21 Day Journaling Course Day 0: Set Up For Safety and Success

Some simple tips to help you enjoy journaling so you don’t need willpower to continue.

Habits and permission to explore are heavily predicated not on repetition of an action but on how we feel when we perform or complete said activity.


So let’s set ourselves up to have the best chance of enjoying this journey. And if cultivating a daily habit is in fact, one of your goals, I’ll show you how you can stack the deck in your favor.

Let’s work our way through our journaling success checklist:

  1. Safety: A shocking number of people who want to journal but don’t are folks who’ve had their privacy violated in the past. In order for journaling to be healing and deep, it needs to be safe. Which means you need to take an honest look at your circumstances and create that safety for yourself.

    You might choose a hiding place for your journal (like your purse or a locked drawer), you might choose a locked journal (on that literally locks shut and has a key you can wear around your neck or a combination lock).

    You might also want to have a conversation with anyone who you believe might violate your privacy and explain your wishes to them. If, in doing this, you get the sense that they wouldn’t respect your privacy, you’ll need to take additional precautions, like using locks or finding hiding nooks. And (I need to say it), evaluating whether your relationship is a healthy one.

    No matter what, do NOT let anyone rob you of your safe space. Get creative and find a way to connect with yourself and keep your thoughts safe.

  2. Your Journal: Do you have a journal you want to spend the next 30 days in? Do you love it? Is it too fancy where you feel like you can’t be your true messy, imperfect self in? Get one that’s simpler then. Dollar Store or Target notebooks can often be just what the doctor ordered. Remember, once you shift your relationship with journaling, this particular choice won’t feel as fraught. More on that later in this course.

    Is it half written in and carrying the weight of projects past? You have permission to start a fresh one.

    Does it have paper that’s really nice and smooth and a pleasure to write on? No? Get a different one. Or start in this one so you don’t procrastinate and get a nicer one as soon as you are able.

    Find some suggestions for choosing a journal here. We’ll need a blank one for this process since the course itself is the “guide”.

    A note on journaling on a keyboard or phone:

    You can absolutely journal digitally if you prefer, but know that one accesses different thoughts when one puts pen to paper and handwrites. I’ll share the science and studies deeper in the course, so you can decide for yourself if it’s worth the discomfort of building these neural pathways and hand strength. For now, choose whichever path is easiest for you but know that enduring the discomfort of handwriting might very well be worth it so try and stay open to trying it.

    Oh, and no matter what you choose now, you can always change your mind later.

  3. Your pen: This may seem Captain Obvious, but having a pen that you freaking love can really help reduce your resistance when you don’t feel like journaling some night. I love using fountain pens personally, but I have a “no scratchy pens allowed in the house” rule.

    Oftentimes, I feel like I have absolutely NOTHING to say but get started purely to enjoy the feeling of moving my fountain pen nib over the page. It’s silly but it works for me and seems to work for a lot of the folks I’ve interviewed.

  4. Your environment: At some point in the future, when your relationship with the process is solid, environment will matter a lot less and you’ll be able to journal everywhere. But in the early days, you need to design for pleasure and comfort.

    Think about where you can journal so you’ll be comfortable and safe and hopefully uninterrupted (more on that in the next section). Where do you like sitting and is it ergonomically sound (so you don’t get up from your session with a crick in your neck or a sore back)?

  5. Schedule: This is a biggie. Even veteran journalers like me can get derailed when there’s a change in routine. Oftentimes finding a nice place to park your journaling habit can take some trial and error. Most people design their schedule for an ideal day and then fall down a guilt and shame spiral when things inevitably collapse. And this deters them from trying again.


    Instead, imagine a really crappy day. Where you’re likely tired or overwhelmed. When would you likely journal on that day? Is it on the subway on your way to or from work? Is it while the baby is napping? Is it at the end of the day when your kids are in bed? Is it at 5am before life gets frenetic? Is it sitting in your car before you commute home? Is it right when you get to your desk after kids have been dropped off at school and before you dive into email? Is it on your lunch break to center yourself so you eat mindfully and support your weight loss goals?

    There is a core mindset shift that is required to make journaling (or any transformative habit) stick:

    Remember, you’re going to be guessing at first. Your reality might not match up. In order for any long term change to happen, you must give yourself permission to fail.

    And fail frequently.

    And be such a good, true friend to yourself that you will continue to try even after your hundredth failure in 4 days. There is no limit to how many times you get to start. No limit to how many times you course correct.

    Remind yourself that more than wanting to journal, what you’re really after is to be a true friend to yourself. There’s no statute of limitations on that.

  6. Volume: How much you journal each day is going to vary wildly. This is normal. Don’t do that silly overachiever thing and make it all or nothing. Examine any unconscious word counts or milestones you might be carrying without realizing it.

    Based on behaviour science, I highly recommend that you commit to no more than ONE SENTENCE PER DAY.

    I know, that seems almost stupid. Like what could you possibly get out of writing down just one sentence?!

    Read this article by habit guru James Clear on the benefits of writing just one sentence each day and what it did for Oprah herself (though, as we’ll discuss on Day 2, the true goal of this program isn’t to have you create a journaling habit). It’s to become a better friend to yourself.