How to Start Talking About Money With Kids, Even If You’re Still Learning
Jamila Souffrant505 travellers
Diana Isern shares how reviewing her spending changed her finances and why curiosity is enough to start teaching young people about money.
Diana Isern’s early money story was shaped by scarcity: clothes arrived in donated garbage bags, and the family’s refrain was that there wasn’t enough. That history helps explain why her later shift matters. She began teaching in New York City at 21 with student loans, no savings, and open bar tabs she rarely thought about. A two-week no-spend challenge and a close review of her statements helped her see where her money was going and start changing course.
That change grew into work beyond her own budget. Teachers, students, and parents began asking Isern money questions. She developed finance courses that teens returned to, started a girls’ investing club, wrote Money Talks: An Educator’s Guide to Teaching Financial Empowerment, and eventually left a secure job with a pension. The arc is more significant than it may look: financial education here began with an ordinary moment of noticing, not with expertise or a perfect plan.
For parents and educators, Isern’s central point is practical: you don’t need to know everything about money before talking about it with young people. Curiosity is enough to get the conversation started.
In this episode, Diana Isern discusses:
How a childhood shaped by a sense of financial scarcity influenced her, and what helped her change that outlook
How a two-week no-spend challenge and a review of her spending helped her regain control
How teachers can use 403(b), TDA, and 457 plans alongside a pension
Ways parents and educators can approach money conversations with curiosity rather than expertise
YNAB – Start budgeting toward your financial goals with a free 34 days trial of YNAB, my go-to budgeting app, through my referral link.
Wondering what stage of the financial journey you’re in, from financial stability to work flexibility? Take this free assessment and get 10 suggested episodes for your stage here!
Diana Isern says her first real shift came from trying a two-week no-spend challenge after reading about it in a book. The point wasn’t simply to spend nothing. It was to notice why she ordered food and where small purchases were taking her money. Her mother had long urged the family to buy food in bulk and cook at home, so Diana drew on advice she already knew but hadn’t put into practice.
She paired the challenge with a review of her previous month’s bank statements, sorting each expense into categories. That exercise still informs how she works with clients. Jamila Souffrant agrees: reviewing your spending can help when you’re starting out or when you need a reset. You need to see where your money goes before you can decide what to change.
Here’s the thing: shame makes that first look harder. Diana says people often feel embarrassed when they review their purchases with her. She encourages them to treat the numbers as a doctor might treat symptoms: examine what happened, without turning spending choices into a verdict on their character. That shift can help people move from avoiding their finances to working with them.
Diana also used goal setting to save for a home. Drawing on the way teachers plan backward from a learning goal, she set a target and worked out what she’d need to reach it. Her plan called for $20,000 toward a down payment and a $20,000 loan from her pension plan. She wasn’t sure whether borrowing from the plan was a good idea; one person she asked thought it seemed fine. She eventually bought the home, but the savings took a couple of years to build. The numbers here are more useful as a record of her own path than as a template: she says she learned the approach from books, and the fragment doesn’t establish whether that pension loan would suit someone else.
Money conversations moved from the staff room into class
While she was still teaching, Diana began bringing personal finance books to school. Colleagues asked about what she was reading, and conversations grew into questions about credit, retirement and the TDA. By her last year as a teacher, just before becoming an assistant principal at age 26, she was talking about money with colleagues during lunch and after school.
Students started asking about investing, stocks and real estate, and parents followed with questions about credit scores. Diana felt educators deserved a better chance to understand their own money: teachers put enormous effort into their students, but often haven’t had formal money education themselves. With another teacher, she developed a standalone course at her school about 12 years ago. Later, as students asked about topics including budgeting and cryptocurrency, she created a course called *Making Money Moves*. The program drew interest from organizations and companies including Bloomberg and Wall Street. Diana says students, parents and teachers all wanted to learn.
Souffrant’s next question is practical: what can teachers do to save and invest beyond a pension? Diana describes several options, while stressing that benefits vary by employer and location. In New York, a teacher’s pension is automatic, but the available system depends on the job and region. She mentions New York City, BERS for some paraprofessionals, and state systems for Long Island and upstate New York; systems in other states differ too.
Diana describes the 403(b), called the TDA in New York, as an optional tax-deferred annuity. She says New York teachers have a fixed rate of 7%, while administrators have a fixed rate of 8.25%, and that contributions can reach $24,500 this year. Those figures are tied to the arrangements she’s discussing; teachers should check their own plan’s terms. She also points people to the nonprofit [403b.org](https://403b.org), which rates 403(b) plans around the country. Diana names Dan Otter and says teachers in other states may have several plan choices, some of which may not serve them well.
The other option she highlights is a 457 plan, or deferred compensation plan, which can offer traditional and Roth accounts. Diana says withdrawals after leaving service before age 59½ are still subject to taxes but avoid the 10% early-withdrawal penalty. She says she only learned about the 457 three years ago, despite actively reading about money. Souffrant recalls finding one through her own research: while working in corporate America, she and her husband used available workplace plans, including a 403(b) and 457, to increase their saving and investing. They eventually invested more than half their income, though they hadn’t always been able to save at that rate.
The account limits and plan rules can change, and the conversation doesn’t spell out the details of every teacher’s plan. But Diana’s larger point is straightforward: not knowing an option exists can cost you the chance to consider it. And you don’t have to contribute the maximum to begin. After she posted a video about the plans, she received about 200 direct messages from people asking whether they’d started too late, what they could do, or whether small contributions mattered. Her answer was to start with what you can afford—even $5—and build the habit. If a future raise gives you room to contribute more, you can increase the amount then.
Teachers can earn more from skills they already have
Souffrant also raises ways teachers might increase their income, from earning certifications and pursuing school leadership roles to taking summer school or coaching work. Diana points to skills teachers already use: organizing, creating learning materials, explaining subject matter and connecting with students. Those skills can translate into tutoring, consulting, curriculum work, homework help, SAT preparation and college essay support. Teachers can also sell curriculum or packages online and share their work through social media. Diana’s view is that teachers should recognize the value of this work and charge accordingly.
The conversation then turns to teaching children about money. Souffrant says more states are passing requirements or approving personal finance education in schools, with New York’s changes expected to take a couple of years to implement. She asks Diana how teachers and parents can make money lessons engaging and useful for kids.
Souffrant also promotes her book, *Your Journey to Financial Freedom: A Step-by-Step Guide to Achieving Wealth and Happiness*, for readers seeking more money, options and independence, including people considering a career change, marriage or starting a family. She directs listeners to [yourjourneytofinancialfreedom.com](https://yourjourneytofinancialfreedom.com), where the book is available through Amazon, Bookshop.org, Barnes & Noble and local bookstores.
Make money conversations safe to start
The point of teaching kids about money isn’t to have every answer ready. It’s to help them talk about money without shame. That’s more significant than it may sound: parents and teachers bring their own histories and emotions into these conversations, and children can absorb those habits along with the facts.
Diana Isern’s approach is to make curiosity the starting point. When a student asked detailed questions about the Federal Reserve, she could have tried to bluff. Instead, she admitted she didn’t know and learned with the student. That led to a class trip to the Federal Reserve. The lesson for educators is practical: gather students’ questions, use them to shape the material, and keep learning as the topics change. Investing, real estate, cryptocurrency, stock trading, apps and sports betting can all prompt questions that a teacher may not have anticipated.
Parents can use the same approach at home. When a child asks for a toy or wants to know whether the family is rich or poor, a quick “we can’t afford it” may end the exchange but leave the child with little understanding. Try connecting the choice to a shared goal instead: explain that the family is saving for a Florida trip, decide together whether to redirect the $20, and make progress visible with a thermometer on the fridge. The aim is to turn a limit into a conversation about priorities.
There are resources, and room to adapt
Schools are adding personal finance requirements in different ways. Advocates often favor a standalone semester course for every high school graduate. New York State, by contrast, allows personal finance to be integrated into another class, such as economics or algebra. The details vary, but educators have free curriculum resources to draw on.
Isern and host Jamila Souffrant mention Next Gen Personal Finance (NGPF), Get Your Financial Life Together, Bonsai, Jump$tart, Intuit for Education and the Council for Economic Education. NGPF offers a base of units teachers can adapt; Get Your Financial Life Together provides 10 lessons, which Isern used with an investing group. Intuit for Education has tax materials, and the Council for Economic Education offers teacher webinars and professional development. These programs give teachers a place to begin, while leaving room to choose what fits their students and community.
A career change built around the work that mattered
Isern’s book grew out of repeated conversations with educators who wanted to teach financial literacy but also wanted to feel more confident about their own money. After a conference attendee urged her to write the book she wished existed, she spent about two and a half years developing it. She rewrote the opening chapters to include her family story, interviewed people working in financial education and spoke with teenagers for a chapter on Gen Z. Chapters six through 11 cover practical subjects such as credit and investing, with activities teachers can adapt to their students.
That work also helped open a new career path. Isern had worked as an assistant principal and thought of herself as a city employee with a secure job and pension. She consulted for Stackwell Capital, a robo-investing firm, for roughly six to eight months before the company offered her a full-time role. She says she chose it because the work—helping people feel more capable as investors—pulled her toward what she most wanted to do: teach, present and connect with students. She sought advice before leaving, and the decision carried real uncertainty, especially given her family’s preference for job security.
The financial trade-off was not all or nothing. Isern said city employees’ health coverage is vested after 10 years, and she expects a partial pension at retirement. She described the pension formula as 1.67% for each year worked until 20 years of service, then 2% per year after that. Those figures are her account of the city plan, and anyone weighing a similar move would need to check the rules that apply to their own benefits.
A career pivot won’t work the same way for everyone. But Isern’s story makes a useful point: security deserves a place in the calculation, alongside the work you want to do and the impact you believe you can have. For families and educators, the same principle applies to money conversations. You don’t need perfect answers to begin; you need a willingness to talk, listen and learn together.
