Lifehacking the Print, Sign, and Scan Debacle

By Jonathan Roseland

Getting what we want in life at crucial junctures requires applying ink to paper and when we are not in physical proximity to the other signatories of our endeavors it can be damned inconvenient.

Dealing with printers

For the longest time remedying this situation was a frustrating combination of fax machines, downloading PDFs, killing trees by buying reams of printer paper, and the dreaded refilling of the printer toner. Below are several free and freeish digital tools that will liberate your valuable time permanently from this unpleasant experience.

HelloSign for Gmail


This free app for Gmail is the first tool in my line of defense against documents requiring my John Hancock. It takes about 3 clicks and 45 seconds to install on your Gmail account and the signature option will appear next to the View and Download links. If you are originating and emailing the document that needs to be signed...

  1. Send it to yourself: Just enter one of your email addresses that forward to your Gmail as the recipient.
  2. It will show up in your email inbox with the sign option.
  3. Sign it with HelloSign and then download it to your computer.
  4. Re-upload it with your signature and attach it to an email to the other signatory.


A slightly more clunky option is this free website that allows you to upload, sign, and initial PDFs, JPGs, and even PNGs.


For several years this was my favorite tool for digital signatures, then they started charging (actually quite high) monthly rates for their PDF hosting and signatures tool, but it does a bunch of cool stuff that the others don't and it works consistently - I've never had a problem with it. So if you are looking for a business-class solution, this is it.

I use these tools even when I am meeting someone in person to sign contracts. I do this because sometimes when you meet someone to sign contracts you still need to negotiate some fine points of the deal. If you are using hard paper contracts you will either need to reprint the contracts or write on the paper contracts. With these tools and digital contracts, all you need to do is make the changes to the actual contracts and sign them digitally.

What kinds of uses have you found for digital signatures?

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