This series of posts by the Born Freelancer shares personal experiences and thoughts on issues relevant to freelancers. Have something to add to the conversation? We’d love to hear from you in the comments.

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As an old year ends and a new one begins, my thoughts are alternately joyful and ever-so-slightly melancholic.

Joyful, in that the new year promises new hope and a new start, drawing a line under last year’s shortcomings and failures.

Melancholic, in that it is a time to remember plans unfulfilled and also those who have passed.

For purposes of this post, my mind turns to the passing of a colleague with whom I had collaborated on a number of scripts many, many years earlier.

His family called and wanted help in assessing his work archives.

I went over and to my horror found a lifetime’s work in a complete jumble. Files were uncategorized and haphazard, boxes of written materials unsorted and unlabeled, hard drives locked down by unknown passwords and inaccessible.

Attempting to help prioritize and organize such monumental chaos proved beyond my abilities, aside from a superficial tidying up and pointing out of the obvious. (The week of his death he had finally appeared in a favourite national publication. His payment lay amongst the unopened mail on his home office desk.)

The experience shook me up, but more importantly, it forced me to confront the question I am asking you today: If you passed away tomorrow would your estate know what to do with your work archives?

For the vast majority of freelancers, I would posit the answer is a resounding “no”.

Consolidation, Organization, Direction

Death remains the ultimate taboo topic.

Sex, drugs, and rock ‘n’ roll are all fodder for daily conversation. Death still seems to freak out a lot of people. I know folk who refuse to make a will or power of attorney out of irrational fear it will somehow hasten their demise.

Well, I have news for them. One day, ready or not, we’re all going to snuff it.

As a working freelancer, and registered control-freak, I’ve concluded I want to decide what happens to my body of work after I’m no longer around to curate it.

And so I have worked out a three-phase plan: Consolidation; Organization; and Direction.

Although I feel no particular rush I recognize the sooner I put it fully into effect the sooner I can forget about it and redirect all my efforts back again into the daily glorious grind we call living.

  • Consolidation

Bottom line: What is worth keeping? What is only fit for throwing away?

This is harder to assess than you think.

On one hand, if you are like me, you might think everything you’ve ever created has merit. Even the terrible failures were learning exercises that have usefulness as timely reminders.

On the other hand, who are we fooling?

Much of what many of us have created, even materials published or broadcast, has dubious lasting value beyond our own affection for it.

So it must be triaged.

And who better to do that than you?

You must ruthlessly go through your archives, physical and virtual, and ask yourself: Does this have any value? Does it represent any significant breakthrough or connection to something of importance in the outside world? (Outside of your own world, I mean.)

Conversely, does it say something profound about who you are or what you believe in? (Sometimes the work most important to us personally has had very little success in the external world).

Then it is a matter of choosing work that is representative of these values.

(Of course, you will also keep all work that can be potentially repurposed and resold while you are still alive. Trawling your archives may reveal much you had forgotten.)

It is hubristic to assume posterity will be at all curious about our work (unless you are a renown author). To try to guess what posterity will find of interest is as impossible as trying to envision what our descendants will find of interest in our body of work. (My guess: It will rarely be what we think it is.)

All we can do is use our gut instincts in selecting what we wish to leave behind to speak for us when we are no longer here.

Repeat annually.

  • Organization

Once we have our body of archived work triaged down to a possibly more manageable size, the next step is to organize it.

This could involve physically filing material in cabinets or boxes, meticulously labeling what it is and why it is being kept.

It could also involve scanning material and digitizing it onto a dedicated archive hard drive that would be easily accessed after passing. Files should be clearly labeled and significances noted.

It might also involve donating materials to relevant libraries, academic institutions or professional organizations. Or at least investigating the possibilities to be activated after passing.

Passwords should be copied down and stored securely but remain ultimately accessible to your estate.

Online work can be copied onto archive-dedicated hard drives physically in your possession as well as printed out into the hard copy format.

Never assume your digital archives will be readable by future generations unless you keep a copy of the relevant device with your archives.

At one point I had hundreds of reels of tape, dozens and dozens of older format floppy discs and similar out of date media that could no longer be played.

Do you bother to try to access it or do you just bulk erase and throw it all out? The answer will depend upon if you think there might be anything worth saving.

Update annually.

  • Direction

The final phase of this plan requires you to direct your estate on how to deal with the body of work you have triaged and selected.

For this, you must consult a lawyer and have a will drawn up.

If you are a member in good standing of the Writers Guild of Canada, the cost will be covered by your associated insurance plan. Other unions may offer similar coverage.

If it is not offered, there is no point in scrimping. Without a properly executed will with the full authority of law your wishes may never be realized.

This is not being morbid; this is being wholly pragmatic.

Things you can include:

* Your digital legacy. How do you wish your online presence to be preserved? A “digital executor” can be appointed to implement your directions posthumously. Websites you created can be paid to keep running; free sites can be turned into memorials. (The specifics are constantly changing so I am only dealing in generalities)

* Donations. Do you wish your body of work, or portions thereof, donated to some relevant collection? Does the donation of work also require a donation of cash in order to see it properly preserved?

* Copyrights. Do you wish any copyrights bequeathed to a particular individual or institution?

* Have you made extra copies of all your triaged work to leave with family? Immediate offspring are rarely curious but if you have grandchildren or eventually great grandchildren they may one day demand to look at your work.

This just scratches the surface of what you can direct your estate to do. Your own circumstances, work history and disposition will suggest many others to you.

Review annually.

The takeaway

With digital memory so cheap it’s easier than ever to save absolutely everything.

But that can result in leaving a heavy burden for those you leave behind.

In the end, with no specified direction or criteria with which to judge my colleague’s lifetime of work, I heard much later that the vast majority of it was simply thrown away.

Having known him, he probably would not have cared all that much.

But I also know it was a devastating heartbreak for his family and close friends who will forevermore feel they have somehow failed him and betrayed his legacy.

And so the real lesson I learned was this:

Any forward planning you do is not just about preparing for your death…

It is also about helping to prepare those who survive you to live.

New Year’s shout-outs

I’ll continue to share more stories from life in the freelancing trenches throughout 2020.

Just room to thank you, my freelancing colleague, for another year of reading this column.

Please remember to look over my backlist by clicking on “The Born Freelancer“. There’s now over 125 posts from which to choose!

Thank you to my editor for making these words so presentable and my task so enjoyable.

Thank you Don Genova for all your good work on behalf of freelance members in the CMG.

Thank you too Karen Wirsig for having faith in The Born Freelancer in the first place.

And so – a very healthy and Happy New Year!

May all your hard work and dreaming pay off in 2020 to advance your career and enrich your life.

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