Summary: The hard questions of life fall between the philosophical 1st-order questions (Who am I? Why am I here? Where am I going?) and the important everyday questions (Which car should I buy? Why is my relationship with my teenager so difficult?). In this post we list five of the ‘hard’ questions.

Note:  This post is a companion piece to my last post.  My husband, David, and I have written it together. 

Warning:  We expect a reaction to this post.  It will be so much better if you contribute to it.  See our request at the end.

(Dave) When my father was in his eighties I asked him how he approached the end of life. A bold, may be even insensitive question which he took well. Jasper’s response was succinct, immensely practical, and somewhat fatalistic.

“I’ll hang on till something happens.”

(Dona) But years later, when we had our last conversation, he was more reflective, hopeful, and life affirming. He asked me, “Why have I lived so long?” His conclusion? To learn gratitude.

“I am a living paradox — deeply religious, yet not as convinced of my exact beliefs as I ought to be; wanting responsibility yet shirking it; loving the truth but often giving way to falsity. . . . I detest selfishness but see it in the mirror every day.”

Bill Clinton (written when a teenager)¹

(Dave)  For 25 years, Richard Leider interviewed more than 1,000 senior citizens, asking them to look back over their lives and talk about what they have learned. These seniors were successful in their jobs, having retired from leading companies after distinguished careers.

Leider writes, “Almost without exception, when these older people look back, they say the same things – things that are instructive and useful for the rest of us as we make decisions going forward in our lives.

First, they say that if they could live their lives over again, they would be more reflective. They got so caught up in the doing, they say, that they often lost sight of the meaning. Usually, it took a crisis for them to look at their lives in perspective and try to reestablish the context. Looking back, they wish they had stopped at regular intervals to look at the big picture.”

(Dona) Facing mortality or a deep crisis can set the stage for questioning the meaning of life, build depth in spiritual reflection and self-examination.

In a recent article for TIME, Jamie Ducharme reports that “the COVID-19 pandemic appears to have spurred a collective reckoning with our values, lifestyles and goals—a national existential crisis of sorts.”

Why don’t we stop and look at the big picture before we face a life-threatening event or realize we have well-exceeded a normal lifespan? Is it Leider’s seniors, who got too caught up in the doing to catch the meaning? Or, another reason, which I wrote about in an earlier post: ‘mythical immortality’; the belief that other people die, I don’t.

Whatever the reason: busyness, belief we will live forever, or simply just a lack of humility, we need to stop occasionally and ask ourselves those hard questions about what we are about. So, we (Dona and Dave) have drawn up a list of life questions, the questions we don’t ask ourselves but should. These questions fall between the philosophical 1^st-order questions (Who am I? Why am I here? Where am I going?) and the important everyday questions (Which car should I buy? Why is my relationship with my teenager so difficult?).

Here are our top five, but we want to hear from you, too. 

1. (Dona) First on my list would be the question my father-in-law asked me two weeks before he passed, “Why have I lived so long?” Notice, again, that he had moved from just “hanging on till something happens”, to asking, essentially, “What does God want you to know or experience before you die?” And, of course, this is a question for any age; the earlier the better.
2. (Dave) What are you pretending not to know? I love this question posed to Jason Nazar. He writes, “This was perhaps the most powerful question I was ever asked (by my best friend). All possibilities open up when we stop deceiving ourselves.” When we get really serious about this question then we start asking really serious questions about the meaning and purpose of life. The corollary question is, “Are you doubting your doubts?” For example, if I doubt God exists, have I seriously examined that doubt or am I just using ‘doubt’ to sidestep or avoid the hard work of researching and facing the issue head-on?
3. (Dave) Are there broken or unhealthy relationships (spouse, family, friends) that are within your power to mend? This is my least favorite question. Easy to answer, difficult to act on because of the risk. But many books written, and movies produced around this theme testify to its importance.
4. (Dona) If you were dying would you worry about this? I devoted a post to this two years ago when I learned my cancer had spread. When I thought I would live forever everything mattered; from the inanest to the most profound. There’s little wiggle room to separate out the important opinions and worries from the trite.
5. (Dave) If you were not scared what would you do? (Another question from Jason Nazar.) “Use the rocking chair test. What would your 90-year-old self, looking back on your own life, advise you to do in the moment?” We are not talking about bungee-cord diving here. (Although if you want a little levity then check out the video below of fearless grandmas taking great risk.) Referring back to Leider’s interview with seniors, he found they would, first, be more reflective, and second, take more risks. My father told me late in life that he wished he had not been afraid to take risks in pursuing some of his entrepreneurial ideas….in other words, spend more time at the office, not less. I am so grateful for all the time my dad spent away from the office and with me when I was young, but I got the point. Is there an opportunity out there waiting that requires effort and risk to pursue? I have a close friend who at 72 spends much of his waking hours developing entrepreneurial programs at a charity providing work readiness training in under-served neighborhoods. The effort great and there is risk, but the reward is great. That is life.

Okay, it is your turn. Please share some of your life reflection questions in the comment bar or send me an email donaeley907@gmail.com .

Footnote 1: Bill Clinton wrote this reflection for an essay in high school. Regardless of what you think of the 42nd president, this is a pretty unflinching look in the mirror for a teenager.