Why Doing "Everything Right" With Money Still Isn't Enough for Many Granite Staters

For many people across New Hampshire, managing money feels like a constant uphill climb. You go to school, work hard, pay your bills and try to save, but financial security still feels out of reach as housing costs rise alongside student loans and everyday expenses. According to New Hampshire financial strategist and entrepreneur Sean Dempsey, that frustration isn't about laziness or poor choices. More often, it's about following financial advice that no longer fits today's realities. Dempsey has spent years building businesses and investing across New England, and through that experience, he's come to question many of the money "rules" people are taught to follow. Today, he uses what he's learned to help people better understand their financial options and build confidence. His latest book, "Financial Cheat Codes: How to Win the Game of Finance," stresses that financial success isn't about perfection or simply working harder. It's about understanding the system, questioning outdated advice and making intentional choices. To keep things approachable, Dempsey uses a video game-inspired framework that compares financial decision-making to discovering shortcuts and tactics that help players move ahead faster. He calls these "Cheat Codes," and they're designed to take people from following whatever's considered "normal" to striving for "exceptional." For instance, one of the biggest misconceptions he sees is the belief that doing everything by the book automatically leads to long-term security. This often includes steps like going to college, working 9-to-5, investing in a 401K and trying to pay down your mortgage early. "This is what 99% of America is doing. So why not do what's 'normal?' Well, the problem is — it's all wrong," Dempsey says. From default retirement plans to one-size-fits-all education paths, he encourages people to take a closer look at whether those conventional approaches truly support their goals. Because for many households in the Monadnock Region, where affordability and income pressures are real, outdated financial advice can quietly hold people back. Among the most common myths Dempsey challenges is the goal of paying off your mortgage early. "Most homeowners these days have a low-interest mortgage. It's not just low. It's epicly low," he describes. And then he poses the question: "So why is someone's low-interest mortgage more valuable than their house?" In his experience, there are myriad reasons, including financial leverage. "This low cost of borrowing allows homeowners to allocate their money to other investments that most assuredly will offer higher returns," he explains. He also adds that these kinds of fixed-rate mortgages provide inflation protection, financial flexibility and even tax benefits. "Every dime you spend 'paying down' your mortgage is a dime that can't be used for far bigger and better investment opportunities," Dempsey describes. And he definitely has ideas about what those opportunities might be. One of the strategies he teaches involves creating personal lending systems that allow individuals to borrow from their own money rather than relying solely on traditional banks. Those funds can then be used to build passive income streams over time. The goal is to keep money working within your own financial ecosystem, instead of constantly sending interest and growth opportunities elsewhere. "Most people are trapped in a scarcity mindset, where they believe that money is limited and hard to come by," Dempsey says. But if you can adopt the mindset of an investor instead of a consumer, it can be incredibly empowering. What it takes is a clearer understanding of how money flows, grows and compounds over time so you can put it to work. With ongoing economic uncertainty and rising costs affecting households throughout New England, Dempsey's work has resonated strongly during community discussions. His book talks across the state have been drawing audiences interested in a new kind of financial literacy. You can find more at about his work at seandempsey.com and join the conversation at the Toadstool Bookshop in Peterborough on Saturday, Feb. 7 at 11 a.m. Dempsey will share strategies he recommends for fellow Granite Staters, offer an inside look at his book and lead a Q&A.