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.

Day One Encryption

(Repost from Medium)

When Day One launched in 2011, I knew that privacy would be an essential part of a great journaling app. We pour our deepest thoughts and feelings into this app, it should give us the assurance these remain private and secure.

In 2015, we launched Day One Sync as a replacement for iCloud and Dropbox sync, knowing we wanted to eventually offer web services (IFTTT, API, etc.) and applications on other platforms (Web, Android, Windows). Most importantly, it was the only way to create a proper solution to our most requested feature, end-to-end encryption.

We set a high bar for our small team, sync is hard, encryption is hard. It took two years for us to complete this project. During this time, we continued to move forward reading every 1-star review requesting encryption come sooner.

Today, I’m pleased to announce Day One Sync with private-key, end-to-end encryption is now available in version 2.2 of the Mac and iOS apps.

Day One is a trusted source for your personal data, thoughts, ideas, dreams, memories, etc. You own your data.

Day One iOS App Security Settings

“End-to-End” is a journal settings toggle alternative to “Standard” encryption on a per-journal basis. This approach allows us to continue developing additional applications and services for Day One, like our web and Android apps (curently in beta), without requiring the advancements of our encryption design. We will expand support for end-to-end encryption to all applications in the future.

You can learn more about end-to-end encryption, including our 3rd-party audit in our FAQ.

Thank you for your ongoing patience, trust, and support.


Day One iOS App Security Settings

The Way I Journal: Amit Gupta

Traveler and entreprenuer Amit Gupta doesn’t want to miss a moment

Photo Credit: Helena Price

Who are you and what do you do?

My name is Amit Gupta. I’m a designer, entrepreneur, and occasional investor. I’ve worked on a lot of different things — started a couple companies, helped start a non-profit, wrote and contributed to a couple books, started a coworking movement called Jelly, and starred in a TV commercial with my dog. Most recently, I ran a company called Photojojo, which I sold a couple years ago.

When and why did you start journaling?

Doogie Howser. I loved that television show, and loved even more how he ended every episode by making pithy & poignant observations about his day on his computer. I started journaling on an Apple IIGS after seeing that show. I gradually went from that to paper, to a Newton MessagePad 2000, to a Mac.

What is your journaling routine?

I journal sporadically. I’ve gone months where I journaled daily, and I’ve gone months without journaling at all. Nowadays, I’m journaling when something momentous happens and I want to remember it.

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

I like to write stream of consciousness for the most part. Similar to the Morning Pages practice of simply sitting down and writing whatever comes to mind. It’s a lot of personal reflection that effectively helps me think through things going on in my life.

Occasionally what comes to mind is a business idea or an essay topic, so I write on that.

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

For the past couple years I’ve been traveling nearly non-stop. Spending only days or weeks in a place makes it difficult to develop habits.

When I was living in Portland for four months last year, it was first thing on the kitchen couch after breakfast each morning. I didn’t let myself leave that couch until I’d written for at least an hour.

Establishing a morning routine that includes journaling has been the most reliable way I’ve found to keep it going.

What was your first entry in Day One?

I’ve actually imported journal entries, the ones I could find, from other platforms, text files, websites I used to journal (like my friend’s and even scraps of paper I found rooting around in my childhood bedroom.

So the first entry I have stored in Day One is from June 1997, and it’s a very emo letter to my future self from when I was 17, about to go off to college. I confessed my high school crushes, described in detail my first kiss at summer camp when I was 15, and talked about how I wasn’t going to go to prom, but that when I was a “famous geek or TV/movie star” I’d tell interviewers I didn’t go to prom as a badge of honor. Apparently I also really hoped that Newton would win out over Windows CE.

The first entry I typed into Day One itself is from 2012. It was the day before my brother’s wedding and I jotted down notes for a wedding toast I wanted to give.

How many entries do you have in your journal?

458 entries, 299 photos.

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

I love how simple it is and that my entries are synced everywhere. I like adding photos, but I wish I could add long videos.

Photo Credit: Stephan Ango

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

iPad. I find it to be a perfect full-screen, distraction-free writing environment. But I use it on all three.

Do you follow any journal organization rules?

I’ve try to end each entry in my personal journal in recent years with one thing I’m grateful for. That one snippet has been an interesting way to look back at the changes in my life from day to day.

I’ve started to practice creative writing recently, and I’ve started a second journal that’s more of a daily log of that process. There, I’m recording I’m doing each day to improve writing, links to things I’m finding helpful, etc.

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

I find it really helpful to go back and understand what I was thinking or feeling in the past about certain things. We tend to rewrite our personal histories in head. How we feel or think today is how we assume we’ve always felt or thought. But real life is so much messier. Looking back and understanding my evolution helps me understand my weaknesses and be a more forgiving and generous person (towards others and towards myself).

Why Multiple Journals Are Better

A few weeks ago, I talked about how creating multiple journals was an essential tip to developing a journal habit.

The premise was pretty simple: If you have multiple journals, it’s easier to to know what is and what is not a journal entry. In my experience, with one journal, it’s easier to forego completing a journal entry in the sake of maintaining a uniform journal than it is to actually write the journal entry.


Of course, there are other reasons to maintain multiple journals. Here are a few that may help you get into your journal rather than wishing you were in your journal.

1. Search and Find

Unless you use a digital journal like Day One, searching for a specific entry can be a nightmare.

For instance, I find I am at my most creative when I use a pen and paper to brainstorm. If I put my brainstorming sessions into one, over-arching journal, going back to find that brainstorming session can be incredibly difficult if I don’t remember exact dates or know exactly where to look.

I’ve found breaking apart my giant, catch-all journal into specific scopes and topics can simplify finding old information. Of course, you could use a digital journal and do a quick “CMD + F” to find a term anywhere in your journal, but this might not be how you work at your best.

For anyone using physical mediums to maintain a journal, creating multiple journals will greatly expand your ability to find old entries.

2. Cues and Indicators

If each of your journals has a specific scope, determining when to write in your journal becomes much easier.

Let’s say you keep your own personal “Movie Reviews” journal. What better time to write that review than moments after you watch the movie, right when you are digesting the hard-hitting climax of the story? The ending of the movie or walking out of the theater can act as a sort of “trigger” to ensure you write in your “Movie Reviews” journal.

Triggers or cues to write can occur throughout the day, which makes having a quick access journal fairly necessary. If you’re into physical mediums, keeping a small memo book in your back pocket works quite well. Or, again, if you keep your journal inside a digital format, having your iPhone handy is the ultimate way to capture a journal entry when the trigger occurs.

3. Efficiency

In all honesty, designating a set time of the day to journal is a very inefficient use of time. Days and events change, and changing up your schedule just to ensure you have journaling time is, well, a waste of time.

Maintaining multiple journals is a far superior way to use your journaling time efficiently and effectively. If you have a journal at the office, you can undertake any work journaling at a downtime during the day. If you have a photo journal, you can snap a photo and create a journal entry on the spot, or, if you have a travel journal, you can add entries as you go through your day rather than at the end of the day when you’re exhausted.

4. Multiple Formats

This one is as self-explanatory as it gets — both physical journals and digital journals each have their own shortfalls, so maintaining at least one of each should be the preference.

Don’t have a photo printer? Keep your photos in a digital journal. Same goes for travel maps, water consumption tracking, or workout routines.

If you’re a creative type, keeping your drawings and sketches inside a physical drawing book seems pretty natural. Spare notes and messages may also call for a physical notebook.

Whatever the case or however you work, maintaining multiple journals comes with a nice side effect of being able to cross over mediums and platforms with relative ease.

5. Growth

I’m a stickler when it comes to uniformity and consistency in my journals — all journal entries within a journal need to look the same, or have the same types of content, or have the same general theme. As life changes and new themes occur, I need room to expand my journaling habit to fit the new type of content.

In my experience, adding a new journal is a lot easier than going back and trying to reformat everything with the new type of content inside. For example, if I have a “Travel” journal but want to add photos to the journal, it’s easier to create a new “Travel Photography” journal than it is to go back and insert photos into every entry.

Obviously, this might be an example for the most obsessive journalers out there. But the idea applies: It’s always easier to add a new journal to your habit than it is to go back and try to fix old entries. What’s done is done and the past is in the past — creating a new journal for going forward is always the best option.

In The End, It’s About Journaling

Maintaining multiple journals may not be for everyone. My mind works in compartments, with clear, delineated lines between different spheres of my life. One general, catch-all journal just doesn’t fit how I think or work, and I suspect many people would feel the same way.

If you work best by putting everything into one giant journal that encompasses all areas of your life, more power to you. I just want as many people as possible to know the power of keeping a journal.

But if you think keeping multiple journals might improve your journaling habit, there’s no better digital platform for journaling than Day One. I mean, it even has “Multiple Journals” as a headline feature in its latest update. You can create as many journals as you’d like and not have to worry about carrying them around everywhere you go.

Pretty efficient, if you ask me.

Journaling Can Jumpstart Your Creativity

Journaling Can Jumpstart Your Creativity

Practicing creativity can be difficult, but keeping a journal is a great way to make creativity a daily habit.


As a writer and graphic designer, it’s a skill I consider integral to my work. Every day, I’m asked to create something that will inspire others to take action. If I’m not creating something, I’m not accomplishing anything.

If you’re not a writer or designer, don’t worry! Creativity is integral to your work as well. Beyond the world of artists, writers and musicians, creativity is solving problems, identifying patterns, and using information in new and unique ways. The most successful people I know are highly creative thinkers. These people also know that creativity takes practice.

Practicing creativity, however, is difficult. Often we’re expected to be creative and given no time to practice. This is where journaling can come in handy. I have found that when I keep a record of my thoughts, ideas, and experiences, I am more likely to apply my creative skills to my daily tasks.

Here are five ways keeping a journal has helped me improve my creativity:

1. Record your best ideas

“Keep in mind that ideas are generally fleeting and must be captured as they arise. Some will hang around and let you mull them over, but most are like a flash of lightning and need instant attention.” –Bill West, The Imagineering Workout

I know—this one seems obvious. What else are journals for? However, I’ve found huge creative value in keeping a record of things I’m thinking and doing. Often my best ideas come when I’m not able to act on them. There have been countless moments when I have sat down to write something and wasted most of my time trying to remember the idea I had in the shower that morning. Writing down inspiration when it strikes is the fastest way to build a library of your best ideas.

2. Practice thinking freely

“The best way to become a producer is to sit down every day and create. If you do that enough, you’ll consistently open yourself up to creating awe-inspiring work.” –Blake Powell

If creativity is the process of making connections and solving problems, a creative person should be used to thinking freely. Journaling is a great way to let your ideas flow unhindered. Whether that involves a daily dump of the day’s accomplishments, jotting down your dreams in the morning, or an evening creativity exercise, giving yourself time every day to think freely without any fear of judgement will improve your ability to generate ideas freely on a regular basis.

And, as a bonus, you might be able to add to your library of best ideas.

3. Refine your best ideas

“Just (make) something. It might be something crummy or awkward or not ready for prime time. If you make something, you are creative.” –Sonia Simone

Sometimes it’s easier to create ideas than it is to act on them. During my freshman year of college, I began writing recaps of college football games. These recaps were crude at best, but more than anything else, this weekly exercise in critiquing helped me learn how I write. I learned how to research a topic quickly, the importance of letting my thoughts collect, and the art of editing my writing. I found my writing voice by consistently expanding on one of my best ideas.

Like the exercise of letting your ideas flow, a journal can be a great place to practice a specific creative goal. Take one of your best ideas and flesh it out. Start setting goals to help you bring that idea to fruition. Recording your progress on a regular basis is a great way to remind yourself that you are a creative person.

4. Trigger your best ideas

“Creative refers to every single aspect of life, not only what you do, but how you do it, and how you think about the world.” –MK Haley, The Imagineering Workout

The greatest enemy of creativity is the dreaded rut. It’s very easy to get into a routine and forget the benefits of free thinking. Keeping a journal is incredibly useful when I’ve encountered these ruts. By keeping a log of what I do on a regular basis, I have a record of what might have gotten me into that rut. I also have a record of where I was and what I was doing when some of my best ideas arrived. I can analyze my routines and discover what got me into a particular rut or I can recreate a specific creative environment. Journaling helps me make creativity a process instead of a checklist.

5. Refill the tank

“The brain is like a muscle — sometimes it
needs to be relaxed.” –lazyguru

Creative thinking is hard work. Often, when I’m in a creative rut, I’ve found it’s because I need to take a break. You can only create something if you have the resources to make it. Just like a journal is useful for recording your best ideas, a journal is also useful for relaxing. Meditate on your experiences. Pick up a new hobby and document your progress. Take a vacation and keep a travelogue. The best creative thinkers know when to take a break. Keeping track of those breaks in your journal will make them more memorable and effective.

Creativity is waiting

These five tips are just a few ways that keeping a journal can improve your creative abilities. The most important piece of creativity is regular practice, and keeping a journal is a great way to ensure that practice happens. Start journaling, and make creativity a habit instead of a talent.

The Way I Journal: Kelly Hodgkins

Who are you and what do you do?

My name is Kelly Hodgkins. I am a journalist covering the outdoors sector and cutting edge technology for Digital Trends. I also work part-time as the Program Coordinator for the Western Foothills Land Trust.

When and why did you start journaling?

I started journaling a year ago when I started the Maine Master Naturalist program. This year-long program trains individuals to become naturalists — teaching them about the bugs, trees, plants, animals and more that are found in Maine. The overall goal of the program is to produce trained naturalists who can share their knowledge with the community by leading nature hikes, writing blogs and so on. The 12-month-long class required me to keep a nature journal — I had to document flowers, identify trees, and track seasonal changes at a natural site, which for me was a local pond. I ended up using Day One for everything — I used it to log more than 50 flowers, identify 30 trees, and record the seasonal changes I saw at the pond. I even used it to do my homework exercises and to create study guides for each quiz in the course.

What is your journaling routine?

I write in my journal at least weekly, sometimes more. I often use my iPhone to record in the field and then finish the writing at home on my Mac.

Do you focus on long-form writing, or in capturing small memories of life?

It’s a mixture — it’s mostly catching the little things and then doing some long-form writing when I have the time. I also do a lot of sketching on my iPad and import those sketches into Day One as well.

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

Yes, anywhere outside that is quiet. In the forest, in the fields or at the edge of a pond.

What was your first entry in Day One?

My first entry was a photo of a tree growing on a rock. I used this photo to illustrate and describe the ecological layers that created such an unusual place to find a tree.

How many entries do you have in your journal?

Over a hundred.

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

The ability to import a photo quickly and easily. I also appreciate the location and weather information. These can be handy when trying to figure out why I saw a bunch of deer one week and none the next week.

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

I use a combination. I use my iPhone to capture photos for Day One. I use my iPad to draw sketches that I import into DayOne. And finally, I return home to do most of the writing on my Mac.

Do you follow any journal organization rules?

Not really, I write when and how I feel in my main journal to keep it stream of consciousness. I do add tags to help find entries more easily. I also use more than one journal — I have a journal just with flowers, one with just trees and so on.

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

All the time! It’s great to be able to look back and compare last year to this year. For example, I first saw the Indigo Bunting bird in April last year according to my journal, but this year, the Indigo Bunting didn’t appear until Mid-May due to the colder weather. I also use it to look up passages that I had written — one time I wanted to recall a detail about an otter’s behavior that I learned in class. I searched and found the answer in an essay I wrote six months ago. Invaluable!

Journal from here, there, everywhere.

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Day One app on iOS and Android devices

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