56. How to Establish a New Habit (w/compassion!)

Join me this week as I share exactly HOW I create new habits compassion and self-kindness. I share:

  • My exact four step process
  • How to uncover WHY you want to have a specific habit, and what knowing WHY opens up for you
  • How to make a habit so easy to do you’ll still do it on your busiest days
  • The habit tracking process I’ve developed, tinkered with, and refined over the past 10 years

I walk you through step-by-step, telling you where to pause me. Give establishing a new habit with compassion a try – I tell you exactly what to do, and where to pause me, along the way.


  • In today’s episode, I mention the Daily Writing Prompts that I created – they can help you establish a daily writing practice that is easeful and fun. They are an amazing way to discover what you believe deep down, and befriend yourself along the way. Learn more HERE
  • Tap into your intuition before making creative work. Sign up for my newsletter and receive my Intuitive Journaling Prompts – four questions to connect with your intuition before making art. Sign up HERE

If you enjoy listening, please subscribe, rate and review, and forward this episode to a friend who would benefit from it too.

Let’s become a generation of creative women who are examples for the people in our lives of what it looks like to prioritize our work (AND recognize our impact).

x, Jen

Full episode transcript below:

Welcome to today's episode, How to Establish a New Habit. 

Today, I'm going to share exactly how I establish new habits. I have found the best success in creating a sticky habit happens when a few things are going on -when you know why you want the habit, when you make it really easy to do, and when you set yourself up to check in and track it for yourself. 

Last week I covered, in-depth, uncovering why you want a habit and also how to make it easy, so if you want support around that, go back and listen to episode 55, and then come back and listen to this one to learn exactly how to break it down and track it. 

Okay, here we go. Here's how I establish new habits:

 the first thing I do is I think of things that I want to start doing, and I make a list. Sometimes there's one thing that I'm thinking about, sometimes there's a lot of things. And I think that especially happens around transition so like when you would start a new school year, if you were still in school, or in the new year, or around your birthday, or a milestone. 

So, whether it's just one habit or there's a lot of habits that you're thinking about, list them out, like actually take the time to write or type them out. 

 And then once you've done that, and if you're doing this along with me, which I would encourage you to do - I think it's helpful to have the built-in accountability - you can just pause me, complete the step that I share with you, and then come back and press play when you're ready for the next bit of information. So, if you're doing this in real time, pause me right now and make that list of habits that you're thinking about. 

And then the second step is take a moment to pause and consider: why do you think you want to do these new habits? And if you've tried to do them in the past, why haven't you done them? That's like a two-part question. So why do you want to be doing them? And then if you have been trying to establish this habit, or you've tried in the past, why didn't you do them? There's lots of wisdom in there. 

What need might this habit be meeting for you? 

And then this is such a good question, this is a great question to consider whenever you want something, whether it's a habit or something else,    whether it's an achievement or an object or to do something or identity, whatever: who do you think you'll become? If you have this habit fully intact? Basically, who do you think you'll become if you get this thing that you want? In this context, we're talking about habits, it applies to a lot of other things, too. 

 It's really important to know the answers to these questions. They will uncover your inner motivation, your intrinsic motivation for wanting to have, or do, these habits. And also they will be fuel that drives you to show up for the new habit when you're working on establishing it, and making it sticky. 

Okay, so again, pause me right here if you're going to answer those questions. 

Okay, and so now I'm going to review. So the first thing you did was make a list of habits. And the second thing is you paused and considered a few questions to get at your internal motivations for these habits that you're wanting to establish. 

And now step three is you're going to put on your experimenter hat and brainstorm. With the list of habits that you're considering, do you foresee any challenges? What are they list them out? 

An example I can think of is let's say that you want to write first thing in the morning. 

But you know that you have, maybe you have little kids or you have to get up early and go to work, or you just know that you don't have a ton of time in the morning. That's a potential challenge. 

Okay. So once you have evaluated the potential challenges that you foresee right now, then I want you - this is where your experimenter hat comes into play - I want you to consider this question: how might you solve for these challenges? What are two to three things that you could do to support yourself, to make it easier, to make it smaller, to solve for the potential challenges that you're first seeing? 

And I just want to say here - you will run into roadblocks and challenges. 

If you weren't going to, then it would be the most easy thing in the whole world to create a new habit, but we all know that it takes perseverance and some time to make a new habit sticky - to have it - as like something that's just in your arsenal. 

So this step, you might be feeling some resistance to it, and I can actually see that myself, like several years ago, I would have been feeling resistance because I'm like, I'm not going to have any challenges. This should be like easy and fun and great for me to do. But now I know that when we try to change the status quo, we're going to run into some challenges, whether it's logistical in our life or whether there's some internal resistance or internal growth edges that are going to be rubbed up against. 

So planning ahead for the challenges, the roadblocks, will help you navigate them. 

And this is important for you to build self efficacy, self trust, that you give yourself the gift of planning ahead and foreseeing some potential roadblocks. And knowing that you can navigate them if you know what they are, you can also navigate them real time, but if you know, a little bit ahead of time, you may be able to support yourself at navigating them. 

And that is one way of building that self-efficacy and self-trust that we're all desiring, rather than getting caught up in life or getting overwhelmed or trying to do too much at one time or too much at once as far as new habits go. And falling off, I put that in air quotes, falling off, and then believing that you are someone that just can't do this. That's not available to you, or it's not available to you right now at this stage of life. 

 Okay so, if you're doing this in real time, pause me right here and go through your list of potential habits that you're considering, and then putting on that experimenter hat - so we're dropping judgment and we're just going into like experimentation, problem solving, if this was a puzzle or a game how might I figure this out? That's the ethos that I'm encouraging here. Answering the question: do you foresee any challenges? What might they be listing them out? 

And then once you have evaluated the potential challenges, then answering the question, how might you solve for these challenges? What are two to three things that you could do? Per challenge. And getting creative.  It doesn't even have to be something that you think you would necessarily do, it's just, let's like, look at this really creatively as like creative problem solving and seeing what wisdom comes up for you. 

So pause me right here. If you're going through this in real time. 

Okay. So, so far, I'm going to review this again because I know this is a lot of information and this is presented in an audio format, so I want to make sure that we're continuing to review it so that this information becomes sticky. 

So far you've listed out your desired habits. You've uncovered WHY you want to do them, and if you have a history with them, why you haven't done them in the past? What need they might be meeting? Who do you think you'll become? Getting in touch with that intrinsic motivation. You've thought through potential challenges and you've created a list of possible solutions. 

So now that you've done that. Now I want you to go to that list of habits and I  want you to go through the list of habits that you're considering and narrow it down to four. 

I strongly, strongly encourage you to do four or less habits at one time. 

 You know yourself best and you might actually do best if you let yourself start with just one, or you might be someone that likes variety and  you might enjoy having three to four, and they may be something that you do daily-ish - this concept that I created where you don't necessarily do it every day, but you do it daily ish. 

I say no more than four, because I want you to set yourself up for success. And limiting yourself to four  requires temperance. And temperance will help you systematically build the experience of your life that you want. 

Temperance is kind of the opposite of rushing and urgency and just like overwhelming yourself by trying to do everything at one time. Instead it's like a brick by brick process, right. You're going to create up to these four habits, make them sticky, and then you can invite in another habit or a couple more habits. 

And we're like slowly turning the ship instead of like, big ships do not turn like 90 degrees in one turn of the wheel. They  change direction, a few degrees at a time and they end up in a completely different place. I think that that's such a beautiful metaphor, actually, for this idea of creating new habits. 

You can get to an entirely new destination by just allowing yourself to slowly migrate, or it's slowly turn, towards it. You don't need to like do a 180 turn in order to end up in a completely different place. And actually this is a side note, but that would probably be very jarring for your nervous system and might not actually be the experience of life that you want. So that's like probably another topic for another time, but just wanted to include that. 

  I want to emphasize again, to please trust me. I don't try to squeeze extra habits in. The whole reason why you want to start a new habit is an act of care for yourself, right? So trying to do too much at one time is not actually in service of that greater goal. There's no rush and there's no hurry. 

You have time and you can experiment if you give yourself this space and this temperance to move on this path. And allow yourself to experiment and move at a pace that feels good in your nervous system. You will continue to build these new habits, you can work on that whole list that you created. But you can let yourself do that over a period of time, rather than trying to do it all at once. 

This is a tip from episode 55, but one of the most important things you can do - I guess I should say I explore this in depth in episode 55, but I'm going to mention it here too. One of the most important things you can do is to scale each habit down to the smallest step that you can take.  I'm going to share some examples with you. 

So a really common example that I hear around this is if you want to start flossing your teeth every night, then you just commit to flossing one tooth before you brush your teeth. 

That sounds really silly, but if you're like not a flosser and you start thinking about, you just feel, start feeling all the resistance to flossing your teeth. But if you I'm sure, actually, as I say that you can feel that in your body. Instead, if you just consider like flossing one tooth, it's like, yeah, no big deal. Most likely you'll keep going, but you're committed to just flossing one tooth. And here are some of my examples that I have experimented with in the past,  some of them became habits and some of them didn't: read one page of a book before looking at my phone, read one page of a book before watching TV. 

I've done all sorts of experiments with meditation and length of time, and one of them has been just one minute of what I think of as being time. So being with myself rather than practicing a specific type of meditation. 

 And if there was any resistance, right? I'm going to go with this flossing one tooth versus flossing all of your teeth, so if one page reading one page before looking at your phone or watching TV, you start to feel any resistance to that, then you would scale back to one sentence. 

 you felt resistance when I said one minute of being time, then you might scale back to 30 seconds.   Another one that I teach with the writing prompts that I have, and The Daily-ish Writer program that I have, is to write the day and the prompt and one sentence.  And that fulfills the requirement of daily-ish writing, right. 

We're scaling this way, way down. That doesn't mean that every day that's all you do, it just means that even on the busiest days are when you have a lot going on or you just feel 'whelmed' by everything, you can still succeed at the habit by doing these smallest, by achieving that minimum baseline. You still won at the habit because you set yourself up for success by creating these minimum baselines that are the threshold for success. 

Okay so if you've been working along with me in real time, while you're listening to this, you now have your up to four habits that you want to establish. And now I want to share with you my favorite way to track habits.

Tracking is so important is what keeps you on task and actually keeping them top of mind so that you remember to do them. And after many years of experimenting, I come back to a very simple tracking method. The simplest. But it's simple and functional and that's exactly what you need for a new habit. You don't need something that's exciting and difficult. And something that you're just going to forget to do actually. I mean, that's such a huge part of it is just keeping it top of mind. 

So my favorite, oldest way of tracking my habits is really simple.  

I'm going to explain exactly how to do this.  So I create a table in Excel or in Google sheets and I list my habits in the first column. The habits that I'm keeping track of either habits, I already have new habits, you get to decide how you want to do this. 

And then in the very first row at the top of the table, I list out the days of the month. I like to do this by the month so right now this is September. So. Today is September 20th so I would list out September 20th through September 30th, and then I would create a new one for October. That's how I like to do it, you can do it however you want. 

 Then I create the outline of the table so that each cell is outlined. And I printed out at less than a hundred percent, and how small it depends on you. But I want it to be on ideally half of the page. I like it to be small. 

And then I keep that Google sheets table on my end table. And every night before getting into bed, I check off what I did. 

It's so simple, but I have so many of these tables from the past 12 years. It's just my favorite way to track. 

 There are definitely higher tech ways of doing this and fancy apps and all the things that you can pay for now but I like the physical reminder and the analog nature of tracking this way. It works for my very visual brain. 

 Okay, that's what I have for you today. If you have a habit that you want to create, act on that energy and excitement and give this method a try. All you have to do is go back to the beginning and then we'll do it in real time together. And I love doing things like that with that built-in accountability. And as always, I recommend that you give my way, the way that I shared with you today, a try, and then adjust it and make it yours. And test it and see if it works for you. 

I am so glad that you were here and that we get to walk our paths together. See you next time. Same time, same place. Bye for now. 



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