Best Results Organizing

In the olden days, if you wanted to send an important message, you could send it in the mail, and it might go by steamboat, stagecoach, or train to get to your recipient. Hopefully, your Pony Express rider wouldn’t lose it in a saloon. Perhaps if you were from a family of means (the Bridgertons, for example?), you might entrust your very urgent message to your ladies maid, who would give it to the hall boy, who would run through the streets to deliver your a note. 

The telegraph was invented in 1837 and by the second half of the 19th century, it was widely used for messaging. But priced by the word, it was essential to limit what you wanted to say to the fewest number of words. As a classic Borsht Belt joke ran, “Start worrying. Details to follow.”

And for those of us of a certain age who recall pay phones, you could place a collect call for “Mom, I need you to pick me up at the mall” or “I arrived safely” and the operator looked the other way. Or, there’s this classic:

HOW TO SHARE SMALL AND MEDIUM FILES

At this point in the 21st century, things are much the same. The truth is that when you have a (relatively) small piece of information, it’s “no big whoop” to transfer that kernel of knowledge inexpensively and easily. The bigger the slab of data (what we’ll generally call “a file,”) the more expensive and complicated things are, and the more strategy you need to keep the cost and effort down.

Methods for Sending Small and Medium Files

For small files, like photos, PDFs, a resume, or a quick video, you can relay information by:

• Text — Whether you use iMessage, SMS, Whatsapp, or Slack, you can quickly relay information or and attach to those texts.
• Email attachments — As long as when you say “attached, please find,” you actually attach the file you intend to share, you’re good to go.
• AirDrop — This works as long as you’e in the same room or area as your recipient and are using an iOS device (or, as of late 2025, are able to duplicate the process on Android using QuickShare).
• Physical media — While tangible media method isn’t as convenient or as quick as a digital transfer, if you have lots of files, it can be helpful to download your files to a USB drive, external hard drive, or SD card, and then carry it to someone in a different location or even ship it to them.

The advantages of these non-tangible methods are that they are generally fast, and there’s little to no set-up needed. You just find the file, click a few buttons or drag-and-drop the file, and you don’t need to be particularly tech savvy as a sender or recipient. If you’re using tangible media, no internet is required, you have total control over the physical file, and it will work anywhere you’ve got the hardware into which to plug it.

The main disadvantage of the first three of these methods are that you’re limited as to the size of whatever file you wish to use, particular to share via text or email.

For example, last week, I had a funny experience when a client had a pregnant pig at her house. The pig had lived at her barn, with horses and chickens, but during a recent cold snap a few weeks prior, the client made a safe, cozy space in her home for the mommy-to-be.

With my client’s permission, I shared a photo in a group text thread with colleagues, and someone said they wanted to see a video! My client provided an adorable video of the pig’s first day in her new space; we were both using iOS, and there was no problem texting it. However, when I went to send the same video to our group thread, I got the message that because it was a mixed iOS/Android group thread, the video was too long to share. Harrumph.

In addition to size limits for file text/email/AirDrop filing sharing, you (or the post office) could lose a thumb drive, hard drive, or SD card in transit, or your recipient could lose it between plucking it from the mailbox and the moment they intend to use it. And none of these methods are particularly useful if you want to ensure that a file is backed up or easy to collaborate upon.

And what you if do you have a BIG file? Certainly text and email are out, as is AirDrop. 

For bigger files, the two main methods to get important information from one location (yours) to another (theirs) will be through cloud storage or file transfer platforms. 

SHARE FILES IN THE CLOUD

You probably upload files to the cloud (or create them in the cloud in the first place) all the time. This method works best for families and friends sharing documents and photos, professionals sharing client work, ongoing personal and work projects, and providing long-term access to content. As long as you don’t remove the file from the cloud, recipient(s) can re-access it as many times as they like.

How File-Sharing in the Cloud Works

This method involves the following steps:

• Upload a file to your cloud account.
• Set the permissions for the file. Sometimes, you just want the recipient to be able to view a file; other times, the permissions might allow them to edit and even share it with others. 
• Share the link with the people or teams who need access. This could be photos of the baby so Great-Grandpa can see how much junior’s smile is like his, or the latest TPS report your staff needs before the next Monday meeting.
• Your recipient then views and/or downloads the file.

The advantages of sharing files in the clouds are:

• Large file support — Cloud storage means that you can upload multi-gigabyte files. Sharing videos, folders of files, and project archives is easy-peasy lemon squeezy.
• Easy sharing — File attachments can be a sticky wicket. If you attach five files to an email, and someone downloads them but then can’t figure out whether the files have ended up in their attachment folder, their desktop, or the most recent folder to which they moved something, it’s a headache. But if you’re just sending someone a link, it’s just a matter of one click to get what they need.
• Ongoing security — With cloud sharing, you can change the permissions at any time. So, if you don’t want your now-insignificant other to access that photo, or your mother-in-law can’t be trusted to not post photos of your little angel to social media per your stated boundaries, or your former employee is “former” for a reason, one quick click denies access to files you no longer what them to have.
• Backup as a perk — When you upload files to the cloud to enable sharing, those files stay conveniently stored until you decide that you don’t want them there anymore. You never have to worry about a crashed hard drive or an accidental local deletion.
• Collaboration made easy — When you upload a file, multiple people can access it (if you wish) and you can keep track of version history, which is great at work or if you’re collaborating with others on a screenplay or story.

Of course, there are drawbacks to the cloud method of sharing files.

• Storage limits — The free tiers for storage sites can fill up fast, so if you do a lot of file sharing and never purge your account, you’ll hit your free limit quickly and need to upgrade to a paid plan. Free tiers with enough storage space will let you upload content, but watch to see if there’s an upload limit on individual files. 
• Account registration requirements — Yes, I heard you groan. Nowadays, almost everyone has too many accounts and too many passwords. It may not be a big deal to you (because if you’re uploading, you probably already have a cloud or two that belongs to you), but if your recipients don’t have cloud accounts, they’ll usually have to register to gain access. Note: some accounts will allow recipients to view files without accounts, but not edit or share.
• Learning curves for setup — Unfortunately, the less tech-savvy recipients might be frustrated if they aren’t accustomed to navigating a cloud space. Additionally, some users are inexperienced at setting up permissions, so it’s important to pay attention to the difference in permissions between view, edit, and share.
• Privacy depends on settings — With some cloud accounts, you can create public links for file sharing. That’s great if you want everyone in your neighborhood to have access to a file, but if you meant for only the members of “I hate the dude who leaves his Christmas lights up all year” club to view the link but it’s available for public consumption, it’ll make the next block party a bit awkward.

The Main Players in Cloud Sharing of Files

You’re likely already familiar with the big names in the cloud arena for sharing files, even if you’ve never used them for file sharing. 

Google Drive — Every Google user has 15GB of free storage; beyond that, there are different file upload limits at different paid tiers. Just upload your file to your Google Drive, get a link to share, and provide the link to your recipient.

However, there’s also a nice mix of the “attach” method I mentioned for small files and the cloud method.

As a Gmail user, if you start a new message with an attached file that’s over the 25MB limit for an individual file, Google automatically creates a link to that file in your Google Drive. When you go to send the email (the one you mean to attach), Gmail will ask you to grant your email recipient access to that file and prompt you to set the permission (view or edit). The default setting, wisely, is just to allow them to view your file. However, your recipient will need to have a Google/Gmail account. 

iCloud — You automatically get 5 GB of iCloud storage for free, but an upgrade of just $0.99/month yields 50GB; $2.99/month provides 200GB; and for $9.99/month, you get a whopping 2TB! Store your files, share the link, and you’re all set. 

However, as with Google Drive and Gmail, if you use Apple’s Mail, try the Mail Drop feature to send large files up to 5 GB via iCloud Mail on Mac, iPhone, or iCloud.com, without it counting against your storage quota. Read more about Mail Drop.

It will generate a secure download link that lasts for 30 days. Just attach a large file in Mail, and it will automatically offer to send it via Mail Drop if the file exceeds standard email limits.

Dropbox — You probably know Dropbox for its cloud storage with file syncing and collaboration tools. Their plans range from a free 2GB storage option up through premium business plans 15-freaking-terrabytes of storage. But that 2GB lower end storage limit for free accounts (with a 2GB file upload limit, isn’t going to win any beauty pageants. However, in addition to the storage 

(In addition to the basic cloud storage method, Dropbox also has it’s own File Transfer protocol for large files.) 

Microsoft OneDrive — Upload your file to your OneDrive cloud account; granting access to others is straightforward. OneDrive allows individual file uploads and downloads of up to 250 GB for both personal and business accounts, and while there isn’t a strict total data transfer limit, syncing oodles (like 300,000+ files can cause performance issues). They recommend using the OneDrive desktop app to accomplish large transfers rather than using browser uploads.

Note, Microsoft does something similar to Google and Apple, in that if you use Outlook 365 and try to send a too-large file as an attachment, you’ll be prompted to upload the file to your OneDrive and share a link to it in your Outlook email (rather than attaching the file, itself). You’ll just use the “Upload and Share as a OneDrive Personal Link” option. Recipients can click to open the file and view it from your OneDrive.

SHARE FILES USING FILE TRANSFER SERVICES

I like to think of this approach as a “send it and forget it” method. It’s great for when you want to send videos to family members or the tour group friends you made on your last cruise vacation, submit creative files to a client or virtual assistant, send one-time deliveries of a massive file — or if you know the person getting your file is a bit of a grumpus about dealing with tech.

Fewer people will be familiar with file transfer service method than the methods I described above, but it’s really efficient for the one-and-done file transfers, plus it’s surprisingly easy for the sender and the recipient.

Upload a file, then enter the email address of the person or people you want to receive it (or, alternatively, you can get a link to put in your own email, text, newsletter, blog, etc.). That’s it.

From there, it’s up to the recipient to click on the link, which takes them to the file transfer site. They click a link, and the file downloads to their computer, where it waits for them to open and use it. The best part is that the file auto-expires after a set period (like a week), so you don’t have to clean up after yourself or purge files or worry that someone you later part ways with could still have access. 

I have a friend from high school who was always the most in-the-know person about music. Four decades later and he’s a professional in the music industry, but he still makes mix tapes, or at least the high-tech version. For years, he’s been sending his own little funnily-named, curated “albums” of music for his personal email list to enjoy. Only instead of a fiddly cassette requiring us to have a pencil at the ready to fix it when everything unspools (hello, 1983!), he sends a big MP3 file every month or so. 

My music industry friend was my introduction to the file transfer service option, but certainly not my only experience. A few years ago, when I had to create a video presentation an online summit, my colleague had me submit my video via a file transfer service, and I was delighted with how easily it worked.

The advantages of file transfer services are:

• No account (generally) is necessary — Just like you don’t need a UPS account to have UPS deliver a package to your door, file transfer services deliver the sender’s file to anyone.
• Low-friction transfer — Remember how I said that some people can be overwhelmed by having to navigate cloud accounts to find a file? That doesn’t happen with file transfer services. My musical friend sends me to a big, splashy webpage with a big, obvious button to click to start the file download.
• Big-file friendly — These services were designed to tackle large transfers. Did you write the Great American Novel? Produce your own album? Make a movie? Share it easily.
• Automated file cleanup — Because the file auto-expires, once you tell the file transfer service to send to your recipients (or you’ve sent them the link or published access to it), you’re done.

There are a few potential drawbacks to file transfer services, though:

• This is temporary storage — For those who prefer cloud storage to warehouse their files, it’s important to recognize that what’s a boon to some (the automated expiration of the files) means file transfer services do not store your files indefinitely. 
• You have limited control of your file — Because there are few (if any) options for permissions with a file transfer service, once you send that file, it’s out in the wild. Someone has it and can copy it, share it, change it and then share it, wear it as a hat, etc. Don’t provide access to your file to someone you don’t trust to have that access. Duh.
• It’s not ideal for super-sensitive data — File transfer services are secure-ish. They use varying methods of encryptions, so if you need ultra-encryption or password-protection, don’t send your super-secret spycraft through a platform that doesn’t offer that. OK? OK!
• Consider the money, honey! — As with everything in the era of late-stage capitalism, you get what you pay for. Free platform tiers work, but if you want bells and whistles, like password protection, longer-termed storage, and higher size limits, you’ll have to shell out the money.

The Big Names in File Transfer Services

There are a variety of file transfer platforms. As a professional organizer, I am not an expert in the technology, and none of these should be considered recommendations. Rather, they are a starting point for your own research into the right file sharing solution for you.

We Transfer — This is the platform my musical friend uses, and it’s the one that seems to be the best known.

Share and receive up to 3 GB/month (10 transfers/month) for free, with transfers expiring after three days. With a paid subscription ($25/month), you get unlimited transfers, unlimited file sizes, no expiration of (uploaded) files, custom branding, and automatic malware scanning. 

FileMail — Send large files, up to 5GB, for free, to up to three recipients, with up to ten downloads per transfer. Just drag-and-drop the file from your desktop onto the website. Of note, they impose no restrictions on commercial usage. There are multiple FileMail tiers: Beyond the free Basic plan, there are paid personal ($6/month), professional ($14/month), and business ($24/month) account levels, with each level offering increased file size, storage capacity, and customization.

Smash — The free tier lets you send an unlimited-sized file, has no upload limits (vs. 2 per 24 hours for FileMail), offers password protection, and files are stored for seven days. At the paid tiers, $4.90/month for Pro and $12/month for ten users, 1TB and 2TB of storage, respectively, for 30 days of file storage. (I also think the platform has a more user-friendly experience than FileMail, but your mileage may vary.)

Drop Send — At the free level, send files up to 2GB, up to two files per week, and get 250 GB online storage. At the paid levels ($5/month for basic, $9/month for standard, and $19/month for professional) you get faster transfer speeds, can send 50GB files, increasing numbers of sent files per month and increased amounts of online storage.

Other popular options include:

My Air Bridge — This European platform is best for professionals and teams. Their service is free for individual transfers up to 20 GB in size, with multiple paid plans. 

Wormhole — Right now, this is a free services. They note: “For files up to 5 GB, Wormhole stores files on their servers for 24 hours. For files larger than 5 GB, Wormhole uses peer-to-peer transfer to send your files directly from your browser to the recipient. So you’ll need to keep the page open until the recipient downloads the files.”

Send Anywhere — At the free level, send a file up to 50GB; the Lite tier is $5.99/month and the Standard tier is $9.99/month, with additional perks related to downloading, speed, and link management. 

BEST PRACTICES FOR ORGANIZING YOUR LARGE FILES FOR SHARING

Before you send your files, consider some tactics for keeping the whole experience organized.

Name your files clearly — If you’re sending a photo, change it from IMG15678 to “Baby’s First Ice Cream.” If it’s a file for work, consider the nomenclature rules and best practices/guidelines your company generally uses for documents. If you’re a solopreneur, this is a great time to develop rules for how to organize and label files so that you know WHAT they are and WHEN they were created. “2026 1Q Earnings Report” tells your recipients at a glance what they’re getting.

Use folders when sending multiple files — Don’t send 3 (or 33) files all higgledy-piggledy. Group them in a folder with a clear name.

Check to make sure you’ve removed duplicates or changed the names — If your recipients are poking around in a cloud folder you’ve created and to which you’ve linked them, and you’ve got 16 iterations of ClientProposal.Final.Final.Final, that’s going to cause confusion.

Add a README file — If your recipients need to know more details about what they’re getting in files or folder, tell them what it’s all about.

Consider file compression — If your files are too big to send as-is for free, consider zipping those large files (or folders) so in order to reduce the size before you send it. Save money by putting your files on a diet, but only if your recipients are tech-savvy enough to know to double-click on a file to unzip them. 

• Zip Apple Files
• Zip Windows Files

What do you do when you have a massive file and need to get it to someone quickly, efficiently, and safely? Have I omitted your favorite method? Please share your thoughts in the comments.