Disclosure: Our attorneys would like us to remind you; this hypothetical scenario is for illustrative purposes only and does not represent the experience of any specific client. It is not indicative of future results. No guarantee of specific outcomes is expressed or implied.

Context

Many people reach their 50s or early 60s with a solid savings base but a complex financial picture: several retirement plans from past employers, equity compensation from a long career, a pension benefit, and taxable investment accounts. As retirement gets closer, questions often shift from “How much can I save?” to “How do I turn what I’ve built into a reliable, tax‑aware income stream, and how do I handle healthcare along the way?”

Our role in this stage is to help organize what they have, clarify what retirement might look like, and create a structured approach for drawing income that can be monitored and adjusted over time.

How We Might Help Someone Getting Ready to Retire

When we work with someone preparing to retire in the next few years, our process might include:

• Clarifying timing and retirement vision
  We start by discussing when they are considering leaving full‑time work, what “retirement” means to them (travel, part‑time work, relocation, family time), and any non‑negotiable goals they want to prioritize.
• Organizing accounts and benefits
  We gather information on workplace retirement plans, IRAs, pensions, stock options or restricted stock, employee stock purchase plans, and taxable accounts. From there, we create a consolidated view that shows where assets are held, how they are invested, and how each account may be used in retirement.
• Designing a retirement income strategy
  Using planning tools, we outline a sequence for how income might be generated (from cash reserves, taxable accounts, retirement accounts, pensions, and Social Security) over different phases of retirement. The objective is to build a framework that seeks to balance reliability, flexibility, and tax awareness, recognizing that markets and circumstances will change.
• Integrating tax‑aware planning
  In coordination with the client’s tax professional, we analyze how different withdrawal strategies, Roth conversions, and the timing of pension or Social Security benefits may affect projected taxes over time. The goal is to be intentional about when and where income is taken, within the constraints of evolving tax laws.
• Addressing healthcare and pre‑Medicare years
  For those retiring before Medicare eligibility, we help estimate and plan for healthcare costs during that gap period, and consider how those costs fit into the broader retirement income and investment strategy.
• Establishing a structure for ongoing review
  We set up a schedule for periodic reviews, use planning software to monitor key data points, and revisit assumptions as markets, spending, tax laws, and personal goals evolve. Retirement is treated as an ongoing process rather than a one‑time event.

What This Type of Engagement Can Provide

For someone nearing retirement, this type of engagement is intended to provide:

• A clearer picture of financial resources and how they may support different retirement timelines and lifestyles.
• A structured, tax‑aware framework for turning savings into income, rather than making ad‑hoc decisions year by year.
• A plan for navigating pre‑Medicare healthcare costs and integrating those expenses into the broader retirement picture.
• An ongoing process for working with an advisory team and other professionals to adjust the plan as life unfolds.

This description is a general illustration of how we might work with someone preparing for retirement. It is not a description of any specific client or family and does not reflect or guarantee any particular outcome.