Skip to Content
Personal Finance

Why I’m Reimagining My Retirement

My sandwich-generation crunch changed how I’m planning to live and invest in my later years.


I thought I had a clear vision of my retirement years. Then, within a span of a few days, I helped my firstborn child move to college and my mom find a retirement community. That shifted my perspective.

My husband and I follow a do-it-yourself, low-cost, keep-it-simple financial strategy. We haven’t faced complicated situations calling for professional advice. Until recently, we never stopped to consider buying an annuity to provide a guaranteed income stream in retirement—annuities seemed too arcane and expensive to be worth the bother, and we figured we could manage withdrawals from our retirement accounts on our own.

When we talked about what life in retirement would look like, we focused mostly on the fun stuff, like travel. Beyond that, we knew we’d downsize someday.

But as we balance parenting our children with caring for our aging parents, we’ve realized that we may not want to go it alone in retirement.

These recent milestones made us reconsider our retirement plans in several key ways:

  • We’re now planning for the expense of a continuing care community.
  • We’re considering buying an immediate or deferred-income annuity.
  • We’re thinking of working with a fee-only financial planner.

Our goal is to make managing our care and finances easier as we age—not only for ourselves but also for our children.

A Sandwich-Generation Juggle

This fall, I traveled to Washington, D.C., to bring my daughter to college and help my mom relocate nearby in Maryland. My parents had retired from the Northeast to Florida, near family and friends. But after my dad and aunt died, it was time for my mom to find a home near my sister.

Friends had warned me that dropping my daughter at school would be rough, and I was braced for it. But that was the easy part. She’s an independent and capable 18-year-old, and I shared her excitement at setting out on her own.

The harder part was figuring out the right living arrangements for my mom. She’s an independent and capable 80-year-old. After my father died, she learned how to use a new laptop to bank online and how to send us pictures from her phone. She doesn’t drive anymore, but she doesn’t need assistance with anything else. She was game for any nice apartment complex with a patch of outdoor space.

My sister made us appointments to tour several options within a reasonable distance from her own home, as she would now be driving Mom to the grocery store, doctor appointments, and church. My mother and I worried that would be hard for her to manage, as my sister is also juggling work and other family obligations. Meanwhile, my sister and I worried about Mom being lonely in a new setting where she didn’t have an established social network.

Why a Continuing Care Retirement Community Is Right for Us

Our first stop was a large continuing care retirement community on a tree-lined campus. My mom was hesitant because there was a sizable upfront entrance fee (about the price of a two-bedroom condo in the area), the additional monthly payment would be higher than rent for a larger apartment elsewhere, and she didn’t feel ready for the kind of cramped lifestyle that the term “retirement home” often evokes.

But after our tour, we canceled the rest of our appointments. This community would solve all the difficulties we’d been worrying about—and a sunny one-bedroom with a balcony would be available soon.

My mother would live independently in her own apartment, with pull cords in case of emergency connecting her to on-site staff. A shuttle bus would take her to the grocery store, but there are restaurants on-site if she doesn’t feel up to cooking. The array of daily activities includes many of her interests—gardening, tai chi, pinochle, volunteering—and would help her make a circle of friends. Then there are day trips to D.C., plays in the complex’s own theater, a weekly Episcopal service, and even a geriatric healthcare practice on-site.

All that was well worth the extra monthly cost, my mom decided. The sale of her Florida condo would help cover the entrance fee, and 90% of that fee will be refunded someday. It could be used toward increased monthly costs should she need to move into the on-site assisted-living facility someday. Whatever she doesn’t use for the cost of care will be part of the estate she’d like to pass on to her children and grandchildren.

My husband and I are sold on the idea, too. As our parents get older, we are learning firsthand how different age 60 is than 80 and how quickly health can take a turn for the worse. We are now planning for the expense of a continuing care community for ourselves someday. And we’ll make the move while we are still relatively young and able. We’re grateful my mom was able to make this decision on her own and that she’s still active enough to enjoy the amenities the community offers.

Annuities Can Provide the Stability of a Pension

My husband and I are also rethinking how we’ll handle our investments once we are in retirement. Right now, we prioritize independence and flexibility. One day, we and our children might prefer the comfort of stability. Buying an immediate or deferred-income annuity would provide some stability.

After my father died, my mother and I sat down to tackle her finances with some trepidation, as my father had been in charge of their banking and investing since the world went digital.

We were relieved to learn that the predictable income from Social Security, her teacher’s pension, and the survivor benefits from my father’s pension would readily cover her expenses. And these payments will last her lifetime. I was grateful I could take over managing her investment portfolio without the pressure of needing to wring a certain level of living expenses from it every year.

My husband and I have 401(k)s, however, not pensions. And 401(k)s don’t generate predictable income on their own. They need to be managed to safely produce dependable withdrawals without running out of money. There may come a time when we may not be able to do that on our own—and we don’t want to turn that burden over to our kids.

Social Security will be a source of predictable income, of course, but that alone may not meet our income needs, particularly if we require assisted living. Additional reliable income from an annuity would give the kids some breathing room to figure things out.

Advisors Can Help Adult Children Take the Reins

Seeing my daughter step out into the adult world led me to picture her in my shoes someday, dealing with her own sandwich-generation scenario. I want to make it as easy as possible for her and her younger brother.

Establishing a relationship with a financial advisor is another way we could smooth their path. If our children needed to manage our finances someday, they’d have guidance from someone who is already familiar with our situation and preferences.

Mom just moved into her new community, and she’s enthusiastic about the opportunities to learn and connect ahead. We joke that she’s gone to college, too. When I consider a continuing care community for my own retirement plan, I think about my later years with equanimity, and even enthusiasm: I’m planning to sign up for yoga, canasta, and Chinese cooking.

The author or authors do not own shares in any securities mentioned in this article. Find out about Morningstar’s editorial policies.

More on this Topic

7 Great Investing Books for Beginners
7 Great Investing Books for Beginners
These books cover everything a beginner needs, from the basics of personal finance and investing to how the markets influence our money decisions.