The final five years before retirement can be the most important, and the most dangerous, years for your financial future. In this episode of Vision Wealth: A New View on Retirement, Ben and Megan Smith discuss why the years leading up to retirement require a different mindset than the decades spent building wealth. From lifestyle creep and spending habits to Roth conversions, tax planning, market risk, and retirement readiness, they explore the decisions that can have an outsized impact as retirement approaches. The conversation also highlights the importance of understanding your goals, defining what retirement actually looks like for you, and creating healthy financial boundaries before crossing the finish line. Retirement success starts long before retirement begins.

Schedule your discovery call with Ben to help calculate the future costs of current decisions at MyVisionWealth.com or call or text 503-831-9011.

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What do $22,000 red-carpet beauty bills, Corvettes, and Amazon purchases have in common? They all reveal how lifestyle creep can quietly shape your financial future. In this episode of Vision Wealth: A New View on Retirement, Ben and Megan Smith explore the subtle ways spending habits evolve over time and why even small changes can have a major impact on retirement planning. From everyday conveniences and subscription services to luxury purchases and family spending, they discuss how lifestyle creep affects people at every income level. The conversation also highlights the importance of intentional spending, opportunity cost, and aligning your financial choices with the retirement lifestyle you truly want.

Schedule your discovery call with Ben to help calculate the future costs of current decisions at MyVisionWealth.com or call or text 503-831-9011.

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Is retiring early really the dream or is there more to the story? In this episode, Ben and Megan Smith unpack the idea of early retirement and why it’s not as simple as following a checklist. The conversation explores the importance of stress-testing your income, defining your purpose, and understanding what you’re actually retiring to, not just from. They also highlight the balance between enjoying life today and planning for tomorrow, along with the role of meaningful work, community, and lifestyle choices. It’s a thoughtful look at how retirement is less about timing and more about creating a life that feels fulfilling at every stage.

Schedule your discovery call with Ben to help calculate the future costs of current decisions at MyVisionWealth.com or call or text 503-831-9011.

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Are you and your partner truly on the same page about your future or just managing day-to-day life together? In this episode, Ben and Megan Smith explore why so many couples spend more time on logistics than meaningful conversations about their goals, especially when it comes to retirement. The discussion highlights how differences in spending habits, priorities, and vision can quietly create misalignment over time. They also share why having honest, sometimes difficult conversations early can help couples better understand each other’s expectations and build a shared path forward. It’s a thoughtful look at communication, planning, and how aligning today can shape the retirement you both envision.

Schedule your discovery call with Ben to help calculate the future costs of current decisions at MyVisionWealth.com or call or text 503-831-9011.

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What if being “ready” for retirement has less to do with your nest egg—and more to do with your life? In this episode of Vision Wealth, Ben and Megan Smith explore the emotional side of retirement and the often-overlooked signs that it may be time for a change. They discuss why purpose, relationships, and lifestyle expectations can matter just as much as financial readiness, and how differing visions of retirement can create challenges for couples. The conversation also highlights the balance between responsible saving and meaningful experiences, along with the risk of retiring “from something” without retiring “to something.”

Schedule your discovery call with Ben to help calculate the future costs of current decisions at MyVisionWealth.com or call or text 503-831-9011.

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What if a small $1,000 investment at birth could grow into millions and change how the next generation thinks about money? In this episode of Vision Wealth, Ben and Megan Smith unpack the concept of “Trump Accounts” and how these government-funded starter accounts aim to spark early investing habits. They explore how compound interest can transform modest contributions over decades, why education may be the real value behind the program, and how families—especially grandparents—can use it to build long-term financial habits. The discussion also highlights how self-reliance and early planning are becoming increasingly important in shaping future retirement outcomes.

Schedule your discovery call with Ben to help calculate the future costs of current decisions at MyVisionWealth.com or call or text 503-831-9011.

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Annuities might be one of the most misunderstood tools in retirement—and that confusion often leads to strong opinions. In this episode of Vision Wealth, Ben and Megan Smith unpack why annuities spark so much debate and why the answer to “are they good or bad?” is almost never black and white. The conversation covers what annuities actually are, why they’ve earned a negative reputation, common red flags to watch for, and how guarantees, fees, flexibility, and income needs all factor into whether they make sense. The episode emphasizes asking better questions, understanding your lifestyle needs, and avoiding one‑size‑fits‑all solutions.

Schedule your discovery call with Ben to help calculate the future costs of current decisions at MyVisionWealth.com or call or text 503-831-9011.

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What if your retirement money looks like it’s yours—until the fine print says otherwise?
In this episode of Vision Wealth: A New View on Retirement, Ben and Megan Smith explore the often‑overlooked rules attached to retirement accounts, taxes, and DIY financial strategies. Using a fun Oscars analogy, they unpack why “owning” your money isn’t always as straightforward as it seems, where well‑intentioned do‑it‑yourself planning can go wrong, and how missed tax strategies can quietly cost families over time. The conversation highlights the importance of knowing your limits, understanding nuance, and planning ahead before major financial decisions are locked in.

Schedule your discovery call with Ben to help calculate the future costs of current decisions at MyVisionWealth.com or call or text 503-831-9011.

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