How to Overcome the ‘What If …?’ Regrets of Life

Larry Tomczak
Larry Tomczak

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 70th 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.

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SOURCE: The Christian Post
Larry Tomczak is a best-selling author and cultural commentator with over 40 years of trusted ministry experience. His passion is to bring perspective, analysis and insight from a biblical worldview. He loves people and loves awakening them to today’s cultural realities and the responses needed for the bride of Christ—His church—to become influential in all spheres of life once again. He is also a public policy advisor with Liberty Counsel.