Reasons Financially Secure People May Be Afraid to Retire Anyway
Upticks: A Financial Planning & Investment Podcast
Release Date: 04/17/2026
401(k) Rollovers, Private Equity, and Roth Conversions
Upticks: A Financial Planning & Investment Podcast
What should you do with a 401(k) after leaving an employer? Should private equity be included in workplace retirement plans? And when does a Roth conversion deserve consideration? In this episode of Upticks, Jake and Cory discuss three financial decisions that are often treated as automatic answers. They explain why each choice should instead be evaluated within the context of an individual financial plan, including investment strategy, access to retirement funds, taxes, liquidity, and long-term goals. --------------- Get your complimentary guide to retirement Get Jake’s weekly blog...
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Leverage, Concentrated Stock, and Is Early Retirement Overrated?
Upticks: A Financial Planning & Investment Podcast
What happens when leverage, confidence, and speculation collide? Jake and Cory begin this episode by discussing a highly leveraged hedge fund and the risks of investing with borrowed money. They also explain how options strategies may help executives manage concentrated company stock before turning to a deeper question: Is retiring as early as possible really the right goal? The conversation explores the difference between financial independence and leaving work, why purpose remains important in retirement, and why a complete retirement plan should address what you are retiring to—not only...
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20 Years of Retirement Planning Taught Me These 5 Things
Upticks: A Financial Planning & Investment Podcast
What separates a successful retirement plan from one that's simply invested? In this solo episode of Upticks, Jake shares five practical lessons he's learned from more than 20 years of helping clients prepare for retirement. He explains why financial organization, tax planning, flexibility, and aligning your investments with your personal goals often matter more than chasing market performance. Whether you're approaching retirement or simply looking to improve your financial plan, this episode offers practical ideas you can apply today. --------------- Get your complimentary guide to...
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When Money Stops Changing Your Life
Upticks: A Financial Planning & Investment Podcast
In this episode, Jake and Cory begin by revisiting the growing conversation around private investments inside 401(k) plans and why they remain skeptical of the trend. They also discuss the rise of index investing and understanding what you own. They debate whether high earners should own vacation homes, when renting may make more sense than buying, and ways lifestyle decisions can have a bigger impact than financial projections alone. Finally, at what point does money stop changing your life? Drawing from years of client experience, they discuss the differences between financial security,...
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What Can Really Put Retirement at Risk?
Upticks: A Financial Planning & Investment Podcast
In this episode, Jake and Cory react to a listener-submitted article about proposed 401(k) changes that could make private equity and other alternative investments more accessible. They explain why they believe retirement plans should stay simple and discuss the risks of adding complexity to long-term investing. The conversation then turns to retirement planning, including a debate on the biggest risks retirees face, the challenge of “golden handcuffs,” and why decisions about retirement can often involve more than just money. They wrap up with a discussion on mega backdoor Roth...
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Smart People Can Make Terrible Investment Decisions
Upticks: A Financial Planning & Investment Podcast
In this episode, Jake and Cory dig into reasons smart, successful people still make bad investment decisions. Pointing to recency bias, overconfidence, and financial media that markets fear and greed instead of sound strategy. They break down their belief of compound interest (not stock picking) being a better path to retirement, and ways “save first, spend second” can solve more money problems than people realize. The conversation wraps with a candid look at money in relationships. Reasons joint vs. separate accounts matter less than actually talking about finances, and ways...
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Reasons People Can Go Broke Trying to Look Rich
Upticks: A Financial Planning & Investment Podcast
What does financial freedom really look like? Are we chasing wealth or just the appearance of it? In this episode, Jake and Cory dive into the psychology behind money decisions, from homeownership and lifestyle inflation to raising financially independent children and resisting the urge to keep up with the Joneses. The conversation also tackles a question many parents wrestle with: when does helping your children become enabling them? Jake and Cory share perspectives on teaching financial responsibility, setting healthy boundaries, and preparing the next generation for independence....
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Does Spending Drop in Retirement? Here's What We Found
Upticks: A Financial Planning & Investment Podcast
Are Roth conversions a smart tax strategy or one of the most overhyped ideas in retirement planning? Should retirees stay invested aggressively? Do most people really need an annuity? And when is the right time to claim Social Security? In this episode of Upticks, Jake and Cory tackle some of the biggest debates in retirement and financial planning. Drawing from decades of combined experience working with retirees, they break down popular financial strategies and explain reasons the right answer often depends on your personal goals, cash flow needs, and long-term plan. The discussion covers...
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SpaceX, OpenAI, Anthropic: Will They Crash the Market?
Upticks: A Financial Planning & Investment Podcast
In this milestone 400th episode of Upticks, Jake and Cory celebrate how far the show has come and dive straight into what matters most: answering listener-driven questions shaping today’s financial landscape. This episode is packed with sharp insights on one of the biggest themes in investing right now: the surge of AI-related IPOs. With companies like SpaceX, OpenAI, and Anthropic dominating headlines, Jake and Cory go beyond the hype to help investors explore whether these record-breaking debuts could actually move the market or simply fuel speculation. They tackle the growing...
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Teach a Man to Fish
Upticks: A Financial Planning & Investment Podcast
Teach a man to fish… or give him everything? In this episode of Upticks, Jake and Cory tackle one of the most misunderstood truths in financial planning: there’s no one “right” answer—only better questions. We break down the real trade-offs behind major financial decisions, including: • Is real estate better than stocks—or just more work? • How much international exposure could your portfolio need? • Are “boring bonds” still worth owning in today’s market? • Should you retire the moment you can… or wait? • ...
info_outlineMany people assume that once you’re financially secure, retirement should feel easy.
In reality, some of the most financially prepared people struggle the most with the decision to retire.
In this episode of Upticks, Jake and Cory break down the real psychological reasons financially secure individuals might be afraid to retire—even when the numbers say they’re ready.
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Upticks is your podcast for financial planning insights. Hosted by Jake Falcon, CRPC™ and Cory Bittner, CRPC™, who discuss the philosophy of wealth management, exploring tailored retirement plans, tax planning, and timely industry topics. Join us for concise, understandable discussions that help empower your financial literacy.
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