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Preparation for Retirement Checklist: 10 Things Every High-Net-Worth Individual Needs to Do Before Retiring

By February 19, 2021September 12th, 2022Retirement

You have found yourself planning for an entirely new chapter of your life, retirement. Wonderful, but where can you look? Where do you start with preparation for retirement? Churchill Management Group has a holistic approach to retirement planning and our services can assist you along the way as you plan on your own terms. Retirement planning takes time and patience to get right. Here at Churchill Management Group, we can help you prepare with a retirement checklist that will make getting ready for retirement manageable. You’ve spent countless years working towards retirement, let our knowledgeable team stand with you as you enter this new journey in life utilizing our expert tools and advice.

Preparing for retirement begins with the crucial step of reducing debt. Debt doesn’t have to be a roadblock on the path to a comfortable retirement with the right tools and assistance. Of course, debt can have its benefits and be maintained when appropriate.  However, knowledge is power and knowing exactly where and how much debt you have is vital.

Vehicles and Lifestyle Debt

Do you owe on any cars, RVs, or other lifestyle vehicles? What about your home mortgage? Will you owe any debt on homes you own by the time you plan to retire? Make sure to check in on any business debt you may have incurred and if you plan on keeping ownership of any business after retirement, let your financial advisor know.

Personal Debt

Other areas of personal debt can include but are not limited to any credit card or membership debts and student loans. Medical debt is also a very important area to consider when reviewing your personal debt. If you and a loved one have any significant medical living costs, make sure you plan to address it.

Protecting Against Unexpected Debt

We all want to live out retirement in comfort and Churchill Management Group aims to make sure retirees plan accordingly for any long term care or assisted living for a parent or spouse. Life is unpredictable sometimes, and our team understands divorce or child support payments can affect your retirement goals and add on debt. Our team of experts will help you put in place forward-thinking measures to protect your retirement goals.

2. Determine Retirement Lifestyle/Needs & Monthly Income

A large part of compiling a pre-retirement checklist is figuring out how you want to live once you leave the office for the last time (that is if you decide to quit your career altogether.) Take time to think through where you’d enjoy living out your retirement. Be sure to recognize theexpenses your lifestyle will incur at that time. Do you want to work during your retirement? While that question may sound counterintuitive, some enjoy a bit of work on the side. Is that the right choice for you?

Proactive Retirement Planning

Another important factor to consider when planning for your retirement is the age at which you want to retire. The length of retirement affects the amount of money you need to save. Churchill Management Group understands life is unpredictable but it’s worth listing rough estimates when planning. What sorts of cash flow will be incoming during your retirement?

Review Company Accounts

Carefully review your Social Security account, any employee-sponsored retirement accounts, personal retirement accounts, any wages and pensions.

Don’t forget to factor in taxes when considering any cash income and then evaluate your current budget for retirement. Our expert advisors at Churchill Management Group are here to walk every step of this journey with you to help you make the best decisions for your individual retirement needs and finances.

3. Figure Out Your Insurance

A large factor of budgeting for your retirement plan is allocating enough money for healthcare in your retirement. Insurance for healthcare is going to be one of the largest expenses you need to plan for in retirement. You’ll want to take time to consider where you want to have healthcare coverage.


Those who retire at age 65 or older can qualify for Medicare during retirement. Medicare does not cover all needs, so it’s crucial to research and see if you may need supplemental insurance. You can learn more at the website

Retiring Early

Retiring before the age of 65 has its own unique hurdles and finances to consider, but may be entirely possible. If you are not covered by your, or a spouse’s, employer health insurance, you’ll need to take advantage of individual healthcare coverage. Insurance can have hidden fees and out-of-pocket costs. Plan ahead and know the exact terms of your health insurance coverage and any deductibles that will need to be met, so you can balance your money accordingly.

4. Plan Your Estate

Planning your estate is not the most lively part of retirement planning, but it is important to have an estate plan for when the time does arise. Having a solid estate plan aims to allow for your family and loved ones to not be burdened with financial debt and helps ensure the desired allocation of your money.

Power of Attorney

An estate plan includes not only a will but an assigned power of attorney and proxy in the event you become unable to carry out your own wishes. Plan to have life insurance beneficiaries picked out and guardians in place for any dependents. Once again, don’t forget to factor in taxes in any financial planning for inheritances and funeral arrangements.

5. Take Inventory of Your Assets

Any good retirement planning checklist includes taking inventory of your assets and income. How do you define a comfortable retirement? That means something different to everyone and living expenses are unique to all.

Retirement Goals

What are your goals for retirement? Get as detail-oriented as you can when planning your cost of living. This examination will involve your current income and financial expenses, your present investment accounts, net-worth, and the amount of income needed to achieve and maintain your retirement home and living goals. Churchill Management Group has the right financial planner and advice to help you aim to be the best manager of your goals by retirement age. 

6. Maximize All Annual Contributions

With a high-net-worth, you may want to consider maxing out your annual contribution limits and investing in your 401 k, Roth IRA, HSAs, employer retirement plans, savings account, and any other applicable accounts you may own. Churchill Management Group can help you decide where to best place your money investments, aiming for the maximum long-term outcome.

7. Build An Emergency Fund

Any sound retirement plan includes a hearty emergency fund. Life catastrophes occur no matter how we plan, and a good emergency fund covers such events. Depending on your own individual retirement goals, plan to invest six months to a year of expenses in such a fund.

Life Happens, Be Prepared

401 k, healthcare, and taxes need to be factored in because this fund will be transferring over to retirement with you. A more conservative account may be a good place to securely store your emergency fund as it can earn interest while being easily accessible.

8. Set Aside Money for Heirs

Do you have children and or heirs you wish to set aside money for? An inheritance is a set amount in your retirement investment portfolio and it is valuable to consider how much you will set aside. These amounts can impact your achievement of long term goals and you should plan accordingly.

9. Investigate All Retirement Investments

The steps taken when getting ready for retirement do not stop once you are retired. Many people create investments and budgets geared toward when they plan to retire. That is they plan to have enough income to get them to that goal. But a healthy retirement plan includes ongoing reviews to make sure you can continue to live the life-style you prefer as life changes over time.

Plan For Your Investment Options

There are many investment strategies to consider when planning for a comfortable retirement. Churchill Management Group is here to help assess risk with your investments to allow you to make the most informed decisions concerning your financial planning.

10. Make Accurate Models

We here at Churchill Management Group are firm believers in compiling a holistic image of your retirement situation. Knowing how much cash flow is coming and from where helps you determine your monthly portfolio withdrawal limit. It’s crucial, as a high net worth retiree, to understand your own individual financial circumstances to make the best choices now to set yourself up for success later.

Take Steps Now Towards Your Retirement Future

Churchill Management Group understands each retirement journey is unique. You’ve worked hard to ensure you can retire in the way you deserve. Our expertly trained team will take note of your present financials and future financial goals to compile some helpful guides, like a pre-retirement checklist and a retirement checklist. Here at Churchill Management Group, our advisors believe in being proactive in retirement planning. Factoring considerations, such as your health status, the strength of your retirement accounts, and the amount of social security benefits you qualify for, helps in the creation of a holistic strategy for reaching your goals. Your retirement plans are too precious to leave in the hands of just anyone, speak with one of our financial advisors today to help you prepare for retirement the smart way.

Financial Planning Disclosure

Churchill provides financial planning services to Clients that specifically engage Churchill for that service. The planning can include defining goals, designing a plan, assisting with implementing the plan, and evaluating and adjusting the plan over time, at the request of the client. The financial planning includes advice regarding securities investing and may include discussions of a client’s tax, insurance, employee benefits, estate planning, and other issues. Churchill, however, does not provide legal, insurance, employee benefit, estate planning, tax, or accounting advice, and the client must rely on legal, insurance, and accounting professionals for that advice and documentation.

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