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Ben Brandt, host of the Retirement Starts Today Podcast and Founder of Capital City Wealth Management, joins me to discuss his new book, Retirement Starts Today. Together we explore fresh perspectives on retirement planning, focusing on mindset shifts, financial strategies, and emotional preparation for a meaningful post-career life.
Here are notes from my conversation…
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(01:45) Abundance vs. Scarcity in Retirement Planning
When most people approach retirement, their thoughts often revolve around one thing: the fear of running out of money. This fear, while valid, can lock retirees into a mindset of scarcity—constantly worrying about worst-case scenarios and guarding against financial shortfalls. But Ben argues that this kind of thinking is only half the equation.
Scarcity thinking, he says, keeps people focused on avoiding risk rather than pursuing fulfillment. It’s the voice in your head that says, “I can’t afford that” or “What if something goes wrong?” The alternative, and what Ben encourages retirees to embrace, is an abundance mindset. This approach shifts the focus from preserving every dollar to using your resources—financial and otherwise—to build a meaningful life.
“Abundance is about more than just having enough money,” Ben explains. “It’s about being excited about the future you’re creating, about having the confidence to turn your savings into memories, experiences, and the things that matter most to you.”
The challenge, of course, is that shifting from scarcity to abundance isn’t easy. After years of saving and deferring gratification, many people struggle to start spending, even when the numbers show they can afford to. And this, according to Ben, is where many retirement plans fall short—not financially, but emotionally.
Retirement, Ben points out, comes with two major risks: running out of money and dying with regrets. Most financial plans obsess over the first, but what about the second? What about the family vacations that were put off, the dreams that were postponed, or the time with loved ones that was never prioritized?
“If all you’re doing is avoiding the fear of running out of money, you’re missing the bigger picture,” Ben says. “It’s about finding a balance. Yes, you need to make sure your money lasts, but you also need to make sure you’re making the most of the time and resources you have right now.”
So, how do you make that shift? Ben suggests focusing on what you’re retiring to rather than what you’re retiring from. It starts with asking yourself what truly excites you about the years ahead. What opportunities or experiences do you want to say yes to? By reframing retirement as an opportunity to pursue fulfillment rather than merely avoid risk, you begin to open yourself to an abundance mindset.
Ultimately, the transition from scarcity to abundance isn’t about ignoring financial realities—it’s about expanding your perspective. Retirement isn’t just a financial puzzle to solve. It’s a chance to create a life rich with experiences, memories, and joy. And as Ben emphasizes, abundance isn’t just a mindset—it’s a choice.
(04:12) The Time Machine Thought Experiment
Retirement is often seen as the final chapter, but Ben challenges that notion by reframing it as an opportunity to rediscover your passions and create a compelling vision for the future. In his book, Ben introduces a unique exercise designed to spark creativity and self-reflection: the Time Machine Thought Experiment.
Here’s how it works: imagine you could travel back in time to your 13th birthday, armed with $500 to spend on yourself by the end of the day. What would you buy? The catch is that you can’t give a practical or altruistic answer—you have to indulge your 13-year-old self’s dreams, no matter how whimsical or frivolous.
At first glance, this may seem like a fun nostalgia trip, but Ben uses it as a tool to help retirees reconnect with the parts of themselves that often get lost in the grind of adulthood and work. He explains that financial independence often arrives at a time when creativity is at its lowest.
“Ideally, we’d be financially independent when we’re most creative—like at 13—but for most of us, it comes at the end of a long career when we’re worn down by the corporate world,” Ben says. The Time Machine Thought Experiment is about reigniting that creativity and figuring out what truly excites you.
For some, this exercise may bring up simple joys, like buying a drum kit (as Ben did) or splurging on baseball cards or video games. For others, it might highlight long-held dreams or hobbies that they’ve yet to explore. The goal isn’t necessarily to act on these exact ideas but to use them as data points for what might bring fulfillment in retirement.
The experiment also underscores a critical lesson: retirement is not just about leisure—it’s about intentional exploration. “Finding out what you don’t like is just as important as discovering what you do like,” Ben explains. He encourages retirees to treat their newfound freedom as a time to experiment. That could mean trying new hobbies, traveling to different destinations, or exploring creative pursuits.
One of the most important aspects of this exercise is its focus on forward momentum. Retirement isn’t just about stepping away from a career; it’s about stepping toward something meaningful. Ben describes this as building a “compelling future,” a vision that pulls you forward with excitement rather than leaving you anchored to the past.
This idea resonated with me as I reflected on my own childhood dreams. When I took the Time Machine Thought Experiment myself, I was reminded of small but meaningful desires I had as a kid—like owning a geode, something I finally indulged in during adulthood. It was a small gesture, but one that reminded me of the importance of saying “yes” to the things that spark joy, no matter how simple they may seem.
The Time Machine Thought Experiment isn’t just a fun exercise; it’s a powerful way to uncover the passions, interests, and values that can shape your retirement into the most fulfilling chapter of your life. Whether you find yourself reconnecting with old dreams or discovering entirely new ones, this process is a reminder that retirement isn’t the end of the road—it’s the start of something entirely new.
(10:35) Rethinking Monte Carlo Analysis and Retirement Success Rates
Retirement planning is often driven by numbers. Spreadsheets, projections, and success probabilities dominate the conversation, creating a sense of security around the idea that everything can be calculated down to the last dollar. But Ben offers a thought-provoking critique of one of the most widely used tools in financial planning: Monte Carlo analysis.
For those unfamiliar, Monte Carlo analysis is a simulation used to predict the likelihood that your retirement portfolio will last through various market conditions. It’s an invaluable tool for financial planners, but Ben believes it’s often misunderstood and misused—sometimes to the detriment of retirees.
“The problem isn’t the analysis itself,” Ben explains. “The problem is how we interpret the results. People see a 90% likelihood of success and think, ‘Great, I’ve won retirement.’ But what they don’t realize is that they might be winning the wrong game.”
Here’s what Ben means: a 90% success rate in a Monte Carlo simulation often means retirees have built significant financial buffers, sometimes at the cost of living a less fulfilling retirement. To achieve that score, people may cut their spending, downgrade their goals, or avoid the risks that could lead to greater joy and fulfillment. It’s a strategy rooted in fear rather than optimism.
Ben challenges this conventional wisdom, arguing that a lower success probability—say, 70%—might actually lead to better outcomes. Why? Because it allows retirees to take advantage of opportunities for upside surprises, whether through market growth or the flexibility to adjust plans later. “The market is up more often than it’s down,” Ben says. “If you’re dialing in a 90% success rate, you’re essentially saying, ‘I’m going to downgrade my dreams so I never have to adjust my plan.’ But life isn’t static, and neither is the market.”
This perspective isn’t just about the numbers; it’s about reframing how we think about risk. Most retirees focus solely on the downside—the 10% chance that something might go wrong. But Ben points out that the same analysis also predicts an upside: there’s a strong likelihood that markets will outperform expectations over a 30-year retirement horizon. By settling for a high success rate, retirees may unintentionally close the door on those possibilities, leaving money unspent and experiences unlived.
This conservative mindset can lead to an unfortunate outcome that Ben has observed repeatedly: retirees who double or triple their wealth during retirement, only to regret never spending it. “I’ve seen clients with significant portfolios who are still living as if they’re going to run out of money,” he says. “And then they pass away, leaving behind untouched wealth that they worked so hard to save. That’s not the legacy they wanted to leave.”
Instead, Ben encourages retirees to think of Monte Carlo analysis as a guide, not a rulebook. A 70% success rate doesn’t mean failure—it means flexibility. It means planning for a future where you might need to make small adjustments, but where you’re also making the most of the opportunities you have today.
At its core, Ben’s critique of Monte Carlo analysis isn’t about dismissing financial planning tools—it’s about using them in a way that aligns with your goals. Retirement isn’t a math problem to solve; it’s a life to live. And sometimes, that means embracing a little uncertainty in exchange for a life that’s richer in experiences, memories, and joy.
(16:40) Creating Memories That Last Beyond Retirement
Retirement isn’t just about financial independence—it’s about creating meaningful experiences and cherished memories. For Ben, this is where retirement planning truly comes alive. Instead of focusing solely on budgeting and investments, he urges retirees to consider how their money can strengthen relationships and leave lasting legacies.
One of Ben’s unique strategies is a thought experiment: tripling your travel budget. While it may sound extravagant, this exercise isn’t about spending recklessly—it’s about breaking free from the “frugality-first” mindset that many retirees carry from their working years.
The exercise is simple: take the budget from your last vacation—flights, lodging, meals, and activities—and imagine tripling it. Would you upgrade to first class? Stay at a luxury resort? Add unforgettable experiences like private tours? The goal isn’t to follow through but to evaluate. Which upgrades would create deeper fulfillment and stronger memories?
“Every decision becomes a data point,” Ben explains. “If you love an upgrade, you’ve learned what enhances your experience. If you don’t, that’s equally valuable—you know where not to spend next time.”
While grand gestures can create memorable moments, Ben emphasizes that the most impactful memories often come from small, intentional acts: family dinners, shared hobbies, or quiet traditions. Peter reflects on his own grandmother, whose grand trips were meaningful, but whose Sunday dinners and birthday outings left the strongest impression.
These “legacy moments,” as Ben calls them, don’t require large financial outlays but can deeply impact loved ones. Whether it’s taking a grandchild to a ballgame or cooking a family meal, these experiences are what endure long after we’re gone.
“Money doesn’t leave a legacy. Memories do,” Ben says. By balancing thoughtful spending with your values and priorities, retirement becomes a time to turn resources into connection and joy. As Ben puts it, “You can’t take the money with you, but you can turn it into something unforgettable for the people you care about most.”
(23:21) Preparing Emotionally for Retirement
When people think about retirement, they often focus on financial concerns: how much money they’ll need, how to make it last, and how to invest. But as Ben points out, the emotional side of retirement is just as critical—and too often overlooked. Retirement isn’t just about leaving a paycheck behind; it’s about stepping away from a significant part of your identity, which can make the transition unexpectedly challenging.
“After decades of working, it’s not uncommon to define yourself by what you do,” Ben explains. “When someone asks, ‘What do you do for a living?’ you have an easy answer. But a few months into retirement, that question becomes harder. Who are you outside of work?”
This emotional adjustment can catch people off guard, especially for those who haven’t planned for it. A fulfilling career often provides structure, purpose, social connections, and accomplishment. Without these, retirees may feel lost, struggling to find meaning in their days.
To counter this, Ben suggests viewing retirement as a new chapter that requires emotional preparation. The earlier you start, the better. He encourages asking yourself: What gets you out of bed in the morning? Reflecting on what brought fulfillment in your career—whether it’s collaboration, mentoring, or achieving goals—can help identify activities that will sustain you in retirement.
For those feeling unsure, Ben recommends treating pre-retirement as a time to experiment. Explore new hobbies, volunteer, or revisit interests you’ve sidelined. The goal isn’t to find one passion but to discover what brings you joy and fulfillment.
Maintaining a sense of purpose is also crucial. Without workplace recognition or goals, retirees can feel adrift. Setting personal objectives—whether through learning, volunteering, or contributing to your community—can provide the structure and accomplishment that work once did.
For couples, retirement is a shared journey. Ben stresses the importance of discussing expectations, fears, and dreams with your partner early and often to ensure alignment as you navigate this phase together.
Finally, Ben emphasizes flexibility. Retirement evolves, and so should your plans. Adapting to changing needs, interests, and circumstances is key to creating a fulfilling life.
“Retirement isn’t just about leaving work,” Ben says. “It’s about moving toward a new version of yourself. The sooner you start imagining who that is, the better your outcome will be.”
By preparing emotionally, you can approach retirement with purpose and excitement. And as Ben reminds us, the best time to start is now—long before the day you retire.
(24:55) Connect with Ben Brandt
Ben’s book, Retirement Starts Today, is available on Amazon and Audible. His podcast, Retirement Starts Today, offers actionable insights for anyone planning their retirement. Keep an eye out for his upcoming YouTube channel, where he’ll continue sharing his expertise.
Retirement is a deeply personal journey, and Ben’s work reflects that reality. His book, podcast, and soon-to-be YouTube channel are all testaments to his mission: helping people create a retirement that isn’t just financially sustainable but deeply meaningful.
So, if you’re looking for practical strategies, fresh perspectives, or just a little inspiration as you plan for the next phase of your life, Ben’s resources are a must. As he puts it, retirement isn’t the end of your story—it’s the beginning of an exciting new chapter.
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The Long Term Investor audio is edited by the team at The Podcast Consultant
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