James discusses a listener’s question about what to do with stock positions and single stock positions, explaining the pros and cons of holding a concentrated stock position.  He highlights the importance of understanding tax implications and assessing your ability to handle financial and emotional implications. 
Questions Answered:
What should you do when you have a large concentrated stock position from an investment perspective?
How do you exit and diversify your position?

Timestamps:
0:00 intro
3:59 Single concentrated stock positions
4:47 The role of taxes
7:07 What’s the biggest risk?
7:52 Two examples
12:10 Takeaway
12:30 Other considerations
15:35 JP Morgan study
20:13 Here’s what I’ve noticed…
21:46 Understanding risk
24:16 What would I look at?
25:52 Outro 

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What's the Best Way to Sell Out of a Concentrated Stock Position?

Ready For Retirement is the podcast dedicated to helping you learn the tips and strategies that will help you achieve your retirement goals. When it comes to retirement planning, it can quickly become overwhelming and easy to not take action. I designed this podcast because I want you to have the knowledge and confidence to create your secure retirement. My ultimate goal for all of my clients (and listeners) is to create peace of mind and that starts with having a strategy. I want you to spend more time thinking about what matters most to you in retirement. I post weekly episodes to keep you up-to-date on all the best tips and strategies to create a retirement that excites you. Everything from investing tips, tax planning, withdrawal strategies, insurance planning, Social Security, and that's just the start! Let's help you maximize your return on life. We use your money and the strategies I share in this podcast to do just that!

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How do you know if you can retire? It seems straightforward, but the answer is far from simple. Beyond portfolio balances and age thresholds, there are other things to consider. James explains his three-step test to determine your retirement readiness.

By pulling together principles from the 4% Rule, straight-line projection, and a Monte Carlo analysis, you can assess whether your portfolio can sustain your desired lifestyle over decades amid various market conditions. However, these tests alone don’t paint the complete picture. James emphasizes the importance of considering other assets like potential inheritances or property downsizing to more fully and confidently evaluate when you can retire.

Questions Answered:
How can I determine if I’m financially ready to retire?
Is the 4% Rule sufficient for determining retirement readiness?

Timestamps:
0:00 - Consider withdrawal rate
2:14 - 4% Rule
5:12 - Not a perfect strategy
7:39 - Straight line projection 
9:09 - Downside of SL projection 
11:07 - Monte Carlo test
13:07 - Understand severity of failure
16:20 - Defining success, 
18:25 - Looking ahead Create Your Custom Strategy ⬇️ 
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3 Simple Steps to Determine If You Can Retire

Jennifer, 54, plans to retire soon. Her husband, 70, is retired, on Social Security, and dealing with some severe health issues. Jennifer worries about possibly becoming single in retirement, which could result in a higher tax bracket for her. 

Jennifer is considering whether to convert her traditional accounts to Roth to lower future taxes or to change her contributions to Roth 403b, even if it means paying more taxes now. James walks us through several factors for her to consider and demonstrates why her future tax situation is likely not as dire as she thinks.


Questions Answered:
How should Jennifer maximize her retirement savings in light of her current financial situation and future tax implications?

What factors must Jennifer consider when deciding whether to convert her traditional retirement accounts to Roth or change her contributions to Roth 403b?

Timestamps:
0:00 - Jennifer’s question
4:46 - Retire early for tax benefits?
6:05 - Roth conversion strategy
8:43 - Consider future expenses 
12:38 - Assess SS strategies
13:56 - Consider living situation
15:54 - The conversion question
17:54 - Main takeaways Create Your Custom Strategy ⬇️ 
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Tax Planning for Widowed Retirees: How to Optimize Your Tax Strategy

Joe is planning for retirement and wants to minimize his tax burden, especially on the interest earned from his three annuities. James explains that non-qualified annuities are purchased with post-tax money and offer tax deferral on growth until withdrawal. When taking out funds, the principal is tax-free, but earnings are taxed at ordinary income rates. 

He explores strategies for tax-efficient withdrawals. He also touches on annuities, options like a 1035 exchange to transfer an annuity into a different product for improved performance, the tax implications for heirs, and early withdrawal penalties before age 59 and a half.

Questions Answered:
How are non-qualified annuities taxed upon distribution, including both lump sum and annuity options?

What strategies can be implemented to keep the tax burden as low as possible when withdrawing from non-qualified annuities?

Timestamps:
0:00 - Joe’s question
1:52 - Non-qualified annuity overview
5:11 - Potential tax strategies
10:02 - Annuitization option
12:31 - Annuity regret
13:22 - 1035 Exchange
14:33 - Things to know Create Your Custom Strategy ⬇️ 
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Lump Sum vs. Annuitization: Tax Implications for Your Non-Qualified Annuity

Deciding to work with a financial advisor is about more than how much you've stashed away. It's also about determining whether an advisor's benefits outweigh the costs. 

In your higher earning years, finances become more complex. More money means more decisions and more chances to make mistakes or miss out on opportunities. That's where a quality advisor can come in handy. They help you steer clear of bad investments, seize the right opportunities, and keep financial stress at bay.

Having more than one perspective to draw from is the key to well-informed financial decisions. Teaming up and talking it out, whether with your partner or a financial advisor, is always beneficial.


Questions answered:
How can I determine whether working with a financial advisor is worth it for me?

What factors should I consider when deciding if I need a financial advisor beyond just my age or income level?

Timestamps:
0:00 - Not an age-related decision
2:43 - Value and pricing structure
4:12 - Natural conflicts 
7:24 - When benefit exceeds cost
10:02 - Cost of mistakes
12:18 - Cost of missed opportunities
14:16 - Cost of anxiety 
16:02 - Thought partnership
21:36 - Summary Create Your Custom Strategy ⬇️ 
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At What Age Should I Work with a Financial Advisor?

Listener Ray is wondering what to do with his home as he embarks on a nomadic, van-life journey in retirement. Should he sell it to finance his travels or retain it for potential appreciation and cash flow? 

James explores the nuances of home ownership as an asset versus an investment. He considers cash flow and leverage as he looks at Ray’s three options – sell, rent, or borrow – while emphasizing aligning financial decisions with personal goals and aspirations.

Questions Answered:
Why shouldn’t I consider my home an investment?

What are the key financial considerations for retirees when deciding whether to sell, rent them out, or explore other options?


Timestamps:
0:00 - Ray’s question
1:56 - Why a home isn’t an investment
4:38 - Do you want to be a landlord?
8:22 - The financials
10:14 - Asset appreciation
11:30 - Cashflow
15:04 - Leverage
19:02 - What should Ray do?
20:33 - Reverse mortgage Create Your Custom Strategy ⬇️ 
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What's the Best Way to Sell Out of a Concentrated Stock Position?

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