Everything in the Cloud: How to Go Paperless, Forever


Cameron McCool


Reviewed by


March 8, 2017

This article is Tax Professional approved


I remember the day I went paperless.

Staring at me was a stack of tax receipts, invoices, and countless journals, the same pile I’d rifle through in angst every time a tax deadline rolled around.

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It took me hours of time, a ruthless mindset, and more caffeine than I’d like to admit, to sort, upload, and store everything online. But once I’d finished, the result was a pure relief.

Years later, I still run my business entirely from the cloud. I can’t remember the last time I wasted money on a printer, I travel light (no training manuals stuffed into my carry on), and whether I’m out of the office for a quick meeting or working from a different country, I can access, search, and share all of my documents with teammates, clients, and my accountant, in just a few clicks.

While it takes some getting used to, I guarantee that going paperless will save you a whole lot of time and hassle during tax season and throughout the year. No matter if your business is brick-and-mortar, or if you’re an office-less entrepreneur, as long as you’ve got a smartphone, a laptop, and access to the internet, here’s how you can make your business semi- or fully- paperless, too.

Scan, upload, shred

When you first go paperless, scanning, uploading, and storing documents online is where you’ll do the bulk of the work.

I use Dropbox to store scanned versions of business cards, receipts, photos, and documents. For bank statements and utility bills, I use FileThis. The app automatically downloads these documents once they’re available and saves them to my Dropbox folder.

If you’ve got a lot to get through, Evernote’s ScanSnap scanner can make your life easier. After scanning, it automatically uploads and stores your documents to your Evernote account. Alternatively, you can outsource the process using Shoeboxed’s Magic Envelope. Just stuff your receipts into the envelope, send it off, and they’ll scan and upload everything for you.

Remember, to keep the IRS happy you need to hang onto tax receipts for three years after the filing date or tax deadline (whichever is later), but you don’t need to keep physical copies. Scan and store the tax receipts you need to keep, and shred the rest.

Store your photos in Flickr

Most people aren’t aware that Flickr gives all users one terabyte of free space – that’s enough to save around 800,000 photos online. Although it’s meant to be used as a public photo sharing network, I use it as a private online storage account. How? During the upload process, I simply set the share settings of my photos to ‘private’. That way, I’m the only person who can view the photos, which I can access and download via my laptop or the Flickr smartphone app.

Also, by storing all of my photos in Flickr, rather than in multiple folders across other cloud storage services, I know where my images are at all times, and I don’t clog up my other cloud storage drives (Dropbox, Evernote) with bulky photo files.

Collaborate on documents with Google Drive

Google Docs has been a godsend for my business. I use it to create and collaborate on documents with clients and others on my team. It’s just like Microsoft Office, but it allows multiple users to simultaneously view, edit, comment on, and even chat together within documents, spreadsheets, PowerPoint presentations, and forms. Oh, and it autosaves every few minutes, so if my computer crashes unexpectedly, all of my work is safe. Take that, MS Word.

Manage your finances in the cloud

I can’t emphasize this enough: keeping my finances hyper-organized in the cloud has been the key to eliminating stress during tax season. I manage invoices through FreshBooks. I outsource my bookkeeping to Bench. And I use Expensify to snap and digitally store a photo of my receipts every time I buy something for my business.

Further reading: The Best Apps for Managing Receipts (2023)

Sign documents digitally

Remember when we used to sign documents by printing them out, signing them, scanning them, and then mailing them back in the post? Today that process seems like such a waste of time. I use this method to digitally sign documents with the camera on my Macbook. If you’re using a PC, or if you need your clients to digitally sign contracts, Adobe’s Sign allows you to send clients a link to a secure page where they can digitally sign documents using a smartphone touchscreen and their finger.

Create an online company library

Sorry, where was that training manual again? If your business calls for the use of internal documents, use Bloomfire to create an online library for your team. Employees can upload documents (guides, manuals, interesting articles that help you get your work done) to your company’s account, for everyone to access virtually. Telling your employee: “You can find it in Bloomfire!” saves everyone from the hassle of digging out documents and sharing them via email. You’ll also end the need to store chunky manuals on your office bookshelf.

Going paperless requires discipline to set up and willpower to maintain, but whether you’re a solopreneur, microbusiness, or mid-sized team, there’s a way for you take some or all of your business paperless and get that sense of relief that only the cloud can bring.

What other paper do you need to kill?

This post is to be used for informational purposes only and does not constitute legal, business, or tax advice. Each person should consult his or her own attorney, business advisor, or tax advisor with respect to matters referenced in this post. Bench assumes no liability for actions taken in reliance upon the information contained herein.
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