Top 3 Things to Know if You Want to Retire at 55
By Matt Held, CFP®
Growing and managing a corporation is hard work, so it’s no wonder that early retirement for corporate executives is becoming a popular option. However, given the complexity of executive compensation, taxes, and retirement benefits, this is not a decision that should be made lightly.
At Clarity Wealth Management, we work with many executives at P&G and GE Aerospace. For these clients, navigating early retirement for corporate executives can be especially challenging because of their unique, detailed compensation structures.
Let’s take a look at the top 3 things corporate executives should know if they want to make retiring at 55 a reasonable goal.
1. Define What “Retirement” Actually Means to You
Before you start diving into the logistics of retiring early, think about what “retirement” means to you as an executive. Do you want to stop working immediately? Gradually step down with a phased retirement? Step down from your company but still take on board and consulting roles?
Are you not sure how to make this important decision? I often tell my clients to think about their personal goals in retirement, their lifestyle expectations, and the long-term sustainability of their plan.
2. Build a Strong Financial Foundation Before You Commit
Early retirement for corporate executives is doable, but before you commit, you need to build a strong financial foundation. This process looks different from person to person, but it often involves the following steps:
- Evaluating your cash-flow needs in retirement
- Estimating the longevity of your retirement income
- Determining whether retiring during your peak earning years could be detrimental to your financial health
- Considering whether your investment strategy aligns with long-term objectives
This is a process you should undertake carefully. Our team can conduct a thorough review for you and help you decide whether early retirement for corporate executives might be the right path for you.
3. Address the Critical Gap from 55 to Traditional Retirement Age
Early retirement for corporate executives has plenty of upside. However, most retirement plans don’t allow you to take distributions without penalty until age 59½. If you retire and no longer have health insurance through your employer, you may need to purchase private insurance until you’re eligible for Medicare.
Understand Your Corporate Benefits and Executive Compensation
If you’re an executive at P&G or GE Aerospace, you probably have multiple retirement plans and incentive compensation. It’s essential to understand vesting schedules, plan rules, and distribution timing before you decide whether you want to retire early.
Considerations for Tax Planning
Distributions from tax-advantaged retirement accounts like 401(k)s are taxed as income, and smart tax planning could potentially save you thousands of dollars in taxes. Getting a complete tax picture is an important part of early retirement for corporate executives, so when I work with clients, I stress-test possible scenarios to help them avoid unexpected tax consequences.
Long-Term Planning: Your Lifestyle and Legacy
When it comes to early retirement for corporate executives, coming up with a holistic plan is absolutely essential. Considering your own goals is important, but so is weighing external factors like market volatility.
Because compensation is so individualized, one-size-fits-all strategies rarely work for executives. When you take the time to build a personalized plan, you are better equipped to build the retirement you’ve been envisioning.
Let Us Guide You Through Early Retirement for Corporate Executives
We at Clarity Wealth Management understand that each of our clients is on a different path. Whether you’re interested in exploring early retirement for corporate executives or you want to extend your working life as much as you can, our team is here to help you build a long-term plan that’s aligned with your goals.
Interested in a no-obligation, icebreaker call? Schedule online here, call (513) 278-9420, or email Info@ClarityWealth.org.
Frequently Asked Questions
Is early retirement for corporate executives realistic at age 55?
Yes, early retirement for corporate executives at age 55 can be possible with careful planning. Success depends on factors such as executive compensation structure, retirement benefits, investment strategy, cash-flow needs, and tax planning. Because executives often retire during peak earning years, evaluating long-term income sustainability is essential before making the decision.
What financial challenges should corporate executives consider before retiring early?
Early retirement for corporate executives involves unique challenges, including managing income before age 59½, understanding vesting schedules, coordinating multiple retirement plans, securing health insurance, and minimizing taxes. The Clarity Wealth Management team helps executives model different scenarios so they can identify potential gaps and make informed decisions with greater confidence.
How can a financial advisor help with early retirement for corporate executives?
A financial advisor can help corporate executives build a personalized early retirement strategy by stress-testing cash flow, optimizing executive benefits, addressing tax exposure, and planning for long-term lifestyle and legacy goals. At Clarity Wealth Management, Matt Held works closely with executives to create tailored plans that support early retirement while maintaining flexibility and financial security.
About Matt
Matt Held, CFP®, is the lead advisor and a founding partner of Clarity Wealth Management, a boutique firm based in Cincinnati, OH. Since entering the industry in 2006, Matt has helped corporate executives, professionals, and business owners uncover opportunities and build long-term financial strategies. Driven by a desire to control his own future and create a lasting brand, Matt co-founded Clarity Wealth Management in 2012. His mission was to build a firm that would provide truly personalized guidance—and become a legacy for his own family. Today, Clarity serves about 100 households and focuses on helping clients simplify and navigate complex financial decisions, particularly those involving equity compensation, tax planning, and executive retirement.
Matt’s approach is rooted in trust, loyalty, and hard work. As a CERTIFIED FINANCIAL PLANNER® professional, he is deeply committed to long-term relationships and believes that clarity doesn’t mean predicting the future, but having the confidence that your plan can handle whatever comes your way.
Outside of work, Matt enjoys time with his wife, Abby, and their twins, Henry and Kinsley. Whether it’s watching sports (they love their Ohio State Buckeyes), hitting the slopes out West, or squeezing in a workout, he’s passionate about staying active and present. He’s also a proud graduate of Moeller High School and The Ohio State University. Matt holds Series 7 and 66 licenses, is licensed for health insurance, and earned his CFP® certification in 2012. He has been named a Five Star Wealth Manager in the Cincinnati area since 2013.* To learn more about Matt, connect with him on LinkedIn.
Clarity Wealth Management is located at 4243 Hunt Road, STE 429 Cincinnati, OH 45242. (513) 278-9420
Securities and advisory services offered through Commonwealth Financial Network®, Member FINRA/SIPC, a Registered Investment Adviser. Fixed insurance products and services are separate from and not offered through Commonwealth. Clarity Wealth Management is neither endorsed by or affiliated with GE or GE Aerospace.
*2013-2018 and 2020-2024 Five Star Wealth Manager Award, created by Five Star Professional. The 2024 award was presented in September 2024 based on data gathered within 12 months preceding the issue date. Advisors pay a fee to hold out marketing materials. Not indicative of advisor’s future performance. Your experience may vary. For more information, please visit www.fivestarprofessional.com.
