Leaving Well

5 Ways to Get Better at Goodbyes

Photo by Mantas Hesthaven on Unsplash

Saying goodbye is hard. Whether it’s the end of a job, a relationship, or a stage of life, our patterns of leave-taking shape how we process loss and transition.

As a hospital chaplain, I witness goodbyes in their most profound form and I’ve learned that how we leave matters.

I’ve written before about final goodbyes that have gone well:

• A mother leaves her children recordings of her wishes for them, reminding them how much she loved them before she died.

• Family and friends surrounding their loved one, singing them a lullaby of goodbye.

And I’ve referenced goodbyes that have not gone well:

• A family arguing over what medical decisions to make when their loved one was at the end of their life. They were distracted by fighting with each other and therefore missed the opportunity to say goodbye to the dying patient. This led to fractured relationships, added guilt and unprocessed grief.

Because I see it so frequently, I often remind people that death is inevitable. So too, everyday endings are a part of life. As are beginnings. We cannot begin again until we have left well.

I’m usually not one for Stoic philosophy, but Seneca’s statement is true: “Every new beginning comes from some other beginning’s end.”¹ If we do not say goodbye well, we cannot embrace what is next.

Many people admit to being “bad at goodbyes.” And I understand why - they can be awkward and weird. But transitions are important. They are worth paying attention to and being intentional about. We can all get better at saying goodbye.

5 Ways to Get Better at Goodbyes

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1. Acknowledge Your Goodbye Style

What’s your Goodbye Style?

Likely, you’ve never thought of this question before. My chaplain students look at me strangely when I ask them at the end of their semester. But take a moment and think about how you approach terminating something in your life. Do you tend to avoid it? Prolong it? Face it head-on?

If you’re unsure of your goodbye style, here are some archetypes for how you might be functioning:

• The Ghoster - Disappears without a word; avoids the discomfort of goodbye entirely and believes it’s easier on everyone this way. May also want to avoid being the center of attention.

• The Overexplainer - Gives long, overly detailed rationales to cushion the pain. Justifies the why behind the leaving, especially if feeling ambivalent about the departure.

• The “See You Soon” Eraser - Refuses to name the ending, avoids final language and minimizes the impact of goodbye. Says “I’ll see you around!” or “This isn’t really goodbye.” Wants to stay connected or can’t face the grief of an ending.

• The Sentimentalist - Writes heartfelt notes, gives tokens of appreciation, and offers long hugs. Embraces the bittersweet nature of goodbye, although may have a rose-colored view of what they are leaving.

• The Efficient Exit-er - Embraces what they can control (packing, organizing, etc) and moves quickly to the next thing. Focuses on being pragmatic and prepared.

• The Slow-Fader - Begins detaching weeks (or months) before the actual goodbye. Wants to soften the blow by letting people know well in advance, but also has one foot out the door and can feel like a lame duck.

• The Bomb Dropper - Right before leaving, drops an emotional bomb or picks a fight to cause a rift. Believes (often unconsciously) that it’s easier to leave when angry, so seeks to rupture relationships, leaving others stunned.

Which of these styles sounds most like you? (It might be more than one)

Where did you learn that way of saying goodbye?

What kind of goodbye do you want to offer (or receive) in this season?

I have embodied different styles at various points in my life. Sometimes I skipped a graduation ceremony, other times I wrote long letters of farewell. I’ve organized and left planning documents for jobs I’ve had and I’ve moved without even telling my neighbors. In my younger years, I ghosted some platonic and romantic relationships. Now I like to think of myself as someone reforming my innate goodbye inclinations because I know how important it is to leave well.

There’s no perfect way to leave, but there are more intentional ones. Whether you are leaving a school, a job, a career, a relationship, or a community, our departure style can help bring closure or prevent it. You don’t have to change your style overnight (or at all). However, acknowledge it, examine it and decide whether you want to continue operating that way.

2. Make Space for Grief, Yours & Others

“Don’t cry because it’s over, smile because it happened” – Dr. Seuss

Apologies to all who read this as my senior quote in my high school yearbook (at least it wasn’t a Dave Matthews Band lyric). I guess it was profound to my 18-year-old self, but now I find it troublesome. It is akin to the irksome religious platitudes I rail against. You can ABSOLUTELY cry because it’s over. Tears can be sacred and healing. To deny the expression of sadness at an ending is to silence your grief.

Grief is a natural part of endings. Even good endings and changes (promotions, weddings, moving to a nicer house) can bring about grief.²

A realtor told me how much of her job is griefwork. While some people dream of buying a new house, it can bring about feelings of sadness. It is a significant change. Even if you are moving on to something bigger and better, it can be hard to say goodbye.

When we bought our hobby farm and house, the previous owners kept stopping by for the first few weeks after we moved in. I suspect it was because they were having a hard time leaving the place where their kids had grown up. It was always under the guise of forgetting to tell us something about the property or wanting to take some cuttings of plants in the garden. It can be difficult to let go of a part of your life that has been so significant for so long.

Goodbyes can be bittersweet. It is important to name that. There can be relief to something ending (a toxic friendship, a tedious project) but there is typically also sadness.

Sometimes we know an ending is coming, which can be a blessing or a burden. But it does give us the time and space to say goodbye.³

So I propose re-writing Dr. Suess to read - “Don’t cry because it’s over and if you’re ready, maybe smile because it happened and then possibly cry some more.”

Not quite as pithy, but more representative of the process of saying goodbye and ALL the feelings that come up.

Allow for others’ sadness, fear or anger

Speaking of feelings, when I left jobs, I was surprised by others’ reactions to my departure.

When co-workers I didn’t know well shared their sorrow about my leaving, I was touched to learn how much they appreciated me, but it seemed incongruent to our relationship. My leaving may have brought up other grief they hadn’t yet processed. One nurse tearfully confided I was the only one she had told at work about her son’s addiction issues. She was losing support amid uncertainty.

“Not you too” was a phrase a former boss used when I gave them the news. Because they feared having to figure out how to lead my department when they had other vacancies in leadership.

When I told a committee I was on that I would not be running for a second term after finishing my first, another member pouted, “that’s not fair, I signed on for doing another term.” I think she was jealous that I was able to say no, whereas she didn’t know how.

They weren’t responding to me in particular, but to what my departure represented for them.

Other people’s reactions to you leaving aren’t always about you.

Sometimes, leaving is painful not just for us, but for those we leave behind. Their responses may surface deep wounds we didn’t cause but can’t ignore.

I learned this the hard way.

I once worked as a social worker with kids aging out of the foster care system. They were going to lose their already unstable, temporary housing placements once they turned 18. Many of them had endured unfathomable abuse and hardship. Most of the teenage girls I worked with opted to have babies so “someone will have to love me.” I dreaded telling them that I was quitting my job to pursue a residency in hospital chaplaincy. The phrase that haunts me still is one 16-year-old girl yelling, “I knew it, I knew you were going to leave me too, just like everyone else in my life.” She lunged at the wall of my cubicle, scattering papers everywhere before running into the stairwell.

Abandonment issues run deep, not just for those who have had severe trauma. What we can do is respond empathetically, listen where appropriate and tend to others’ hearts that are breaking because old wounds or new fears are surfacing. These reactions aren’t always about us, but they are real and worthy of compassion. Recognizing that helps us respond, not retreat, and leads to more meaningful farewells.

Created by Holly Stapleton, this image appeared in the NY Times as a Picture Prompt, encouraging readers to share their stories about it here.

3. Stay Present until the End

When the decision has been made that an ending is coming, you may find yourself pulling away. That is a natural reaction, and yet, I encourage us to stay engaged as much as we can.

Leaving well might mean leaving it well for the next person taking over our home, job or role.

With my chaplain interns, I see their reluctance to visit new patients as their last day draws near. It is a combination of exhaustion and the mental energy of preparing one’s mind for the next thing. I have had my own experiences of counting down the days until I was done with something and I was ready to leave. It is a struggle to remain grounded and motivated.

Even though we know something new and potentially desirable might be on the horizon, being good at goodbyes means finishing strong.

My ten-year-old son had his first track meet the other day. He was running an 800m race after finishing a 400m just a few minutes earlier. I could tell that he was gassed. He was holding his side with a cramp for much of the run. He told me afterwards he just wanted it to be over and thought about stopping mid-race. Being the ever-embarrassing mom that I am, I went to the fence and yelled, “You’re doing great, you’re so close to the end, finish strong, fast as you can!” To my surprise (and his), he sped up and overtook the kid next to him and placed third.

How can you cheer yourself on in the final throes of a season or a task to stay in it and cross that finish line with pride?

“Don’t count the days, make the days count.” - Muhammad Ali

4. Say Goodbye & Mean It

We tend to avoid saying “goodbye.” Instead, we say, “I’ll see you later” or “We will stay in touch on social media, etc.” Sometimes we are in denial about the fact that this is an ending. We water down our goodbyes to lessen the emotional impact. But if we don’t fully acknowledge the ending, we don’t honor it.

I never spent summers at a sleepaway camp, but I’ve heard others describe the dynamic that occurs after that intense type of bonding. No one wants to say goodbye. They say they will call all the time, or make plans to be there next summer, etc. And those things might happen, but the truth is that next summer won’t be the same. This summer is over.

When guiding families or patients who are preparing for their final goodbyes, I often return to Palliative Care Physician Ira Byock’s concept of The Four Things That Matter Most. He proposes phrases for end-of-life conversations.⁴ The phrases are simple and profound. They are:

Thank you.

Please forgive me.

I forgive you.

I love you.

Although intended for deathbed goodbyes, I think these phrases need to make their way into our everyday goodbyes as well.

We can tell others what it has meant to us to be with them in this space, we can ask forgiveness for how we may have wronged them. We can say thank you. And use the term goodbye.

Implement Boundaries

Many of my students, friends and Spiritual Direction clients are clergy and have denominational rules to follow when it comes to leaving a congregation where they have served. I know far too many people who have ignored these limits and continued to be in close contact with former parishioners. I get it. It’s hard to go from caring about people so intensely and then flipping a switch to not knowing what is going on in their lives. That’s why it is important to communicate with everyone beforehand about your departure and ongoing expectations. It is also incredibly difficult for the new person in leadership if these relationships are still ongoing.

“Daring to set boundaries is about having the courage to love ourselves, even when we risk disappointing others.” - Brené Brown

But even beyond the congregation, leaving well requires that we fully leave something. We can’t leave a job and then continue to come back and fill in from time to time, or take phone calls answering questions, etc. We can’t break up with someone and then keep seeing them all the time. We can’t graduate and then continue to hang out at the school. If we are having a hard time keeping boundaries, then it is an indication that we still have some emotions to sort out around that particular departure.⁵

5. Mark the Moment with Ritual

There is a reason our society has traditions or celebrations to demarcate major occasions. For example, graduation ceremonies, Bon Voyage parties, housewarmings, retirement dinners and funerals are all ways for us to honor major transitions. But we don’t have ways of honoring some of the other transitions and goodbyes in our lives.

What are we to do when:

• An important relationship ends

• Our children leave home or need us differently

• We let go of certain beliefs, values or coping mechanisms

• We change spiritual communities

• Our bodies change in various ways

• We give up a hobby we can no longer pursue

• We let go of a dream we once had for ourselves

Or any other situation you are experiencing that you can add to this list.

I encourage you to create a ritual around any goodbye you are going through. Just because something has not been established by society for a proper life cycle event doesn’t mean it cannot be acknowledged in a meaningful way. Everyday endings often go unmarked, but creating simple rituals can help bring closure, honor what was and make space for what’s next.

For example, in recent years, people have started throwing divorce parties to commemorate the ending of a marriage. Or parties in advance of a mastectomy or hysterectomy to honor those parts of our bodies before medical intervention requires a goodbye.

But it doesn’t have to be a large fete. Ritual can also be a smaller moment of remembering and letting go. It can involve others or it can be a private, individual effort that no one has to know about.

• Maybe it’s a simple pause or moment of silence in your day to acknowledge this monumental shift.

• Perhaps you write letters/cards/emails to the people involved in that change (even if you don’t send them).

• It could be walking through a space you are saying goodbye to and saying goodbye aloud to everything you see (Think of the children’s book, Goodnight Moon!) Or blessing a new space.

• Maybe you ponder what it’s like to be on a new/different threshold or liminal space of being in-between something.

When I am leaving something in my life, I write out a list of things that I will miss about that person/place/role and things that I will not miss about it! Especially when I have been wavering in my decision, this has been a helpful practice for reminding myself of my intentions and my values.

Goodbyes aren’t just moments in time, they are also spiritual practices. When we pause, acknowledge, bless and release, we honor what has been and what is coming next. As you navigate transitions, may you find strength in presence, truth in grief and meaning in the ways you say farewell.

I leave you with this blessing, which we share with chaplaincy students as they graduate. May it speak to you in whatever you are saying goodbye to this season. ⁶

This Day We Say Grateful
A Sending Blessing by Jan Richardson

It is a strange thing
to be so bound
and so released
all in the same moment,
to feel the heart
open wide
and wider still
even as it turns
to take its leave.

On this day,
let us say
this is simply the way
love moves
in its ceaseless spiraling,
turning us toward
one another,
then sending us
into what waits for us
with arms open wide to us
in welcome
and in hope.

On this day,
in this place
where you have
poured yourself out,
where you have been
emptied
and filled
and emptied again,
may you be aware
more than ever
of what your heart
has opened to
here,
what it has tended
and welcomed
here,
where it has broken
in love and in grief,
where it has given
and received blessing
in the unfathomable mystery
that moves us,
undoes us,
and remakes us
finally
for joy.

This day
may you know
this joy
in full measure.

This day
may you know
this blessing
that gathers you in
and sends you forth
but will not
forget you.

O hear us
as this day
we say
grace;
this day
we say
grateful;
this day
we say
blessing;
this day
we release you
in God’s keeping
and hold you
in gladness
and love.

What’s your goodbye style?

What rituals have you used in saying goodbye to something/someone?

What are you leaving or getting ready to leave in your life right now?

How do you want to say goodbye differently moving forward?

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Related Posts:

The Grief Before the Grief

Turning it "On" & "Off"

Loss 101

1. Depending on your age, you might be singing the lyrics to Semisonic’s Closing Time now!

2. For more on this concept of grief existing even when there are happy changes, see this post on Loss 101.

3. For more on anticipatory grief, see this post.

4. I’ve featured these phrases before in this post.

5. If Boundaries are difficult for you, here’s a post that might help.

6. Thanks to my colleague, A, who introduced this blessing to me. Jan Richardson’s work is always a balm to my soul and makes a great gift!