Meet Mark & Jennifer
Now in their early 50s, they’re ready to make work optional.
Mark and Jennifer don’t have a set retirement date.
They love what they do, and they don’t know when they’ll want to stop working.
Mark is a tenured professor, and Jennifer is a respected physician. Their careers continue to bring purpose, fulfillment, and meaning to their lives. They’re not ready to step away from that simply because they’re nearing traditional retirement age.
At the same time, they know this chapter brings important planning questions they can’t afford to ignore:
- Is it possible to lower our tax bill?
- Is there room for improvement with our investments?
- How can we create a steady income stream in retirement?
The Challenge
Mark and Jennifer aren’t trying to correct major financial mistakes, but they understand that gaps in planning can be costly.
In fact, they’ve been doing all the right things, including:
- Generating high six-figure incomes
- Maxing out retirement vehicles and other investments
- Growing sizeable equity in their primary home
- Protecting themselves with the right types of insurance
But as they look ahead to the next stage of life, they want reassurance that they’re on the right track. They want an expert to help them make smart, strategic decisions with the wealth they’ve built. While they aren’t in a rush to retire, they want the confidence of knowing they could when the time comes. And with a substantial nest egg, they also know the tax decisions ahead will only become more important.
The Approach
Mark and Jennifer weren’t sure where to begin—and truthfully, they’re busy people with limited free time as it is.
They recognize the value in not having to figure out everything on their own. A comprehensive plan was put together that addressed all of their needs and concerns:
Tax Planning
To lower lifetime taxes, Mark and Jennifer incorporated strategies like a 351 Exchange and Roth conversions paired with charitable giving. That early coordination created more flexibility around future income and helped reduce unnecessary taxes in retirement.
Investments
Using evidence and academic research, they slowly repositioned their portfolio to support retirement. The result was a superior, more intentional investment strategy designed to reduce unnecessary risk while staying aligned with their long-term goals.
Retirement Income
Even without a fixed retirement date, Mark and Jennifer now had a plan for turning their assets into reliable retirement income. They continued contributing to retirement accounts, evaluated withdrawal strategies, and coordinated the timing of Social Security.
The Results
At the outset, Mark and Jennifer were focused on more than just their investments. They wanted clarity across their entire financial picture, especially around taxes and how their decisions today would impact the future.
With a more coordinated plan in place, they now have a clearer understanding of how everything fits together—from taxes and investments to income and long-term decisions.
As a result, they can focus more of their time and energy on what they enjoy, knowing that retirement is no longer a question of if, but a choice they can make on their terms, when the time feels right.
What Do You Need to Make Work Optional?
Let’s figure out what’s standing in the way
between you and retiring on your terms.
Disclosure: The above case study is hypothetical and does not involve an actual Define Financial client. No portion of the content should be construed by a client or prospective client as a guarantee that he/she will experience the same or certain level of results or satisfaction if Define Financial is engaged to provide investment advisory services.

