Jonathan continued, “Okay, so we’re back to managing your disappointment, and trying to avoid it. And how will things go here if we just had that be the way this went?”

Dennis thought about this. “Well, I can say that we’d basically not do this. I don’t think it’s any more complicated than that.”

“Yah, that makes sense — that’s what I was thinking too. And finally, where else in your life is this same thing happening?”

Dennis thought some more. “Well, what I can see is that this is basically what’s happening at work. I think about delegating, or having a conversation with a client, and I end up continually putting it off. And then eventually I’m just doing it on my own at the last minute.”

Dennis paused, and then exclaimed, “Wow… I’ve been thinking that procrastination was my issue, and that the solution I needed was another productivity system. Or reading books like Eat the Frog, or stuff like that. But I’m seeing here that this is actually all designed to avoid disappointment. No amount of productivity is going to make a difference if I can’t be with what we’ve been talking about — I’ll just keep finding new ways to avoid the thing.”

Jonathan was inspired — Dennis was doing some really deep work and creating some big insight. He gave Dennis time and space to be with what he was opening up.

Dennis sat in silence for a few minutes before speaking again.

“Okay, so this seems pretty big. I’m seeing a lot here. Where do we go from there?”

“Well, let me see if I can summarize where we’re at,” Jonathan responded, “We’ve got a bunch of stuff on the table. First, we’ve gotten clear on some of what’s getting in your way: avoiding being disappointing and disappointed, and everything that comes with that. Second, we’ve gotten clear on what might shift if we moved that out of the way: your relationships would change, work would become easier, you’d find yourself with more time, you’d have more space and time with your wife, etc.”

Jonathan checked in with Dennis, “With me so far?”

“Yup, absolutely.”

“Okay. Third, we’ve gotten clear on what your commitment will look like, if you want to shift this, at least if you want to use me and this kind of work as the structure to support you doing so. And fourth, that’s driven up a bunch of fear and feelings — which we’ve discovered is the same stuff that’s getting in the way of you creating the breakthrough you talked about. So basically, what’s getting in the way of you saying YES here, is also what’s getting in the way of all that other stuff you said you wanted everywhere else in your life. We still on the same page?”

Dennis thought for a moment before responding. “Yes, that sounds exactly right. So now what?”

“Well, that’s what I want to hear from you Dennis — what do you see is the way forward from here?”

Dennis thought. “Hmm. Do you offer any kind of guarantee or refund with your work? Like, what if I totally screw things up? How do I know that won’t happen?”

Jonathan smiled, “It’s actually much worse than that. There is zero guarantee that that won’t happen. And in fact, what I’ve heard from you is that we will almost certainly wind up in a situation where you are creating disappointment. The reason I can say that with so much certainty is because you’ve shared that that is the thing you can’t be with, and avoiding that is what is messing everything up for you. Are you able to see that the place you’re asking your question from is actually more of that avoidance?”

Dennis felt uncomfortable, but sat with that, “Umm. Basically because I’m trying to set things up so that I don’t wind up disappointed or disappointing other people?”

“Exactly! And the truth is, you probably will experience disappointment here. We actually want to walk you through that. The real difference here is that as that happens, we’re going to be in conversation and relationship, and support you in showing up differently in the face of that disappointment.”

Jonathan kept talking, “So, even if I was somehow able to offer you a guarantee, I really don’t think that would be in service of you or the work in front of you. That would just hold off disappointment for longer, and effectively keep you away from the breakdown that will precede your breakthrough.”

Dennis hadn’t heard Jonathan use that word before. “What do you mean breakdown?”

“Thanks for asking — I just realized I haven’t clarified that part. The breakdown is basically the experience you’re avoiding. The thing that you can’t be with that is keeping you stuck. In your case, it’s disappointment. So if the breakthrough available is for you to create a new way to experience and be in the face of disappointment, the breakdown is what you will experience before you create that. It’s the moment when things stop working, because you’re practising something new. It’s the part where you haven’t yet created the new way of living, and all you can see is how you’re losing.”

Jonathan paused and checked back in, “Am I going too fast?”

“Nope, I’m with you — thanks though.” Replied Dennis.

“Great. So, the breakdown is an essential part of the process. It may not look traumatic for you — you might experience it like anger, frustration, sadness, grief, not having an answer, feeling like something’s wrong, feeling like I’m wrong, feeling like you’re wrong, etc. Ultimately, we’re going to expect that that will happen, and that’s the eye of the needle that you and I will travel through on the way to creating your breakthrough, should you want it.”

Dennis sat with that. “Okay. So no guarantee, and in fact, it sounds like what you can guarantee is that things will suck?”

Jonathan laughed, “Boy, I love your sense of humour Dennis. Yes, in a way, you’ve got it. I can promise you that we will create something new, if you’re willing to go into that breakdown. And I can promise you that we’ll have fun along the way, and that at times it won’t necessarily be fun. And I can promise you that once we’re a YES to each other, I am one-hundred percent on your side, in your corner, and committed to supporting you in creating this breakthrough.”

“And most important of all Dennis, I want you to know that I believe you can create this. I wouldn’t be a YES to you if I didn’t feel that way.”

Dennis chewed on that. “Okay, this all makes sense. Why is it so scary though? I want to tell you YES, but I’m having a really hard time.”

Jonathan answered Dennis’s question, “It’s scary for the same reason it’s scary to delegate or do any of the other stuff that is going to set you free. Hiring a coach, I believe, is going to start you creating a breakthrough right out of the gate. There’s a leap of faith here, into possibility, and into our fear. That’s where we’re at. So the two questions I have are: one, am I the coach, is this the structure, and are you a YES to this? And second, if the answer to the first question is YES, then what support do you need to step into that possibility?”

Dennis thought. “Jonathan, I definitely want to take this on with you. I don’t understand your business model at all, and I would have called you insane if you described this to me at the conference we were at, but there is something about being with you that is completely different and opens things up for me. Everything we’ve talked about makes complete sense. I am a YES.”

Jonathan felt tears welling up in his eyes. The opportunity to work with someone was always a sacred experience for him, and anytime a human being was willing to step past their fear into possibility, it moved him.

Dennis continued, “As for your second question, what I need to do is talk to my wife and make sure she’s on board. And then I’d really like to have you do this same work with our executive team, but I’m still a little foggy on that one. Can you support me with how we might approach that?”

“Sure. Let’s start with the leadership team. Here’s what I propose: let’s start by getting you supported. Your commitment will be fifty-thousand, and once we’re doing some work together, part of what we look at can be enrolling your team in the same work. If and when they are ready, I’ll honour the original commitment I mentioned of one-hundred and twenty-five thousand, so we can remove any urgency or need for you to choose right now.”

Dennis broke in, laughing, “Thanks for another terrible business decision Jonathan — you know, you could be using urgency and taking the deal off the table to force my hand here!”

Jonathan burst out laughing. “I know right? Anyhow, does knowing we’ll work towards bringing your team on board, together, have that question feel handled to you?”

“Yes, totally, that feels great. I’m so glad you suck at business.”

“Hey, watch it. We haven’t said YES yet.” Jonathan laughed with Dennis and continued, “As far as the conversation with your wife, totally, we want her on board so that she is in support of this work, rather than working against it. What do you see you need to do to get her on board?”

Dennis thought for a minute. “Well, probably make sure she’s okay with me spending that money. I think I just need to explain why I want to do this.”

“Great. And, is there anything predictable about how that might go? Predictable things you might end up doing, or that she might end up saying?”

Dennis responded, “Mmmm. Well, I will probably put it off for a long while, because I’m scared she’ll say NO. And to avoid that, I might try to convince her. Basically bring a really well-formed airtight case and keep her on the back foot.”

“Good awareness Dennis. So, two things for you: let’s get a declaration on the table here, so that you aren’t prone to make this one more thing you procrastinate on. By when will you have the conversation with your wife?”

“Well, the sooner the better. We’ve got a dinner planned with friends tonight, but tomorrow I think we’re both free, so I’ll have it then.”

“Beautiful. Nice work. So, let’s see. That’s a Thursday evening. Will I hear from you on Friday then?”

“Yes, I’ll let you know how it went either way.”

Jonathan continued, “Okay, perfect. Here’s the last thing for you — my invitation is to put your attention in the conversation on what you see is possible from this work. Rather than convince her about the money, or try to browbeat her into this, tell her everything you and I have talked about, and what you see is possible. Share what’s possible in your life, possible in your relationship with her, possible at work, etc. Make this about enrolling her in a possibility, rather than convincing her to let you do something. Make sense?”

Dennis nodded to himself. “Yeah. I think that does make sense. I’m kind of excited!”

“Right on, me too! Before we wind down, is there anything else for us to talk about to have the conversation today feel complete, Dennis?”

Dennis thought quietly, before responding, “No, actually. This conversation has been so much more than I expected. Thank you so much for the time and supporting me through all of this Johnathan — I’m really excited to get started and actually looking forward to sharing with my wife what we looked at today. I’ll send you an e-mail on Friday!”

“Excellent. I’m looking forward to hearing how it goes — and remember, if you find yourself stuck, or afraid to have the conversation with your wife, or anything else, feel free to reach out. I’m happy to support you either way.”

Jonathan and Dennis ended the conversation and hung up the phone.

Excerpt from Coaching With Love