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Emailing Your Future Self

Send-later functions aren't just ways of disguising your sleeping and working habits. They're an opportunity to confront your past and your future.
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Here's hoping the hotel computer lounge of the future is nicer. (Photo: larskflem/Flickr)

Here's hoping the hotel computer lounge of the future is nicer. (Photo: larskflem/Flickr)

Perhaps you've heard of Bruce Farrer, the retired high school English teacher from Saskatchewan. In a lovely profile last year, Sarah Boesveld of Canada’s National Post detailed how the 72-year-old is fulfilling the promises he made to thousands of former students by mailing them letters they wrote to their future selves. One by one, Farrer is tracking down all of the students he encountered since his teaching career began in 1961 in order to reunite them with letters they wrote as high-school freshmen.

It’s a masterful project, in design and execution, one that Farrer says was always designed to promote loyalty to self and to others. “We say we’re going to do something,” he told the National Post last year, “whether it’s in a marriage, or with our kids or maybe even with our organizations we join, and some little thing ticks us off and we think ‘Enough of that, I’m walking out.’”

But Farrer added,“I think it’s important to have a sense of commitment, and maybe in a minor way, the kids see I value that.” The letters, then, show his commitment to his students, and inspire their renewed commitment to past selves and current obligations, future dreams and present ambitions.

You can schedule an email every six months for the next few years to see if you really have finished that novel or found the courage to propose.

I was thinking of Farrer and his letters the other week when I scheduled an email. By scheduled, I mean that I wrote an email which would send at a later, fixed time. This was two or three in the morning, one of those crazed early hours when no one should be writing emails to anyone she doesn’t desperately love or completely loathe. I was writing to a friend about something sort of serious that was to happen to her three days later. I didn’t want to forget to send something for the occasion, but I also didn’t want to send something at that very odd hour. A draft wouldn’t do since I was likely to forget, so I used Boomerang to do it.

Boomerang is an extension for Gmail, but there are several other ways of scheduling emails too: Microsoft Outlook has a send later function, while provides the same service. All of these add-ons and features allow you to schedule emails that you have already written to be actually sent minutes, hours, days, or even years later. You simply type the content of the email, identify the recipients, and then choose the exact minute, hour, and day when it will send. You can also make their sending conditional, so that the scheduled email sends only if you haven’t received a response from the future recipient.

Boomerang and these other services are quite useful for business and the banalities of things like bills and taxes, but they also hold some possibility for personal use as well. Perhaps you only need to email yourself next Wednesday to remember your dentist appointment or your neighbor three Wednesdays from now so he doesn’t forget to move your car for you when you’re out of town. Maybe a relative of yours died this year, and next year you want to receive an encouraging note on what would have been his birthday.

These send laters can disguise your schedule and habits from others, but also allow you to interact with your future self. Search Twitter for Boomerang, and you’ll find professors who don’t want their students to know they’re awake at four in the morning, workaholics who don’t want their customers to know they were working on Christmas, and night owls who despair over their desire to be known as early birds.

But these send later options are quite useful for goading yourself as deadlines approach or encouraging yourself as milestones near. They can be used, for instance, to replicate Bruce Farrer’s letter experiment. You can schedule an email every six months for the next few years to see if you really have finished that novel or found the courage to propose. You can write an email now to yourself that you will receive two, five, maybe even 10 years from now.

Time capsules needn’t only be objects, and their intervals needn’t be decades. Like Ulysses with the Sirens, we can decide whether to trust our past or future selves simply by confronting them. Send later features and functions aren’t just ways of disguising our sleeping and working habits, but opportunities for challenging the present with the past and the future.