EP. 24 | Ending Well: How to Navigate the Closing Chapters of Discipleship

Chris Johnson (00:02.557)
Ladies and gentlemen, welcome to the Ordinary Discipleship Podcast. My name is Chris, with me as always, the one and only Jake, Ub, and of course, the genius of the group, Jessie. Today, we are talking about endings, and nobody likes to talk about endings. People like to romance the beginning of a discipleship relationship, but can discipleship relationships end on a good note?

Do they just naturally flame out? Or how do we discern when a discipleship relationship should maybe change in focus? These are the questions we're gonna be looking at for the next 19 minutes. I don't have any answers whatsoever. So I'm gonna hand it over to the two experts, Jessie and Jacob. Jessie, how do I know when a relationship like this, a discipleship relationship is kind of changing in?

And I don't know, speak into this. Like, I'm sure you've discipled plenty of people, and I'm sure you're there's some people that you discipled that you're still not discipling. Did it end okay? What did it look like? How did you know when it should kind of change? So many questions.

Jessie Cruickshank (01:16.744)
Well, let's start with like your fear. let me ask you question. some snake same. If you have somebody who comes in and says, hey, will you mentor me? Will you disciple me? What is what are you afraid of? Like, do you naturally think that, I can do this for a season or does that even occur to you?

Chris Johnson (01:20.543)
Yeah. I have a lot of fears. Snakes. Bears and trash cans.

Chris Johnson (01:44.012)
Now, so number one, it's like the inside voices. It's like, are you smart enough to do this? Are you going to act? Is this going to be fruitful? Is it going to be worth your time? Do you think you can accomplish anything? What are you going to do? And then I get intimidated by how many hours do I spend with this person? And then the final thing is, is this going to be like, am I tethered for life with this human being or do they, you know, like

turn into a dark Sith and strike me down. I don't know, you know, like, I just don't know at this point.

Jacob (02:18.142)
You're figuring that you are Luke Skywalker, whoever got framed by Kylo Ren?

Chris Johnson (02:23.145)
I'm eating.

Yeah, and then I got a little Kyle Oren coming up trying to strike me down. I don't know. No, but seriously, think the intimidating thing is that sometimes when somebody asks me that, I guess my mind races to how long am I promising to do this? And that's intimidating.

Jacob (02:30.668)
Right.

Jessie Cruickshank (02:48.574)
Right, what's my commitment look like? Right? These are all like, what are the parameters of our commitment to each other in here? And I think it's a super important question that if you can do a formal or at least have the conversation, we call it a DTR. I'm super old school. So we have a define the relationship. We call it the DTR. And the DTR question is, what are we going to commit to each other? And we somehow we treat discipleship like it's marriage or

Chris Johnson (02:54.355)
Yes.

Jessie Cruickshank (03:17.04)
you know, you have this apprentice until they strike you down and take your place, nefariously or better, know, for good or for evil, depending on which one you were. Good luck choosing that one. But a healthy discipleship relationship understands that God has seasons that people are in. we're not, our story has chapters. Our story has sections.

Chris Johnson (03:25.493)
Who knows? Right.

Jessie Cruickshank (03:44.688)
And sometimes it's like multiple books. Right. And so each one of those has a beginning point or an ending point. And there are chunks to it. So discipleship is the same way a person is brought into your life for a season. And you don't necessarily know how long the season is. Sometimes you do because you're like, I can commit three months to you or a year to you. then and then a known change is happening in my life because I'm going to move or

you know, something marks it to be different. And so maybe you know that upfront, but usually we don't. Usually we don't know how long the season is. And so for me, discerning the season is paying attention to one, that they're in a lesson, like what lesson are they in? And when have they learned that? If discipleship is just information, then you're like, I'm in 101 class, I'm in 201 class, I'm in 301. And it goes on per...

Chris Johnson (04:39.956)
Right.

Jessie Cruickshank (04:43.572)
forever because there's infinite amount of Bible and cosmos of God to study. But if you think about it rather, it's centered around the lesson that they have, the aha moment, the revelation that heaven wants to teach them or the way that God wants to recreate them, then you can discern the season has changed or the season's about to change when they learn that lesson. Like when did they get that? And so for me, my commitment to somebody is, okay, I'm here for this.

Nugget in your And when they have that aha and I hang on even if I think they're taking forever sometimes they do but like You hang on and then they have that and you're like, okay We're on the other side of the mountain. We climbed the mountain and got back down again What's our new week we get to redefine the relationship again. It's a good marking point for for resetting the the relationship

Chris Johnson (05:40.627)
Okay. Yeah. What do you think about that, Jake?

Jacob (05:44.014)
Yeah, and I think that like, what that allows us to do, you know, in another episode, we talk about how do these relationships begin. And in that episode, we were talking a little bit more about organic beginnings, but here we've talked a little bit about what if somebody shows up and says, I want this relationship. does it like, I think it's, it's a trite phrase, but begin with the end in mind allows you to set up the relationship fruitfully at the beginning. So in this scenario that you just outlined, Chris, it's like,

somebody comes to you and says, hey, will you mentor me through this season of my life? And you're like, wait a minute, is this a lifetime commitment? Well, no, let's begin with the end in mind. Hey, so what is it that you're working on right now that makes you say you want someone to walk with you in that? Then you begin to get an understanding of what's the lesson that God is teaching them and how can I come alongside of them? Or am I even the right person to come alongside of them for that season? So I think being able to see that ending from the beginning,

allows you to enter in even more mindfully.

Chris Johnson (06:46.355)
OK, that makes sense. Yeah.

Jessie Cruickshank (06:49.12)
So this has happened to me in a few, like I've experienced this just to give some examples of the ways that this can go. One person I was mentoring in discipling, she was a young lady, she was in a dating relationship and I kind of walked with her through that dating relationship. She gets married, so then some of the early marriage part and then she gets pregnant and she starts having kids and I don't have kids. So it didn't.

she needed somebody else in her life that could help her think through that. And what does it mean to be a mom and everything? so, you know, we celebrated the years that we had spent together. And I was like, yeah, you need somebody, a different voice for this season of your life. So her life season had changed. On the other hand,

Chris Johnson (07:19.939)
Chris Johnson (07:34.531)
who?

So Jessie, who discerned that? Who discerned that? Did you discern that or did she or did you kind of come together and discern it together? Like, I mean, it sounds like a really healthy break at the end. I'm just wondering how that came about. You know what mean?

Jessie Cruickshank (07:44.32)
That was a good one.

Jessie Cruickshank (07:50.496)
Well, to overly romanticize it, we discerned it together. But honestly, I was like, I don't know how to help you. And I was like, I don't know how to give you anything. I passed on the lessons. I had wisdom for what you were going through. I don't have any wisdom anymore for you. And you need somebody else because we just went somewhere I don't know. And I would...

Chris Johnson (07:51.765)
Yeah.

Chris Johnson (07:59.083)
Gotcha.

Chris Johnson (08:10.731)
Gotcha.

Chris Johnson (08:15.104)
Okay.

Jessie Cruickshank (08:16.954)
There might have been more fear or insecurity that led up to the conversation on my end, but we lived in the same town, so we weren't ending our friendship. We were just changing the nature of our relationship. And she wasn't going to come to me for advice anymore.

Chris Johnson (08:31.989)
So it just kind of changed. Right, it changed from like a mentor to a true friendship at that point. Right, right? Yeah.

Jessie Cruickshank (08:38.548)
Yeah. Yep. Now on the other hand, like, so this one's a little more recent. There's a person I've been discipling for about seven years. And I found that when she would reach out to me, the way that I felt about seeing her name on my phone with the phone call started to change. And I had had like a lot of grace for her.

I had a rule that I wouldn't skip her call more than once. So if I had a situation going on or my life or whatever, and I couldn't take her call, like the next time that she would call, would at least say, even if it was bad, I'd be like, hey, I hear you, I see you, let's set up a time I can talk to you. And I didn't have an aversion to that. And she even went, she went through some very difficult things and she would call in the middle of the night. mean, it got, her life got real intense with some of her situation and

Chris Johnson (09:27.657)
Yeah.

Jessie Cruickshank (09:33.566)
I had all this energy and all of this compassion and patience and everything. And then

She was through that and I didn't know that that was the lesson that I didn't know that was what I was there for. But on the other side of that, you know, about six months after she had come through that and was doing really well, her name would come up on my phone and I'm like, I just don't have anything for this. And my life was getting a little more stressful, a little more full and I didn't have grace for her, like emotional margin and grace.

Chris Johnson (10:00.693)
Mm-hmm.

Jessie Cruickshank (10:11.648)
I called her and I said, hey, my life is so I said, I can't, I have to change the nature of our relationship. You can still call me and I will answer if I can, but my commitment to you to be this available to you, I can't fulfill anymore. So we can still have relationship like, well, I was really nervous about it because of how

Chris Johnson (10:31.701)
that go over.

Jessie Cruickshank (10:39.796)
big of a role I had spent in her life, like seven years mentoring her. And you know what? bet she went home and cried. I bet she had to process that with someone else, but I can't manufacture grace where grace isn't. And that was a lesson I had taught her and we had talked about from the very beginning. There would be an end at some point to this. And she knew that.

Chris Johnson (10:42.165)
Sure. That's what I'm saying.

Chris Johnson (10:52.373)
That's That's fair.

Chris Johnson (10:58.985)
Right. Yeah. Yeah.

Jacob (11:01.902)
Well, think, I think like, let's talk about how that would have gone with people who weren't as spiritually emotionally as healthy. Because what Jessie described, I think a lot of us have experienced is there's someone in our life, we see their name come up on our phone and we've let it go to voicemail.

Chris is laughing because that happens, right?

Chris Johnson (11:27.881)
most of the phone calls I get. No way, No, no, not Jacob. I'm just saying that happens to me on a daily basis. Like I get so many phone calls. I just let them go through and then I have this moment of guilt, you know, and then I'm like, but then everybody knows if they call me twice, I'm going to answer. I mean, that's just the thing.

Jessie Cruickshank (11:27.968)
Chris Les Jacobs' voice go to voicemail.

Jacob (11:37.315)
Right.

Jacob (11:48.736)
Yeah, so now you just gotta call Chris twice. But I can imagine the scenario that Jessie just outlined going in a way where somebody just starts ignoring the phone calls, the other person starts to wonder what's going on, but they don't talk about it until somebody gets offended. Until somebody gets offended and then they start and the things that have festered come back up and then the relationship ends poorly.

Chris Johnson (11:51.487)
That's it. That's it. That's all you got to do.

Chris Johnson (12:03.371)
think the kids call that goat thing. Yeah.

Chris Johnson (12:13.247)
Right.

Jacob (12:16.342)
And then the risk is all the good work that God has done in that relationship gets lost in the way that it ended. Yeah.

Chris Johnson (12:22.441)
Right. Yeah, yeah, no, that's a good point. Just thankfully Jacob.

Jacob (12:29.486)
And so I think the courage that Jessie exhibited to say, let's redefine the relationship is really saying, let's not lose what's been good, but let's acknowledge the ending of a season. Yeah.

Chris Johnson (12:38.293)
Okay.

Chris Johnson (12:43.091)
If Jacob would have ghosted me during seminary, I would not be a pastor today. That's the bottom line right there. Kids smart. The guy helped me through it. yeah. all right. So, but Jessie, you bring up a good point. Like that's happened to me in 21 years of ministry. There's been a lot of times where you sit down on the couch, maybe after a long day and it's like eight or nine o'clock and you see that call come through and you're like, my goodness. Seriously, what?

could possibly and then you start feeling guilty because you're like, I should take this because that's kind of my gig. And then you start wrestling with all that stuff. So yeah, I feel you. I, you, when you said that, I was like,

Jessie Cruickshank (13:26.752)
And I just try to ask God, you want me to answer? Should I answer this call? And if he says yes, and I'm epically tired, and if he says yes, I'm epically tired, I'm like, okay, well, you need to show up because I got nothing to give right now. But sometimes he says no. Sometimes he's like, you know what, call him back tomorrow.

Chris Johnson (13:30.131)
You

Guys like,

Chris Johnson (13:40.99)
Amen, yes.

Chris Johnson (13:45.769)
Yeah, yeah. Or maybe never call him. No, I'm just kidding. That's not true. Okay. Okay. getting back to what we were originally talking about, like ending it gracefully. And you guys have both mentored multiple people discerning the season. then, and then like sometimes it flames out. Sometimes it goes on.

but you guys talked, both of you two talked about a fruitful ending to discipleship. I'm curious. I saw that in the notes of the podcast and I guess I don't understand. Like, what are you talking about?

Jacob (14:35.342)
So this is where in our community curriculum, we'll talk about the importance of rites of passage. So marking and ending, so you can crystallize what came out of that season.

Chris Johnson (14:47.987)
Okay, so you're going back over it and you're saying this is what we achieved in this season. So it's not it's not about the ending. It's about what you've achieved together. In that season.

Jacob (14:53.345)
Yeah.

Jacob (14:59.34)
Yeah, intentionally marking the moment. So I'll give an example from the Bible and then think Jessie has that example from pop from like culture, not pop culture, but culture. Like I think about the Israelites entering into the promised land and crossing over the river Jordan. And Joshua in that moment leads them to set up a monument to mark the fact that God had brought them out of the wilderness and into the promised land.

And it's after they set up that monument, somebody can fact check me, email us if I'm wrong, but it's after they set up that monument that Joshua says, decide today whom you will serve as for me and my house will serve the Lord. And what he's saying is like, like what's happening in that moment is they're transitioning from one chapter to the next. And they're, and they're like capturing the, the wind of the wilderness season is God rescued us out of the world, out of slavery and brought us through the wilderness.

Now we're going into the next season where what we have to learn is how to set up a household. And so that rite of passage marks the transition from one season to the next and says, this is the lesson we learned and this is the challenge we're now facing. And it allows them to leave one thing behind and engage the next thing.

Jessie Cruickshank (16:17.332)
Yeah, I think about it like ending a chapter or ending a book and a trilogy, you know, depending on how long it is. you know, if the interesting thing is that if you don't do this, then the person, their soul, their psyche, their self narrative never has an end to that season. So one of the ways that we can think about that is like we all still think about life like we're in COVID.

We talk about COVID all the time. We talk about the change that COVID initiated. And y'all, by the time you hear this podcast, it was five years ago.

five years ago. It's like the slowest, longest, fastest five years ever, but it's because we don't have a way to mark that that season is over, that time of disruption and destruction and recreation, and they call that a liminal season. We haven't marked that it's over, and so our souls and our narratives don't exist into the new one.

Chris Johnson (16:56.746)
Yep.

Jessie Cruickshank (17:21.416)
And so if you don't mark the end of something significant and say, okay, now we're in a new time, just like Jacob said, now we're not wanderers in the wilderness with manna anymore. We're gonna create houses and plant crops and live life totally differently. If you don't have that, your soul remains stuck. So part of being a disciple maker is helping people do that. So one way that I did that, that my husband and did that with a couple that we disciple,

is they were having a significant season change. They were moving into a lead pastor position. so they've been mentored and now they're move. They're gonna take a senior pastor role. And so we were like, okay, we're seeing this as a moment of life change. So let's stop and share story around the dinner table of where you guys were when we met you. It had been like 10 years and so like they had been teenagers and they had been dating.

And we just shared story and remembered, you know, what had been and they shared the lessons that we had taught them that were meaningful for them. That was incredibly powerful for us. Like 10 years of teaching them stuff, what it stood out to them, what had changed their lives, what did what what did they what were they carrying forward into the next season? We talked about what a hot mess they were and how we like, I don't know how to help you in this place. And we would like my husband and I would talk about it.

Chris Johnson (18:38.335)
Yeah.

Jessie Cruickshank (18:46.186)
pray God shows up somehow, because we don't know what to do. And we just had this story time around our table and they were going into the next season. And at the time we didn't know what the new relationship would look like. What were they going to need from us? They didn't know, we didn't know. And so we just left it open. The DTR was that the season that Infantentional Mentoring was done and now they were going to be mentoring other people.

And we were just open to however the next season naturally rolled out with all of us. And they don't call us all the time, but we love it when they do. And they don't need to tell us stuff. They don't need advice all the time. Sometimes they're just calling and celebrating things in their life. And yeah, so it's really beautiful. So it was a rites of passage because my husband and I were very intentional about it because we marked it and we remembered.

Chris Johnson (19:25.653)
Yeah.

Jessie Cruickshank (19:44.884)
But it was just dinner, you know?

Chris Johnson (19:46.603)
Well, it's kind of what you just mentioned kind of reminds me of like what I'm going through with my 20 year old girl right now. Like I feel like I went from being a head coach to kind of like an offensive coordinator. Like now she doesn't ask me every question and need it all answered. And like today she just texted me and she's like, dad, I just locked my keys in my car. Like, what do I do? And I'm like, she still needs me. That's nice. But it's not very often, you know, and she's kind of got stuff figured out.

And that's ultimately what we want from a discipleship relationship or from like our kids growing up. Right. Like, I'm glad that you don't have to ask me every single question. And it's really cool that you're kind of like pouring into other people and you feel like you can do that at this point. So that's cool. That's, that's really cool. And I saw that you got kind of emotional there. Like, that's beautiful. Like when you spend that much time, it's hard not to, right? Like,

That's pretty awesome. OK, well, we just hit the 20-minute mark. That's going to do it for this episode. I think it was a gem. I think after we shine this up, it's going to be a diamond. And so thank you for joining us on the Ordinary Discipleship podcast. Please do us a favor. If you're listening to this, whether it's wherever you listen to podcasts,

Go and write a review. Give us five stars. If you feel like anything less than five stars, then just, you don't do it. And then after that, share it with a friend. And Jessie, if people want to learn more about everything in Hoology and what you and Jacob do, can you give them a little description?

Jessie Cruickshank (21:36.906)
Yeah, we love to walk with people in the journey and that could look like the Bible study class that you can buy on our website and it's got videos in it that could look like a team training, coaching, the podcast webinars, all that sort of thing. So you can learn more about what our current offerings are at whoology.co that's W-H-O-O-L-O-G-Y.

Chris Johnson (22:01.959)
Awesome. Thank you guys so much and thanks for listening. God bless guys. We'll see you on the next episode of Ordinary Discipleship Podcast.

EP. 24 | Ending Well: How to Navigate the Closing Chapters of Discipleship
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