Day One / Blog

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 750words.com) 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).