The Way I Journal: Kendra Wright

Blogger Kendra Wright doesn’t want life to whizz by

Who are you and what do you do?

Kendra Wright. I’m a writer at, a speaker and creator of The Year of Fear Project. I specialize in helping others break through uncertainty, take consistent action, and embrace the rebel they were born to be.

When and why did you start journaling?

At the end of 2014 after a pretty startling revelation. At a New Years event, I was asked to sum up 2014 in one word. That year I had tackled quite a few incredible memories, like starting my consulting business, buying a one-way ticket to live in a city I had never been to for a month, white water rafting, participating in the “World’s Longest Yoga Chain” world record, riding in a hot air balloon, getting my writing in front of hundreds of thousands of people, and so much more!

However, when asked to wrap the year up in one word in front of a group of people I felt guilty. The word I wanted to use was “underutilized.”

A few years earlier, had I seen my the hit list of accomplishments and experiences I would have in 2014 I would have been totally jazzed. Instead, I felt inflated.

I had a giant revelation.

We think life is vacations, trips, and big moments like buying a house or falling in love, but what I discovered is big moments are a small percentage of everyday life. Ten to fifteen percent if you’re lucky.

What happened in 2014 was between the “big” moments I was head down in work. All the days blended together. In 2013 I had created The Year Of Fear Project where every day for a year I did something new, different or outside my comfort zone. I made every day count in little ways. In 2014 I still did a lot of amazing things, but I didn’t stay as present daily creating new memories and lessons.

When I got to the end of the year, I realized that I only remembered the big moments. All these tiny accomplishments, experiences, lessons and memories were lost.

This lesson hit me hard and I made a pact that not only would I not let my life whizz by and be forgotten but I would also document it daily to keep myself accountable to create new experiences, remember the lessons I learn that I don’t want to forget, and watch myself grow.

This realization also led me to kick off my second “Year Of Fear.” I have now gone on to complete over 850 self-assigned comfort zone challenges (I track them in Day One!), and built an entire brand and online business that helps others do the same.

What is your journaling routine?

  1. I “active journal” throughout the day using the menu bar shortcut on Macbook. As things happen, whether that be accomplishments, experiences, or conversations I want to remember, I quickly jot them down so I can return to before bed to flesh them out. I use the mobile app on the go.
  2. I also paste text conversations, micro-pieces of content I write or create for the day that log my thoughts and lessons I’m learning or sharing with students since most of my content comes straight from what is happening in my real life.
  3. At the end of the day, my evening routine includes journaling. Some days I have a list of ideas or thoughts to start with by active journaling throughout the day. Occasionally, it’s a blank page.
  4. If it is a blank page, I pull out my list of “Daily Reflection Questions.” As I built my journaling practice, I found staring at a blank page to be uninspiring and wanted a way to avoid having writers block (one of the biggest reasons people cite not journaling).

A few of my Daily Reflection Questions are:

  • What was my favorite thing about today?
  • What am I looking forward to in my life right now?
  • What incredible gifts or lessons did life deliver to me today?

You can get the full list of questions here.

If you have a hard time journaling because you struggle with building from a blank page, create your own list of Daily Reflection Questions.

Pro-Tip: I suggest keeping your DRQ in a note on your phone or using Text Expander to quickly insert them into your journal. Pre-format your list with bolds, markup, etc and it will make your journal organized and beautiful.

Do you focus on longform writing, or in capturing small memories of life?

I focus less on how much I write and more on what I’m capturing. The number one reason I love DayOne is the tagging feature. Using tags, in a click of a button I can track what is important to me. I’m very self-devlopment focused so my tags reflect that.

  • #YearOfFear:self-assigned comfort zone challenges for The Year Of Fear Project.
  • #Accomplishments: to track when I hit goals or things I want to be proud of later.
  • #Lessons: these are things I learn throughout the year. These could be those I’ve learned personally, or big ah-ha’s others shared with me that I don’t want to slip away in the chaos of life.
  • #Travel: every time you travel and where.
  • #Quotes:powerful quotes you read or love throughout the year.
  • #Books:when you complete a book. I also like to add a summary of my big takeaways or pull a few of my favorite highlights from my Kindle.

Other items you may consider tracking:

  • #Moments:track incredible memories with your kids or significant other. It would make a great list to surprise them with at the end of the year. #Content:if you’re a creative, brainstorm content ideas in your journal on the go that you can later write or create.
  • #Milestones:small steps you complete along the way to a big goal

Pro-tips: When you structure your journal to track objectives that are important to you it makes doing your year in review a breeze. In two clicks you can see your accomplishments, travel, lessons you want to remember, etc.

I also recommend setting a reminder to review your journal once a month. It’s incredibly powerful when you’re taking actions toward goals. I’ve also been able to uncover why life has felt chaotic — we often forget all the things we are doing on a day-to-day basis!

Do you have a favorite spot where you like to journal?

Nope. Life happens everywhere. Although, in my bed at night in my PJ’s tends to be my go-to. I’ve found journaling the day of events is more effective. I’m more emotionally connected with what happened that day.

What was your first entry in Day One?

I documented a comfort zone challenge. It was the day I sent out a survey to my email list about creating my first digital product. The first three years as a blogger I made no money. I was terrified of selling. So this was a big step for me!

That survey was the start of what would later become my flagship course (Facing Fear) that now teaches students across 8 continents how to face fears, take action, and make time for what matters most to them in their life.

How many entries do you have in your journal?

867 entries, 157 photos.

What is your favorite or most-used feature in Day One?


Do you write mostly on the iPhone, iPad, or the Mac?

Both. I heavily use the shortcut menu to active journal during the day and the app when away from my computer.

Do you follow any journal organization rules?

Tags to make goals and priorities easy to track. In two clicks and I can see what is happening in my life (lessons, travel, comfort zone challenges, etc).

Journal daily so that I remember the small moments in life later. At the end of the year it is incredibly fulfilling to see how you actually spent your time and what you accomplished.

Have you ever relied on Day One for something unexpected, or used it to recall details about a specific event or date?

YES! All the time. I often track when I meet people. I’ve been able to recall when and where I meet people by searching their name for my journal. I also use it to search for powerful quotes I later want to recall for writing and recommending to students.

About Kendra Wright:

Kendra Wright is a blogger, speaker and location independent entrepreneur. Since creating the Year Of Fear Project in 2013, she has completed over 850 self-assigned comfort zone challenges. Kendra specializes in teaching others how to break through fear and uncertainty, productivity slumps, and create better work-life balance (without abandoning their inner hustle).

Get 100 of her simple and unconventional comfort zone challenges here.

Journal from here, there, everywhere.

Download the Day One journal app for free on iPhone, Android, iPad, Mac, and Apple Watch.

Journal from here there and everywhere mobile devices image.Journal from here there and everywhere mobile devices image.