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High Net Worth Retirement Planning Tips

Posted on September 27, 2021 By

You’ve proven you are an expert at running a successful business, and you know how to make money. But are you an expert when it comes to retirement? There are certain financial factors that high-net-worth individuals should consider leading up to retirement.  

What Do You Have? 

Make a list of all sources of retirement income you have available to you. This includes:

  • All checking, savings, and money market accounts and CDs
  • Traditional and Roth IRAs. Note that these differ for tax purposes. 
  • Company tax-deferred accounts such as 401(k)s 
  • Projected Social Security benefits
  • The net value of any businesses that you plan to sell 
  • Real estate assets, net value, debt, and rental income. This is when you will need to decide if you are selling any assets or earning passive income from them after retiring. 
  • Health savings accounts
  • Stock options
  • High-value assets such as vehicles, fine art, coins, antiques, or jewelry  
  • Pensions from all previous employers. You may need to check on this because it is common for companies not to communicate about these pensions. 
  • Life insurance other than term life
  • Annuities

It is also crucial to optimize a well-diversified portfolio to gain the best possible returns with the least amount of risk. You should know the expected return of your assets and how much risk you are taking. It is not uncommon for wealthy individuals to have many investments and not be clear on how much it costs in the long term. 

You should also have a tax diversification plan. Money taken out of retirement accounts for living expenses is considered federal taxable income, often taxed at the highest tax bracket. IRAs and 401(k)s can help you to save on taxes while contributing to them, but when you withdraw, you can end up paying a hefty tax. Roth IRAs and certain insurance products can offer more tax-efficient solutions that give you a stream of tax-free income once you are retired. 

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What Do You Owe? 

In addition to what you have, it is crucial to account for what you owe. Make a list of all your sources of debt, such as:

  • Home mortgage debt
  • Debts owed by any businesses you own, such as rental properties that are not paid off 
  • Vehicles such as cars, boats, RVs, etc. 
  • Medical debt for you or a family member and any future long-term care costs
  • Divorce-related costs such as spousal or child support
  • Any personal debt 
  • Audit your portfolio for any hidden fees

What Are Your Retirement Plans?

You will have to consider out your possible expenses heading into retirement. How you plan on spending your time will dictate how much it will cost and how much money you need to plan on having in order to maintain the lifestyle you desire. This can be rather unpredictable and not easy to figure out. Just try to get a sense of what you can see yourself doing and consider the possibilities:

  • Traveling, including frequency, duration, and destinations 
  • Philanthropy, such as starting a foundation
  • Helping your children or grandchildren with finances such as college tuition or buying a home
  • Being a socialite and hosting events
  • Purchasing more high-priced material items 
  • Setting aside money for your heirs

You may also want to assess your current health and your life expectancy. Today people are living longer but are not necessarily planning for it financially. This also depends on at what age you are retiring. Obviously, the younger you are, the longer you will need to plan. And don’t forget to account for inflation when you’re planning far into the future. 

What Should You Be Doing Now? 

It is never too soon to start planning for your retirement. There are certain strategies that you need to be focused on now and moving forward:

  • Maximize annual contributions to all possible investment accounts
  • Understand how your accounts will be taxed for withdrawals
  • Create a living will, estate plan, revocable living trust, and power of attorney
  • Make sure you have the right kinds of insurance
  • Consider getting the help of a wealth advisor, retirement planner or M&A advisor
  • Start doing everything that’s included in this article of tips!

Ready for Your Next Move?

Whether you’re considering retirement, exit planning, or growth strategies for your company, please reach out to our M&A experts at Benchmark International to discuss how we can help you define your legacy.


Schedule A Call


Americas: Sam Smoot at +1 (813) 898 2350 /

Europe: Michael Lawrie at +44 (0) 161 359 4400 /

Africa: Anthony McCardle at +27 21 300 2055 / 


Benchmark International’s global offices provide business owners in the middle market and lower middle market with creative, value-maximizing solutions for growing and exiting their businesses. To date, Benchmark International has handled engagements in excess of $7B across various industries worldwide. With decades of global M&A experience, Benchmark International’s deal teams, working from 14 offices across the world, have assisted hundreds of owners with achieving their personal objectives and ensuring the continued growth of their businesses.


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