Beyond Numbers: The Human Element of Retirement Planning

What if the most important lessons about retirement aren’t found in a spreadsheet, but in the stories we live and the people we love? For over two decades, Harry Abrahamsen has sat across the table from pre-retirees, retirees, and families, listening not just to their retirement planning goals and wealth management questions, but to their dreams, fears, and the “what ifs” that keep them up at night. In a recent episode of “Talking Retirement,” hosted by Ken Connolly of NJ Life & Health, Harry opens up about the journey that shaped his philosophy—and why, for him, money is never just math.

The conversation begins not with numbers, but with a moment of reckoning. After 9/11, Harry, then a business owner, found himself questioning everything: “Did I have this set up right? Did I have that set up right?” The answer was no. That vulnerability, and the mentorship that followed, set Harry on a path to help others prepare for the unpredictable—those black swan events that can upend even the best-laid plans.

Money Isn’t Math—And Why That Matters

Early in the interview, Ken asks Harry to expand on a phrase that’s become central to his work: “Money isn’t math and math isn’t money.” Harry’s answer is as simple as it is profound: “Math is perfect—one plus one will always be two. But with money, a dollar today plus a dollar a year from now is never just two dollars. Taxes, inflation, and other wealth-eroding factors eat away at value over time.”

He likens money to oranges: leave them on the table for a year, and they rot. “Money behaves more like an orange than a number,” Harry says. This isn’t just a clever analogy—it’s a reminder that retirement planning and wealth management must account for erosion, uncertainty, and the realities of life, not just tidy equations.

Retirement Planning: The Stories Behind the Strategies

Harry’s approach is deeply human. He’s seen how what makes sense financially might not make sense emotionally. “You could be totally right, but the person is just going to be like, ‘I don’t want to do it,’” he shares. Whether it’s the comfort of a paid-off home or the desire to give to charity, Harry knows that emotion often trumps logic. He’s learned, through countless client conversations, that “numbers don’t retire—people do.”

He recounts stories of clients who, after reading his book Money Rules, come back with questions about retirement planning, life insurance, building a financial legacy, and how to support their families through effective wealth management. “I’m a terrible mind reader,” Harry admits. “I can’t assume what matters most to my clients, so I ask, I listen, and I build plans around their real lives.”

Building a Legacy, Not Just a Nest Egg

Ken’s questions throughout the episode reveal a deep empathy and expertise. He doesn’t just ask about products or returns—he asks about the “why” behind the plan. “At the end of the day, it’s really a way for you to support the lifestyle you want and to support the people that you love,” Ken observes. Harry agrees: “It’s different for everyone. Every client is entirely different. I’ve learned one thing—I’m a terrible mind reader. We have a lot of conversations. Really listening to what they’re looking to achieve is important, and making sure you can provide solutions that fit into their world.”

For Harry, a true financial legacy is about more than leaving money behind. It’s about ensuring that, through proactive retirement planning, families are protected and futures are secure. He shares personal stories—like why he owns 12 life insurance policies, not just for tax or investment reasons, but as an act of love and protection for his family.

Debunking Myths and Mainstream Advice

The conversation doesn’t shy away from challenging the status quo. Ken invites Harry to critique the advice of mainstream educators like Dave Ramsey and Tony Robbins. Harry is candid: “General rules, like withdrawing a fixed 8% from your portfolio, can be dangerously misleading. Markets are volatile, and what works in theory can fail in practice.” He emphasizes that advice must be tailored, and that “math isn’t money”—a mantra that challenges the oversimplification rampant in popular finance media.

Harry also warns against the allure of “tax-free money” schemes and urges viewers to scrutinize products and advisors carefully. “There’s no magic bullet. True financial security in retirement planning and wealth management comes from understanding your options, questioning assumptions, and working with professionals who put your interests first.”

Tools, Tactics, and the Macro Advantage

After decades in the business, Harry’s retirement planning and wealth management toolkit is broad and nuanced. He’s seen firsthand how retirees can be blindsided by taxes, inflation, and the hidden costs of longevity, all of which impact your financial legacy. Here are just a few of the insights he shares:

• Social Security Optimization: Harry doesn’t just run break-even charts—he helps clients weigh the real-world value of money today versus tomorrow, factoring in inflation and personal needs as part of a holistic retirement planning strategy.
• Required Minimum Distributions (RMDs): Many retirees are shocked by the tax impact of RMDs, especially after years of diligent saving. Harry’s planning anticipates these surprises, integrating tax strategy, income needs, and lifestyle goals.
• Expense Planning and Inflation: Using advanced software, Harry models how expenses will grow over time, ensuring clients aren’t blindsided by rising costs ensuring your wealth management plan accounts for rising costs.
• Insurance as Love, Not Just Leverage: Harry’s advocacy for life insurance is deeply personal. “It’s about love,” he says. Paid-up policies, living benefits, and permanent coverage provide peace of mind and flexibility for whatever life brings.

Facing the Unpredictable: Conversations That Matter

One of the most powerful moments in the interview comes when Harry talks about the importance of having tough conversations early. “Real risk is everything that nobody’s talking about,” he says. Black swan events—major health issues, sudden loss, or simply the desire to step back from managing your own finances—are inevitable. Harry urges clients to build relationships with trusted retirement planning and wealth management advisors before they’re needed: “You don’t want to be interviewing for advisors when you’re in your 70s dealing with cancer. Establish a relationship now, while you’re on top of your game.”

Ken echoes this sentiment, noting that too many people wait until it’s almost too late to talk about legacy, long-term care, or what happens if cognitive decline sets in. The lesson? Start the conversations now, and don’t underestimate the power of planning for the unknown.

Education That Empowers: From Webinars to “One Minute Medicare”

Both Harry and Ken are passionate about education. Harry hosts weekly webinars focused on emerging issues—like new tax laws, the Secure Act, and inflation—ensuring clients stay ahead of the curve. Ken, meanwhile, produces “One Minute Medicare” digital segments, breaking down complex topics for seniors and their families. Their shared mission: empower individuals and families to make informed, confident decisions about retirement planning, health, wealth management, and building a lasting financial legacy.

The Power of Partnership: Why Collaboration Matters

This episode is more than just an interview—it’s a collaboration between two professionals who care deeply about their clients and their communities. By sharing the stage, Harry and Ken demonstrate the value of cross-promotion and partnership in the financial world. If you’re looking for more expert perspectives or want to connect with professionals who put people first, check out NJ Life & Health for Medicare education and resources.

Key Takeaways:

• Retirement planning is about people, not just numbers.
• Building a financial legacy requires proactive, personalized strategies.
• Wealth management must adapt to life’s unpredictability and evolving goals.

Meet Your Guides

Harry Abrahamsen
Founder & CEO of Abrahamsen Financial Group, Harry is a leading voice in personal financial economics and the author of Money Rules – 9 Rules to Massive Wealth. With a background in marketing and finance from the University of Tampa and advanced entrepreneurial training at MIT’s Birthing of Giants program, Harry built his firm on the principle that macro-level, personalized strategies are essential for true wealth protection and growth. He collaborates with attorneys, CPAs, and bankers to deliver holistic plans for individuals and families, always prioritizing personal relationships and client values. Harry lives in Little Silver, NJ, with his wife Jennifer, their seven children, and one granddaughter.

Ken Connolly
Marketing Director, Licensed Life & Health Insurance Specialist
Ken is an Ohio State Business School graduate who has helped hundreds of people over his two years with NJ Life & Health. He spent his twenties in the music industry, running his own record label and learning the art of marketing. Today, Ken brings that creative energy to helping seniors understand the complexities of Medicare, saving them money and avoiding pitfalls. He’s the face of “One Minute Medicare,” and when he’s not working, you’ll find him producing music, spending time with family and friends, cooking, working out, or taking on Spartan races.

Ready to Rethink Retirement?

This isn’t just another financial podcast. It’s a journey through the real-life stories, hard-won lessons, and deep insights that only decades of experience can bring.  Whether you’re navigating your own retirement planning, helping your parents with wealth management, or just looking for a fresh take on building a financial legacy, Harry’s conversation with Ken is a must-watch.

Watch the full episode of “Talking Retirement” featuring Harry Abrahamsen and Ken Connolly:

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For more expert guidance, visit NJ Life & Health. Empower your retirement and build your legacy.
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