A Retirement Planning Case Study

By Joe Dowdall, CFP®, RICP®, CRPC®, CCFC

Retirement planning can often feel like a moving target. You’ve worked hard, saved diligently, and now the big question hits: What’s next?

That’s where Steve (age 62) and Jenna (age 66)1 found themselves. After decades of building a career, Steve was suddenly laid off. His severance package was winding down, and most of their savings were tied up in company stock. They weren’t sure how or when they could confidently step into retirement.

In this case study, I walk you through the steps we took together to sort through the noise and put a plan in place. From navigating concentrated stock positions and tax surprises to deciding on Social Security timing, we focused on building a retirement income plan that made sense for their situation.

My goal with stories like this isn’t to show off some magic formula. It’s to give you a glimpse into how integrated tax and retirement planning can make a real difference by reducing lifetime tax bills and maximizing retirement income. 


The Client

After more than 40 years with a Fortune 500 company, Steve was unexpectedly laid off. It was a major emotional blow and a financial wake-up call. Most of their savings was tied up in company stock from Steve’s long career, including restricted stock units (RSUs) and incentive stock options (ISOs). With his severance package winding down and so much of their future riding on a single company’s performance, Steve and Jenna felt overwhelmed and uncertain about what retirement would look like. That’s when they reached out to me. My role was to help them sort through the chaos, make sense of their options, and bring some much-needed clarity to a difficult time.

 

The Retirement Planning Goals

After carefully walking through their finances—including income, investments, taxes, and healthcare—we landed on the following retirement planning goals:

Social Security Optimization

  • Determine the optimal time for Steve to claim Social Security benefits.
  • Analyze how Social Security payouts interact with their other retirement income sources. 

Investment Diversification

  • Manage and diversify the concentrated stock positions from Steve’s former employer.
  • Strategically handle their RSUs and ISOs.

Tax Planning

  • Mitigate their overall tax burden during the transition and retirement phases.
  • Understand the tax implications of Social Security benefits.
  • Manage their Modified Adjusted Gross Income (MAGI) to lessen Medicare premium increases.
  • Determine the optimal distribution ordering per IRS rules for which funds should be withdrawn first.

Retirement Income Planning

  • Create a sustainable retirement income plan to replace the lost income from Steve’s job and severance package.
  • Design a strategy for Steve and Jenna to transition from receiving employment and severance payments to living off their investments.


How I Helped Steve and Jenna Navigate Retirement

When Steve and Jenna came to me, they had a lot of moving pieces and even more questions. With Steve’s severance ending soon, they needed to figure out how to create steady income in retirement without triggering surprise tax bills or draining their savings too quickly.

We started with a Social Security analysis. We looked at different claiming scenarios and how each option would affect their overall income and tax situation. Timing that benefit right can make a big difference, especially when it’s coordinated with other sources of income.

Next, we tackled their investment concentration. Much of their nest egg was tied up in Steve’s old company stock. We put together a plan to gradually diversify their portfolio while being mindful of tax consequences and market timing.

From there, we focused on tax strategy. We mapped out how different income sources would be taxed and explored ways to manage their Modified Adjusted Gross Income (MAGI) to avoid unexpected hits, like higher Medicare premiums. Small decisions, like where to pull income from first, made a big difference here.

We also built out a retirement income plan. This wasn’t just about replacing Steve’s paycheck—it was about creating a sustainable, flexible approach that could adjust with life. We walked through how to transition from a working salary to drawing income from savings in a way that felt manageable, not overwhelming.

And finally, we reviewed their stock options. RSUs and ISOs each come with their own rules and tax timing quirks. We put a plan in place for exercising and selling shares in a way that fit their broader goals.

This kind of planning isn’t one-size-fits-all. It’s about listening, educating, and helping folks like Steve and Jenna feel more confident about the road ahead.

 

Get Retirement Planning Support Today

I work with a wide variety of clients facing unique needs and situations. As a fiduciary financial advisor, I guide each client through a proactive process that focuses on understanding their personal circumstances, addressing their concerns or fears, and creating strategies designed to help them reach their goals.

If you’re experiencing a situation similar to this case study or face an entirely different need, I encourage you to reach out to me. I’d be happy to evaluate your situation and share how I can help.

Get support today with a 15-minute introductory call. I can be reached at (469) 423-1989 or by email at joe@worthassetmgmt.com. 

 1Names changed for confidentiality purposes.

About Joe

Joe Dowdall is a CERTIFIED FINANCIAL PLANNER® professional at Worth Asset Management, a financial services company in Dallas, TX, that provides a wide range of wealth management services. With over 15 years in the financial services industry, Joe is a fiduciary who creates tax-focused financial plans for people nearing or in retirement—to help them build and safeguard their wealth through all life stages. He desires to offer clients the best financial planning experience while developing a friendship based on mutual respect. Joe’s philosophy as a financial planner is rooted in his experience as a teacher, where he learned the importance of explaining complicated concepts in understandable terms. He’s passionate about working with a select group of clients to help them achieve their financial goals with confidence and clarity.

Joe has an education degree from the State University of New York and an MBA in finance from Saint Joseph’s University. In addition, he has obtained the CERTIFIED FINANCIAL PLANNER®, Retirement Income Certified Professional®, Chartered Retirement Planning Counselor℠, and Certified College Financial Consultant (CCFC) designations. Joe resides in Frisco, TX, with his wife, Leila, and their two daughters. During his free time, he enjoys traveling with family, exercising, and hiking the national parks. To learn more about Joe, connect with him on LinkedIn.