Navigating money as a wife, mom, and breadwinner with Jessica Norwood

Written By Emily + Cassidy

What happens when you're the higher earner in your marriage? When your 401(k) keeps growing while your spouse builds their own business? When you're navigating motherhood, career ambitions, and being the breadwinner all at once?

We love talking about money and relationships, and we’re not the only ones. This episode features Jessica Norwood, who co-hosts The Sugar Daddy podcast with her financial planner husband, Brandon. What began as an outlet for his expertise has turned into something bigger: a source of honest conversations about money that break down the jargon and shame that usually come with financial advice.

In this episode, Jessica breaks down the reality of out-earning her husband, how they’ve navigated tricky money conversations, and why they decided to get a postnup after nine years of marriage.

Episode Highlights

[7:00] Why Jessica and Brandon decided to get a postnup after nine years of marriage — and what changed their minds

[10:00] The real financial dynamic of being the breadwinner when your spouse is an entrepreneur

[17:00] How prenups and postnups actually strengthen marriages (not weaken them)

[24:00] Breaking traditional expectations: What it's like when the woman out-earns her partner

[29:00] The awkward money conversation about living with Brandon's mom — and why speaking up mattered

[33:00] How to normalize talking about money with friends without making it weird

[36:00] Why women who talk about money with other women are 2x more likely to invest

[40:00] The investing mistake Jessica wishes she could undo from her 20s


When Your Income Changes Everything

Jessica's journey to becoming the higher earner wasn't exactly planned. She started out as a teacher. Brandon was managing a shoe store. Financially, they were pretty evenly matched.

Then Jessica shifted into tech — where she had stock options, RSUs, and a generous 401(k) match. Around the same time, Brandon got his financial planning credentials and left the big firms to start his own independent practice. As an entrepreneur, he reinvests heavily in his business, pays for his own insurance, and handles all the costs that come with being self-employed.

The result? Jessica became the higher earner. And in their household, that's never been a source of tension. They consider any money coming in as "our money," regardless of whose name is on the check.

The Postnup Decision

Even though they’ve always communicated pretty openly about money, Jessica and Brandon did something most couples don't: They got a postnup… After nine years of marriage.

Their reasoning? Insurance for their love.

They have life insurance. Homeowners insurance. All kinds of policies protecting different parts of their lives. Why not write their own rules for what happens if their marriage ends — while they still like each other?

After having the Prenup Guy, Aaron Thomas, on their podcast, everything clicked. Prenups and postnups aren't about planning to fail. They're about having difficult conversations when you're calm, rational, and still genuinely care about each other's well-being.

In this episode, Jessica opens up about what exactly their postnup includes — everything from provisions about retirement accounts, their house, student loans, and even thoughtful details like furniture funds and inheritance protection. More importantly, they talked through their expectations and values around money in a way that strengthened their relationship.

How to Start Talking About Money with Friends

One of the most valuable parts of this conversation was Jessica's advice on normalizing money talk with the people in your life. Her approach is low-pressure and accessible: 

  • Reference something you heard. "I was listening to this podcast and they mentioned backdoor Roth IRAs. Do you know anything about that?"

  • Ask about specific situations. "Did you choose the HSA or PPO during open enrollment? What made you pick that one?"

  • Be honest about your own budget. "Hey, I've been looking at my spending and I think tonight I'm just going to cover my own meal. Are you good with that?"

  • Talk travel budgets upfront. Before planning a trip with friends, have an honest conversation about what everyone's comfortable spending.

Jessica's also the friend who reminds people to negotiate their salaries, who shares market rate information, and who gives pep talks about asking for more. Her friends appreciate it — because underneath all the societal awkwardness around money talk, most of us are desperate for these conversations.

The Advice She'd Give Her 25-Year-Old Self

As an elder Millennial, Jessica has lived a little more life than us (and honestly, she’s got lots of great advice to show for it). So we asked her, if she could go back and tell her younger self one thing, what would it be?

Her answer was painfully simple: Invest more.

At 25, she was a teacher with a 403(b). Whatever came out of her paycheck automatically was all she contributed. She didn't look at it. Didn't adjust it. And didn't even totally understand it.

Her parents had taught her to save money and not live beyond her means. But there was zero conversation about investing or growing wealth through the market.

Looking back 15 years later, she could probably be retired by now if she'd been more intentional about investing early on. Her advice? You don't need hundreds or thousands of dollars to start. Cut out a few coffee runs a month and put that money into an IRA. Get your employer's 401(k) match. Increase your savings rate by one or two percent each year.

Where Jessica Is Now

These days, Jessica's proudest money wins involve booking trips using points and miles. She and Brandon put everything on credit cards and use the rewards strategically. Her upcoming Mexico trip with a friend? Completely free accommodations and flights through points, miles, and a companion pass.

She also shared how she and Brandon want to be work optional in their 50s, and why it’s so important to them. It’s obvious they have big dreams in life and see money as a tool for achieving their goals. This is something that can be easy to forget in the grind and hustle of your prime working years, so we were inspired to hear how much of a focus it is for Jessica. 

The Bottom Line

Jessica and Brandon's story isn't about being perfect with money. It's about being intentional. It's about having the hard conversations before resentment builds. It's about designing a partnership where both people feel valued, regardless of who brings home the bigger paycheck.

Whether you're the breadwinner, considering a prenup or postnup, or just trying to figure out how to talk about money without it being awkward — this episode is packed with practical wisdom from someone living it in real-time.

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Emily + Cassidy
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Prenups for modern couples with divorce attorney Aaron Thomas