As you approach retirement, you may find yourself daydreaming about how you will savor your newfound freedom and flexibility. Perhaps you will spend this next phase traveling to far off lands or just meeting up with friends on a whim. While many people do spend this next phase of their life doing just that, many retirees overlook the realities of multigenerational families, including (sometimes simultaneously) supporting adult children financially and caring for aging parents.
While you might have considered how you will provide for other generations in your estate planning, many pre-retirees frequently overlook the aspect that they may be called upon to sacrifice their own autonomy or financial security to support the people they care about. In fact, 50% of parents reported providing regular financial assistance to adult children,1 while 75% of caregivers of aging parents reported using their own money for caregiving expenses.2 This combination of financial and emotional demands, whether driven by obligation, love, guilt, or all three, can create competing priorities that make it challenging to truly enjoy retirement. Through a balanced approach, you can continue to support the people you love without losing sight of your goals.
Does your current retirement plan allow you to care for yourself while also caring for others? And do you know what caring for yourself even looks like?
Family Obligations Versus Self-Preservation
Have an honest conversation about the kind of support you need or want to provide. Thinking about your financial and emotional limits, as well as boundaries and motivations for giving can also help keep everyone’s expectations aligned. What family responsibilities are you willing to take on?
Here are some questions to get the conversation going:
- Will I pay for a long-term or ongoing expense, e.g., paying their cell phone or insurance bill?
- Will I cover a one-time or short-term expense, e.g., helping during an illness, job loss, or down payment on a house?
- Do or will my parents require care, financial assistance, or long-term care services?
- Is my support helping or is it enabling?
- Are there ways I can support my loved ones beyond (or instead of) financially, such as with my time?
Considering the extent of your assistance ahead of time is important. Rather than assuming your loved ones won’t need assistance or their problems will fix themselves, this preparation allows you to give as needed with confidence that you’re still looking after yourself.
A financial partner can help you work through this process and calculate a realistic budget for anticipated family expenses alongside your personal expenses, including fixed costs, emergency reserves, and funds for your long-term care needs.
Make Space for Your Retirement Dreams
Having a plan in place to support you and your family financially provides tremendous peace of mind. As we like to say, the plan becomes permission. When you’re realistic about obligations that aren’t going away once you retire, and you give space to reflect on the emotional side of the transition, you can begin to give yourself permission to design your dream retirement.
Retiring and being part of the Sandwich Generation present a host of psychological challenges that often make the transition difficult, including emotional exhaustion, a loss of routine and structure, and questions about meaning after work. It’s important to think about how you will find purpose and community that fulfill your emotional needs too.
You know what you’re retiring from — do you know what you’re retiring to? Many people find out too late that much of their identity, relationships, and social interactions revolve around work, making an abundance of time in retirement particularly lonely. During your working years, take time to evaluate the role your career has in your life (daily structure, friendships, mental stimulation, status) and take steps today to build or replace what it’s provided.
We recently worked with a couple that cultivated a great mix of things that they would do individually, such as restoring vintage cars for him and crafting for her, but also shared interests, like pickleball and traveling to local concerts. The goal is not to fill every hour but to create a life that brings you joy and eases the transition.
What does an ideal month in retirement look like to you?
Surprisingly, relaxing by the pool every day may not be as fulfilling as you think. This is why we encourage pre-retirees to practice retirement before making the transition. If you can take several weeks of vacation or your job offers a sabbatical, it’s helpful to practice what your retirement will look like, from how you’ll spend your time to your anticipated budget and spending.
Doing a test run is an effective way to tell if you’ll actually enjoy what you’ve been envisioning. Do you like golfing every day, or are you bored out of your mind by week three? If the latter is true, it may be time to refine your vision for retirement.
How Your Financial Plan Can Provide Balance and Fulfillment in Retirement
A strong financial plan can help bring your priorities for yourself and your family together. You don’t have to sacrifice one priority for another. By understanding the trade-offs, you can align your decisions so you can feel secure while continuing to show up for those who matter most to you. This often includes developing a sustainable spending plan, ensuring your current investments support your goals, and stress-testing against various scenarios. Additional strategies, such as timing withdrawals and managing tax liability, can create opportunities that extend the life of your savings, providing more room to give.
While you can’t plan for every unexpected family challenge or personal circumstance that may arise, you can create enough financial flexibility and clarity to enjoy retirement and offer help when you choose. Our team regularly guides clients in these conversations and the various personal decisions — financial and emotional — that accompany retirement. Retirement planning isn’t just about building the biggest pile but about designing a post-career life that reflects your goals, values, and unique family dynamics.
What would it look like to support your loved ones while also giving yourself permission to enjoy the retirement you’ve worked decades to build?
Sources:
1 Klongpayabal, B. (2025, March 21). Percentage of parents financially supporting adult children reaches a three-year high. Savings.com. https://www.savings.com/insights/financial-support-for-adult-children-study.
2 Kerr, N. (2021, June 29). Family Caregivers Spend More Than $7,200 a Year on Out-of-Pocket Costs. AARP. https://www.aarp.org/caregiving/financial-legal/high-out-of-pocket-costs/.
