I Was Afraid I’d Get Hurt Again

Some Conversations Can't Wait Forever

Is there something significant you know you should do in a relationship, but you've been putting it off? That was the heart of a question my pastor asked at the end of his sermon last Sunday. And I immediately knew what it was.

For more than eight years, I hadn't spoken to someone who'd played a significant role in my life. Our relationship had hit some rough patches involving substance abuse and repeated choices they'd made. That's how my week started.

When a significant relationship goes sideways, it doesn't just disappear from your thoughts. It sits in the background and surfaces at random times without your permission. At least that's what happens for me. Not a week had gone by that I hadn't thought about this person and prayed about our relationship.

If you've been in a situation like this, you understand what I'm saying. Sometimes, no matter how much we'd like to resolve things or how often we've tried, the relationship stays frozen in limbo. Hope had been lost a long time ago, or at least that's how it felt.

For seven and a half years, it wasn't the right time. But for about six months, I'd had a recurring thought: this person was getting older, and there might not be enough time left to try again. I kept thinking about it, and I kept putting it off.

On Sunday, it became clear that it was my time to try again. I was nervous about reaching out and how it might go. After talking with a few very trusted friends and my wife, I realized that my biggest fear was that I would get hurt again.

Even with that, I mustered up the courage and reached out and asked if they'd be willing to meet. In an effort to rip the band-aid off as fast as possible, I made an appointment for Monday at 1:00 p.m. I felt a sense of urgency and the Holy Spirit nudging me, and I didn't want to put it off.

If my Apple Watch was any indication, I was, to say the least, a bit nervous. My pulse was significantly higher than normal as I walked from my car to their front door. But I'm happy to report that, after eight years of wondering, the first steps of reconciliation went really, really well. In fact, I don't think I could have asked for anything better.

A few minutes after 2:00 p.m. this last Monday, I was walking back to my car, feeling ten pounds lighter. So much time had gone by that I hadn't realized how heavy the weight was that I'd been carrying.

Some of the most important conversations in our lives don't feel urgent — until we no longer have the opportunity to have them.

It was only Monday, and I had a busy week ahead of me. I didn't realize that the significance of what had just happened would be reinforced two more times before the week was over.

Thursday: An opportunity that was gone

On Thursday, I was speaking at a Christian business leaders' event in Sacramento, with about fifteen people in the room. The day began with everyone sharing challenges in business and life and how God was moving in their lives. As the guest speaker, I ended up being the last to share.

I talked about vulnerability and being radically human in leadership development, and I was also teaching about it that day. I decided to practice it myself and shared what had happened on Monday. (It was a bit risky sharing something so personal with a bunch of strangers, but I decided it was a risk worth taking.)

At the first break, a leader of a large company came over. He thanked me for what I was teaching and for sharing my story. Then he told me about his relationship with his father.

His father hadn't passed away, but he had Alzheimer's. It had progressed so far that the conversation he'd hoped to have about their difficult relationship was no longer possible. His father was still alive, but that opportunity was gone.

He encouraged me to be thankful that I'd been able to have my conversation while I still could. I could see and feel the emotion behind what he was sharing.

After he walked away and sat down, I was struck by how vulnerable and special that exchange had been. God had used the story of what He'd done in my life on Monday. And the conversation with that leader helped me appreciate even more the opportunity I'd had to try again.

Friday: A different kind of goodbye

Then Friday morning, I ran into an old friend I hadn't seen in a while at Starbucks. We had a chance to catch up, and she told me her mother-in-law had just passed away.

About six weeks earlier, her husband had gone over to say hi to his mom. He found her lying on the couch, not feeling well, and took her to the hospital. In the six weeks that followed, they spent time with her and cared for her before she would go to be with Jesus.

Their relationship was healthy. Their time together was difficult but beautiful. It reminded me of how I hope relationships come to an end.

I want the things that need to be said to have been said, with forgiveness and acceptance and a chance to say goodbye knowing nothing's left on the table. Our story might not be a perfect storybook ending, but I want to get there without final regrets in the relationship. Ideally, I don't want to regret not sharing the important stuff if at all possible.

My friends were fortunate. They were there, and they had those six weeks. Standing in front of Starbucks on Friday morning, just a few days after my own life-shaping conversation, I was even more grateful I'd acted on Monday. I hadn't known what the rest of the week would bring or how those two encounters would reinforce the importance of what I'd done.

We truly never know what the future holds. We don't know what tomorrow holds, or even what the rest of today holds. Sometimes it's mundane, and sometimes it's life-altering.

Your Turn

In leadership, some of our most important work involves things that are important but not urgent. They help us build the company and the life we're hoping for. But it's easy to keep putting decisions or conversations off because something else feels like it's a bigger fire.

I walked away from Monday's conversation and went straight back into a busy week. That's what we do. And unless we're intentional, the demands of business and life can keep taking priority over the relationships that matter most.

So, I'm asking you now, is there something significant you know you should do in a relationship, but you've been putting it off?

Maybe it feels too big or too risky. Maybe everything else keeps demanding your attention, and you keep telling yourself you'll get to it. If someone came to mind as you read this, please don't neglect it.

Monday reminded me how important it is to be vulnerable and have the conversations that matter. Thursday showed me that we can wait too long and lose the opportunity. Friday gave me a picture of the way I want my story to end, wherever I'm able to influence it.

And because I care about you, I wanted you to hear that. I hope you're doing well and have a great weekend. I'll talk to you in the next issue.

Until next time,

Keep learning. Keep growing. And God bless,

Michael

Half a Bubble Out (HaBO) Business Consulting | Leadership Coaching

This article was originally published on October 10, 2026 on https://www.halfabubbleout.com/post/i-was-afraid-id-get-hurt-again