After decades of building a career, transitioning into retirement can feel both exciting and overwhelming. For many individuals, retirement is not about “stopping work” — it’s about redefining purpose, control, and how your wealth can serve you, your family, and your legacy.
At Shepherd Financial Partners, we specialize in helping clients navigate this pivotal stage with confidence and clarity. Below are the key considerations—both financial and emotional—that are essential for a successful transition into retirement.
1. Redefining Identity and Purpose
One of the most overlooked challenges in retirement planning isn’t financial—it’s emotional.
A Harvard Business Review study found that retirement often leads to a loss of identity for professionals whose self-worth has been closely tied to their careers. Psychologists call this the “retirement transition crisis,” where structure, social interaction, and daily purpose vanish overnight.
Our perspective: The best retirement plans go beyond income projections. We encourage clients to proactively define what fulfillment looks like—whether it’s philanthropy, travel, mentorship, family leadership, or pursuing passions that were once postponed.
2. Creating a Reliable Income Strategy
While most clients we serve are not worried about “running out” of money, the shift from accumulation to distribution creates new complexity.
Key considerations include:
- Tax-efficient withdrawal sequencing across taxable, tax-deferred, and tax-free accounts
- Roth conversions during lower-income years
- Social Security timing strategies to maximize benefits or defer for spousal planning
- Required Minimum Distributions (RMDs) and their impact on Medicare premiums
Best practice: Implement a multi-account, multi-year income replacement strategy—what we call the Shepherd Living Plan—that adapts as your needs evolve.
3. Managing Healthcare & Longevity Risk
A Fidelity study estimates that a 65-year-old couple retiring today will need approximately $315,000 for healthcare expenses in retirement, excluding long-term care.
Key strategies we employ:
- Medicare gap analysis and proper plan selection
- Evaluating long-term care coverage vs. self-insurance
- Stress-testing your plan for rising medical costs and longevity scenarios
What you can do now: Include health-related expenses in your retirement projections, and evaluate family medical history and lifestyle to realistically model longevity.
4. Planning for Legacy and Family Dynamics
Retirement often triggers important estate and legacy conversations. This is especially true for multigenerational families, where wealth isn’t just passed down—it’s stewarded.
Common goals include:
- Structuring trusts to protect heirs while promoting family values
- Educating children and grandchildren about responsible wealth
- Aligning charitable giving with your mission through Donor-Advised Funds (DAFs)
Tip: Don’t wait. These conversations are more powerful—and less stressful—when they’re proactive and values-based.
5. Building a Retirement Roadmap with Flexibility
The best retirement plans aren’t static—they evolve. Life changes, markets change, tax laws change. Your plan should, too.
Our dynamic planning approach models various “what-if” scenarios:
- What if you sell a property?
- What if your child needs support?
- What if the market declines early in retirement?
- With regular reviews and clear action plans, our clients approach retirement with resilience, not rigidity.
In Closing: Retirement Is a Beginning, Not an End
At Shepherd Financial Partners, we believe your retirement should reflect the life you’ve worked so hard to build—one of confidence, contribution, and continued purpose. Whether you’re five years out or already transitioning, having a personalized, forward-looking strategy in place is essential. Let’s create a roadmap that empowers you to live—and give—with clarity.
Ready to start your retirement transition plan? Contact us today!
Disclosures
Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual. All performance referenced is historical and is no guarantee of future results.
The economic forecasts set forth in this material may not develop as predicted and there can be no guarantee that strategies promoted will be successful.
The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. There is no guarantee that a diversified portfolio will enhance overall returns or outperform a non-diversified portfolio. Diversification does not protect against market risk.
All indices are unmanaged and may not be invested into directly.
Investment advice offered through Shepherd Financial Partners, LLC. A registered investment advisor. Registration as an investment advisor does not imply any level of skill or training.
Securities offered through LPL Financial, member FINRA/SIPC. Shepherd Financial Partners and LPL Financial are separate entities. Additional information, including management fees and expenses, is provided on Shepherd Financial Partners, LLC’s Form ADV Part 2, which is available by request.
The content is developed from sources believed to be providing accurate information.
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