How to Start a Journaling Practice: Tips, Tricks, Rewards & Challenges

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For as long as I can remember I have always wanted to have a daily journaling practice. For some reason, this hobby has always held value to me. I’d envision myself curled up in the corner of a couch, writing in a beautiful journal, using a perfect pen that effortlessly highlighted the uniqueness of my penmanship, my thoughts would flow onto the page, over time notebooks would fill one after the other, and I would proudly display them on  a bookshelf somewhere. It’s a lovely thought, but in reality implementing a daily journaling practice is a little bit more…complicated. 

It took a long time but, finally, in 2015 I made my vision a reality: I began writing daily, and the notebooks and bullet journals did start filling up. I would like to share my journey to journaling in the hopes that it will help others cultivate their practice. So, keep reading! I’m about to share almost 20 years of tips and tricks, AND be totally honest about the rewards and challenges you’ll face along the way.

How to Start a Journaling Practice: Tips, Tricks, Rewards & Challenges

The Attempts

I attempted to become a diary keeper at least 10 times over my lifetime. The first few attempts were when I was a teenager, the majority of the attempts were when I was in my early twenties, and the last attempt (which was successful) was in my early thirties. Each attempt was met with a  brand new fancy notebook which would cost waaaay more than I am willing to admit  (I’ve had a fondness for fine stationery my entire life). 

As each day came to a close, I would write about it. I quickly realized that my day to day life wasn’t actually all that exciting. Exciting events accumulate over time, and an isolated daily page of writing doesn’t actually reveal all that much at the start.

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Remember: journaling implies handwritten. Truly getting into the details of your day using a handwritten medium is a time investment. Just filling one page, depending on the size of the notebook, can take upwards of 20-30 minutes.

The Realities of Keeping a Daily Journal

The First Reality: The Negativity Bias

Initially, starting a journaling habit is not nearly as rewarding as one would think. That is,  until you have a really bad day. Suddenly, you can’t wait to get home and write everything in your journal… to vent, to let it go, and have an audience that will always be on your side.

 On a bad day, I can remember picking up my pen and filling pages effortlessly. I’d write until my hand hurt and my letters became blurry from either exhausted penmanship or tears. 

When writing daily, there seems to be an involuntary pull to express the negative. Journaling is cathartic in this way. In my experience, I was always more likely to vent about a bad day than I was to brag about a good day. 

The Second Reality: The Joy is in the Writing, not the Reading

One of the beauties of journaling is that as you write you truly begin to get a sense that your thoughts are flowing freely onto the page. The pen that writes is the conduit to your innermost feelings. As you free write it feels like there could never be any errors. Unfortunately, re-reading entries will prove this feeling false. Hand written pages are not magically highlighted with spelling or grammar errors. I know I have a tendency to leave out words when I handwrite. Sometimes reading my entries can sometimes feel like putting together a puzzle.
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The joy in journaling is the writing, not the reading. I don’t suggest never reading your old  journals, but I would recommend allowing a few months to pass before venturing backwards into your experiences. Here is an excerpt from my journal regarding an experience I had re-reading an entry: 

 “Looking back, it amazes me how fragmented this is! At the time, I remember feeling like I was being so in depth. It probably took me well over an hour to write this [entry] ! Writing 6 pages felt like such an accomplishment, but now all I want to do is edit!”

Giving yourself time before reading will allow you to gain perspective and hindsight about what you were experiencing and feeling as you wrote.

How To Get Started: 3 Do’s & 3 Don’ts

Lets start with the Don’ts:

  1. Don’t use an expensive notebook. Investing in something fancy will put pressure on you to have a perfect journaling practice. You will feel like you need to write neater because you want to maintain the niceness of the notebook. Censoring your handwriting censors your thoughts. Get an ordinary notebook. Don’t be afraid to be messy, cross things out and carry it around with you. The more used and tattered your notebook looks at the end, the more successful your practice!
  2. Don’t let filling notebooks be your end goal. This was a trap for me. I was too future focused. I created an all or nothing statement in my mind that if I was filling notebooks I would then be an avid journaler. Writing is meant to be an activity that connects us with the present moment, which can only be measured in progress (not success or failure). My first filled notebook took about 8 months to complete!  
  3. Don’t write about your day. All of my ‘start and stop’ attempts at writing occurred when I was only filling my pages with daily events. Using a structured style of journaling can increase your dedication to the practice. I had much more success using journaling prompts to guide me (more about that below). 

And now the Do’s:

  • Do find a pen that you love. If you are going to be writing a lot you should love the way your pen feels and writes. Personally, I prefer finer tip pens (0.7 tip is my ideal). Finer tip pens are less likely to smudge because not as much ink is expelled with each pen stroke. Thicker tip pens and gel pens are prone smearing and bleeding through the pages of your notebook. This will annoy you, trust me!
  1. Do keep your journal in sight. You may have the urge to keep your journal hidden to protect your privacy, but if it’s too well hidden you won’t be reminded to write in it. Store your journal in a place where you will encounter it. I kept my journal in a bathroom cabinet for almost a year because I would see it every time I needed to get toothpaste.
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  2. Do use specific types of journaling. As mentioned earlier, writing about your day can be a trap. There are many types of journaling and all of them do reveal insight into your life over time, despite not documenting daily occurrences. Here are a few different styles of journaling to try:
  • Line a Day: Simply write one line a day everyday. Short, sweet and to the point.
  • Morning Pages: A writing practice that takes place first thing in the morning before getting out of bed. Without happenings to dwell on, morning pages can reveal clarity about what you’d like to accomplish each day. Morning writing tends to also have a more positive tone should you choose to re-read your entries.  
  • Gratitude Journal: Write 1 to 5 things that you are grateful for everyday 
  • Journaling Prompts: Answering daily questions that may or may not have a theme to them. Pinterest is loaded with various types of journaling prompts. For 3 years I used the same monthly journaling prompts. It was fun comparing how I answered each question differently from year to year. This is my preferred method to journal.

Almost six years later, I am happy to say that I am still journaling. Sure, my practice ebbs and flows but ultimately I am committed to it. I’ve allowed my writing to evolve and I use different styles of journaling for variety. I have now filled 15 notebooks. Just as I envisioned, I display them proudly as I hope one day you will too. 

By: Cheryl Tobin

About the Author

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Cheryl is the author of the blog Spiritually Premeditated. She describes herself as a spiritual enthusiast, avid journaler and wannabe morning person. She relies heavily on coffee and oracle cards to get through the day. 

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20 thoughts on “How to Start a Journaling Practice: Tips, Tricks, Rewards & Challenges

  1. I know that you recommend not using a fancy note book but those paper blank notebooks. They are some of the most beautiful notebooks I’ve ever seen and the only thing that made me journal consistently unfortunately too expensive to keep buying and justify not finishing them 😦 I just can’t stick journaling.

    1. Hi there! Thanks for reading 😊
      Yes, the journals in the pictures are quite pretty lol
      My journals have become simpler overtime. I usually opt for a Moleskine or Leuchtturm 1917 now. Nice paper, simple design, perfect size to carry around.

      Have you tried Bullet Journaling? Its a fusion between a journal/planner/sketchbook. Its quite fun and a great organizational tool.

      Thanks again for reading and taking the time to comment 🙂

  2. I love that idea! The um bullet journaling because sometimes I want to just doodle and I cant write something everyday. Not everyday is something you want to write down and read about later and it sounds pretty transferable from university planners. Thanks for that idea I may have to do it sometime. Yeah those journals are very pretty I always get stuck looking at them in the stationary section but get put off by the price a nice paper journal with a decent cover sounds like its probably the better option like you say.

  3. These are wonderful tips! I love writing in my journal daily, it has changed my life!
    Thank you for sharing your great advise.
    Alyssa
    The Sacred Space AP

  4. I could completely relate to this post, Cheryl.
    Just like you I’ve struggled with getting myself to journal regularly and finally fell into the habit when I devoted myself to writing a gratitude journal everyday.

    I completely agree journal writing isn’t as exciting on a daily basis unless you assign a theme to it. That’s why I have separate journals for my gratitude practice, fitness and daily musings.

  5. Good tips! I don’t do journaling but I am a diary keeper since 2005. I write a little everyday (not in the diary though). One nice notebook for that and two notebooks: one normal sized with all my research and work-related writings; and a small little booklet for my creative ideas and little tid-bits. It does get a little messy in the normal notebook 🙂

  6. I have the hardest time sticking to journaling. I start and stop and start and stop again. I know it’s a good practice though, if for nothing more than venting and focusing. I’m going to try again to incorporate this into my 2020 lifestyle. 🙂

  7. Reblogged this on DG Speaks and commented:
    These are some great tips to help you on your journaling journey. I have the hardest time sticking to journaling. I start and stop and start and stop again. I know it’s a good practice though, if for nothing more than venting and focusing. I’m going to follow these tips and try again to incorporate this into my 2020 lifestyle. Let me know if you do too! 🙂

  8. This is great. I journaled for my PPD, and just wrote letters to the baby when I felt overwhelmed. I used rainbow pens to set it up like a mood tracker. Really should get back into the habit. It helped my mood tremendously.

  9. I really like the gratitude journal idea. Having an attitude of gratitude, actually putting it in writing, can have very powerful positive effects on a persons life.

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