This journal shares an abridged transcript of the conversation between Hollis and her assistant, Kimmy Anne Dunn, as they answer a question from the TDL Community: How Do I Quit Quitting?

In their conversation they explore the habit building process and the difference between linear and circular mindsets when building habits or practices. By clarifying our ‘why’, taking it slow, and finding resilience, we can quit the quitting cycle and better support ourselves in the motivation process. 

Listen to their conversation.

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Hollis: This is so exciting. This is so much fun. Leading up to this, I couldn't stop thinking about Conan O'Brien and his assistant, Sona Movsesian, on their podcast. I know this is an entirely different genre and dynamic, but I think about their relationship, and it feels similar to ours. They've known each other for so long, and they're like family more than employer-employee. That's how I feel about our relationship because we go way back at this point.

Kimmy: I know, I know. Every time we expand our relationship in some way, like me coming on the podcast with you, it makes me so happy. I'm so excited to be doing this.

Hollis: Amazing. Well, I think this is a great subject for us to talk about because you participated in the illuminated course last year, right?

Kimmy: Right, right. It was the winter session.

Hollis: Yes, the winter session. OK, so this is definitely something that we talked about a lot in our work together. So, you have hands-on experience with testing out these tools we'll talk about today, and it's pretty recent. So, I guess let's first get into what it means. Like what quitting quitting means which, when I think about it, you know, I think the word quit, kind of already has an aura around it of either giving up or it's relief in some way. Do you also have the same experience with the word "quit"?

Kimmy: Yeah, yeah. When I think about quitting, I immediately feel bad. I definitely related to a negative feeling, like I couldn't finish it, and it's a reflection of my failing. But thinking about quitting in terms of allowing yourself to find relief from things that aren't for you is a nice distinction. There's often intense pressure when starting something new, whether it's a routine, a project, or a new habit. Even more so when it's something you feel you should be doing, like to be more interesting, smarter, or to advance your career. Starting and following through with something naturally carries a lot of pressure.

Hollis: Completely. Knowing if something is right for you and dealing with the emotional roller coaster of cultivating something new isn't linear. It's not like we just add something new in and then it’s there consistently. There's a journey of understanding how it fits into your life and how it changes. So, let's talk about integrating something new into your life. Like running, you want to start with a slow jog, getting comfortable there, and then increasing slowly. And then, once you increase, you stay there and hold steady until you're comfortable there with your heart rate, with your breathing, and everything. And then you maybe add on a little bit more. And I always like to think of habit building or integrating something new in that same way. It pushes your edges at the beginning because your life is already full. You have to reorganize and create space for the new element, which can be uncomfortable.

For example, consider a morning meditation practice. You start with meditating three days a week for 10 minutes each time. Once you're comfortable with that, maybe increase to four or five days a week. You know, whatever feels more comfortable there. But assuming that you're going to jump into everything all at once - that you're going to go from a jog to a sprint and be able to hold it for 30 minutes, it not only would be extremely difficult, but it would also be too much to ask for yourself.  It can make you feel like you didn't do well enough, leading to a sense of failure.

Kimmy: For me, the hardest thing about building any habit is starting. Like if we’re using running as an example, when I imagine starting, I envision the end goal: a strong, powerful runner. But I don't want to imagine the exhaustion and the difficulty of the early stages. But, yeah, you definitely want to give yourself grace and also be realistic when starting something new. You know? You don't have to run the full mile on the first day. Listening to your body, understanding what it can handle in that moment, and being patient with yourself. And I think that the same applies to creative projects. If writing feels daunting, start with just two sentences. Even if that's all you do for the day, great. I think setting parameters is super helpful when starting anything, but it's also one of the hardest things for me to do. I say all this, but I don't really do it as often as I would like. But the reminder is really helpful and it takes the pressure off of whatever the new habit is in a big, big way.

Hollis: It's interesting because I feel like even when we have the motivating energy to start something, we have that end goal in mind. And that adrenaline rush is really essential to begin. The excitement is a sign that it's something you should do for yourself. So, holding onto that end goal while being realistic about the initial challenges is crucial. 

For instance, when you start writing again after a long time, it might feel clunky at first. You need to understand where you are and meet yourself there rather than assuming you'll immediately be the person at the end goal. Everything is a process, and you must meet yourself where you are every day. And that motivation will likely fade, so it's important to revisit your 'why' to remind yourself why you're doing it, even when it's tough.

Kimmy: Right, right. Something we discussed during The Illuminated Course is the deeper 'why' behind what you do, and understanding this motivation as an essential part of following through with anything. Can you talk more about finding the deeper 'why' and how to initiate it? It's really helpful, but often gets lost when we start something new.

Hollis: Yeah, yeah, of course. Let me use myself as an example. I've recently started something I'm excited about, but I know my motivation will probably wane in the future. I've always wanted to paint and draw regularly. There is a lot of creativity in my family, and it's something I've done throughout my life. Going to art school extended the passion, but it dropped off in my 20s. And over the last year, I've felt a growing urgency to access that part of myself again. I've had several moments of frustration with my skill level not matching my vision. But over the past few months, I've clarified my 'why.' I want to paint and draw as a way to reconnect with a playful version of myself I've dismissed. Even if it doesn't seem practical, it serves the purpose of connecting with myself and doing something purely for pleasure. 

And I’m using this as an example to emphasize finding your 'why.' There may be a surface-level desire, but allowing yourself to explore it and understand the deeper reason can be really enlightening. Reflect on why you're feeling the urgency and using that in connection with the end goal vision that you have for yourself keeps that motivating force going. Does that make sense?

Kimmy: Definitely. It just adds more play and flexibility to what you're doing. And I think it's really important to have structure when building habits, but then also adding a bit of spontaneity and fun to the process. Something that has been really helpful for me is my self-talk when starting something new. Bringing in some of that fun and some of that sweetness while I'm doing something. Celebrating the small and big wins and letting go of things that didn't go as planned. Being kind to yourself can make the process of starting and sticking with something way more fun.

Hollis: Exactly. What you're describing is so key. Especially if it’s something like a health habit or something that you "have to do". It can feel heavy and daunting. We're not taught to make these activities more enjoyable. And I am so not about that. Why not make them pleasurable? For example, when you're trying to move your body more, what kind of movement is enjoyable—dancing, running, yoga, group activities? Or when you're writing, what creates a supportive environment —snacks, a warm tea, a journal? At the beginning, give yourself the grace and support to let things unfold naturally.

Okay, so let's discuss the middle phase, where you've established a routine, but the initial motivation has decreased. The phase when thoughts like "I can take a break" or "I don't need to do this today" start to emerge. What comes to mind for you when we're talking about all of that?

Kimmy: Well, what immediately comes to mind is that I've been trying to meditate more, but the motivation has faded. Initially, it was going strong and I was reading a book on meditation. I was really making it my personality. I was meditating for 20 minutes a day. But then I started feeling bored and like I didn’t feel like doing it each day. And so I’ve been giving myself a meditation break, and I've gone back to it occasionally for 10 minutes or so on random days, but I don't know if I should maintain the routine or take a break altogether. I keep hearing a little voice in my head questioning whether I should be meditating or not. But it’s like the initial excitement and peacefulness I was feeling from the practice has shifted. 

And as I'm saying this, I'm just thinking about what we were just talking about, the importance of adding fluidity and personality into the process. And I haven't really been thinking about that. I haven't been allowing myself some of that pleasure, or at least not in the past couple of weeks.

Hollis: Your example is perfect, and it brings up the question of knowing when something is for you and when it's not. There's a lot of pressure to finish and stay consistent with things, but some things (most things) require an ebb and flow. And I think that the challenge is recognizing if you need to apply more emphasis, structure, or devotion to a process or if it's something you can let go of and perhaps pick up again in the future, or maybe not at all. It's about differentiating between them. So, can I ask a couple of questions about your meditation practice?

Kimmy: Yes, yes.

Hollis: When you initially started meditating, what was the source of that motivating force? What made you want to integrate meditation into your daily routine?

Kimmy: I wanted to bring more meditation into my day because I was waking up in the morning with a lot of anxiety. It felt chaotic. I really wanted the first 20 minutes of my day to center myself, and find some ease and peace to carry with me throughout the day. 

Hollis: And when did you start feeling that it was dissipating? 

Kimmy: Yeah, well I would wake up, think about sitting down for 20 minutes and think, "Do I need this? Could I be more useful or productive with my time?". There's often resistance when it comes to meditation.

Hollis: OK, so this is exactly where I was hoping you would go with this because what ends up happening for a lot of us is we start something, and then we get to a place where we feel like the motivating energy is sort of dissipated, or we experience some initial relief or change, and then question whether they need it anymore. You might feel you've reached a level of comfort or growth and wonder if you should continue or not.

And here you can think, maybe I gave myself what I needed and I don't need to do this anymore. Maybe it was just a momentary thing that I needed to do for myself. Or you can recognize, well, is this actually something that I want to do? Because I want to push my growth edges a little bit more and maybe this is really a part of who I am. And continuing means stepping into a new version of yourself, which can be uncomfortable. It can cause growing pains. And I think, as humans, we naturally avoid discomfort. We don’t want to be in pain. But by taking small steps, making it enjoyable, and being patient with yourself, you can manage the discomfort.

Kimmy: Yeah, that's exactly what's happening. I couldn't quite articulate it, but I began to feel that the meditation served its purpose. I got what I wanted. I checked it off. And now I'm feeling the resistance, wondering if I should continue. And I feel like, with me, I can easily see how meditation has been beneficial to me. I find it helpful. I do feel like it adds peace. I can see how keeping up with the practice would be very helpful to me. But I’m wondering, how do you differentiate sitting with the resistance and realizing something is not for you or maybe just not for you at this moment?

Hollis: Yeah, I think that there are a few ways to explore that. If you feel resistance right away, it could be an indication that it's not for you anymore but you won't know until you experiment a bit. Maybe it just needs to evolve into a new version. Explore it further, see if it's uncomfortable in a growth-inducing way, or if it's uncomfortable in a confining way. In either case, it might be time to let it go or develop a new relationship with it. By exploring it and testing it a few more times, you can discern whether it's right for you now or in the future, or whether you should walk away from it completely. 

And this is where paying attention to your physical reactions can also help you distinguish which path is right for you. If it feels like you’re pushing a boulder up a hill, that’s a good indication that it might be time to let go, at least for now.

Kimmy: Right. When starting something new, it naturally leads to personal growth and how we interact with the new habit will change and evolve as we change and evolve. And it's so important to allow space for that evolution and checking in on whether or not the habit is still serving its purpose.

Hollis: Yeah, you took the thought right out of my head. That's exactly what I was going to say. This is where we should check in with the deeper why. Is this habit still serving its intended purpose, even if you’re experiencing resistance? And I think that working through resistance can make us feel more capable. After doing something challenging, acknowledging how it feels, the joy, the endorphins, and appreciating ourselves can make it easier to tackle hard things in the future. 

Kimmy: Yes, one of the biggest reminders I always come back it is to work with myself rather than against myself.

Hollis: Can I put you a little bit on the spot about your meditation practice? How do you see yourself moving forward in supporting it or possibly relieving yourself from it?

Kimmy: Yeah, I think what this conversation made me realize was that I wasn't enjoying the rigidity of my 20-minute meditation routine. It started feeling stale, and I think what I really need is to find a different routine that's more fun and exciting. I definitely feel like the practice is for me and I still feel like it's something that I want to do, but it needs to be more enjoyable and nourishing.

Hollis: At the very beginning we were talking about how habit building or integrating something new into our lives, we assume it to always be this linear process, but what I'm hearing from you is the ever applicable growth process, which is really more of a spiral. Knowing that a new habit might take on a few different evolutions before it really finds a solid version of itself can be an expected part of the process. Letting go of the idea that it must look a certain way forever and allowing it to evolve with you can be liberating. Keep the "why" as your foundation, but allow the "how" to change.

Kimmy: I love the idea of being an explorer, of it being an ongoing journey rather than a rigid end goal.

Hollis: Absolutely. Is there anything you'd like to add to wrap up this conversation? I feel like we really went into a lot of the nuances. I hope that people took away a lot of insight from what we discussed, and your personal experience with meditation.

Kimmy: No, no I don’t think so. I mean, I just feel grateful because I think that I have a little bit more understanding of how to move forward in my own resistance.

Hollis: Wonderful. Well I hope that listeners hearing your personal experience will be able to see themselves in your experience and, you know, replace meditation with whatever it is that they're personally working on and hopefully be able to explore their own journey with resistance or picking up the process that they might have left it at some point. Thank you for sharing, and I look forward to having more conversations like this in the future.

Kimmy: Thank you!