How Writing to My Future Self
Changed My Life

For four years, I answered OhLife’s question: “How did your day go?”

Kara Cutruzzula
Human Parts

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A few weekends ago, I received a distressing email. Subject line: “OhLife is shutting down.”

Judging by my wailing, neighbors probably thought The Mindy Project was endlessly buffering. But no, it was just the sound of the last four years of my life crashing to an end.

For the uninitiated, OhLife.com is a free personal journaling service start-up, founded in 2010, that had one simple mission: to help people remember what happened in their lives.

This was navel-gazing for the laziest of lazybones. OhLife emailed users every day at a self-appointed time (mine was 8 p.m.) with the simple question: “It’s Monday, Sep 22 (or whatever the date was) — How did your day go?”

When users responded their thoughts were filed away on a website, accessible only to them via password. Every day I would receive OhLife’s friendly question. All I had to do was reply and then promptly purge the day’s events out of my mind.

At first it was a chore. Then I became freakishly diligent. I have 1,418 entries dating back to August 18, 2010 and can find what happened nearly every day for the last four years. (Yes, this is as horrifying, humiliating, and hilarious as one might imagine.) Some responses are brief: “ughhhh” or “worked 15 hours today” are frequent offenders. But others are whirlwinds about promotions, spontaneous trips, and those fantastic, once-in-a-blood moon kind of days when everything just works. Taken together, they chronicle the killer peaks and mundane valleys of a subject matter that holds interest for exactly one person: me.

I’m a newish convert to productivity/habit-forming exercises. Getting Things Done is my favorite cult, Zen Habits acts as a welcome port in the daily storm, and though I don’t outsource my life, I’ll admit Tim Ferriss makes some decent points (mainly about not checking email so often). However, OhLife is the only routine that has consistently stuck. There was no app to open. No public comments. The service brilliantly infiltrated email — the one place where every procrastinator hides — and every day, ever so gently, prodded you to record something. Anything.

After a year or two I began to see the appeal of my little nighttime introspection. Throughout my endless preaching about the site, friends usually volleyed back, “Why would I want to write down all the boring stuff I do?” But OhLife’s secret weapon was revealing patterns in mundane events; it was an ideal and persistent reminder to reflect on your own changing nature. At the bottom of every email was this illuminating bit: “Remember this? One year ago, you wrote…” followed by your entry from the same day last year.

OhLife’s emails were sneaky reminders of Steve Jobs’ 2005 commencement speech at Stanford during which he revealed his morning routine: “For the past 33 years, I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today?’ And whenever the answer has been no for too many days in a row, I know I need to change something.”

Yes, this may be a refrigerator magnet-worthy sentiment. But for people without the self-discipline of Jobs (or those afraid of their own reflections), OhLife laid it out in black and white. Here is the mirror. Here is how you spend your days.

Two years ago, after replying in a seething mood for too many consecutive days (fine, months) I had to ask: Was I happy? Do I like what I’m doing? It is very easy to keep your head down and trudge through a never-ending series of mediocre days. It is very easy to forget to ask yourself “How did your day go?” which is puzzling because, as Annie Dillard writes, “How we spend our days is, of course, how we spend our lives.”

And so I stopped doing things that I didn’t like. Maybe don’t get roped into office politics so ruthless they’d make Olivia Pope lunge for the nearest bottle of red. Maybe don’t work in an office at all. I started paying attention to the entries where I sounded happy and fulfilled, and began doing those small things more often. Run. Call your grandparents. And for the love of god, eat breakfast. The annoyed responses lessened, which was nice, considering I was my only reader.

Perhaps the key to a happier, more productive life is to participate in self-imposed therapy sessions — to make a conscious effort to reflect on what it is we actually do every day. It’s a task that’s easier said than done. As George Eliot’s Middlemarch observes, “If we had a keen vision and feeling of all ordinary human life, it would be like hearing the grass grow and the squirrel’s heart beat, and we should die of that roar which lies on the other side of silence. As it is, the quickest of us walk about well wadded with stupidity.”

Think for a second. Is it possible for you to conjure up your exact emotions from one year ago? Would your tweets tell you the truth or merely what one-liner you found funny that day? What about Instagram — can you zoom in on that photo of a sunset and find between the pixels what you were thinking? These outlets, fun as they may be, are purposely filtered for the public: all wheat, no chaff. OhLife was personal, private, and — fine — maybe a touch adolescent…but you had nothing to prove to anyone.

Except yourself. Case in point: An old entry recently showed up in my inbox, reminding me that 365 days ago I was training for a marathon, writing, editing and traveling like a fiend, reading four books, and sleeping eight hours a night. I looked around for that person: Is she on vacation?

Suddenly I was held accountable for my actions. There are no more hours in any given day in 2014 than there were in 2013. I was just choosing to use them in a different way. And after OhLife (or rather, a past version of myself) reminded me who I could be, I got back to work.

So after all of that obsessive chronicling, now we’ve come to the end. The shutdown isn’t causing thousands to pick up their digital pitchforks. A few fans have tweeted R.I.P., including Brainpickings’ Maria Popova, who called it a “simple, brilliant tool of introspection.” Of course there are similar start-ups to fill the void: Little Memory, DailyDiary, MailDiary, Dabble Me, etc. Maybe I’ll commit to a new one later, but for now that feels adulterous.

All I know is this: On October 11, 2014, users must export their entries (secrets and all) and say goodbye to OhLife forever. This is the ultimate test of my most hard-earned and longest-lasting habit. After four years, will I have the discipline to ask myself every night: “How did your day go?”

Will you?

Follow the writer on Twitter @karacut. She’d love to hear about your day.

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