Knowing why, when, and how to say goodbye

Saying goodbye

One of the hardest things for me as a young priest has been knowing when to say goodbye. That’s been the case for me both personally and professionally. So I wanted to share some observations that hopefully will be helpful. And you’ll see I deliberately shift perspectives, from being on the receiving end of good bye to the other end of goodbye. That’s not an accident, as in many cases we can be on both sides of the issue at the same time.

For starters, the past few years have been ones fraught with goodbyes for many of us. Whether it’s unemployment, loss of loved ones, or the end of old ways of doing things, we’ve had more than our usual numbers of goodbyes.

So, let’s look at why it’s essential to be able to say goodbye and why we need to know when to say goodbye. I’m thinking especially of the goodbyes that happen in our relationships.

Being able to say goodbye is essential if we want to be healthy and stay healthy. 

Why? Because it allows us to focus on the important things in life. “For everything, there is a season, and a time to every purpose under heaven.”

As life changes, what is important changes. For example, in high school it might be all about getting good grades, having fun playing sports, and making friends. But 20 years later, our priorities might be our careers, our relationships, or finding a spouse. But to have room for these new priorities, we have to say goodbye to the old ones.

When we can’t say goodbye, we not only get trapped in old ways of doing things, but we can also get pulled into toxic situations. 

Whether it’s an abusive spouse, an emotional vampire who drains our energy, or a supervisor or coworker who makes life miserable, we choose fear, loneliness, and anger when we cannot bring ourselves to say goodbye. We may even put our physical safety at risk.

Even worse, the longer we stay in a toxic situation, the more skewed our reference point becomes until we don’t know which end is up. In those cases, we lose ourselves and become a jumbled heap of misery and confusion.

We all know someone in that situation—someone who has no path, direction, or way out. These people become black holes, drawing others into the swamp, spending all their time and energy spinning in circles, even as they struggle to survive.

When that happens, we as Christians can help, but only with rigorous boundaries. 

That’s why, for example, I’m only allowed to meet four times with the same person on the same issue. After that, I have to refer them to a professional. That arrangement protects me by keeping me from getting too involved, and protects the parishioner by helping me stay objective. 

Of course, I don’t stop caring about that person and their situation, but I’ve handed the problem off to someone better equipped than me to deal with it. Handing off also prevents the other person from becoming codependent—a situation where they are worse off than ever, because they depend on me to make decisions, to plan for them, to help them.

In short, it becomes a case of necessary loss, where we need to let go for everyone’s sake.

Knowing when to say goodbye

By now, you might be saying, “Fair enough. But how do I know WHEN to say goodbye?”

That’s a good question. It’s also a complex question to answer.

Sometimes, the answer is obvious. 

If you have experienced physical violence in a relationship, even once, it’s time to make tracks. Exit, stage left. Head for the hills. No stopping on the way out.

Other times, the answer is less obvious. For example, in cases of coercive control, spiritual, or emotional abuse, we may want to give the other person the benefit of the doubt. Or we may doubt our own judgment. Or may not want to lose our investment in our church, the relationship, or the community.

But it’s time to say goodbye if we feel like we’re constantly walking on eggshells. In those cases, we need to say goodbye sooner rather than later.

Or if we regularly feel oppressed, unhappy, or burdened. Or if we see others behaving badly on a consistent basis, with no hope that they will change their ways. These are all signs that it’s time to cut loose.

Even trickier are cases where the issues are insidious. These situations often involve boundary violations, where someone does something repeatedly that they know offends us or causes problems for us.

In those cases, it’s helpful to ask, “Have I told the other person what my concerns are? Where my boundaries are?”

If we have made our boundaries clear, and the other person is running roughshod over those boundaries, either they can’t honor our requests or don’t want to. 

In either case, it falls to us to maintain those boundaries, usually by making ourselves scarce.

On the other hand, if we haven’t made our boundaries clear, then it’s our bad. 

For instance, I try to make clear that my Friday nights are valued time away. If someone who knows about this boundary calls me, I may ignore them. I may growl at them. Or I may respond if it is an emergency. 

But if someone doesn’t know about my boundary, that’s an entirely different situation, and I try to respond quickly. Even if it’s just to say, “I try to take Friday evenings off. Would you be free to talk tomorrow morning?”

Implicit boundaries

There’s also a set of implicit boundaries in every relationship. These include trust, compassion, caring, loyalty, and discretion. Those boundaries are real. They’re vigorous. And we violate those boundaries at our peril.

My experience is that many relational issues come to a head in this space.

Sometimes, the other person regularly tells us, “You need to….” 

Other times, the person, totally well-intentioned, barges in for the very reason that they are a friend. Or they may be the Johnny-come-lately to a situation and want to assist. Or they feel that they can help in difficult circumstances.

In those cases, it can be helpful to back up and ask ourselves if we’ve overstepped, worn out our welcome, or overplayed our hand. Or maybe we’re blundering around in a situation far more complex than we understand. Or we’ve gotten inaccurate information.

Or maybe it’s just the whole bull-in-the-china-shop-thing, where we’ve busted up the place without realizing it. 

It happens.

Sometimes, we can’t quite put our finger on it, but something always feels off.

In these cases, we may reinforce our boundaries. But if this fails, we must say goodbye because people who violate boundaries almost always get worse over time on these issues.

My observation is that these situations often arise in times of tension. People become entrenched in their positions, without taking time to evaluate the situation or to listen.

As an example, one friend of mine, then employed by a Fortune 10 company, hired a freelancer to help on a project. The first several months were arduous, with the freelancer regularly denouncing issues involving candor, accuracy, and transparency on the project.

Time and again, my friend responded with, “I agree. We already raised that issue with the senior vice president, and she said no.”

Finally, one day the freelancer had a moment of epiphany and exclaimed, “Oh, why didn’t you tell me that this already had been discussed?”

The answer, of course, was that he’d told her dozens of times, but she was so caught up in raising her concerns that she wasn’t listening to the responses.

Fortunately, the two are close friends to this day, and the underlying gap in communication didn’t result in hard feelings.

Relationship breakers

We also can say and do things that immediately cause a relational meltdown. I call them relationship breakers because they instantly bring the connection with the other person to a screeching halt. Or to be more accurate, they shatter the relationship in often irreparable ways. Like a baseball through a window, we can replace the glass, but we can never put the original glass back together.

These relationship breakers include:

  1. Adultery or cheating.
  2. Theft.
  3. Bullying.
  4. Inappropriate accusations.

The first three are obvious, so I’ll focus on the last one.

Several years ago, while serving as an interim, I had a parishioner jump up in the middle of a vestry meeting and loudly accuse me of having an affair with his wife. 

I’ll spare you the gory details, but I can tell you that after a stunned silence, the other vestry members burst into raucous laughter. The kind of laughter where people have tears rolling down their faces they are laughing so hard.

Yes, I am single, but being openly gay, chances that I would have a fling with his wife were zero. None. Zilch. Nada. 

In fact, I’d never met his wife. 

The accuser later apologized, but there wasn’t much to discuss after that noisy debacle.

Was I angry at him? Not at all.

In fact, the whole scene was really funny, and when I have a bad day, I sometimes cheer myself up by thinking about the looks on people’s faces when this parishioner made his announcement. It’s been a highlight of my career, and I’d pay serious money to have a video of the vestry meeting.

But at the same time, I didn’t have room for his toxic behavior and drama in my life. Simply put, there are some things that happen in life that are the nuclear option, and once the explosion happens, there’s nothing more to be said. No going back. No starting over. Just done, done, and done.

So, in these situations we need to be absolutely certain before we take the plunge. 

Once we jump over that cliff, we can’t turn around. Nor is the person we’ve accused likely to discuss the matter with us or continue the conversation. In fact, in most cases, they’ll be so ticked they’ll simply take a pass, then and there, and keep right on trucking.

We also want to make sure we understand the situation, even if we think we have the details correct. Or most of the details.

One couple I’m friends with owns an art gallery, and they got into a knock-down, drag-out fight about the details of the lease when it came up for renewal. Things went on for days and it looked like they were headed for a divorce. In fact, they didn’t simmer down until someone, a third party, looked at the proposed lease and asked, “Did you guys realize this lease is for the storefront next door? They sent you the wrong lease.”

So yes, the terms in the lease were onerous and unhelpful. But the lease in front of them was someone else’s problem. They had overlooked the most important issue, which is that they were reading the wrong lease.


Another relationship breaker is when we offer unsolicited advice, especially about mental health and wellness. It’s easy to want to help, and we may even feel like we can see an issue that the other person is missing.

But unless we’ve been asked, we can’t go there.

These are tricky issues; clergy, social workers and psychologists know how even the most loving, gentle advice can leave the recipient boiling with rage. In fact, that’s common, even when we have been asked for advice. So we save all involved a lot of wear and tear when we simply ask, “Would you like my thoughts on this situation?” before plunging in.

Another tricky area is when confidentiality is involved. 

Every priest out there has horror stories about going to a cocktail party, being in the middle of an enjoyable conversation, and suddenly realizing that the other person is fishing for confidential information.

In those cases, the priest is in a tough situation because she can’t even implicitly confirm the existence of the confidential information, let alone share the details.

In fact, we may have every detail of the situation wrong, but all the priest can do is to politely say they can’t discuss the matter. Or she may try to talk about inconsequentia, like our last vacation, in an effort to get the situation out of the weeds.

But it’s a safe bet that the priest will not be at our next party and probably won’t even agree to officiate at weddings or other future events.

She’ll likely be too polite to say anything, and she’ll be absolutely professional about things. But she’ll do everything humanly possible to maintain that boundary.

In other words, we’ve  just shattered our relationship with that priest.

Trauma and goodbye

Another important point relates to trauma. We live in a society scarred by trauma. Inflation, the pandemic, the death of loved ones, isolation, and more contribute to deep and lasting trauma.

Many times, this trauma isn’t obvious. Every day, we see people who seem like they are on top of the world, but right beneath the surface, they are having a tough go of it.

Or we know about it, but because the other person seems happy, we don’t factor their trauma into the equation.

In those cases, we may love the other person, care deeply for them, and yet cause immense trauma, often without realizing it. When that happens, the person we’ve hurt may have to say goodbye as a matter of self-preservation.

If so, there’s no moral judgment to be made. All we can do is to continue to care about the other person and pray for health and wholeness.

As an example, I’ll use the recent death of my grandmother.

She and I grew up running together, reading books, whitewater rafting, and more. And when I was little, I loved to cuddle in her lap, happy in the feeling of safety, security and love.

Given her age, her passing was hardly a surprise. But some of her friends have tried to become friends, and I just can’t go there. I’m still working through her loss, and while I’m doing okay with it, I’m not ready to add complexity. It’s nothing personal; it’s just a matter of finding my own path forward.

Forgiveness and goodbye

Faith communities, particularly the Episcopal Church, have a tough time with the theology of forgiveness.

Often, there’s a desire to forgive and forget, even though the offender shows no sign of true repentance. That’s a problem; it doesn’t lead to health and wholeness for anyone.

On the other hand, many in the church also expect cheap grace. One awful priest I know likes to say, “Well, I’m sorry,” with the expectation that the other person will instantly let him off the hook—even though his voice makes clear he’s anything but sorry. He treats the words “I’m sorry” like a magic spell, a get-out-of-jail-free, collect-two-hundred-dollars-while-you’re-at-it card. It doesn’t work that way.

In situations involving goodbye, looking at ourselves and considering whether our behavior has fallen short can be helpful. In some cases, if the other person hasn’t said they want no further contact, apologizing may make sense. But it’s up to the other person to decide if and how to respond, and we cannot force the issue. Nor should we try to force it.

When someone else says goodbye

A related issue is when someone else lets go of their relationship with us. It may be gradual, or it may be sudden. But in either case, there are good and bad ways to handle things.

If we value the other person in our lives and hope they will continue to be in our lives, we must tread very carefully. Indeed, if we don’t get it right, the other person will head for the door even more quickly and we will make any hope of future reconciliation impossible.

So what things should we not do in these cases? The list is long, but it includes:

  • Digging in our heels.
  • Berating the other person, calling them an “ass” or otherwise being abusive.
  • Insisting that they have further communication with us.
  • Lecturing them.
  • Giving them advice.

Instead, in these situations, we need to take a deep breath and ask ourselves about our own conduct. 

Perhaps we violated that person’s boundaries.

Or maybe we failed to heed warning signs that they are tired and stressed.

Or perhaps we were just too strenuous at a time when the other person needed us to be chill.

Or they may not have a reason. It may just feel right to them, and that’s okay.

Sometimes, we may not see where we are making our mistakes. If the other person is still open to contact, we might ask, “I feel like I might have made some mistakes. Would you want to tell me how you see things?”

But in every instance, the common denominator is we failed to listen, and we failed to ask questions. In fact, most people outside of abusive relationships are quick to tell us when things are headed south. Yet if we’re not listening, we may feel like we’re blindsided when the other person says goodbye, despite ample warnings.

In those situations, we may be able to fix the problem. We might not. But if the other person chooses to respond, we may get valuable insight into ourselves and the other person. And if they don’t respond, we may still have someone out there with warm feelings for us, even though they have moved on.

Looking forward

Organizations in decline inevitably experience elevated levels of conflict. That’s particularly true in highly conflictive organizations like the Episcopal Church.

We must also remember that many of our sisters and brothers have left the Episcopal Church in the past decade, and many more will do so in the coming years. 

Thus, we must learn to say goodbye in healthy ways for us, ourselves, and the communities in which we live. By doing so, we maintain right relationships and leave the door open to future healing, renewal, and resurrection.



  1. Honestly, why would anyone take mental health advice from a priest? If they have a degree in theology (magic) then we can safely ignore most of their advice without anything else at play. As said in this piece, the church is a high conflictive organization, What healing can they offer? I will give this to the Episcopal priest, they are very good at saying goodbye. Soon the world will say goodbye to this whole “church” and we will all be better off.

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