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Retirement Planning Questions — PillarWM

If your retirement years are drawing closer, you might be wondering how the next phase of your life will play out. Perhaps you have a long list of retirement planning questions, many of which are too complicated to answer yourself. If your wealth exceeds $10 million, you may find the answers to most of your questions in our guide titled 7 Secrets to High Net Worth Investment Management, Estate, Tax, and Financial Planning. Even better, seek retirement planning advice from Pillar Wealth Management, which specializes in wealth management services designed for individuals who own between $5 million and $500 million in liquid assets.

7 Secrets minified

7 Secrets To High Net Worth Investment Management, Estate, Tax and Financial Planning

The insights you’ll discover from our published book will help you integrate a variety of wealth management tools with financial planning, providing guidance for your future security alongside complex financial strategies, so your human and financial capital will both flourish.

Clients frequently share with us how the knowledge gained from this book helped provide them tremendous clarity, shattering industry-pitched ideologies, while offering insight and direction in making such important financial decisions.

In this guide, you’ll learn about some of the most crucial retirement planning questions to ask yourself or your financial advisor to secure your retirement:

Table of Contents
Nine Retirement Planning Questions

Nine Retirement Planning Questions

1.     At What Age Should I Retire?

According to the National Academy of Social Insurance, the full benefit age for those born in 1955 is 66 years and 2 months, but for those born in 1960 or later, it will gradually rise to 67. When it comes to what Americans actually plan to do, over 54% plan to keep working beyond 65, even though the average retirement age stands at 61.

Many retired individuals later choose to return to work and then retire again after a few years; some  keep working part-time; others even go on to pursue a second career such as launching a startup.

Understandably, many of these numbers reflect individuals who can no longer work due to health issues or can’t find work. Knowing that early retirement squeezes income, you may not want to retire before your full benefit age. If you’re in good health and are self-employed, you may continue working through your 70s.

Everyone’s situation is different. We recommend taking into account the following factors when determining what retirement age makes the most sense for you:

• Net worth

• Financial goals

• Investments

• Expenditures

• Debt

• Cash flow

If you’re a high net worth or ultra-high net worth individual, you may be able to stop working at the age of 60 (depending on your lifestyle and expenditures) and benefit from passive income, which means your existing wealth earns enough money for you, perhaps through smart investments. If you’re still unsure about when is the right time to retire, seek expert advice via a video consultation meeting with our wealth managers.

2.     How Much Money Do I Need to Retire?

This is one of the most asked retirement planning questions, and if you’re anywhere close to retirement, you’ve probably asked yourself this question at some point in time. Gone are the days when you could totally rely on government- and company-funded pensions. With more and more Americans retiring with less money than what they need, retirement planning has become more of an individual responsibility than a governmental or corporate obligation.

Using online calculators can give you a basic idea of how much you need, but don’t rely on them exclusively because most tend to be overly simplistic. Again, an appropriate answer to this question depends on several aspects, including your age at the time of retirement, the amount you get from Social Security or pensions, and most importantly, your lifestyle and expenditures.

Some folks spend very little and may have worked at the same job their entire life. Not only do they need very little money to comfortably support their post-retirement lifestyle but also have accumulated a sizable monthly income or pension in their retirement account. Others who like to spend a lot but have no retirement account or pension will either need to find a way to live on less after retirement or need a large amount of retirement savings.

We recommend budgeting on the conservative side when devising your retirement plan to ensure that your social security income, retirement accounts, and savings support your post-retirement lifestyle. If your liquid assets exceed $25 million in value and you’re looking to secure and further increase your wealth for retirement, read our book titled The Art of Protecting Ultra-High Net Worth Portfolios and Estates: Strategies for Families worth $25 Million to $500 Million.

3.     How Does Medical Care Affect My Retirement Savings?

Most people underestimate the medical bills they may incur after retirement, and to be honest, long-term medical care can consume a massive chunk of your retirement savings. According to Annuity.org, a 50-year old couple retiring at the age of 65 back in 2019 expected to pay around $405,000 on healthcare in retirement.

Once you reach age 65, you’ll certainly qualify for the federal health insurance program called Medicare, but it won’t cover everything. It will pay for your doctor visits, prescriptions, and hospital stays, but won’t cover long-term health care, hearing aids, dental care, and vision services. Therefore, you may need the following types of health insurance:

Long-term care insurance: This is an insurance product offered in the US that will cover long-term healthcare costs that aren’t covered by healthcare plans.

Supplemental health insurance: Among the most important sources of supplemental coverage include Medicare Advantage plans, employer-sponsored plans, Medigap policies, and Medicaid.

Health Spending Account (HSA): This is a flexible spending account that enables you to save pre-tax money for your future healthcare expenditures.

When budgeting for long-term healthcare costs, be sure to take into account the medical costs in the area you retire because costs can significantly vary from one geographical location to another. To accurately forecast your medical expenses, consider both your current health condition and your genetics. By making the right, growth-oriented investments now, you can easily cover your long-term healthcare costs after retirement. For more inspiration, take a look at our free book titled 5 Critical Shifts For Maximizing Portfolio Growth Strategies – For Families Worth $5 Million To $500 Million.

4.     When Is the Right Time to Claim Your Social Security?

While you can claim your Social Security retirement benefit as early as age 62, it’s best to wait until your full retirement age. This is because claiming your benefits at any time before your full retirement age means you’ll receive a reduced benefit. Not only can that reduction cost you in the long-run, but when your spouse claims your benefits after your death, they will receive only the reduced amount.

On the other hand, delaying claiming your Social Security until the age of 70 should result in an 8% increase in the benefit. But if you anticipate having a shorter-than-average life owing to some known health conditions, it might be rational to claim earlier. For deeper insights into when exactly should you claim your Social Security retirement benefit, conduct a video consultation meeting with our wealth managers.

5.     Where Do I Invest for Retirement?

This is among the most crucial retirement planning questions. If you plan to retire early, perhaps in your 50s rather than your 60s or 70s, you’ll need more funds to maintain the same lifestyle after retirement. Understanding your investment options should help you in setting up your financial nest egg. The simplest place to start is to participate in a workplace investment plan like a 403 (b) or 401(k).

Regardless of the products you invest in, be sure to take your risk tolerance into account and develop a well-diversified investment portfolio.

Take the time to determine your investing timeline. If retirement is near, you may want to consider less-volatile investments. But if you still have decades before retirement, you can go for a more aggressive investment strategy. While there’s no guarantee with investments, with an extensive investing timeline, you have a lot more time to recover from market downturns. Consider allocating a greater proportion of your portfolio to stocks that have the potential to offer higher returns than bonds or cash.

When making investment decisions, however, don’t forget to account for inflation, which can eat away at the purchasing power of the dollars you’re saving today. To make meaningful gains at the time of retirement, make sure that your money’s growth surpasses the expected inflation rate. You’ll also need to closely monitor the performance of your investment portfolio over time. To ensure consistently high portfolio performance study our Performance Guide.

retirement planning questions

6.     How Do I Apply for Social Security Benefits?

You can apply for Social Security benefits in the following three ways:

• Visit the Social Security Administration website and complete an online application

• Call 1-800-772-1213 and submit your application by phone

• Apply in person by visiting your local Social Security Administration office

7.     Should I Acquire My Pension as a Lump Sum?

When it comes to receiving pensions, choosing between a lump sum option and an annuity option is entirely your choice. Make this decision carefully and thoughtfully. Some retirees acquire their pension as a lump sum when an annuity is a more rational choice. This leads to financial instability in the long run. You must examine your choices in light of your overall financial picture as well as your life expectancy. The best approach is to seek expert advice. Hire a financial advisor to help you make the correct decision.

8.     Is My Debt Interfering with My Retirement Planning?

When it comes to investing in your future, debt can seriously hold you back. Remember, the money you use to pay off your debt is not going toward investments, making no contribution to retirement planning whatsoever. In fact, letting yourself get into debt now can make you rather financially unstable during retirement.

Many American seniors are burdened by a massive amount of debt. Don’t let that happen to you. During your working years, stick to your budget, and educate yourself and your family on the costs of debt, which extend far beyond the benefits of immediate purchases. Use consistent contributions to 401(k) and IRA accounts to optimize the amount you save for retirement. Following these steps should ensure that your major retirement expenses, like healthcare, are covered by savings. For more comprehensive advice on how prevent your debt from interfering your retirement planning, schedule a video consultation meeting with our wealth managers.

9.     Can a Financial Advisor Help Me with Retirement Planning?

As you can see, it takes a lot of careful planning and consideration of numerous things to secure your post-retirement life financially. This is where the role of financial advisor fits in. From when to start collecting your benefits to predicting your financial needs and making investment decisions, an experienced financial advisor can help you tackle every step of retirement planning. However, with so many companies out there, it can be difficult to choose the right financial advisory services. If you’re not sure how to hire a financial advisor, read our guide titled Ultimate Guide to Choosing the Best Financial Advisor for Families worth $5 Million to $500 Million.


You’ve worked all your life and are finally looking forward to the golden years to retirement. To get ready for the post-retirement adventure, it’s important to understand that the five to ten years approaching retirement are critical for retirement planning. To live a happy retirement life, you must diligently plan, forecast, invest, and make careful strategic decisions now. While the aforementioned answers to most asked retirement planning questions should have addressed many of your queries, nothing matches the power of professional advice. To make your retirement life financially secure, hire a financial advisor from Pillar Wealth Management, which offers high-quality retirement planning services to individuals with $5 million to $500 million. To hire a financial advisor, book a video meeting today.


To be 100% transparent, we published this page to help filter through the mass influx of prospects, who come to us through our website and referrals, to gain only a handful of the right types of new clients who wish to engage us.

We enjoy working with high net worth and ultra-high net worth investors and families who want what we call financial serenity – the feeling that comes when you know your finances and the lifestyle you desire have been secured for life, and that you don’t have to do any of the work to manage and maintain it because you hired a trusted advisor to take care of everything.

You see, our goal is to only accept 17 new clients this year. Clients who have from $5 million to $500 million in liquid investable assets to entrust us with on a 100% fee basis. No commissions and no products for sale.

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