
Roth IRA Tax-Free Withdrawals: 5-Year Rule Explained
12/05/23 • 19 min
2 Listeners
James explores the nuanced aspects of Roth IRAs, shedding light on intricacies that can confound even experienced investors.
Through a listener question from Manfred, a retiree contemplating a $50,000 conversion from a 401k to a Roth account, James dissects the crucial five-year holding period and the order in which contributions, conversions, and earnings are treated during withdrawals.
James also provides clarity on distribution rules, exceptions, and strategic considerations, offering a comprehensive guide to navigating the complexities of Roth IRAs for optimal retirement planning.
Questions Answered:
How does the timing of subsequent conversions impact the application of the five-year rule?
In Roth IRA withdrawals, what is the specific order of operations, and what implications does that have?
Timestamps:
0:00 Manfred’s question
1:39 Get the cheatsheet
2:37 Understanding source nuances
7:01 The five-year rule
8:37 IRS’s order of operations
11:59 Exceptions to the rule
13:49 Only a small impediment
16:14 Back to Manfred’s example
Create Your Custom Strategy ⬇️
James explores the nuanced aspects of Roth IRAs, shedding light on intricacies that can confound even experienced investors.
Through a listener question from Manfred, a retiree contemplating a $50,000 conversion from a 401k to a Roth account, James dissects the crucial five-year holding period and the order in which contributions, conversions, and earnings are treated during withdrawals.
James also provides clarity on distribution rules, exceptions, and strategic considerations, offering a comprehensive guide to navigating the complexities of Roth IRAs for optimal retirement planning.
Questions Answered:
How does the timing of subsequent conversions impact the application of the five-year rule?
In Roth IRA withdrawals, what is the specific order of operations, and what implications does that have?
Timestamps:
0:00 Manfred’s question
1:39 Get the cheatsheet
2:37 Understanding source nuances
7:01 The five-year rule
8:37 IRS’s order of operations
11:59 Exceptions to the rule
13:49 Only a small impediment
16:14 Back to Manfred’s example
Create Your Custom Strategy ⬇️
Previous Episode

Retire Happy: How to Navigate Your Retirement Transition with Joe Kuhn
When we think of retirement, it often evokes dreams of leisure, relaxation, and the freedom to pursue one's passions. Yet, the decision to retire is not merely about leaving a career; it's about embarking on a new chapter filled with purpose and fulfillment. Joe Kuhn, a seasoned retiree and creator of the "Joe Kuhn Loves Retirement" YouTube channel, shares valuable insights gained from his personal journey.
Retiring to Something, Not Just From Something
Rather than focusing solely on leaving behind the stresses of work, Joe advocates for retiring to something meaningful. His emphasis on having specific plans, hobbies, and activities in retirement resonates with the idea that the transition isn't just a departure; it's an arrival into a new, purposeful phase of life.
Slow Travel and the Joy of Unplanned Adventures
James and Joe discuss the concept of "slow travel," an approach that involves savoring the journey rather than rushing to the destination. By embracing the beauty of unplanned adventures, he emphasizes that retirement opens up the possibility for individuals to explore at their own pace, fostering a deeper connection with the world around them.
Adaptability and Embracing Change
Joe shares the evolution of his retirement plans, demonstrating the importance of being open to change. Unforeseen events, such as the COVID-19 pandemic, forced him to reevaluate his consulting work, inspiring his YouTube channel’s transformation into a retirement coaching platform. Joe's story underscores the resilience required in retirement, encouraging individuals to navigate the uncertainties with flexibility and a willingness to explore new paths.
Slowing Down and Recognizing Stress
Joe reflects on the shift from a high-stress, task-oriented mindset to a more relaxed and balanced lifestyle. The act of slowing down, evident even in routine tasks like mowing the lawn, becomes a metaphor for the broader shift in priorities during retirement. Joe's candid revelation about being unaware of the stress he carried during his working years prompts listeners to reconsider their own well-being and the impact of stress on health.
Spending Less and Financial Realities
Contrary to expectations, Joe reveals that he is spending significantly less than initially estimated. Adjustments in car usage, changes in insurance, and a transition to streaming services contribute to this surprising revelation. It is important to carefully assess finances and the need to adapt spending habits in retirement based on changing circumstances.
Confidence to Spend and Seeking Support
Joe addresses a common fear amongst retirees – the confidence to spend money. Despite having sufficient resources, many individuals hesitate due to economic uncertainties. Joe advocates for seeking support, such as from financial advisors, to gain confidence in financial decisions. Retirement is not just about financial planning; it's about developing the confidence to enjoy the fruits of one's labor.
Joe Kuhn's journey through retirement offers unique insights for those contemplating or navigating this significant life transition. From the importance of retiring to something meaningful to the adaptability required in the face of unforeseen challenges, Joe's experiences provide a roadmap for creating a fulfilling retirement anchored in purpose, flexibility, and financial mindfulness.
Timestamps:
0:00 Emotional prep for retirement
1:34 Joe retires at 54
4:54 Fear versus time
10:04 Retire to (not from) something
14:57 Try different paths
19:44 Adjust to a slower pace
24:42 Release hidden stress
26:55 Spending in retirement
3
Create Your Custom Strategy ⬇️
Next Episode

When Should You Collect Social Security if Your Spouse is Much Older?
James addresses a listener's question regarding Social Security strategies in retirement. Sasha, aged 59, seeks advice on when to start collecting Social Security, considering her husband's benefits and their overall retirement plan.
James emphasizes the importance of considering spousal benefits, survivor benefits, and age gaps in making this decision. He explores the complexities of Social Security analysis, encouraging listeners to run break-even calculations based on the assumed age of the first spouse's death rather than just life expectancy.
James also shares a real-life example where delaying one's own benefit and collecting a survivor’s benefit early can be a strategic move. When choosing a Social Security claiming strategy, evaluate the broader impact on taxes, withdrawal rates, asset allocation, and legacy considerations.
Questions Answered:
How does the age gap between spouses impact the Social Security claiming strategy?
What factors should be considered when deciding on your Social Security claiming strategy?
Timestamps:
0:00 - Sasha’s SS question
2:19 - Analysis of Sasha’s situation
5:51 - The challenge
9:08 - When assumptions don’t pan out
12:29 - General principles
16:08 - Look at the whole picture
Create Your Custom Strategy ⬇️
Ready For Retirement - Roth IRA Tax-Free Withdrawals: 5-Year Rule Explained
Transcript
Roth IRAs can be a powerful tool for retirement savings , but there's some tricky things about them that can also be quite difficult to understand . In today's episode of Ready for Retirement , we're going to go over some of these lesser known aspects of Roth IRAs , some of these tricks , so that you know what to avoid and how to make the most of these in your Roth IRA strategy
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