Do You Have Enough Courage For These 5 Retirement Challenges?

It takes courage to juggle. “As I’ve grown older, I’ve come to see life as a game of juggling—except instead of balls, it’s responsibilities, relationships, and personal growth,” says Chip Conley, founder of the Modern Elder Academy. This quote seemed particularly relevant during a recent conversation I had with some alumni of Modern Elder Academy. One woman, Cynthia Starz, made a statement and asked a question of the group: “The stage of life after retirement takes a lot of courage. Do you have enough courage to get through it successfully?”

Since I could not stop thinking about her question, I set up a time to talk with Starz in-depth about courage. We had a conversation worth sharing.

If we are going to do what we hoped to do when we retired, we need to do it now because we have a shorter runway. But there are challenges to following our dreams and the through line tends to be a difference of expectations.

Starz said, “Boomers have a history of living out loud and not being quiet about what we want from life.” She continued, “Boomers often led the trends that were happening. We were protesting and as retirees we have more time to protest. We often say, ‘We are not going to live a retired life as our parents’ did. But it takes courage to live the life we have desired for so long.” These challenges assume your health is well enough to live your life as planned.

Claim Your Time

We have worked hard and now it is our time. Is it really? Not everyone may be supportive. Starz reminded me that even the people we love can be placed on a continuum between supportive and distressed. Do we have the courage to be ourselves or do we give into the pressure of the status quo. We can feel selfish if we do what we want to do and have had it planned for years. We may still be part of the sandwich generation—taking care of elderly parents and being present for adult children and grandchildren. Our loved ones may have expectations of how they want us to spend our time that are different from how we want to spend it.

Live Differently

We may want to downsize and sell the family home. This requires packing up and distributing some physical assets and often family heirlooms and history. Downsizing may require time and effort on the part of family members. But they may prefer we keep the home so they can visit and for nostalgia reasons. According to Starz, “It is easier to live life quietly, not make waves, and keep the peace with the stakeholders in our lives than to push back.” At the end of the day, however, you are the one living your life.

See The World

Travel is often a high priority for retirees. If you have adult children who live close by, then you don’t need to travel to see them or your grandchildren. If not, then there is often an expectation that traveling to visit family will be high on your priority list. But you have dreamed of seeing the world and have many places on your bucket list. But you still only have 24 hours in a day!

Now you have the time and money to travel and there may be an expectation for you to babysit—regardless of where the grandchildren live. Do we focus on sustaining the relationships in our lives or pursuing our dreams?

Redefine Your Roles and Relationships

The expectations for our roles and responsibilities may not be congruent with what you want them to be. For most of your life, your job structured how you spent your time. Even as a stay-at-home parent, your day was structured to accomplish your goals. If you have aging parents, they can remind us of what is to come. We see our futures before our eyes. We need to demonstrate grace and patience with our parents and not freak out about what is to come.

Observing our aging parents can make us question how long we want to live. Do we want quality of life over quantity. There is often an expectation of taking care of our parents and this takes time that we had planned for travel, leisure, or other activities. We feel responsible to take care of our parents as they took care of us, but caregiving can be stressful.

And women can never do enough for our parents as the caregiving role often falls on the daughters or daughters-in-law. According to a 2023 study, “Nationally, 60 percent of caregivers are women. Closer to 70 percent of caregivers for people with dementia, are also women.” Since I only have three sons and none of them live in my state, it is unlikely my husband and I will have family caregivers.

Yet, there is an expectation to be joyful while our parents are still alive. But the reality is it can be hard to always be joyful. Caregivers need care too. In our hearts, we may want to claim our town time, live differently, and see the world. But we feel the pressure to be a caregiver and the responsibility to use our time and energy for activities and not our lifetime dreams.

Be Financially Literate

Navigating social security, Medicare, long-term health insurance, and other financial decisions is not easy. It requires some financial competence. It is not straight forward and can be a challenge for anyone and especially for the average person who may not have a financial advisor. Starz warned me, “It takes a sophistication. The systems are not user friendly for the average person. While there are tools for lower- and middle-income levels that are often available for free, especially online, older people are susceptible to advertisements and scams.” And she added, “Not understanding your financial situation can have a profound impact on your peace of mind and health.”

Navigating the financial and medical systems requires an awareness and understanding that many people don’t have. It takes courage to deal with the burdensome and scary systems. And it takes courage to reach out for help when you need it.

So What Should You Do?

Too many people choose to go back into the box of unlived life and live the expectations of others. Bronnie Ware, author of Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing, discovered that “the number one regret her clients had was not living an authentic life.” Ware defined living authentically as “acting and making choices based on what you truly want and on the values you believe in.”

This time of life can feel as if we are on a teeter totter, with family expectations and financial obligations on one end and pursuing our goals and dreams on the other end.

There is pressure to keep the peace. Don’t make waves. Stay in your lane. It is unique to this stage of life because we often have freedom to choose how we spend our resources—time, energy, and money.

And no one can predict the future. Carol Orsborn, author of “The Making of an Old Soul: Aging as the Fulfillment of Life’s Promise” and “Older, Wiser, Fiercer: The Wisdom Collection,” explained her challenge this way. “Just when I thought I’d be harvesting the bounty of a serene and stable stage of life, I’m finding many of my hopes and plans upended. Faith takes courage and I’m working all support systems to the max to row as steady a boat as possible through turbulent seas and a seemingly receding horizon.”

The time to face these challenges is now. If not now, then when?