Are you delaying retirement, working for "just one more year" to feel ready? In this episode, Ari and James dive into goalpost planning—the tendency to postpone retirement over financial or emotional uncertainties. Learn how to prioritize life goals over arbitrary benchmarks, like saving $1M or following a generic 60/40 portfolio strategy.

🎙️ Highlights from the conversation:

• The emotional challenges of leaving work and finding purpose in retirement
• Why cash flow matters more than hitting a specific savings number
• Real-life example: a mid-50s teacher couple weighing part-time work, pensions, and travel
• The truth about 60/40 portfolios and inflation-proof investing

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here 

Timestamps:
0:00 - Goalpost planning
3:09 - Procrastinating finding meaning
4:42 - Tradeoffs
6:43 - An example
9:20 - Initial analysis 
12:48 - Roleplaying
15:09 - Use your PTO 
18:01 - Allocation
20:39 - No cookie-cutter formula

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In today’s episode of Ready for Retirement episode James covers when to adjust your portfolio as retirement nears—a crucial step for balancing growth and security. If adjustments happen too late, market downturns could delay your plans; if too early, you might miss out on potential growth.

The focus is on reallocating stocks to more stable investments like bonds as you approach the time you’ll need to start drawing from your portfolio. Historical data shows that while the stock market grows over the long term, short-term volatility can be risky close to retirement. Timing this transition, often starting about 10 years before needing funds, provides a smoother adjustment and reduces risk.

Besides financial factors, psychological comfort with market swings also matters. Striking the right balance helps ensure your retirement funds last while maintaining your peace of mind.

Questions answered:
1. When should I start adjusting my investment portfolio as I approach retirement?
2. How can I balance growth potential with stability in my retirement portfolio to minimize risks and ensure financial security?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here 

Timestamps:
0:00 - Protect against stock market decline
2:22 - Investment fundamentals and market trends
6:12 - When will you need the funds?
8:06 - Risk capacity
10:55 - Consider dividends and interest from bonds
14:20 - Use bonds for a specific purpose
17:07 - Risk tolerance
20:59 - 5-10 years before retirement
24:36 - Goal: minimize risk and regret

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Meet Ari Taublieb 👋 If you didn’t already know, Ari and I work together at Root Financial, and we thought it was finally time to launch a podcast series together.

In our very first episode, we dive into a topic that many people shy away from: talking to your parents about money. Whether it’s discussing their estate plans, long-term care, or the tough conversations around wealth, these talks can feel awkward—but they’re absolutely essential.

In this episode, we break down:
▪️ Our personal stories and insights on how to approach these conversations
▪️ Tips for handling these talks with grace and understanding
▪️ Strategies to ensure peace of mind for everyone involved

If you’ve ever felt uncertain about talking money or navigating estate planning with your parents, this episode is for you.

Subscribe to Ari’s YouTube channel

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here 

Timestamps:
0:00 - Ari and James
2:03 - A listener's question
5:54 - Approaching parents
9:26 - Focus on the parent's needs/desires
11:13 - Start with long-term care
14:33 - Initiating conversations
18:03 - Have questions? Ask!

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Roth IRAs offer great tax-free income benefits, but to make the most of them in retirement, here are seven things you need to know:

1. Contribution Limits: In 2024, you can contribute up to $7,000 annually ($8,000 if 50+), across both Roth and traditional IRAs.
2. Access to Contributions: You can withdraw your contributions at any time, tax-free and penalty-free. Only earnings are subject to penalties if withdrawn early.
3. The Five-Year Rule: To withdraw earnings tax-free, the Roth IRA must be held for at least five years.
4. Income Limits & Backdoor Roths: High earners may not be able to contribute directly, but a backdoor Roth strategy can help. Consult a financial advisor for guidance.
5. No RMDs: Roth IRAs don’t require minimum distributions, allowing your funds to grow as long as you want.
6. No Impact on Social Security: Roth IRA withdrawals won’t count toward your provisional income, potentially lowering your Social Security tax.
7. No Medicare Surcharge: Roth withdrawals don’t affect your adjusted gross income, helping you avoid higher Medicare premiums.
   
   

By understanding the points above, you can use a Roth IRA to manage taxes and increase flexibility in your retirement.

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here 

Timestamps:
0:00 - What is a Roth IRA?
1:38 - Free withdrawals
3:15 - The 5-year rule
4:49 - Income thresholds
6:01 - Backdoor Roth contribution
8:18 - No RMDs
9:26 - Not provisional income
12:10 - Not part of IRMA calculations
13:06 - Income requirement nuances 
14:49 - Wrap-up

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Have you thought about what moving to a new state might mean for your retirement budget and lifestyle? In this Ready for Retirement episode, the focus is on preparing for an out-of-state retirement. James outlines three essential considerations for retirees planning a move:

1. Housing Costs and Expenses: From property values and local property taxes to potential capital gains from selling a current home.
2. Overall Cost of Living: Everything from groceries to utilities varies widely between regions. It’s also wise to consider personal lifestyle goals—like travel or access to nature—as these can impact ongoing expenses
3. A Solid Tax Strategy: Particularly if moving to a state with different tax laws. Retirees can benefit by adjusting their tax strategy based on the state they’ll be in, potentially saving thousands over time.

These tips offer invaluable guidance for anyone considering a fresh start in a new state after retirement.

Questions answered:
How can moving to a different state impact my retirement expenses?

What tax strategies should I consider if I plan to retire out of state?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here 

Timestamps:
0:00 - An overview
1:27 - Compare housing costs
4:04 - Moving to higher property tax state
6:32 - Moving to lower property tax state
7:12 - Compare cost of living
10:48 - Dial in your tax strategy
13:44 - Consider state tax rates
14:51 - Summary

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Many dream of retiring early, but you would be surprised to learn that many people who retire early regret doing so. James reveals five things that lead people to regret early retirement and provides practical tips to avoid these pitfalls.

He explains why many individuals who retire before 65 struggle due to a lack of planning, overly conservative investment strategies, and failure to envision life beyond work. He highlights the importance of aligning financial plans with personal goals, maintaining a balanced portfolio to outpace inflation, and considering part-time work as a transitional phase. He also encourages listeners to “practice” retirement before fully committing and cautions against adhering to common retirement “rules” without understanding their context. By addressing these critical aspects, listeners can make more informed decisions and transition into retirement, at any age, with confidence.

Questions answered:
Why is it important to have a life plan in addition to a financial plan when retiring early?

What lifestyle adjustments should early retirees be prepared to make to sustain their retirement long-term?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here 

Timestamps:
0:00 - Defining early retirement
1:15 - Not knowing what you’re retiring to
4:14 - Being too conservative
7:51 - Not considering part-time work
12:25 - Not practicing retirement
14:05 - Relying on retirement “rules”
17:26 - Being too dependent on 401(k)

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James sits down with someone who’s financially set to retire—mortgage paid off, kids through college, and investments in place—but he’s still grappling with one big question: what’s next?
Instead of focusing solely on financial strategies or retirement planning, James gives him some unexpected advice: start journaling. This led to a deeper conversation about finding purpose beyond optimizing your portfolio.

What would your life look like without constraints? What actually matters most to you? And how can you ensure your future is filled with meaning, not just money?

It’s not just about retiring from something but retiring to a life you love.

Questions answered:
How can I avoid feeling unfulfilled in retirement, even if I have all the money I need?

What are some practices I can do now to flush out what I really want out of life?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here 

Timestamps:
0:00 - A pertinent conversation
1:53 - Journaling prompts
3:00 - What matters
4:47 - Imagine no limitations
6:43 - Best, second-best, worst scenarios
10:00 - Addressing fears steps 1&2
13:22 - Addressing fears steps 3&4
16:43 - Take action
18:50 - Wrap-up

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For many, Social Security makes up a large portion of their retirement income, so it’s important to know how to maximize your Social Security benefit. James explains how Social Security works, diving into some important foundational aspects. He then explains four key strategies for maximizing benefits:

1. Work for 35 years to avoid zero-income years in the calculation.
2. Delay benefits, if possible, until age 70, increasing payments by 8% annually after full retirement age.
3. Leverage spousal benefits, allowing a lower-earning spouse to claim up to 50% of the higher-earning spouse's benefit.
4. Plan for survivor benefits, where a surviving spouse can receive 100% of the deceased spouse’s benefits.

By understanding how these factors work, retirees can make informed decisions to maximize their Social Security income, reducing pressure on their savings and ensuring a more stable retirement.

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here 

Questions answered:
How is Social Security funded, and how does it affect my retirement income?
How are Social Security benefits calculated based on my earnings?


Timestamps:
0:00 - How SS works
4:16 - Drilling deeper
6:27 - Full retirement age
8:08 - Work 35 years
10:08 - If possible, wait
12:17 - Spousal benefits
14:03 - Survivor benefits
17:39 - Summary

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ames responds to a question from Chris regarding restricted stock units (RSUs) and how to avoid costly mistakes when managing them. He explores whether it’s wise to hold onto company stock or diversify for a safer financial future. He breaks down how RSUs work, from vesting schedules to the tax implications of receiving stock as part of your compensation package. He also explains the critical considerations you should make when deciding whether to hold or sell vested shares and how this decision fits into your broader investment strategy.

Questions answered:
Should I hold onto or sell my vested RSUs?
What are the tax implications of RSUs, and how can I avoid mistakes?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here 

Timestamps:
0:00 - How RSUs work 
4:24 - Like a cash bonus
7:17 - Question your performance assumptions
12:25 - How RSUs are taxed and paid
15:14 - Default withholding rate and wash sale rules

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Patrick and Mary will soon both be retired. They are curious about what their withdrawal strategy should be as they balance various retirement accounts, including a pension, IRAs, and a brokerage account. They've been using tax gain harvesting to minimize taxes and plan to eliminate gains by 2024. A key question is whether to withdraw from their IRAs or brokerage account first, considering their state’s tax exclusion. James explains that by managing withdrawals and Roth conversions strategically, some retirees can reduce tax liability, optimize income streams, and preserve the tax-free growth of Roth accounts during retirement.

Questions answered:
Should retirees withdraw from their taxable brokerage accounts or IRAs first to minimize taxes?

How can Roth conversions and state tax exclusions be used to optimize income and lower taxes during retirement?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here 

Timestamps:
0:00 - Meet Patrick and Mary
3:14 - Retirement taxes are different
6:37 - Consider combined tax rates
8:42 - Tax gain harvesting
12:35 - Strategizing income in retirement
16:48 - Realized gains
20:12 - A twist on traditional thinking
23:47 - The bottom line

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Ben has been a saver his entire life, which helped position him for an early retirement at the age of 53. Yet, he faces a big challenge. Having maintained his modest lifestyle, Ben’s comfortable portfolio has continued to grow and has nearly doubled in value. James and Ben discuss the challenges of making mindset shifts and the proactive steps Ben has taken to encourage himself to spend more.

Questions answered:
How did Ben decide to retire when he was in his peak earning years?

What are the steps Ben has taken to force himself to spend more? 

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here 

Timestamps:
0:00 - Meet Ben
2:36 - A lifetime saver
5:28 - Confidence to retire early
6:41 - Retirement reality vs expectations
9:12 - The appeal of retirement
11:46 - The biggest challenge - spending
14:13 - A growing portfolio
17:33 - The lure of subsidies

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