Retirement Countdown: Essential Dates and Milestones to Remember

Planning for retirement can be an exciting yet complex journey. It’s a time when you finally get to enjoy the fruits of your labor and embrace a life of freedom and relaxation. However, to ensure a smooth transition into this new chapter, it’s essential to be aware of the important dates and milestones that can significantly impact your retirement experience. In this video, we will delve into these crucial aspects and provides expert insights to help you make informed decisions along the way.

Taking Social Security

One of the primary considerations in retirement planning is determining the optimal time to start taking Social Security benefits. Our expert host, Walt, shares valuable talking points on this topic. He explains that while the earliest age to start is 62, for most individuals, full retirement age (FRA) falls between 66 and 67. However, waiting until age 70 can result in higher benefits. Factors such as life expectancy, health, spouse, SS benefit amounts, and other sources of income should be carefully evaluated. It’s important to note that the decision to claim Social Security benefits is highly individual and requires a thorough analysis.

Long-Term Care Planning

Addressing the need for long-term care is another critical aspect of retirement planning. Walt emphasizes the significance of understanding how to handle the associated risks. This involves considering whether to transfer the risk or self-insure. Early planning is essential due to factors like health, age, and coverage limitations. Walt highlights the importance of becoming educated about the various options available beyond traditional plans, which have become increasingly costly. To illustrate this, he shares a real-life client story that sheds light on the escalating costs of coverage after two decades of paying premiums.

Withdrawals from Retirement Accounts

Determining when to start withdrawing money from your retirement accounts is a crucial decision that varies based on individual circumstances. Walt emphasizes that there is no one-size-fits-all answer. Factors to consider include other sources of income, age (with key milestones at 59.5, 73, or 75), the purpose of the money, lifestyle needs, and tax implications. Understanding how and when to take retirement assets can make a significant difference in your overall net worth over time.

Investment Allocations for Retirement

As retirement approaches, it’s essential to reevaluate your investment allocations. Walt highlights the importance of setting objectives, understanding your risk tolerance, and going beyond traditional conservative, moderate, or aggressive approaches. Losses matter, and diversifying beyond the traditional 60/40 split between stocks and bonds is crucial. Walt introduces the endowment model, which includes strategic, tactical, and alternative allocations, and emphasizes the significance of considering risk-adjusted returns. He also touches on the famous 4% rule, a guideline for sustainable withdrawals in retirement.

Roth Conversions, 401ks, and Estate Planning

The video further explores topics such as the ideal timing for Roth Conversions, managing 401ks from former employers, and the importance of early estate planning. Walt provides insights and considerations for each of these areas, such as the need for funds, legacy planning, tax implications, investment strategies, and the significance of naming beneficiaries.


Retirement planning is a multi-faceted process that requires careful consideration of important dates and milestones. By understanding when to take Social Security, planning for long-term care, making strategic withdrawals from retirement accounts, adjusting investment allocations, considering Roth Conversions and managing 401ks, and initiating estate planning early, you can pave the way for a successful and secure retirement.

The comprehensive video discussed in this blog post offers valuable insights and expert advice to help you navigate these critical aspects of retirement planning. By staying informed and making well-informed decisions, you can ensure a comfortable and fulfilling retirement journey.

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  1. Good information for the confused and concerned, esepecially as it pertains to SSN and consideration for long term care. Very similar to what is presented at the Prepare Institue classes!

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