Ultra-High Net Worth Retirement Planning Guide

Study this 29-point retirement planning guide before you begin preparing for retirement.

If you are in your 50s or early 60s, now is an ideal time to work through this checklist. For each item in this retirement planning guide, it is helpful to write a few notes to organize your plans and priorities. You may wish to print a copy of the checklist or keep a journal to record your thoughts as you go.

Taking the time to carefully consider each step can help ensure that your retirement strategy is well-aligned with your long-term goals.

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.

The purpose of this retirement planning guide for ultra-high-net-worth individuals is to gather all the essential information needed to begin thoughtful retirement planning.

Until you fully understand your financial numbers, it is difficult to create an effective plan. Once you have completed this retirement planning checklist, you will be better prepared to start developing a strategy for your “after-work life” and confidently manage your retirement nest egg.

In this sense, this guide serves as a retirement pre-planning checklist. If you have not yet started formal retirement planning, the insights provided here can help you take the first important steps.

Creating a Well-Organized Retirement Plan: Steps You Need to Follow

Creating a retirement plan is a complex process that often benefits from the guidance of a financial advisor. A thoughtful plan must account for active and passive income, retirement savings, assets, debts, mortgages, and more. Assistance in defining an investment strategy may also be helpful, especially if you hold stock market investments.

Before creating a retirement plan, it is important to first complete the following step:

Step 1: Know What You Have – Sources of Retirement Income

The first step in this retirement planning guide is to identify all sources of retirement income. For each item in this section, you should:

1. Confirm whether this source of income is part of your current financial portfolio. If not, simply move to the next item.
   
2. Record the approximate value of each source you do have.

Key sources to review include:

• Regular Bank and Retirement Savings Accounts
  Be sure to account for all savings, including online accounts, branch-based savings, money market accounts, and certificates of deposit (CDs) established over the years. Establishing consistent savings habits early is a key factor in successful retirement planning.
  
• Roth IRA and Roth 401(k)
  Many ultra-high-net-worth individuals exceed the income limits for contributing to Roth accounts. However, some individuals reach high-net-worth status by maintaining disciplined savings over many years, even with moderate earnings. If this describes your situation, you may have accumulated a significant balance in Roth IRAs or Roth 401(k)s.
  
• Traditional IRAs
  In this retirement planning guide, it is recommended to keep traditional IRAs distinct from Roth accounts due to the significant tax differences. When planning for retirement, understanding the tax consequences of withdrawing from different types of accounts is essential, as the impact on after-tax income can vary widely.
  
• Company Tax-Deferred Accounts (e.g., 401(k), Defined Benefit Plans, SIMPLE, SEPP, etc.)
  Be sure to account for all employer-sponsored retirement accounts you may have accumulated. If you have worked for multiple employers, it is possible you have several of these accounts, including some established many years ago. For reference, the employee contribution limit for 401(k) plans is $19,500 (subject to annual adjustments).
  
• Projected Social Security Benefits
  You can estimate your future Social Security income by setting up an account on the official government website. Benefits vary depending on when you begin collecting them — which can occur anytime between the ages of 62 and 70 — and the timing of your claim will significantly impact your monthly benefit amount.
  
• Business Net Value
  If you own any businesses that you plan to sell or transition during retirement, it is important to determine the net value of each. For owners of highly valuable businesses — those valued in the eight, nine, or ten figures — assembling a specialized team of advisors will be critical to managing the transition successfully.
  
• Real Estate Net Value and/or Rental Income
  As part of this guide, list out all your real estate assets. For each property, record the outstanding mortgage balance and estimate a realistic sale price. Subtracting the outstanding debt from the estimated sale price will give you an approximate net value.
  
  If you intend to retain any rental properties for ongoing passive income, note those separately and list the expected monthly rental income they will generate during your retirement.
  
• Health Savings Accounts
  If you have contributed to a health savings account (HSA) over many years, you may have accumulated a valuable reserve that can help cover healthcare expenses, such as prescription drug costs not fully covered by Medicare.
  
• Stock Options
  You may have been awarded stock options during your career, possibly from multiple companies. Review the status of these holdings and consult with your wealth advisor regarding the financial implications and potential tax consequences of retaining or selling portions of them. Preparing for retirement requires making strategic choices about investments well before retirement begins. Retirement accounts typically offer a range of investment options, including bonds, mutual funds, and stocks.
  
• High-Value Assets
  If you are a collector, you may own valuable items such as artwork, vintage cars, yachts, or other specialty assets. Ideally, you should have professional appraisals estimating the current value of these assets. Include these figures in your retirement planning to ensure a complete financial picture.
  
• Pension Plan
  Some companies still offer pension plans with vesting periods, although communication about these benefits can sometimes be unclear. It is important to confirm whether you are eligible for a pension and to understand the details. Pensions can play a significant role in your retirement income planning.
  
• Life Insurance
  If you have purchased permanent life insurance policies (such as whole life or universal life) rather than term policies, you may have cash value benefits available during retirement. Review your policy details to understand when and how you can access these funds, and include them in your overall retirement income projections.
  
• Annuities
  If any portion of your assets has been placed into an annuity, determine when benefit payments are scheduled to begin and the expected monthly payout. Annuities can provide a steady source of income in retirement and should be factored into your financial planning.

 

Step 2: Know What You Owe – Sources of Individual Debt

When evaluating your financial situation for retirement planning, focus on identifying major outstanding debts. There is no need to account for every minor expense — concentrate on significant obligations you currently have or expect to carry into retirement. These may include:

• Vehicular Debt
  This includes any outstanding loans on vehicles such as cars, boats, recreational vehicles (RVs), or other specialty vehicles.
  
• Home Mortgage Debt
  If you will still have mortgage payments due on any properties after retirement, this fixed monthly expense should be clearly tracked and incorporated into your financial planning.
  
• Business Debt
  Business-related debts include outstanding loans tied to rental properties or businesses you own and plan to retain after retirement. Ensure that any significant debts tied to business operations are noted.
  
• Personal Debt Scenarios
  Other personal debt obligations — including personal loans, financing agreements, or other contractual debts — should be documented. For retirement planning purposes, every significant debt should be accounted for.
  
• Known Medical Debt
  If you or a family member have substantial recurring medical expenses, such as ongoing treatments, medication costs, or long-term care arrangements (including assisted living), make sure these are included in your debt planning.
  
• Divorce-Related Costs
  Divorce can introduce long-term financial obligations such as spousal support or child support. If a divorce occurs close to your retirement, assets and debts may be affected, and adjustments may be necessary to your overall retirement plan.

Step 3: Know Your Retirement Lifestyle Plans – Possible Expenses

This part of the retirement planning guide checklist can be the most unpredictable. You may have plans for how you want to spend your retirement years, but those plans may evolve over time due to changing circumstances. While some individuals maintain their envisioned lifestyles, others find their priorities shift.

That said, you know your preferences and what is most important to you. This insight can help you create a foundation for your retirement lifestyle planning. Before finalizing your retirement strategy, consider your projected expenses, time horizon, risk tolerance, and tax implications.

Review the lifestyle elements below. For each item you expect to include in your retirement, it may be helpful to estimate an approximate annual cost.

• Travel
  Travel plans can vary widely, from domestic trips and international vacations to extended excursions, safaris, or luxury resort stays. When estimating future travel costs, be generous in your projections. Anticipating significant travel expenses ensures you can fully enjoy your experiences without unnecessary financial stress.
  
• Charitable Giving
  You may have philanthropic goals, such as donating to charitable organizations or even establishing a foundation. Estimate how much you intend to give annually to support the causes that matter most to you.
  
• Social Activities and Hosting
  If you envision hosting parties, social events, or regular gatherings during retirement, consider the associated costs. Expenses for entertainment, venues, catering, and travel for guests can add up, so estimate the number and scale of events you would like to host each year.
  
• Buy New Items
  Retirement may be a time when you choose to upgrade or invest in new possessions, such as furniture, jewelry, home security systems, pools, technology, or even disaster preparedness supplies. These costs can add up across various categories of physical goods.
  Consider your plans and desires carefully. If you anticipate becoming a frequent big-ticket purchaser in retirement, list a few examples and estimate the potential expenses. A retirement planning guide encourages setting clear expectations for future spending — particularly on items that enhance your quality of life.
  
• Help Children and/or Grandchildren
  Many retirees take joy in supporting their children or grandchildren financially. This support can range from hosting celebrations, contributing to educational expenses, assisting with a first home purchase, or providing other meaningful gifts.
  Think about the types of support you would like to offer your family members and estimate the costs involved as part of your retirement planning.
  
• Set Aside Money for Heirs
  Every retirement planning guide should include a decision about how much you intend to leave to your heirs. Identifying this amount early allows you to factor it into your portfolio planning, ensuring that your legacy goals are clearly accounted for alongside your personal retirement needs.

Step 4: What You Should Be Doing Now – Basic Strategies

Here are five retirement planning strategies that you should already be working on. If any of these areas have been delayed, it is advisable to begin addressing them now. At this stage, partnering with an experienced wealth advisor — especially one familiar with the unique needs of high- and ultra-high-net-worth households — can provide valuable guidance.

• Am I maximizing my annual contributions to all eligible accounts?
  If you utilize accounts such as Roth IRAs, traditional IRAs, employer-sponsored retirement plans, health savings accounts (HSAs), or other accounts with annual contribution limits, aim to contribute the maximum allowed amount each year.
  A wealth advisor can help you allocate contributions strategically across different accounts to optimize investment performance and tax efficiency.
  
• Do I understand how my accounts are taxed upon withdrawal?
  It is important to have a clear understanding of how different accounts will be taxed when you begin making withdrawals in retirement.
  
  • Tax-deferred accounts such as pensions and 401(k)s are taxed at ordinary income tax rates upon withdrawal.
  • Short-term capital gains are also taxed at ordinary income rates.
  • Long-term capital gains are typically taxed at lower rates compared to ordinary income, providing an important planning advantage.
  • Withdrawals from Roth IRAs, 529 plans, life insurance cash values, and HSAs are generally tax-free, provided the withdrawals meet the qualifying conditions associated with each account type.

Understanding the tax treatment of your various accounts will allow you to plan more effectively and structure your retirement income in the most tax-efficient manner possible.

• Is My Estate Plan in Order?
  At a minimum, it is recommended to have a living will, a revocable living trust, and a power of attorney in place. Consult with your wealth advisor and estate planning attorney to ensure that your estate plan fully protects your assets and provides for your heirs according to your intentions.
  
• Am I Set Up with the Right Insurance?
  Essential insurance coverage may include long-term care insurance, health insurance (particularly before Medicare eligibility), disability insurance, and life insurance. Review your current coverage and identify any gaps that need to be addressed to safeguard your financial security.
  
• Have I Properly Estimated My Monthly Income in Retirement?
  Once you have gathered all the information from this retirement planning checklist, work to estimate your expected monthly income during retirement. A realistic assessment will help you plan more effectively and maintain your desired lifestyle.
  

Completing this ultra-high-net-worth retirement planning guide checklist is an important step toward building a comprehensive and sustainable retirement strategy.

To continue refining your financial planning: