Retire with Confidence: Are You Ready?
A Framework for Navigating Financial Decisions in Retirement
Retirement is not a one-time decision, it’s a shift in how you manage your finances, your lifestyle, and your goals. For individuals and families who have accumulated significant wealth, this transition brings new considerations: How will your income be structured? How can your taxes be minimized over time? How can your financial plan remain resilient across changing markets and evolving life needs?
Whether you’re a physician winding down your practice, an engineer nearing the end of a long career, or a small business owner preparing for a leadership transition or exit, retirement isn’t just about stopping work—it’s about organizing your resources to support the life you envision next.
This whitepaper offers a strategic framework for evaluating your retirement readiness across five essential areas:
- The sufficiency and flexibility of your wealth
- The composition of your investment portfolio
- Tax-efficient income planning
- Social Security claiming strategies
- Overlooked personal and planning gaps that may impact long-term confidence
With the right strategies and support, you can approach retirement with clarity, control, and peace of mind -knowing your financial decisions reflect the life you’ve worked hard to create.
1. Have I Saved Enough to Retire Comfortably?
Capital Sufficiency in the Context of Lifestyle, Longevity, and Liquidity
There’s no universal retirement number. What matters most is whether your accumulated wealth is aligned with your personal goals, expected expenses, and life expectancy. A retirement plan should not just account for the assets in your portfolio , but also give consideration to its accessibility, tax treatment, and ability to hold up under various market conditions.
Key Considerations:
- Use probabilistic modeling to estimate how long your wealth can support your desired lifestyle.
- Include healthcare costs, inflation, and legacy intentions in your planning assumptions.
- Ensure your portfolio includes a healthy mix of liquid assets to provide flexibility.
Hypothetical Case Study:
David (59), an engineer, and his wife Maria (56), a nurse, were evaluating early retirement. They had accumulated over $2 million across retirement and brokerage accounts. A retirement simulation showed
they could meet their income goals—provided they reduced discretionary travel early on and started Roth conversions in the years before required minimum distributions (RMDs) began.
Key Takeaways:
- It’s not just how much you’ve saved—but how and when you’ll use it.
- Flexibility is key: modest changes today can preserve long-term sustainability.
- Stress-testing your plan helps reveal the consequences of the decisions you are contemplating.
2. Are My Investments Suitable for the Retirement Phase?
Aligning Investment Structure with Distribution Needs
The investment strategy that helped you build wealth may not be ideal for generating income during retirement. A sound approach reallocates risk, prioritizes cash flow, and preserves growth potential—while reducing the chance that market swings could force unfavorable withdrawals.
Key Considerations:
- Establish a tiered portfolio (short-, mid-, and long-term needs).
- Reduce exposure to volatile assets needed in the near term.
- Reassess concentrated stock positions or overweighted sectors.
Hypothetical Case Study:
Elaine (64), a retired physical therapist, had $1.8 million invested, with most in equities. She wasn’t comfortable with the amount of market risk in her portfolio so close to retirement. Her plan was restructured into a “bucket strategy” that included three years of cash and bonds for spending needs, a mid-term balanced allocation, and a long-term growth sleeve. This reduced her anxiety while allowing her portfolio to remain productive.
Key Takeaways:
- Retirement portfolios should prioritize income stability and long-term sustainability.
- Bucketing investments based on time horizon reduces risk and supports peace of mind.
- Your allocation should evolve as your needs change.
3. Will My Retirement Income Be Tax-Efficient?
Structuring Withdrawals to Manage Taxes and Preserve Wealth
How you withdraw money can matter as much as how you invest it. Retirement income could potentially be drawn from Traditional IRAs, Roth IRAs or taxable brokerage accounts—each with different tax consequences. The scale and sequence of withdrawals can significantly affect lifetime tax exposure.
Key Considerations:
- Coordinate withdrawals to minimize taxable income spikes and Medicare surcharges.
- Consider Roth conversions in lower-income years.
- If you’re charitably inclined, use Qualified Charitable Distributions (QCDs) to fulfill giving goals and reduce RMDs.
Hypothetical Case Study:
Mark (66), a former small business owner, had a $1.3 million IRA and $500,000 in a taxable account. His advisor recommended using the taxable account first while delaying Social Security, enabling Roth conversions before RMDs kicked in. This approach reduced his future taxable income and gave him more flexibility later in retirement.
Key Takeaways:
- Tax-efficient income planning improves the longevity of your wealth.
- The order and timing of withdrawals matter.
- Proactive strategies like Roth conversions and QCDs can reduce future tax burdens.
4. Is My Social Security Strategy Optimal?
Getting the Most from a Guaranteed Benefit
Social Security may not be your largest income source, but it’s a guaranteed one—and often includes survivor benefits and inflation protection. The decision of when and how to claim should reflect your broader income picture and long-term needs.
Key Considerations:
- Delaying benefits can increase your monthly income significantly.
- Spousal and survivor benefits add planning complexity and opportunity.
- Social Security strategy should align with your tax and portfolio withdrawal plan.
Hypothetical Case Study:
Susan (65), a retired dentist, was married to Mike (67), who had already begun taking his benefit. Susan was unsure whether to claim hers or wait. After reviewing their overall plan, the couple decided Susan would wait until age 70, while Mike continued his benefit. The delayed benefit increased their future monthly income and provided stronger survivor protection for Susan if needed.
Key Takeaways:
- Claiming early or late can lead to significantly different outcomes.
- Coordination between spouses is key.
- Model the impact on both lifetime income and survivorship before making a decision.
5. What Else Should I Be Thinking About Before I Retire?
Don’t Let Overlooked Details Derail a Well-Built Plan
Even the best financial plan can fall short if key non-financial aspects of retirement are left unaddressed. Healthcare planning, legal documents, lifestyle structure, and long-term care are often the missing links in otherwise well-prepared retirement plans.
Key Considerations:
- Review and update estate documents: wills, powers of attorney, and healthcare directives.
- Discuss long-term care options before it becomes urgent.
- Clarify how you’ll spend your time—purpose is as important as preparation.
Hypothetical Case Study:
Brian (63), a recently retired project manager, had $2.2 million saved—but hadn’t touched his estate plan in 15 years and had no long-term care plan in place. A review helped him update his documents, earmark funds for potential future care, and define his retirement goals, including part-time consulting and travel.
Key Takeaways:
- Retirement planning includes legal, medical, and emotional dimensions.
- Being proactive about long-term care protects both lifestyle and legacy.
- A sense of purpose can be just as critical as financial readiness.
Final Thoughts: Retirement Planning with Confidence
Retirement is a new phase of life that deserves thoughtful planning and coordination. For individuals and families with meaningful wealth, the focus shifts from accumulation to distribution, from growth to sustainability, and from working income to lifestyle income.
If you would like more information about the terms and strategies discussed in this guide, or if you’re ready to explore how they apply to your specific situation, contact Waverly Advisors. With experience working with individuals, families, and executives managing significant wealth, we specialize in creating tailored strategies with the goal to help you grow, protect, and transfer your assets effectively.
MEET THE AUTHOR
Chris Register, CFP®
Partner, Wealth Advisor
Chris Register joined Waverly Advisors in March of 2024 after the acquisition of EFP Advisors. He serves as a Partner and Wealth Advisor. Chris brings 19 years of experience focused on investment management, financial planning and retirement plan consulting to the firm. He enjoys building strong relationships with his clients and helping them develop a comprehensive plan for their desired future… Learn More
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