Why Your Old E-Mails Matter

Encryptomatic LLC
4 min readAug 21, 2015

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When my grandmother past away, she left behind a box of old letters, post cards, and pictures that she had received from others. She had seen fit to preserve these treasures, which captured snippets from her life, and the lives of those she cared for. A life time of communication, some mundane, some of it quite personal.

At any point she could have discarded it all, but instead she chose to leave it for us as a way to know her better. Some of the letters documented conversations that slowly played out over decades. Some of the letters were from me as a small boy; pictures and notes, and “thank you’s” for the $5 bill she would send me faithfully every birthday through the year she died.And while her boxes did not hold copies of the many letters she had sent to us (she didn’t make copies of the messages she sent, afterall), that she saw fit to preserve what we sent to her was humbling.

Anectdotally, I believe the time I began to send fewer letters was around the time that e-mail began to take over as my main mode of communication. Although my grandmother never had an e-mail address, in the 90's sending “electronic mail” to friends and connected relatives became the instant, free and convenient way to communicate.

I’ve clearly been sending email for at least twenty years now. Although many of my emails, especially work emails, have been lost, I still retain many gigabytes of email communication from all sorts of people who have crossed my life path.

An examination of my Outlook .pst files (email databases) reveal messages accumulated from dozens of personal and professional email addresses that I have used. Although most of the messages are routine, mundane, involving issues, clients and priorities that may no longer exist, there is a wealth of revealing personal information. Many of the emails contain pictures that were sent to me from friends, while many others are just pure spam and viruses that were emails.

The question then becomes: should I keep these? Is there possibly more historical interest to my decendants in retaining these emails versus the short term personal risk involved? Some companies have email retention policies that delete emails as soon as they are reasonably able to do so, in order to thwart legal discovery requests. Should I have a personal retention and deletion policy of my own?

The answer to these questions are undoubtedly personal. If I had been faithful in separating my email communications into discreet channels, it would be easy: just keep the personal .pst/email files, and remove the business files. But like many people, my private and work lives are not so separate. Personal and business emails mingle together.

The right answer for me is to try and preserve the e-mails that I have. Although I’m not so vain as to think that anyone (who isn’t trying to sue me) would be interested in my emails, I do enjoy sometimes mining my stash of e-mails for pictures and other interesting reminisces.

Twenty years of e-mail communication may soon be an anomaly. The huge shift to cloud storage of e-mails could make it difficult or impossible for people to bring their e-mail messages under their physical control as email providers come and go, and email accounts get hacked, or passwords become lost. Email is no longer the preferred channel for communicating with close friends and family.

Our communication is scattered across a far flung range of services. Pictures now are uploaded directly to Facebook and Instagram, and home videos to YouTube, disposable short videos to Snapchat. Personal text messages seem to persist forever, but still are not easily amenable to long term storage (except to police agencies, it seems). Communication that was once funneled reliably into e-mail now persists in various states of accessability across disparate channels.

It could very well be that storing these snippets of our lives on cloud services will preserve them from hard disk crashes, or it may turn out that they become inaccessible to loved ones after my death. It’s difficult to know with any certainty where all this may be headed.

But a couple of things are undeniably true:

Any box of letters I leave behind for my children will be quite small, and probably only consist of a few birthday or holiday cards.

Any reliable e-mail record that I leave behind will probably be a) too large, and b) not very interesting after about the year 2010, when my email seems to have become mostly spam and business related.

How about you? Do you every think about the electronic record of your life that will leave behind for your decendants?

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Darren Leno is CEO of Encryptomatic LLC, the company that publishes this blog. Encryptomatic LLC creates software tools like Pst Viewer Pro, MessageExport, and MessageLock, that people use to manage and transform e-mail communications.

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Encryptomatic LLC

We’re a software company that helps people communicate securely and manage e-mail content. We are based in Minnesota, USA.