What missed chances are you going to regret when it’s too late to change?

The older man at the next table looked a bit as though he was lost. I wouldn’t say he looked sad. He seemed more like a man who didn’t know where to go or what to do — almost like a little boy who had lost his parents. I had no idea that he had actually just lost his wife.

Jim and I struck up a casual conversation, but he didn’t have a lot of enthusiasm at first. If I hadn’t made a passing reference to his wife, I’m sure we wouldn’t have talked any further and I wouldn’t have learned his story. He had been sitting in a booth staring aimlessly out the window for close to an hour as I ate and wrote. Since I noticed he was wearing a wedding ring, I joked that his wife must have kicked him out of the house and he didn’t have anywhere else to go.

“I buried my wife two weeks ago,” he said softly.

Jim is 72 years old and seemed to be in excellent health. His wife had developed some kind of cancer early last year and it moved into more critical organs as the year went along. He had known for months that she didn’t have much time left. It’s still a shock to have her gone, though. He said he doesn’t quite know what to do.

He had once had his own accounting practice, but he hadn’t really wanted to retire, so he had stuck around working part-time for others ever since he sold his firm. For his entire life, his work and his church activities have taken up the vast majority of his time. He seemed to have done well financially, but he started talking to me about the things that have been on his mind since he lost his wife.

As I started asking Jim questions, it seemed as though he had needed to talk about some things, but he hadn’t quite known how. Before long, though, a lot of things were coming out. Regrets. Missed opportunities. Wishing for a chance to change things.

Jim mostly wishes he had known his wife better and spent more time with her. He thought he was doing the right thing for decade after decade by simply working harder and harder to give her more financial security. He said it was just the thing that men used to do. He thought he was supposed to get married and have kids and work hard at his career and work hard in his church, but he was starting to question what it all meant.

Jim said he realized in the last few months that he had never really gotten to know his wife.

“How can a man spend close to 50 years married to a woman — living in the same house with her — and not really know her?” he asked me. “That’s what I did, but I have no idea how or why.”

It wasn’t until the last few months of his wife’s life when he started getting to know her. He said he would have been offended six months ago at the suggestion that he didn’t really know her, because he assumed he did. It wasn’t until she was lying in a bed dying that they started talking in deeper ways. He discovered things he had done over the years that had hurt her — mostly by not meeting her emotional needs and not spending enough time with her — and he discovered that she was smarter and deeper than he had realized.

He said he knew she was bright, but he discovered that she had real insight on things he had never bothered to ask her about. As she lay dying, she talked a lot and he listened a lot. He found that his longtime wife was intellectually smarter and emotionally deeper than he had ever known. What’s more, he found that listening to her — and thinking about all the years they could have been talking like this — had awakened a hunger in himself for something deeper than he had known he wanted.

This is at least the third time I’ve randomly come across a conversation such as this in the last couple of years. I talk to a lot of random strangers in public, but it still seems odd. Is it a coincidence? Or is God trying to tell me something about looking at life’s regrets before it’s too late to do anything about them?

The conversation reminded me of something I read last year by a woman who worked in hospice care in Australia. Bronnie Ware is a writer and songwriter who spent several years caring for dying people in their homes. She wrote a blog post about “Regrets of the Dying” that she later expanded into a book after the blog post was read by millions of people. (Her blog is called Inspiration and Chai.)

I don’t know how Jim would feel about the five items on Ware’s list, but I’d say it’s at least a good place to start a discussion. See what you think:

1. “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

This was the most common regret of all. When people realise that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honoured even a half of their dreams and had to die knowing that it was due to choices they had made, or not made.

It is very important to try and honour at least some of your dreams along the way. From the moment that you lose your health, it is too late. Health brings a freedom very few realise, until they no longer have it.

2. “I wish I hadn’t worked so hard.”

This came from every male patient that I nursed. They missed their children’s youth and their partner’s companionship. Women also 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 a work existence.

By simplifying your lifestyle and making conscious choices along the way, it is possible to not need the income that you think you do. And by creating more space in your life, you become happier and more open to new opportunities, ones more suited to your new lifestyle.

3. “I wish I’d had the courage to express my feelings.”

Many people suppressed 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.

We cannot control the reactions of others. However, although people may initially react when you change the way you are by speaking honestly, in the end it raises the relationship to a whole new and healthier level. Either that or it releases the unhealthy relationship from your life. Either way, you win.

4. “I wish I had stayed in touch with my friends.”

Often they would not truly realise the full benefits of old friends until their dying weeks and it was not always possible to track them down. Many had become so caught up in their own lives that they had let golden friendships slip by over the years. There were many deep regrets about not giving friendships the time and effort that they deserved. Everyone misses their friends when they are dying.

It is common for anyone in a busy lifestyle to let friendships 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. They want to get things in order more for the benefit of those they love. Usually though, they are too ill and weary to ever manage this task. It is all comes down to love and relationships in the end. That is all that remains in the final weeks, love and relationships.

5. “I wish that I had let myself be happier.”

This is a surprisingly common one. Many did not realise 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 their selves, that they were content. When deep within, they longed to laugh properly and have silliness in their life again.

When you are on your deathbed, what others think of you is a long way from your mind. How wonderful to be able to let go and smile again, long before you are dying.

Too many of us are afraid to seek the things we really need or we’re stuck chasing lives that other people have told us should be meaningful to us. I’ve lived long enough to know that living other people’s lives won’t ever make us happy. I wonder, though, how many people are living out scripts that others have given them — playing the roles they’ve been assigned, afraid to take chances to be happy, and afraid to place emotional needs higher than physical comfort.

It’s too late for Jim and his wife to live the life that he’s coming to understand would have been meaningful to him. Maybe he’ll find some other way to make his remaining years worth something. Maybe he can find purpose some other way. I’ll never know.

But what I do know is that a lot of things keep nudging me toward doing something to make my own life more meaningful. The recent cancer scare has forced me to evaluate why I haven’t done certain things (and why I’m alone). It seems as though everything in the universe is pointing toward me and saying, “You have to bring change to your life — or you’ll end up having wasted your time on this Earth.”

I really hope Jim finds some meaning for his life, but I can’t do anything to help him. What I can do is to make sure I keep focused on positive change for my own life. I’m not going to end up like Jim. I hope you won’t, either.