Ultra-High Net Worth Retirement Planning Checklist

Compile These 29 Pieces of Information Before You Start Planning for Retirement

You can’t get all your ducks in a row until you find all your ducks.

If you’re a high net worth or ultra-high net worth household starting to ponder retirement, this retirement planning checklist will help you assess your current financial status and resources, and get you thinking about some basic retirement planning strategies.

If you’re in your 50s or very early 60s, now is the ideal time to run through this checklist. Get a printable version of this checklist For each item on the list, you will need to write a few things down. So either get the printable version by clicking above, or find a place to write it down as you go.


Strategies For Families Worth $25 Million To $500 Million
The Art of Protecting Ultra-High Net Worth Portfolios and Estates

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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.

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The purpose of this ultra high net worth retirement planning checklist is to gather all the information you’ll need to commence retirement planning. Until you know your numbers, you can’t plan anything. Once you’ve completed this checklist, you’ll be ready to start planning. In that sense, this is really a retirement pre-planning checklist.

You need this before you can begin planning.

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

For each item in this section, you’ll want to do two things:

1) Check if you have this source of income in your portfolio. If not, skip it.
2) Write down the amount of money you have in each one

    • Regular bank and savings accounts

Make sure you get them all. This includes online accounts, branch accounts, money market accounts, perhaps some CDs you started years ago. All your low-interest basic accounts.

    • Roth IRA and Roth 401(k)

Many ultra-high net worth individuals make too much money to be able to contribute to Roths. But it’s also possible that you’ve reached high net worth status by just being a really good saver while earning income in the low-six figures for many years. In that case, you may have amassed an ample reserve in your Roth accounts.

    • Traditional IRAs

These need to be kept distinct from Roths because of the tax differences. For retirement planning purposes, the tax consequences of withdrawing money from different types of accounts vary widely.

    • Company tax-deferred accounts like 401(k), Defined Benefit, SIMPLE, SEPP, etc.

Again, make sure you get them all. If you’ve had a prolific career working for many different employers, you may have several of these, some dating back decades.

    • Projected Social Security benefits

You can find out what you’re projected to earn each month from Social Security by setting up an account on the government website. Your benefits will vary widely depending on when you start collecting them, which can begin anywhere between the ages of 62 and 70.

    • Business net value

If you own any businesses that you intend to sell as part of your retirement, you’ll want to determine the net value of each one. If you own an 8, 9, or 10-figure business, you’ll need specialized help with this, which begins by assembling the right team of advisors.

The key thing to remember here, however, is that net value may differ from your likely sale price.

    • Real estate net value and/or rental income

List out your real estate assets. Look at how much you still owe on each one. Estimate the likely sale price. Then, subtract what you owe for an approximate net value. If you choose to sell any real estate to help fund your retirement, you’ll need this information.

If you plan to continue owning any rental properties so you can keep earning passive income from them, note that here too, and list the monthly income you expect to earn.

    • Health savings accounts

If you’ve contributed to an HSA for many years, you may have a nice buffer sitting there which can help pay for any drug costs not covered by Medicare.

    • Stock options

You may have been awarded stock options during your career, and possibly from more than one company. Take a look at these and talk with your wealth advisor about the financial and tax implications of holding on to them or selling various portions of them.

    • High value assets

If you’ve been a collector, you may own valuable artwork, vintage cars, boats, or many other specialty items with great monetary value. Hopefully you have some estimate from a professional of the approximate worth of these items, and can list those here.

    • Pensions

Most companies that still offer pensions have a vesting period. But some of those same companies are pretty terrible at communicating the details. Many people don’t even realize they have a pension because they weren’t clearly told about it.

Check with all previous employers to confirm whether or not you have a pension waiting for you.

    • Life insurance

If you bought any life insurance policies other than term life, you may have some cash benefits coming your way in retirement. Brush up on your policy details and find out when and what you can start withdrawing each month.

    • Annuities

If any of your money got trapped in an annuity at some point, find out when your benefit starts paying out and how much it will be.

Part 2: Know What You Owe – Sources of Debt

No need to get too carried away here with details. Just focus on the large debts you have now or anticipate having. These may include:

    • Vehicular debt

You could owe money on cars, boats, RVs, or specialty vehicles if that’s your thing.

    • Home mortgage debt

If you will still owe money on any of your homes after you retire, this large fixed monthly expense is a simple one to track.

    • Business debt

Business debt would include any rental properties you own but haven’t yet paid off. If you own any businesses and intend to retain ownership even after you retire, note any remaining major debts owed by the business.

    • Personal debt scenarios

You may have entered into many other agreements that entail debt obligations. Make sure you know them all and list them all in one place.

    • Known medical debt

If you have large monthly drug costs for a particular treatment, for you or a family member, list those out. Here you would also include any long term care costs such as assisted living for a parent.

    • Divorce-related costs

You may owe spousal or child support payments. If you divorce close to retirement, many of the assets and debts on this list may be compromised.

Part 3: Know Your Retirement Lifestyle Plans – Possible Expenses

This part of the checklist is the most unpredictable. You may have plans for what you want to do in ten years, but those plans may end up changing for all sorts of reasons. That said, you know yourself. You know what you enjoy and what’s important to you. So you have a sense of how you want to spend your retirement.

Check off the items on this list you are likely to incorporate into your retirement planning. If you feel able to do so, list approximate annual amounts you might spend on them.

    • Travel

Many options are possible: Domestic travel, international travel, weekend trips, months-long excursions, safaris, luxury resorts – you’re limited only by the size of the planet (and maybe not even that before long…).

If you’ve been booking travel destinations in your mind for the last twenty years, anticipate some major expenditures here.

    • Give

You may be harboring generous philanthropic plans, from giving to a variety of causes to starting a foundation. Do your best to estimate how much you expect to give each year.

    • Become a socialite

Hosting parties and social events, when done well, can run up a pretty large tab. If you see yourself doing this regularly in retirement, estimate the number of parties and gatherings you want to host each year.

    • Buy new stuff

New furniture, jewelry, security systems, pools, gadgets, disaster prep – you can run up the costs in just about any of these and many more categories of physical goods. Consider your plans and desires, and if you want to become a big-item buyer in retirement, list out a few things you have in mind.

    • Help kids and/or grandkids

For every item on this list, you could apply it to your kids. You could host parties on their behalf, buy them new stuff, give to their college needs, help them buy a first house – everything you need and want, they will eventually need and want too.

Consider the ways you want to help your kids or grandkids get off the ground, and list out your choices here.

  • Set aside money for heirs

Now is a good time to decide how much you want to leave to your heirs after you die. That number then becomes a fixed amount in your portfolio planning, and you build everything else around it.

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

Here are five retirement planning strategies you should be working on already. If you have put any of these off, get started now. And here is where you will most likely need the help of an experienced wealth advisor who works exclusively with high and ultra-high net worth households, such as Pillar.

    • Am I maximizing my annual contributions to all possible accounts?

If you use Roths, traditional IRAs, employer plans, HSAs, or any other accounts with annual contribution limits – you should be contributing the maximum to all of them. Your wealth advisor will help you with the details of how to allocate your investments in each of these so you can optimize your performance.

    • Do I know how my accounts get taxed for withdrawals?

You want to have a good sense of how this will go when you get into more concrete retirement planning stages.

In general, tax deferred accounts like pensions and 401(k)s get taxed at ordinary income tax rates. Your short term capital gains from equity growth do as well. Long term capital gains have their own rate, which is lower than the income tax rate for wealth households.

And any money in Roth IRAs, 529 plans, life insurance, and HSAs is not taxed at all, unless you withdraw it for reasons other than those intended by some of these programs (such as using a 529 for non-educational expenses).

    • Is my estate plan in order?

At minimum, you should have a living will, a revocable living trust, and a power of attorney. But consult with your wealth advisor and your estate planning attorney to make sure you’ve done everything possible to protect your assets and provide for your heirs, if that’s your plan.

    • Am I set up with the right insurance?

This could include long term care insurance, health insurance before Medicare kicks in, disability insurance, and life insurance. Take stock of what you might need, and fill in the gaps.

    • Have I properly estimated my monthly income in retirement?

Lastly, put all the information from this retirement planning checklist together and try to estimate your monthly income after you retire.

And by the way – once you’ve worked through this ultra-high net worth retirement planning checklist, you’re in the perfect position to seek long term investment planning help from a wealth advisor like Pillar.

This sort of information helps us complete your Wealth Management Analysis report, which details what you need to do to ensure you can live out your retirement to the fullest. Request your Wealth Management Analysis meeting today

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