that drove them to start. She sat down with us on Hello Moxie and what she shared stopped us in our tracks.
The Money Story Nobody Wants to Admit
By the time most small business owners find Monica, they’re frustrated. They’ve had bad experiences. They’re reaching out to their financial team and nobody’s answering. Their books are behind. They can’t make decisions.
And underneath all of that? A feeling that’s almost harder to say out loud: I should know this.
There’s a stigma around money and finance that follows us from our personal lives straight into our businesses. If you carry a scarcity mindset at home — the fear that it could all be taken away — you’ll carry it into every business decision you make. If you’re a “spend now, figure it out later” person personally, that shows up in your P&L too.
Monica’s work starts there. Not with the spreadsheets. With the story.
“The numbers are telling you a story,” she told us. “And it’s about organizing that data in a way that makes sense to you as the business owner.”
That moment when the fog lifts — when a business owner finally sees what’s actually happening in their finances and no longer feels the shame of not knowing — is what Monica chases. It’s why she built Agile Planners. And it’s what keeps her going 13 years in.
The Thing Nobody Talks About at the Top
There’s a loneliness to running a business that almost nobody names. It shows up the same way burnout does in tech — quietly, and then all at once. You can’t go back to your team and tell them you’re worried about payroll. You can’t show the fear. You’re the one everyone looks to — which means you carry the weight of it alone. It’s the same weight Maren Conradi describes when she talks about tying her entire identity to her career — that feeling of over-identification with your work until there’s nothing left outside of it.
Monica named it directly. And in doing so, she gave language to something that thousands of business owners feel but rarely hear acknowledged out loud.
Her answer isn’t a tactical one. It’s a return to the original question: why did you start this? What was the problem so big that you were willing to risk everything to solve it? Because there was a calling. There was a passion. And getting back to that — really back to it — is what changes everything.
“Connecting back to their why is really important,” she said. “That’s what we’re about.”
Providing a Service vs. Being of Service
There’s a distinction Monica makes that we haven’t been able to stop thinking about.
There was a season in her business where she was building something she was good at. Something she could do. Something that, by every external measure, was working. And yet. It’s the same tension Gwen Bortner names when she talks about redefining what sustainable success actually looks like for women entrepreneurs — the gap between building something impressive and building something that genuinely fits your life.
“I was providing a service,” she told us. “But I didn’t know that I was of service.“
That’s the question worth asking yourself. Not just am I good at this — but does this feed me? When your clients win, do you win too? Do you feel it?
For Monica, the answer to that question has shaped every evolution of Agile Planners across 13 years. It’s what led her to add advisory services, executive dashboards, and a bookkeeping arm — following the thread of what actually lit her up, not just what she was capable of.
She Designed This Life on Purpose
When Monica started Agile Planners, her youngest son was 14. She told her husband she was going to be a stay-at-home mom and work part-time. People thought she was crazy.
She did it anyway.
Today she’s a grandmother to two young boys and takes multiple days off every week to be with them. She works weekends. She books client calls on Saturdays — which, it turns out, is her most booked day, because business owners finally have space to breathe when the rest of the office isn’t watching.
She didn’t stumble into this life. She chose it, built toward it, and talks about it openly with her clients — normalizing it so that other women can see it’s possible too. It’s the same permission Beth Mooney gave herself when she walked away from a 30-year corporate career at its absolute peak to spend five months traveling solo across six European countries. Two completely different paths, the same core truth: you get to decide what your life looks like.
“You can live an extraordinary life and still have an amazing personal and business life,” she said. “Yes, you can.”
The nine-to-five structure was built during the Industrial Revolution, by men, for a workforce that looked nothing like us. Monica’s proof that you don’t have to follow it. That you can build something successful, design your days around what matters, and refuse to apologize for any of it.
Serena Williams and the Power of Living Visibly
When Nicole asks Monica which woman has inspired her most, her answer is Serena Williams — still building, still evolving, still refusing to be put in a box.
What Monica loves most about her isn’t the athletic legacy. It’s the willingness to be fully seen across every dimension of her life. The vulnerability about her health journey. The openness about being a mother. The way she’s built businesses and invested in companies with the same ferocity she brought to the court.
“We should have more conversations like that,” Monica told us. “About what it is like being a parent. About how you can still do all the things you want to do and reach the potential you want — and still be a mom.”
In an era where women were told to keep their personal lives out of their professional ones, Serena showed a different way. Monica has lived that same philosophy — and she wants every woman watching to know it’s available to them too.
What Moxie Means to Monica
For Monica, moxie isn’t about being the loudest person in the room or having it all figured out.
It’s about commitment. To the things you said you wanted. To the life you said you were building. And to questioning the voice inside you that keeps insisting it can’t be done.
“Moxie is being committed to the things that you say you want in your life. And not listening to that teeny little voice that says it can’t be. Questioning the voice that says it can’t be.”
Thirteen years of building a business on her own terms. That’s what that sounds like in practice.
Ready to Hear the Full Conversation?
If you’re building something and some days it feels heavier than you expected, this conversation is your next step. Monica and Nicole go deep on money stories, the loneliness of leadership, AI in business, and what it actually takes to design a life and business on your own terms.
🎧https://www.buzzsprout.com/2397037/episodes/18929446
Connect with Monica Roccasada
- Website: AgilePlanners.com
- Book a Call: “Let’s Chat” — available directly on her website
Hello Moxie is a podcast for women in tech and underrepresented industries who are done playing small. New episodes drop regularly — subscribe wherever you listen to podcasts.
