Streak Stories

2,400 Days with Margot Olson

Introducing Streak Stories, a new series that celebrates Day One journalers and their recent milestone of consecutive days of journaling. Each interview features questions about how they built their journaling habit and their best tips for building a long streak. We also explore what they’ve learned from keeping a journal.

Margot Olson

Margot M. Olson recently crossed the impressive milestone of 2,400 consecutive days of journaling. As an analyst for the largest global consulting/financial firm, Margot lives in the beautiful “City of Roses” (Portland, Oregon). Margot has nearly 17 years of experience in Information Technology, and was also in the US Army in Active Duty, Reserve, and National Guard capacities.

In this interview, we asked Margot about the importance of journaling and for advice on how to build a long-term journaling habit.

How long have you been keeping a journal?

I have been keeping a journal/diary since 1998. It started with pen/pencil and paper, and then eventually I found the need to digitize everything, which was a Herculean task in and of itself.

I began using Day One back in November 2014, and have gradually back-filled days based upon a plethora of sources I had (this undertaking is still on-going to date!).

What makes journaling important to you? 

It stems from a couple of different sources really. During my formative years, my maternal grandfather always was journaling and it seemed important. Coupled with the fact that my entire family was active in The Church of Jesus Christ of Latter-day Saints, one of the most important teachings impressed upon me was to record my life.

The other major aspect of my life is that I am a transgender woman—which means I am living a kind of second existence now. Day One has enabled me to be able to vocalize my journey.

What do you usually journal about?

I suffer from severe ADD and OCD, and had addictions to substances that caused me to forget/not be able to remember many days that are now lost to time.

This is a lengthy way of saying I journal about anything and everything I can in my life – minutiae, dreams, important mailed papers, receipts, etc. There is literally nothing that I won’t put in my assorted journaling.

When do you journal each day?

There is no real set timeframe, though I do have hourly reminders set for every hour from 0700-2200 (7:00 am – 10:00 pm).

Really, it depends on what is going on for any particular time.

What tips or advice would you give others who want to build a journaling habit/streak?

This really is dependent upon each person, honestly—what is important to them and why—and then creating some “future-proofing”—setting up loosely-defined criteria and expanding/refining that as time goes on.

What have you learned from keeping a journal for over 2,400 days?

What a question! I really don’t know how to answer this except that I love to see how my life has ebbed and flowed and have gained deep insights into myself.

What is your favorite thing about the Day One app? 

“I love to see how my life has ebbed and flowed and have gained deep insights into myself.”

The ubiquitous nature of it and how you absolutely can mold it as a dynamic tool for your life.

How has Day One helped you journal consistently for 2,400 days? 

It has allowed me to “defragment” the many digital odds and ends that represent aspects of my existence.

What else you would like to share about your journaling streak? 

It has taken a LOT of time and effort to ensure that the digital story of my life and existence is expressed in the most accurate way I can.

Ultimately, Day One is an amazing, digital tool/service that is there for you to mold and bend to your desire and needs. At 45 active, individual journals, I can honestly say that Day One is my most-used app and service.

Start Your Journaling Streak
with Day One

The Day One journaling app makes it easy to build and maintain a daily journaling habit. Daily journaling reminders, daily writing prompts, and journal streaks are designed to help keep you motivated and consistently journaling.

Did you recently cross a journaling streak milestone? We’d love to hear your story! Tell us your Streak Story here.

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