How To Live A Life Free From Regret

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What does a regret-free life look like? Is it even possible? Several years ago, Bronnie Ware attempted to answer that question. She interviewed hundreds of people, most in their final days on earth.

The result of these interviews was her book, The Top Five Regrets Of The Dying. The greatest regret of the dying, according to Ware, was that they would pass from this earth knowing their choices prevented them from honoring even half of their dreams.

It’s a sad reality that most people reach the end of life with regret. Why is that? How come more people in their final days don’t say, “I lived a meaningful life. I pursued my dreams. I made a difference.”

The answer? Most people don’t realize a meaningful life is a counter-intuitive life. The greatest truths, the keys to a full life, are wrapped inside competing ideas.

The first will be last. The greatest will be a servant. Through weakness, you are strong. The humble will be exalted.

You probably recognize these. Jesus spoke them.

I wonder if the greatest factor contributing to regret is our inability to see below the surface, to embrace the counter-intuitive life Jesus offered. Here are several counter-intuitive truths that lead to a meaningful life.

What you fear most reveals what you desire most.

Your greatest fear often reveals your heart’s greatest desire. –Erwin McManus

My first full-time ministry job was at a church in Jackson, MS. The youth group included kids from a local children’s home. No Christian college or seminary prepares you for those stories of brokenness. Most of the kids at the children’s home wanted to be loved and accepted, but they put up walls that kept most of them from experiencing love.

The one thing they wanted was the one thing they feared most.

Some people fear vulnerability. Some fear intimacy. Others failure or losing their job.

If you want to live a regret-free life, fear God. He is the only one who can absorb all of your fear and turn it into love. He is the only one who can resurrect our struggles, forming something new and better.

You can’t love others until you learn to love yourself.  

This counter-intuitive truth is one of the great revelations of marriage. You can and most likely will project the insecurities, anxieties about yourself onto your spouse. But this truth spreads to all types of relationships. Until you come to peace with who you are – imperfections and all – you will struggle to maintain healthy relationships.

Until you come to peace with who you are – imperfections and all – you will struggle to maintain healthy relationships.

To accomplish great things is determined by how much value you add to the lives of other people. 

Everybody can be great because everybody can serve. –Martin Luther King, Jr.

Your legacy, your capacity to change the world will be determined by how much value you add to other people.

The foundational question for a meaningful life is, “How can I serve people?” Everything the world defines as “success” is really a by-product of how well you serve others.

I do not want to be the richest man in the cemetery…I go to bed thinking we have done something wonderful, that I do care.

Jesus was the pioneer of this mindset, right? He came not to be served, but to serve (Matt. 20:28). For some reason, however, I struggle to believe Jesus. I don’t think I must become a servant to impact the world. But what if Jesus was right?

What if you change the world by washing feet, not by climbing the ladder?

The more you practice vulnerability, the stronger you will become.

The past four years, I’ve struggled with Chronic Battle Syndrome. It’s stifled every area of my life. I freaking hate it. I feel worthless somedays, as the pain and fatigue make getting out of bed a Herculean task. I’m jealous of people who continue to progress in their careers. I would love to have published a book or two by now. Maybe traveled around speaking and stuff. But my mind and body won’t allow it.

I’ve found peace, over the past four years, in 2 Corinthians 12:9-10.

“My grace is enough for you. My power works best in weakness…That’s why I take pleasure in my weaknesses, for when I am weak, then I am strong.”

Though I’ve lost a lot, CFS has forced me to practice vulnerability, to ask others for help and prayer. Through it, I feel more grounded. I feel more stable. I guess you call that strength. But it’s not the kind that’s championed in our culture, the hard-hitting linebacker or ironman. It’s the kind of strength that’s on the inside, the kind that grows deeper roots so you can stand firm through life’s ups and downs.

The more you fail, the more likely you are to succeed.

Thomas Edison once said, “I haven’t failed, I’ve just found 10,000 ways that won’t work.” No, Mr. Edison, with all due respect, you’ve failed 10,000 times. And that’s ok.

Maybe I’m naive, but I don’t think people sit around thinking, “You know what? I want to reach my final days with a lot of regrets. That sounds awesome.”

Somewhere in the game, however, fear creeps in and says, “You know those great plans for your life? You can’t achieve them. Don’t even try.”

And, sadly, many people listen. Failing doesn’t mean you’re a failure. The only people who fail are the ones who listen to failure’s lies. So, just for a second, let’s assume failure isn’t part of the equation. If you knew without a doubt you couldn’t fail, what would you do with your life?

Now, if you want to live a life without regrets, actually make decisions like failure isn’t part of the equation. Think about what sets your heart on fire.

Then, go do it.


A counter-intuitive life isn’t easy. It’s dang hard, actually. But it’s the only life that’s worth living. I pray you have the grace and courage to pursue it.

Grace and peace, friends.

Follow Frank Powell:

Frank is a contributing writer and editor for the blog at Bayside church. He is also a husband, father and Jesus-follower. Occasionally he plays golf. Often he drinks coffee.

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