My Mail is a mess — is there hope?

I’m primarily using Apple Mail for both personal and business mail.
Between 5 and 7 active accounts from our biz site, and one forwarded legacy account.
I also have a couple of Gmail accounts for personal and 1 photo club acc’t

In Mail I have mailboxes for the Biz and personal accounts, with Smart mailboxes, and folders for various personal and biz emails. I also have one specific folder where I move some emails to a location on my hard drive.

Over 30K emails still in the system at various stages of Read/Tagged.
I’ve tried mass deletions but have never gotten down to a reasonably tolerable/manageable level

Yup… a real mess!

Is there recommended J.D. solution for getting out of this mess?

Sorry to break it to you, but I’m not sure you’ll like JD’s suggestion. I can’t find it, but somewhere he said when he goes on holiday he sets his auto-respond to “I’m away, and when I return I’ll delete all inbox email, so resend it later if it’s important” :rofl:

2 Likes

:joy: yup it’s in his workbook… and I laughed when i saw it — cuz it’s exactly the way I feel about emails when I’m vacating, and especially about repeat phone calls like… I tried calling yesterday and nobody’s answering — duh :roll_eyes:

Also in the workbook:

[if you’re going to organise your email,] your boss needs to understand that you’re going to spend at least 10% of your day filing email.

Do you want to organise all mail going back in time, or starting now? The second is still a lot of work, but doable. The first would probably need a few months vacation, and probably isn’t entirely necessary.

My other thought would be: can you consolidate email accounts? It’s great to have separate ones, but maybe you can somehow gather the important ones in one place for tagging.

And tagging is important. Or putting the JD ID in the subject line. Then as long as you have full-text search, you’re good to go. The organisation happens in the JD Index (which is elsewhere, not in the email system); as long as that has instructions for how to find the emails (i.e. keywords) then that should get you a fair way there …

I should say that email is still on my list of areas to tackle, so I’m not speaking from experience :smiley: Would love to hear (your and others) experience too.

2 Likes

I’ve mostly given up.

A few special emails I’ll move in to a JD folder. Like we have a current disagreement with the neighbour about a barking dog. That went in 12.52 Neighbours just earlier.

But it’s maybe 1/100. The rest, it’s just too hard. We get too many. Game over.

If I still had a job I’d still be doing this with my canonical timesheets example. Because this helps me later. And, as above, it’s like 1/100 emails.

1 Like

I have a few thoughts here that are not at all JD-helpful:

Email is conversation, like piles of snail mail or voicemails. I’m not sure why email has to be “organized”. It just has to be “gotten through”. I can’t, off the top of my head right now, tell you of any e-mail sent to me from 15 years ago that’s worth saving, but I can give you so many such examples of physical documents. E-mail is not important or worth keeping. That’s my opening argument.

Just as I don’t try to organize everything about my conversations with people, that philosophy informs my e-mail approach. Some times I want to remember to follow up with someone for a reason. That’s a to-do list or calendar item. The original e-mail served as a trigger and can be thrown away (probably after me giving the sender an idea of when I might get around to the task). As far as I’m concerned, that’s it. Someone might say “ah yes but if you delete an e-mail accidentally, then you can’t really hit the same e-mail thread in someone else’s inbox later in the year”. First, to me, 1/500 e-mails may need such crazy months-long follow-through. Second, the other person only cares about the thing getting done or the final response, not if they have to click “delete” in their inbox twice. Just get rid of it all. I’ve been at inbox zero for about two years now because I just ruthlessly omit and delete all the crap.

When new e-mail comes in, I keep in mind that most e-mail is anyway someone else’s delegation or to-do list to me, so I’m perfectly happy mindlessly being an item on someone else’s to-do list instead of holding on to it in my system for god knows whatever reason. Sounds like their mental space has to be occupied for follow-through if they really care enough. I’m not trying to be mean or disrespectful here. Just, my time is mine, I already have life goals I’m attending to, no one else’s goals should take priorities or mental space over mine. If I have extra time and energy to spare then yes I’ll get around to the e-mails that I can. It’s like coffee invitations with people. Sounds lovely, if I have the time, and if all my best friends are already busy.

Finally, I follow the late Tony Hsieh’s system of Yesterbox. Every night before my dog walk I decide what e-mails I’ll attend to tomorrow from today’s list. Everything else gets tossed. Then, no more e-mail for the rest of the night. Luckily I’m not CEO of a Fortune 500 company, so it’s like only 10-15 e-mails coming through my inbox every day with usually 1-3 that actually need time the next day. If an e-mail can barely stick out in a pile of 15 e-mails from that day as “definitely more important than the rest”, how could it possibly have a hope of sticking out in my life as “significant” and “I’m glad I followed up on that”. Delete most of it and don’t respond. I use the dog walk as “decision thinking time” to decide how I will approach those e-mails in the morning for maximum efficiency. I welcome the time sink of those 3 e-mails as my structured procrastination for the next day. If I have already finished “today’s e-mails” when deciding my to-do list for tomorrow, I pick up the previous calendar date that I haven’t gotten around to. This way I slowly catch up over holidays or times when I just didn’t open my e-mail at all. One key insight from the structured procrastination piece is that e-mail has a tendency to become the exact kind of horrific to-do list that drains motivation. Our inboxes would just over time fill up with the e-mails that we have struggled to get around to, creating a sense of dread. Delete it all. Just. Free. Ourselves.

I’ve actually been thinking recently of changing my e-mail signature to be radically clear about all of this, with a bit of Johnny Noble sprinkled in. Something like “I follow the Yesterbox philosophy. I decide by 5pm what gets done tomorrow. My inbox is set to auto-delete all mail received after 5pm to maintain my responsiveness. If it’s important, please message me again within daily working hours.”

E-mail requires philosophical approaches, not organizational. Just like real-world physical mail. Just because there’s 10 times as much of it as physical mail shouldn’t change our overall conclusion of … just throw away 10 times as much e-mail.

Hi Hans
Thanks for the reply. I think the issue is mainly the sheer volume of email that I’ve ’collected’ over the years. That and being afraid to lose the business contacts and conversations (small home based biz).

I admire those, including my wife and biz partner, who have near zero email boxes. I have tried — to no avail.

I’ve tried smart boxes, archiving, and mass deletions. Just when I think I’ve got it down to a manageable level in Apple Mail I realize I have to go through the same process at the server end — and I eventually give up. Perhaps I’m missing a step in the deletion process there?

I am thinking that perhaps a better solution might be to set up a searchable mini JD system for ‘important’ emails on my NAS, and somehow use an Archive process to move them there. Maybe using something like Hazel where at the end of a day/week I could program it to move all Red Flagged emails to JD 18.04 BizMail Orders and all Yellow Flags to JD 18.05 BizMail Estimates and use the date of the email in the title of the email?

Maybe set up a few other such archive folders on the NAS that could be accessed from all my appliances Mobile/Desktop. Might also use KeyBoard Maestro to assist with this if I ever get the time to master it!

Finally, if I could find a way to harvest (ouch, don’t particularly like that thought or word) the contacts that I note with, say, a Grey Flag, into a separate DB, SS or contact app for future use — and then just trash the rest.
:thinking:

:thinking:
Food for thought for sure, @clappingcactus John!
I answered @hans above and have probably included some of your suggestions in my answer there.

Like everything else, everyone has their own needs and wants and the goal is to find a happy medium, or at least something, in my case, that will allow me to get my own time back.

I’m going to re-read your reply several times as I believe it may just give me a whack on the side of the head strong enough to get me back on track.

No doubt I have to be more ruthless with my deletions, although I do have a current practice of deleting close to 90% of all incoming emails.

Vacation time is and has been my time — no biz emails or calls allowed! I like signature both you and Johnny have created and will soon be incorporating something similar into my model.

Over the years we have gone from a home based, eager to please, 24/7/12/365 business to a don’t expect an answer outside of 10 am to 4 pm / never on vacations / call first for appointment business.

It’s been a huge stress reliever and most have complied. The rest we don’t answer, no matter how much they press. We have blocked several of the latter until they ‘get it’.

Thanks again for your well thought out reply.

I read two things in here:

(1) there is value in your archive of emails, no doubt. It would be too much work to extract it all; but since there is value in there, keeping it in its current form is worth it. Here, I would suggest trying to get it somewhere where it’s safe for the future, and fairly searchable, and then if you REEEEEALY need to find something sometime, it will be doable with some time.

to be precise: I’m thinking of scenarios where it’s legally crucial to find some message from ten years ago, and when you extracted the most important stuff before archiving it all, you didn’t realize this particular topic would fall into that category …

(2) The business contacts and conversations currently stored in your email. I think JD (not exclusively, that yesterbox link from @cobblepot is mind-blowing!) offers an approach to not have to rely on email for this anymore (going forward). I’m still very guilty of this myself. This will require effort to consciously create the records for people and topics we find important using JD IDs and Categories, and then train ourselves to get the important information out of the email as it comes in.

It sounds like this is a very clear, high-value project: go through and select the most important contacts and their context, and put those in records in your JD system where they belong. Then archive the rest. (It sounds, from your story about re-orienting your business communications approach, that you have the insight and motivation to do this and to create a clear scope of what to extract, and what to leave in there for the archive).

Note about tone: I’m talking to myself here mostly, not implying I know what you should do in your situation :innocent: .

And note about technical details: it sounds like your stack is so different from mine I can’t really speak to that. But is there some way you can get a plain filesystem dump of your emails (backed up of course), that you know can be queried someway if necessary, so that you don’t have to worry about relying on third-party services for the big ol’ archive?

Thanks @cobblepot, your post is galvanizing.

sorry @cobblepot @clappingcactus for mixing your user names up!!!

The system I (previously) advocated on the website, with very neatly organised folders, was in a work context. Very busy $300M project with dozens of interacting parties, a fiendishly complex schedule, and lots of people who say they’ll do a thing and then don’t.

But then it’s your fault that they didn’t. And this might cost you real money. Aha! Now we have a problem.

It shouldn’t have been this way. It wasn’t ‘healthy’. But that’s how it was. And so being the individual in my team who could recall, almost flawlessly, any email: utterly priceless.

Partially because those emails acted as mini-contracts. You told us you’d have the widget painted red by the 27th July. ‘No I didn’t!’ Slides email across table…

And partially just because so much organisational knowledge exists in email. Again, it shouldn’t. But it does. You ask someone in April how to do [really complicated one-off process] and then you’re not ready to implement that until July and now … dang. Where was it?

This was my primary frustration with email: you know you have the knowledge, but you can’t find it.

(This has got much worse with the advent of MS Teams.)

So in that job, for a few years, I organised essentially every email in to a folder. It probably took 10% of my work day. Every day. But I was the team’s librarian. My boss was well aware. It was a cost of doing business that paid for itself.


Now, that’s quite a unique situation. I do not do that today. Here’s a quick overview of my current strategy, which works okay. I’m inspired by @clappingcactus and will probably adopt his ideas.[1]

1. Never truly ‘delete’ an email.

By ‘delete’ we mean ‘archive’. It’s always over there if you need to recall it with search.

This means that you never have to worry about removing something from your inbox. You don’t have to consider that action for even the briefest moment. Because it’s over there in your archive, just in case.

I do this by having my mail provider forward all incoming mail to another address, archive@example.com. My mail client then POPs (yeah, POP!) that off to a folder, and a rule marks it as read. I never see it. It’s just there.

The key is that this is happening server-side. I can switch mail clients, do whatever else: every email is forwarded, by the server, to my archive mailbox.

2. Use your mail app’s features

I use macOS’ Mail.app just because it’s there and I’m used to it. It’s fine.

I use its ‘Filter messages in this mailbox’ feature heavily. So currently … lol, okay … my personal email, which is mostly junk/mailing lists/receipts, has 1,879 messages. hello@johnnydecimal has 734. But I don’t care, because if they’re read, it just means I haven’t cleaned up yet.

I leave those that need my attention unread and then when I hit the filter button to ‘only show unread’, now I have 3 emails. I use Mail’s unified inbox view so I don’t care which mailbox they’re in.

2,613 to 3. Quite a difference.

3. Don’t forget to clean up!

Okay so I’m probably overdue. I tend to leave at least the last few weeks of history in my inbox because I do flick back to those messages and it’s convenient. But it looks like I’m due a cleanup.

Thanks to rule 1., that’s easy. I’ll do it now. Cmd-A, delete. Gone from the ‘inbox’ … but still in the archive.


This mostly keeps me sane. My relationship with email is that it is a necessary evil.


  1. And honestly I say that but I probably won’t. Because that would be me giving email even more of my attention, at least in the short term, and I just don’t think it deserves it. ↩︎