In this YouTube tutorial, email‑management expert Randy Dean challenges the conventional practice of filing or deleting processed emails. He recounts a conversation with an attendee who, after following his standard workflow (read, act immediately on quick items, convert longer items to tasks or calendar events), simply left the processed messages in her inbox, relying on search to retrieve them later. Dean argues that, if you trust yourself and avoid repeatedly revisiting handled emails, you can keep everything in the inbox and forego filing. He demonstrates how both Outlook and Gmail let users drag‑and‑drop emails into tasks or calendar events, preserving the original message text. He then shows how to apply multiple labels (Gmail) or categories (Outlook) to those emails, and how to use search or label‑based filters to locate them later. Dean also proposes a rolling 6‑month archive system as a safety net. Throughout, he emphasizes a disciplined decision‑making flow: read → decide → if <2 min, act now; else, create task/calendar → label → leave in inbox. The video concludes with a call to action for viewers to try this “brave” approach, download his productivity PDFs, and contact him for more resources.
Chapters
Hi everybody, Randy Dean, Email Sanity Expert here. Hey, this is a video I've been thinking about making for a while, and it's going to potentially be dangerous for some of my viewers because they're going to see, see, I told you. And it's because of some interesting things to think about when it comes to taking those emails and filing them when you're done with them. Which has been sort of one of the major points in my email management program for the last, oh, I don't know, 18 years. And I just want to throw something by you. There is an alternate strategy, but only if you're brave and you absolutely deeply trust yourself. Let's talk about this. All right. And as we talk about this, I actually want to bring up my email management strategy that I normally teach. But I also want to jump back and share a little quick little story with you. So I'm doing an event before the pandemic, must have been 4 or 5 years ago out in Las Vegas. And I get done doing my email management, you know, program up on stage, like 500 people in the room. It was a big crowd. One of the attendees comes up to me after the program. She goes, so, Randy Dean, and I go, yeah. She goes, what's the biggest number of emails you've ever seen in an inbox? Now, this is a question that I get asked pretty frequently after doing my presentations because I guess some people are sort of proud of this. And she comes up to me and she goes— I go, "Well, it was 164,000." She goes, "Oh, I got that." And I go, "Okay." She goes, "Look," and she holds up her iPhone, 248,000 emails in her inbox on that iPhone. And then she says something that really got my attention. She goes, but I don't think I need to change. And I go, really? And she goes, yeah, I just heard what you said and I'm pretty sure I can keep doing what I'm doing. And I said, now you've really got my attention. Can you please explain? And here's what she said. She said, well, you know how you said when you get a new email, you should keep looking at it till you know what you need to do with it next. And I go, yeah, that's just standard. I learned that. From like David Allen, Getting Things Done, like 30 years ago. She goes, I do that. I read it. I figure out what I need to do next. I go, well, that's good. She goes, and you know how you said if it takes a couple of minutes or less, you should do those now? You know, once again, David Allen fans out there. I go, yeah, that's right. She goes, I do that. If it's quick, I handle it. If I can reply or forward, I do it. I go, well, that's good. Then she goes, and you know, you said that if it takes more than a couple of minutes, then you should add that to your task list or your calendar. And I said, yes. She goes, Yeah, I'm putting them on my calendar and if they're a task, I basically just put it on my calendar as a no-time task, you know, so they sometimes show on the— up at the very top. She was using a calendar tool that allowed you to make no-time tasks for the day that are appointments for the day that would basically just sit at the top of the thing. And I go, yeah, that counts. I guess I would count that. She goes, so I'm doing that too. And I go, yeah. She goes, and then I just leave them in my inbox. Interesting. This little area down here, she wasn't doing. She was just leaving them in her inbox. And I go, I go, okay. She goes, yeah, because if they've been read, I see that they're read. They're not unread. They've been read. And then I just never look at them again. But if I need to find them, I can use search to find my emails. And I went, oh, Interesting. Maybe what I just highlighted down here, you don't really need to do. And so I thought about it for a second and I said, you know, you promise, do you promise you never look at your red messages another time unless you're going back to get them for a reference purpose? You're not looking at them over and over again just to see, did I look at it or not? Because that's the big problem that most people have. They look at them over and over and over again. Even though they've already dealt with them because they can't remember if they dealt with them or not. Anybody know the clinical definition of insanity? But now here's the thing though, if you just leave them in there and you never look at them again, except for when you actually truly need to reference them, I don't see a problem with that. I think you got to be sort of brave and you got to be honest. When I say honest, what I mean is this, you don't lie to yourself. I don't care. I don't care. I just don't want you looking at emails over and over again that you've already dealt with because that's crazy, frankly. But if you could leave them in your inbox and never look at them again and you're not bothered by all the clutter, who am I to say that's the wrong way to do it, especially if you're doing this top part up here properly. Open the email, make a decision, handle the quick ones, turn everything else into Tasker calendar. Maybe you don't need to do the file or delete piece that I've been talking about for years. And now here's the interesting thing about this though. Maybe they have actually made it easier for you to consider this new option. Now let's talk about this a little bit, especially when you consider that both Outlook and Gmail allow you to quickly and easily convert your emails into task and calendar items. From the email. Now I've made videos on this that are going to be in the description and in the comments for both Outlook users and Gmail users on how you can quickly and easily convert emails into task or calendar items. I'm going to show it real quick, but if you want to see it in more detail, watch the videos that are linked in the comments in the description. But let's go out and show you this real quick. I go into my Outlook, I have an email. That I need to do something else with. I click on the email, hold the click. Whoops, hold on. I got myself a little messed up there. Hey, look, and I even messed up my camera doing that little maneuver. I'm going to turn my video off for a second, make it easier for you to see. I'm going to click on this email, hold the click and drag it up here to the task icon in Outlook and drop it. That's drag and drop in Microsoft Outlook. And what it does now, I can say, show people I can type how to convert. Due date, we'll say today. Priority, high. And if you take a look, look what's down here, the text of that original message. And so what's interesting about this is by doing it that way, not only have you created a task from the email, you have the text of the email inside the task. And yes, you can do this on calendar too. Let's close this task. Not going to save it. I can left-click on the email, hold the click, drag it up here to calendar. Hey, look, my camera's doing that weird thing again. I'm going to hit stop video one more time and go back out here to this and say title, show how to create a calendar item. This is how you do it in Outlook and you can set the date, you know, for Monday at, 5. Okay, so now I've got this for my calendar. And not only— I'm not going to save the changes on this one either. Not only can you do this in your Outlook, you can do this in your Gmail too. Let's open up Gmail because I'm going to stop that video so you can see this clearly. If you have the task little icon selected on the side of your screen, in your Gmail inbox, you can actually do the exact same thing I just showed you in Outlook. You can click on the email, hold the click, drag it over and drop it, and then come up here and edit it. Show how to convert. I mean, it's that easy. You can set date and time. There's the link back to the original email so you can see the text of the email. And not only that, you can also open the email in Gmail and come up here to the top where it says More and Create Event. And that— it takes a second. But what happens is you can also make a calendar item out of your email. And once again, take a look. It also allows you to do this. I'm having a weird little thing happening with my Zoom video camera, so I'm going to keep stopping the videos. I'll bring them back up every now and then. But the interesting thing is that both Outlook and Gmail allow you to quickly and effectively convert your emails into task or calendar items. Now, what's truly interesting about this, though, I'm going to close this item in my Google Calendar. I'm just going to hit leave. I'm going to come back up here because there's another thing that both Outlook and Google Google allow you to do. And since I'm right here in Gmail, I'll show it to you. Not only can you create the task or calendar item, soon as you do that, you could come up here and— stop that video one more time— you can make a label. Now, the interesting thing is you might already have a bunch of labels that are created. And the nice thing about the way that the label tool works in Gmail is you don't have to just select one label. You could put it in Anna Soccer, Automated Messages, Speaker Match, Taming Email Webinar, hit Apply, and now all of those labels have been applied to this email. Now what's interesting is I've done another video. I'll put that one in the description too, of how that in Gmail you can— the labels and the folders are basically the same thing. See Anna Soccer, Automated Messages, Speaker Match, Taming Email Webinar. But you don't have to necessarily put them in the folders because what happens is now that it's been labeled, what you can do is basically give yourself the opportunity to just leave them in your inbox with these labels because later, take a look at this, you can search. And let's go back to the inbox proper. You can search And one of the things that you can search by is by label. And actually, I would recommend maybe coming up here, search options. And then when you do search options, what you can do is you can take a look. It's called creating a filter, has the words, doesn't have the word, search all mail, etc. And then, you know, you could put it by whoever the person was, Randy Dean, create filter. Et cetera. And then what you can do is you can actually automatically label and do things like that. But the other thing that you can just do is search, search by the labels down here. You can come over to the side because you've already labeled it, and you can just click on all the ones that are speaker match, and boom, it's going to bring everything up from speaker match. So if you've already added the label, you don't even need to do the search. You just come over here and click on the label. You got search options. You've got label options, which means maybe you can just leave them all in your inbox as long as you're not reading them over and over again. So you could have a big full inbox, but the only ones you're looking at are the ones that are unread. Interesting. Does Outlook have a comparable feature? Why, yes, it does. Let's go to Outlook now. And once again, I'll get myself out of the way. Take a look here. So in Outlook, what you have is a slightly different option. Take a look at this. If I click on and open an email, one of the options up here is categories. Once again, I made a video about how to use categories, and I'll watch that video too in the comments. But the interesting thing about the categories, I always tell people these are just labels. And if you click on this, take a look. I've changed the names from red category, blue category, gray category, maroon category. I've come down here to all categories and I've changed those names to my key projects, activities, clients, customers, events. And then what I can do, as you can see, this one I've already got 3 labels, but I could add more. I could add this one to meetings. And I could add this to personal and hit okay. And now it's got 5 labels. See, I'm not limited by how many places I can put it because I can put it in all the labels it's related to. And once again, let's go back here. I'm going to stop my video, go up here and show you something. Let's close this email. Let's go up to search, because in search you can search by label in Outlook. How about that? Which means maybe, just maybe, you could keep your emails in your inbox and only look at the ones that are marked unread. And then you have to, of course, move your focus to your task list or your calendar. Interesting. They give you the tools to label, they give you the tools to search. You can easily and quickly convert to task and calendar in both platforms. Maybe you don't need all these folders. Hmm. I'm wondering if my video card's about to die. Isn't that interesting? Let's go ahead and finish this thing. Maybe, just maybe, let's bring this back up in my Taming Email decision tree, should no longer fully focus on this and instead focus on this. Get the new email, make the decision, couple minutes or less, do it now, more than a couple minutes, task or calendar. And then once it's done or task, label it and leave it. Using categories in Outlook and using labels in Gmail and search and/or the labels in Gmail to find your stuff when you need your stuff. And if you don't have a good label, but you want to label it so you can find it later, maybe you create a label and put it there. I think this could work. But Let me tell you the fail before we finish this. If you find yourself going back and reopening emails you've already dealt with because you can't remember if you dealt with them or not, you need to get them out of your inbox. Now, one last thought before we finish this whole thing up. Maybe the other thing you could do is then start filing emails after every about 6 months and every year make a new year folder and then move the 6 months to a year emails that are in there into that folder. And then in 6 more months, move another 6 months in. So you're constantly rolling with a 6-month backlog of emails in your inbox, and your inbox isn't going back years. You might even be able to talk to your IT team about how to archive those so that it's done automatically for you. But look at the email, make a decision. Quick, deal with it now. Not quick, task or calendar. Label it and leave it. Hmm. No label, make a label. Use search to find your stuff. Use your labels to find your stuff. I think it can work, especially if you're really good and you trust yourself and you keep your focus on your task list and your calendar once you know you've looked at everything. I'm Randy Dean, Email Sanity Guy. Want to get more info? Go check out my website, randaldean.com. You like my videos, please give it a like. I'm going to check out this video card thing and see what's going on with that. That's a little bit funky. And if you want to get my productivity PDF tip sheets on other tips on Outlook, Gmail, Google Workspace, Microsoft 365, smartphones, tablets, send me an email, randy@randaldean.com. Put YouTube PDF in the subject line. And with that, I'm going to say thank you for your time. Let me know your thoughts on this. This is interesting. Maybe I'm just going to make a bunch of you feel Like, it's okay to have that big mess in your inbox because maybe it is. Bye.
