Partner Content

What have been the “Top 10” tax-savings strategies of the last 25 years?

© iStock

Worth Magazine is celebrating a quarter-century of providing valuable information for high net worth (HNW) individuals. Based on the financial climate of any given year, tax-planning strategies have come and gone. However, over those 25 years, several tried and true strategies have remained.

Here is our list of the Top Ten (presented in no particular order) most reliable tax saving strategies for high income earners that have stood the test of time.


HNW individuals often acquire municipal bonds as an alternative to corporate and U.S. Treasury securities. The reason: Munis provide substantial after-tax yields. Used prudently, these investments can be as safe as the taxable U.S. government alternatives.


The Roth IRA was established in 1997. In 2010, Congress lifted the income contribution limit, allowing for unlimited conversions of IRAs to Roth IRAs. Those rules changed the tax landscape: For individuals with substantial tax-deferred qualified plan assets, the Roth IRA conversion has become a beneficial strategy to create tax-free accounts for many generations.


Philanthropic giving helps you, and supports your favorite causes. However, there are many ways to contribute. By making gifts of appreciated L-T capital gains property (stock, for example), you can deduct the full value of the stock and don’t have to recognize the appreciation, or “capital gains tax,” ever.


Tax-loss harvesting is the process by which you sell investments such as stocks and bonds, at a loss. Losses may be used to offset any gains you have recognized during the tax year. Losses offset gains dollar for dollar, and if you have more losses than gains, you can use up to $3,000 in losses to offset other income.

You can implement these strategies yourself, or work with a qualified professional who can stay on top of your individual circumstances.


Because social security won’t be enough to fund a comfortable retirement, it is advisable to maximize all opportunities to fund your retirement accounts. Always fund your 401(k) to the max, and utilize deductible and Roth IRAs, if you’re eligible. Self-employed business owners can also benefit from contributions in the form of profit-sharing and defined benefit pension plans.


The choice of entity to operate your business will have a significant impact on your overall taxes. For example, if you have operated your business as a sole proprietorship or LLC, it might make sense to convert to an S-corporation, since generally there is no self-employment tax on earnings. Under present law, C-corporations are double taxed and might not be the best form for operating your business.


The ability to fund the rising costs of college education has always been challenging. Section 529 allows for long-term tax-deferred growth on education savings-related accounts. Distributions from plans for qualified education are generally tax-free.


Estate taxes can take a large bite out of one’s legacy, making proper lifetime gifting and estate-planning essential. Aside from annual gifting and exemption credit planning, gifting strategies that HNW advisors recommend include grantor retained annuity trusts (GRATs) and intentionally defective trusts.


Even the best investment performance is muted when it comes to after-tax returns. Does the location of your investments in taxable vs. tax-deferred accounts have an impact on your returns? You bet it does! The compounded growth of your assets will benefit greatly from an approach that factors in your particular tax situation.


Providing for heirs on a tax-free basis is the one primary objective that puts life insurance firmly on the top 10 list. With tax-free growth, investment flexibility and tax-free funding for retirement plans, life insuranceis a panacea for the HNW world.


There isn’t much you can do to control what tax bracket you’re in, or what changes occur in the tax code. However, reliable tax-saving strategies can be used no matter how your income or tax legislation changes.

You can implement these “Top Ten” strategies yourself, or work with a qualified professional who can stay on top of your individual circumstances, providing guidance to help you build wealth, while minimizing your tax obligations.

This article was originally published in the February–April 2017 issue of Worth.

Charitable GivingTax Planning Strategies

Disclaimer: Worth magazine is a financial publisher and does not recommend or endorse investment, legal, insurance or tax advisors. The listing of any firm in the 2019 Worth® Leading AdvisorsTM Program does not constitute a recommendation or endorsement by Worth magazine of any such firm and is not based upon Worth magazine’s experience with, or prior dealings with, any advisor. The information presented for each advisor, including but not limited to any related profile, statistical data, presentation, report, commentary, recommendation or strategy, has been provided by such advisor without review or independent verification by Worth magazine. Any such information is the sole responsibility of the advisor. Worth magazine makes no representation or warranty as to the accuracy or completeness of such information, assumes no liability for any inaccuracies or omissions therein and disclaims responsibility for the suitability of any particular investment recommendation or strategy for any person. Nothing contained in Worth magazine constitutes or should be construed as any form of investment, legal, insurance or tax advice or as a recommendation to buy, sell, hold or trade any securities, financial instruments or assets. Readers are advised to consult their legal, financial, insurance and tax advisors prior to making any investment or pursuing any investment strategy. Past, model or hypothetical performance is not indicative of future results.

back to top