How to Overcome Life’s ‘What If’ Regrets

In their twilight years, a senior asked his aging buddy, “Jim, do you prefer boxers or briefs?”

After a pause, Jim smiled and with a wink and a nod playfully responded, “Depends!”

On a more reflective note, as death approaches people are often asked if they have any regrets. Getting older presents fewer opportunities for “bucket lists” or “do-overs” so many folks engage in a little bit more honest life review. The realization sinks in that no one is going to live forever no matter how many “age-defying” products are marketed today.

My father passed away over 30 years ago. He believed God for a happy death and he got it! On a Sunday he attended a church service with my mother; they went to lunch with a Christian friend; they came home where he sat in a chair, opened a devotional book, bowed his head and went to his heavenly home.

My second “father” (for decades I comfortably referred to my father-in-law Joe Grefenstette as “Dad”), passed away last week having lived a remarkable life. He was 93 years old. In two and a half weeks he would’ve celebrated his 70^th wedding anniversary. He had 52 children, grandchildren and great-grandchildren. He served as an elder in the church and officer in the military during World War II. He won many to Christ. He basically died of old age in his bed with family by his side. As a born again Christian, he also went immediately to his heavenly reward.  

It was my honor to officiate at both of these men’s memorial services. Celebrating their legacy, I cited the same passage from the Book of Ecclesiastes 7:2. “It is better to go to the house of mourning than to go to a house of feasting, for death is the destiny of every man; the living should take this to heart.”

In other words, feasting on a meal is short-lived, but attending a funeral affords opportunity for course correction as we reflect on the brevity of life. While both of these men would certainly express some minor regrets and probably wished they had done some things differently, both of their departures inspire me when I ponder passing from this life into eternity.

It really is beneficial to once and for all overcome the “What if …?” regrets that nag us and hinder productive, carefree living.

While the following are not exhaustive lists, these categories can prove helpful no matter where we are in life’s journey.

Areas of Regret

1. Times we were prideful and refused or neglected counsel then suffered for it. How many of us live with consequences from our stupidity?

2. Areas that still bring forth shame and embarrassment—maybe an abortion or some immorality, scandal or legal problem.

3. Times we could have averted a disaster if we had been more prudent and teachable. Perhaps carrying an STD decades later, or the resulting inability to have children or long-standing repercussions from financial debts come to mind. How about a divorce that we caused?

4. Episodes in our life where we acted impulsively, in sinful anger or stubbornness.  

5. Actions that we took that hurt another person in a serious way. Maybe we were inebriated, influenced by drugs or went along with “group-think” to intentionally or unintentionally harm someone.

Scripture is replete with individuals like Paul, Peter, John Mark, David, Moses, Abraham, Jonah and others who sinned and could’ve ruined the remainder of their lives shackled by the burden of regret and guilt. They refused to be defeated by some sort of self-imposed imprisonment and so can we.

All of us can benefit from our failures and mistakes by not only claiming the promise of Romans 8:28, but using negative life experiences to cultivate greater humility, change priorities, seek God more earnestly, share our mistakes for other’s benefit and exhibit greater compassion towards others who are suffering and less fortunate than we.

Aging Regrets

Besides areas of sin, as we age we’re more prone to wish we had done things better earlier in life. Many times this falls into the category of better planning.

Not long ago the National Association of Area Agencies on Aging, National Council on Aging, United Healthcare and USA TODAY engaged in a joint effort to ascertain life regrets of those mature in years. The national survey revealed these five top responses as people wished they had: 1. Saved more money; 2. Took better care of their health; 3. Made better investments; 4. Maintained legal documents; and 5. Stayed closer with their family.

I wonder how many of those in the poll equated financial security with peace of mind? While it is important, we can miss the mark if we think just having more money brings  the peace, happiness and security we desire.

Dying Regrets

Years ago a woman named Bonnie Ware wrote a book entitled, “The Top 5 Regrets of the Dying—a Life Transformed by the Dearly Departing.” For many years this dedicated woman served patients about to die in the field of palliative care. Her meaningful and first-hand experiences with those approaching death were compiled into her insightful book. Bonnie commented, “Patients gained phenomenal clarity of vision as they approached death.”

Here’s what was revealed as the five most common regrets she heard from those in their dying days:

1. I wish I had the courage to live a life true to myself, not the life others expected of me. Multitudes admitted too late in life that they were held back by the fear of man or man-pleasing. At times in my life I’ve identified with this category. I was helped early on in ministry by Jamie Buckingham, a brilliant writer, who shared with me these words: “Larry, you have to come to accept two realities of life. You have to learn to say ‘no’ and know when you do, some people will be offended!”

2. I wish I didn’t work so hard. Bonnie stated that “this came from every male patient that I nursed! They missed their children’s youth and their partner’s companionship. Women spoke of this regret but as most were from an older generation, many of the female patients had not been breadwinners. All of the men I nursed deeply regretted spending so much of their lives on the treadmill of the work existence.”

3. I wish I had the courage to express my feelings. “Many people suppress their feelings in order to keep peace with others. As a result, they settled for a mediocre existence and never became who they were truly capable of becoming. Many developed illnesses relating to the bitterness and resentment they carried as a result.”

4. I wish I had stayed in touch with my friends. “It is common for anyone in a busy lifestyle to let friendship slip. But when you are faced with your approaching death, the physical details of life fall away. People do want to get their financial affairs in order if possible. But it is not money or status that holds the true importance for them. It all comes down to love and relationships in the end. That is all that remains in the final weeks, love and relationships.”

I think it was John Maxwell that said there are four categories of friends: JUST friends—social; RUST friends—older ones (some keep and some let go); TRUST friends—confidants and counselors; and, MUST friends—smaller circle of lifelong gifts from God.

5. I wish that I had let myself be happier. From her many years of experience, Bonnie Watson said the following: “This is a surprisingly common one. Many did not realize until the end that happiness is a choice. They had stayed stuck in old patterns and habits. The so-called ‘comfort’ of familiarity overflowed into their emotions, as well as their physical lives. Fear of change had them pretending to others, and to themselves, that they were content. When deep within, they longed to laugh properly and have silliness in their life again.”

Jesus put little children in the midst of his disciples and told them His Kingdom belongs to such as these (Matt. 19:13-14). It would do us all good to determine to be more playful and fun loving around children and then let this attitude spill over into the rest of our lives. At the reception following the memorial for Doris’s father, one little relative,  with whom I’d been goofy playing hide-and- seek, begged me not to go saying, “If you go I will die!” That same little girl referred to my wife as the “Fun Aunt.” What a badge of honor.

How about you? Are you living with a number of “What if” regrets?

May we glean insights from what we’ve read and make changes to put the past behind while redeeming the time in the present.

Together may we draw inspiration from my just-deceased, 93-year-old father and recall the words from William Wallace in the film “Braveheart”:  “We know that all men die, but not all men live.”

Thanks, Dad, for leaving us a powerful legacy and a life well lived!

Larry Tomczak is a best-selling author of eight books with 43 years of trusted ministry experience. He is a cultural commentator whose weekly articles appear on sites reaching 26 million monthly. He is a public policy advisor with Liberty Counsel. Connect and view short video commentaries at larrytomczak.com.