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Retirement Concerns and How to Address Them – PillarWM

Wealthy investors spend many decades building up their wealth in the pursuit of a luxurious life. However, everyone wishes to hang up their gloves and retire at some point. This is usually the life-stage when many develop retirement concerns. Wealthy investors with $5 million to $500 million in liquid investment assets who are concerned about their wealth and well-being in retirement should turn to Pillar Wealth Management for retirement planning services. You can learn about some of our specialized investment strategies in our guide for investors with $10 million or more.

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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.

Adjusting to Retirement

We tend to think of retirement as some kind of heaven on earth—lots of freedom to do whatever you want, and particularly, lots of free time. But that’s one issue—what to do with all that free time. How will your activities outside of work fill up that time? What happens when the novelty of retirement wears off?

In the early days of retirement, after the “honeymoon” phase, you may feel anxious about having “nothing to do.” You can feel disoriented by not having a planned activity (going to work) for each day and find it difficult to establish a new routine. Feeling a loss of purpose or identity is common, as well as feeling isolated due to losing contact with co-workers.

Whatever challenges you face, here are four tips for adjusting to retirement.     

Embrace change 

Change can be challenging, and retirement is a major life change. So, an important step to take is to acknowledge that this stage of life is a challenge, and a challenge is something to overcome by thoughtful planning and analysis. The challenge is to focus on being aware of what you really want to do at this stage of your life.

Retirement is a new phase and should be given careful consideration by setting new goals and starting to work toward them. Take your time with this but don’t avoid it. It’s your life!

However you feel about being retired, let those feelings happen. Look at them and find their cause so you can find a remedy through action.

You may need support and someone to talk to, so be sure to maintain your existing social ties, such as with your workmates. To maintain connections, don’t give up your current activities until you’re sure about replacing them.

In your community, look around for senior groups or other services for seniors to help with the transition to retirement.

Find new purpose and meaning

Work gives meaning and purpose to life, so ending your work life can feel like a major loss. It becomes vital to find new purpose and meaning.  

You don’t have to give up working completely. You can continue to contribute to society by taking a part-time job in a field completely different from the one where you had a full-time career. The novelty will allow you to expand your capabilities and continue to grow mentally.

Since retirement income is often less than a normal salary, working part-time can add a welcome supplement.

Volunteering is also an option. You can dedicate your time to making life better for others while developing new relationships. As a volunteer, you can remain socially active, reducing feelings of isolation, loneliness, and lack of purpose.

Meaning and purpose can be found in hobbies and other interests, through which you develop skills and remain mentally and physically active. You can develop your interests by taking a course and reading about subjects that are meaningful to you.

Manage stress, anxiety, and depression

The stress and negative feelings that may arise with retirement can be mitigated in various ways.

Relaxation techniques such as yoga and meditation are useful to reduce stress. Form the habit of getting in touch with your feelings every day so that when you feel stressed or anxious, you can act. Find the source of the feeling and get busy with any task that will move your goals forward, which releases the negativity. You challenge the negative thoughts by proving they are not valid. For example, you don’t become lazy and incompetent because you retire.

Look after your health

Retirement often leads to physical inactivity, which is detrimental to your health. As they say, “Use it or lose it.” You certainly don’t want to need a hip replacement because your bones are weak and you fall and break a hip.

Develop an exercise program that maintains an adequate level of activity, preferably for an hour each day. And keep moving; don’t sit for too long without getting up; you can stay active even when at home by keeping up with chores and maintaining a relatively uncluttered environment.

Create a daily and weekly routine that adds structure to your days and, at the same time, gets those chores done! Include regular, healthy meals in your routine. Maintain a regular sleep schedule, such as getting up at the same time every day.

If needed, make some improvements to your diet, and you’ll enhance your health if you eliminate drugs and alcohol from your environment.

What Retirement Concerns Do Wealthy Investors Have?

Wealthy investors experience many of the same concerns that people of ordinary net worth experience. This includes concerns regarding their eventual retirement. Please set up an exclusive free appointment with our wealth managers to learn about the various retirement concerns wealth investors have.

If you have ever wondered “what do retirees worry about,” the following list should offer some insight.

retirement concerns

Running Out of Savings

Believe it or not, people with a high net worth or even an ultra-high net worth spend a fair portion of their time worrying about whether or not they will have enough savings for retirement. After all, retirement is the life-stage during which you are no longer actively earning income and are relying on your savings to keep yourself afloat.

It’s easy to assume that wealthy investors will never run out of money, especially if they have tens of millions tucked away in their savings or assets. However, it is also essential to factor in the cost of their high-spending lifestyle. It’s not uncommon for wealthy investors to grow accustomed to buying nice things or spending large sums maintaining their homes or valuable possessions.

The bill from maintaining a high-spending lifestyle can be quite hefty. Such spending habits may eat into your retirement savings at a quick pace and leave you with far fewer savings than you imagined.

Healthcare Costs

Healthcare costs can also be concerning for retirees. It’s not uncommon for people to develop health problems later in life. Some of these health problems may be genetic, while others may spring up randomly.

Modern medicine has enabled us to cure plenty of diseases and treat numerous conditions. However, the cost of healthcare is always a concern for seniors. An unexpected surgery may cost you millions of dollars and leave a sizable hole in your retirement savings.

Addressing healthcare costs should be a primary concern for retirees. However, many fail to prepare for these costs beforehand.

Providing For Your Children and Beneficiaries

It’s not uncommon for wealthy investors to have children later in life. This personal choice typically stems from wanting to start a family when you are better established financially. However, the major drawback of having kids later in life is that they may still be young when you retire.

This means you will need to draw from your retirement savings to pay for their education. You can try covering their costs for a while, but this process will be more challenging without an active income to draw from. This makes being unable to provide for your children and beneficiaries a significant concern for retirees.

How Retirement Planning Can Help?

The problems mentioned above may keep a significant percentage of wealthy investors up at night. If you are wondering, “How can I retire well?” the answer lies in retirement planning. Please set up an exclusive free appointment with our wealth managers to learn more about how we can help you.

Let’s look at how retirement planning can help with each of the retirement concerns mentioned above.

Running Out of Savings

A good retirement plan will include different budgeting strategies to increase the rate at which you save money. This will allow you to enjoy a larger quantity of savings by the time you reach your retirement. We discuss various wealth growth and protection strategies in our special book for wealthy investors, The Art of Protecting Ultra-High Net Worth Portfolios and Estates – Strategies For Families Worth $25 Million To $500 Million.

Healthcare Costs

Emergency surgeries can leave a significant dent in anyone’s retirement savings. However, it is possible to reduce the amount you owe by choosing the right healthcare insurance. Wealthy investors can choose specialized healthcare plans that offer more comprehensive coverage than ordinary plans. Insurance planners typically provide such plans, but you can incorporate them into your retirement plan too.

Providing For Your Children and Beneficiaries

If your children are still young when you enter retirement, you may be concerned about your ability to provide for them. Luckily, it is possible to offer your family a comfortable and luxurious lifestyle during your retirement by setting up passive income sources.

This involves investing in certain assets that are stable and will continue to provide a source of income during your retirement. We discuss strategies for smart investing in our special portfolio growth guide.

Stages of Retirement

Many people assume that retirement is a single life-phase that remains the same throughout its course. However, retirement can actually be viewed at a sequence of five stages. So what are the five stages of retirement? These are:

Stage 1: Pre-Retirement

The first stage of retirement is the “pre-retirement” phase. This refers to the period before you actually retire and is usually when you first consider what your life may be like in retirement. This is a good time to think about where you want to be and what type of lifestyle you wish to enjoy after closing out your career.

Stage 2: Retirement

The second stage is retirement itself. This is when you have thrown in the towel and want to enjoy the rest of your life without pursuing wealth through a career. Many wealthy investors are usually satisfied during the first two years of their retirement. In fact, it’s not uncommon for this phase to be referred to as a “honeymoon phase.”

You may spend this time reconnecting with your relatives or old friends and simply enjoying life. Some people get into a comfortable routine or travel the world with their partner during this stage.

Stage 3: Disenchantment

The “honeymoon phase” eventually comes to a close, and you are hit with the reality that you are retired. The initial thrill of no longer working and spending more time with your loved ones has worn off. This period can still be enjoyable, but it usually feels different from the earlier phase.

Many of the concerns we discussed above, such as worrying about savings depleting or health problems, arise during this phase.

Stage 4: Reorientation

Stage 3 can be quite frightening initially. However, it also offers retirees a chance to think about how they wish to remap their lifestyle and habits. This is why stage 4 is considered the “reorientation” stage.

Retired investors often readjust their spending habits and retirement to-do lists during this phase. You may find yourself downgrading your spending habits if you notice your savings depleting faster than expected.

Stage 5: Stability

The reorientation stage may take a while for some wealthy investors. However, most individuals eventually adapt to their current situation and attain stability. It may take some time to settle properly into this phase of your retirement. However, you will feel far more content and less worried than before.

You should note that it is possible to fast-track your way to the stability stage by setting up a robust retirement plan along with high-earning assets beforehand. We discuss some useful portfolio performance improvement strategies in our special guide.

Why Use a Retirement Planner for Your Retirement?

You may be interested in creating a retirement plan to ensure a comfortable and sustainable retirement. However, this can be a challenge to do by yourself. It’s not uncommon for wealthy investors to turn to a retirement planner for assistance on this matter.

Some great reasons to use a retirement planner include:

Understanding the Challenges of Retirement

We have already discussed many of the challenges of retirement. However, there are many other challenges you may not know about until it is too late. A retirement planner will be familiar with the various needs and concerns of retirees. After all, their job is to address these problems as quickly and easily as possible.

It is important to assess your retirement planner’s expertise before using their services. You can learn some great questions to ask a retirement planner in our special guide for selecting a financial advisor.

Executing Advanced Strategies

Some retirement planning tasks, such as budgeting, are relatively easy to do by yourself. However, other tasks such as choosing investments that offer passive income can be more challenging. A retirement planner can help you choose the right investments without making the process overly complicated. We discuss some special investment strategies in our guide for investors with $10 million or more.

Learning About Your Financial Position

Retirement planners also understand what is required to achieve a comfortable and worry-free retirement. These professionals can study your finances and portfolio carefully and inform you where you stand. They can create retirement plans that are in-line with your current finances, or they may ask you to adopt specific changes to help meet your retirement goals. Please set up an exclusive free consultation with our wealth managers to learn more.

Why Choose a Wealth Manager From Pillar Wealth Management?

Professional retirement planners certainly do offer great useful services for wealthy investors approaching retirement age. However, we would argue that one of our wealth managers at Pillar Wealth Management would be a better fit for your needs.

Wealthy investors from all over the country choose us to create their retirement plans for a variety of reasons. This includes:


We possess six decades of experience helping high net worth as well as ultra-high net worth clients. Our wealth managers are familiar with the particular concerns that wealthy individuals may have regarding their retirement and can provide services to meet those needs accordingly.

Personalized Services

We offer each of our clients specialized attention because we understand that they have a unique background and understanding of finance. For this reason, we specially tailor each of our plans so that they are easy to understand and follow.

Transparent Pricing

At Pillar Wealth Management, we believe each of our clients should be well aware of our charges before using our services. We charge a straightforward fixed annual fee that is based on the value of your assets.

This fee structure encourages you to use our services as often as needed and without incurring additional charges. We always put our clients’ well-being ahead of profit and strive to provide high-quality personalized services without charging extra. Please set up a free introductory meeting with our wealth managers to get started with the retirement planning process.

Frequently Asked Questions

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Some common issues with retirement include making your money last, dealing with unexpected health problems, staying active, finding a new purpose, and maintaining and developing relationships.

Worries in retirement include having enough income, dealing with serious health problems, finding meaning and purpose, and maintaining and developing social ties.

Retirement generally means less income, which means having to save while you’re still working so you have enough income when you retire.

People may underestimate how much money they’ll need to retire comfortably; their healthcare costs can increase dramatically, and they may not realize how isolated they may become.

Retirement means finding a new identity as well as a new purpose; it means ensuring your budget is sufficient to meet basic needs; and it may mean remaining employed at least part-time.

The decision to retire can be based on the need to explore new activities that may not be remunerative but are expected to be fulfilling, and there is enough money to make that transition.

Be fully vested in a retirement plan and save as much as possible each month while eliminating impulse buying and over-consumption.

The five stages of retirement are pre-retirement, retirement, disenchantment, reorientation, and stability.

Statistically, retirees should be able to spend 4% of their savings each year (adjusted for inflation) and not run out.

For retirement, you should have enough money to meet your basic needs multiplied by your life expectancy in years, as a complement to other income.


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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