Hawaii Retirement Show

In this episode of the HI Retirement Show, Jason explores the overlooked problem of saving too much for retirement.  Jason breaks down why rigid savings rules and fear-based habits can lead to stress and difficulty spending later in life, and highlights the importance of balance, flexibility, and defining your own sense of “enough.” Website: https://www.hiretirementshow.com Email Us: aloha@hiretir...

In this episode of the HI Retirement Show, Jason explores whether it makes sense to roll over your 401(k), TSP, or other employer retirement plan into an IRA. He covers the key benefits—like simplified finances, more investment options, and greater control over taxes—as well as potential drawbacks, such as losing certain early withdrawal options and creditor protections. Tune in to learn what to c...

In this episode of the HI Retirement Show, Jason dives into the essential topic of managing tax obligations in retirement. He breaks down how estimated taxes work, when you're required to pay them, and how the IRS’s Safe Harbor provisions can help you avoid underpayment penalties. Jason also explains how to fine-tune your withholdings from Social Security benefits, pensions, and retirement account...

In this episode of the Hawaii Retirement Show, Jason breaks down the difference between cognitive errors—thinking mistakes rooted in flawed logic or poor information processing—and emotional biases, which stem from feelings, impulses, and intuition. He highlights common pitfalls like conservatism bias, confirmation bias, overconfidence, and loss aversion, explaining how they influence investment d...

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP®, welcomes back Andy Panko, CFP®, RICP®, TPCP®, EA, for a second time to dive into taxes in retirement. They cover a range of important topics, including estate and inheritance taxes, how capital gains tax brackets work, the IRA Pro Rata Rule, the pros and cons of non-deductible IRA vs. taxable brokerage contributions, the dedu...

In this episode of the HI Retirement Show, Jason explores dynamic withdrawal strategies and flexible approaches to retirement income that adjust based on market performance, spending needs, and longevity considerations. He explains how these strategies differ from fixed withdrawal methods, highlighting the potential benefits of greater adaptability in uncertain markets. Jason gives a high-level br...

In this episode of the HI Retirement Show, Jason takes a deep dive into the bucket strategy, a popular retirement income planning approach designed to help retirees manage risk and maintain steady cash flow. He breaks down how the strategy works, including how to structure different “buckets” for short-, medium-, and long-term needs. Jason also explores the advantages and limitations of the bucket...

In this episode of The Hawaii Retirement Show, Jason is joined by Kaipo Crowell, a former senior civilian leader at Pearl Harbor Naval Shipyard, for a deep and thoughtful conversation that goes beyond the numbers. From reframing wealth, to investing in relationships, health, and time, Kaipo offers lessons rooted in real-life challenges and reflections. He and Jason explore themes like influence, a...

In this episode of the HI Retirement Show, Jason takes a deep dive into the 4% rule, a widely used retirement strategy that helps determine how much you can safely withdraw from your portfolio each year. He unpacks the origins of the rule, explains how it works, and explores how it holds up in today’s market conditions. Jason also highlights key concerns and important considerations to keep in min...

In this episode of The Hawaii Retirement Show, Jason is joined by Dr. Tray Spilker, Finance Professor at the University of Hawaiʻi’s Shidler College of Business, for a deep dive into the world of private equity. They explore what private equity really is, how it works, and where it fits into the broader investment landscape.  Tray Spilker, PhD, CFA - Latest Research Paper:  "Private Equity Fund Pe...

In this episode of the Hawaii Retirement Show, Real Estate Broker James Chan joins us to break down the latest trends in Hawaii’s housing market. We dive into how interest rates are impacting buying and selling decisions, explore the current state of single-family homes, condos, and the luxury market, and discuss whether investing in renovations and repairs is really worth it before selling your h...

In this episode of the Hawaii Retirement Show, Jason unpacks the recently passed "Big Beautiful Bill".  He highlights several key provisions including the temporary raising of the SALT deduction cap, the new “Senior Bonus” deduction, the targeted tax breaks for tip income and overtime pay, and much more. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this episode of the HI Retirement Show, Jason dives into the fundamentals of rates of return—what they are, how they're calculated, and why they matter for your retirement planning. He also explores the concept of benchmarking, helping you understand how to measure your portfolio’s performance against appropriate standards. Plus, Jason breaks down common misconceptions and mistakes investors ma...

In this episode of the HI Retirement Show, Jason breaks down what Hawaii State and City & County employees need to know about EUTF medical costs in retirement, highlighting the employer contributions and financial considerations to help you prepare with confidence. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this episode of the HI Retirement Show, Jason explores Hawaii's 529 college savings plan and an exciting new benefit for State and City & County employees, automatic payroll deductions directly into the plan. He explains how 529 plans work, the potential tax advantages, and how this new feature makes saving for education easier and more accessible than ever. Whether you're a parent, grandpa...

In this episode of the Hawaii Retirement Show, Jason is joined by Estate Planning attorney Stacy Takekawa for an insightful conversation on how estate planning fits into a well-rounded retirement plan. They review the basics of estate planning, discuss how to avoid common pitfalls, and explore how to ensure your wishes are carried out. This a must-listen for anyone preparing for the future. Stacy...

In this episode of the HI Retirement Show, Jason takes a closer look at annuities—what they are, how they work, and whether they belong in your financial plan. He also highlights common mistakes to avoid when considering annuities, helping you make more informed decisions about your retirement strategy. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this Episode of the HI Retirement Show, Jason briefly breaks down some things to consider when deciding whether or not to take a pension as a lump sum.   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this Episode of the HI Retirement Show, in light of the recent events, Jason discusses what issues to consider during a recession or market correction.   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this Episode of the HI Retirement Show, Jason breaks down the eligibility and other considerations pertaining to social security benefits for divorced individuals.  Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this Episode of the HI Retirement Show, Jason is joined once again by Chris Naffziger to discuss what retirement means in the modern age. Chris also shares his experience in taking a mini-retirement several years ago. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this Episode of the HI Retirement Show, Jason breaks down the Social Security benefits available to surviving spouses.  "Survivor Benefit" Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this Episode of the HI Retirement Show, Jason discusses how most of us will suffer from cognitive decline as we age, and how this can impact financial decisions.   Jason also touches on how our confidence in decision making remains high as we age and the potential role a Single-Premium Immediate Annuity can play in someones financial plan later in life.  Website: https://www.hiretirementshow.co...

In this Bonus Episode of the HI Retirement Show, Jason discusses some things to consider for any Federal Workers who have recently resigned or were laid off due to cuts.   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this Episode of the HI Retirement Show, Jason briefly breaks down the Social Security Spousal benefits and who is eligible to collect them.   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com