What Executives Planning to Retire in The Next 5 Years Need to Consider Now

Your strategic advantage 

As a business leader, you've mastered strategic planning for your organization. But when it comes to personal retirement strategy, the complexity of executive compensation packages, stock options, and deferred compensation plans creates a planning landscape that requires sophisticated expertise. 

The good news? You likely have access to financial tools that can significantly accelerate your path to retirement—if managed strategically. The challenge? These same benefits can create tax implications and timing considerations that, if overlooked, could cost you tens of thousands in retirement income. 

Your five-year roadmap starts today 

Maximize your compensation package strategically: Your executive compensation is likely your most powerful wealth-building tool, but it requires careful orchestration. If you have restricted stock units (RSUs), stock options, or deferred compensation plans, now is the time to develop a tax-efficient strategy for exercising and diversifying these holdings. 

Consider our client Rick's story: through strategic planning around his corporate benefits, together we were able to create a realistic path for him to retire at 60, telling us afterwards, “WHZ, With your team’s transparency, patience, and sophistication in maximizing my corporate benefits and overall financial plan, I now have a realistic path to retire at 60. Thank you!”1 The key was developing a comprehensive approach that balanced maximizing his compensation package while positioning for long-term growth and tax efficiency. 

1 This statement was provided 3/18/2024 by Rick Harvey who is a client. This statement may not be representative of the experience of others and is not a guarantee of future performance or success. For additional reviews, search us wherever local businesses are reviewed. Read Rick’s full story at whzwealth.com/client-stories. 

Navigate the new tax landscape with precision: The tax planning landscape has dramatically shifted with President Trump's signing of the "One Big Beautiful Bill Act" on July 4, 2025. This landmark legislation has made permanent many of the Tax Cuts and Jobs Act provisions, including lower individual tax rates, increased standard deductions, and enhanced estate tax exemptions. 

For executives planning retirement, this creates both immediate opportunities and long-term planning clarity. The permanent extension of favorable tax rates means your retirement income projections can now be made with greater certainty. However, new provisions like the temporary senior deduction for those 65 and older, modifications to the SALT cap, and changes to business deductions create fresh strategic planning opportunities that require immediate attention. 

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Build your diversified foundation: If a significant portion of your wealth is tied up in company stock, your five-year retirement timeline creates urgency around diversification. Market volatility can be devastating to retirement plans that are over-concentrated in a single company. 

Address the healthcare transition: One of the most overlooked aspects of executive retirement planning is the transition from corporate health benefits to Medicare and supplemental coverage. Healthcare costs can be one of the largest expenses in retirement, and the gap between losing executive-level benefits and Medicare eligibility can be financially significant. 

Create your legacy framework 

Estate planning with enhanced permanence: The One Big Beautiful Bill Act has permanently increased the estate and gift tax exemption to $15 million per individual ($30 million for married couples), indexed for inflation. This represents a significant increase and provides substantial planning opportunities for executives with considerable wealth. 

With the new permanent exemption, many executives now have additional flexibility in their legacy planning. However, this enhanced exemption also means that existing estate planning strategies may need recalibration to maximize their effectiveness under the new tax environment. 

Income replacement strategy: The transition from executive-level compensation to retirement income represents one of the most significant lifestyle adjustments you'll make. Developing a comprehensive income replacement strategy that accounts for Social Security optimization, pension maximization, and systematic withdrawal from investment accounts requires careful coordination and timing. 

Many executives are surprised to learn that maintaining their pre-retirement lifestyle may require 80-90% income replacement, particularly when factoring in healthcare costs, travel plans, and the reality that many retirees actually increase spending in the early years of retirement. 

Your next steps 

If you're an executive planning to retire within the next five years, your window for strategic planning is narrowing. The financial moves you make in the coming months could impact your retirement security and lifestyle for decades. 

Consider conducting a comprehensive review of your current financial position, including analysis of your executive compensation optimization opportunities, tax-efficient diversification strategies, and retirement income replacement planning. 

Remember, you've spent your career making strategic decisions that drive organizational success. Your retirement deserves the same level of strategic thinking and expert guidance. If you’re ready to create your strategic retirement plan, get in touch with our team here at WHZ. We’re experienced in helping executives optimize their compensation packages and develop sophisticated retirement strategies. We understand the unique challenges you face and the opportunities available to you. See how we can help to provide you with “Absolute Confidence. Unwavering Partnership. For Life.” Contact us for a complimentary consultation at whzwealth.com or call (860) 928-2341.    

Authored by WHZ Managing Partner, Advisory Leisl L. Langevin CFP® CDFA®. AI may have been used in the research and initial drafting of this piece. Securities and advisory services offered through Commonwealth Financial Network®, Member FINRA/SIPC, a Registered Investment Adviser. 697 Pomfret Street, Pomfret Center, CT 06259 and 392-A Merrow Road, Tolland, CT 06084, 860.928.2341. http://www.whzwealth.com. These materials are general in nature and do not address your specific situation. For your specific investment needs, please discuss your individual circumstances with your financial advisor. WHZ Strategic Wealth Advisors does not provide tax or legal advice, and nothing in the accompanying pages should be construed as specific tax or legal advice.