I delay writing back to people and then never do it — can I fix this?

by Alison Green on January 15, 2024

I’m off for the holiday, so here’s an older post from the archives. This was originally published in 2016.

A reader writes:

I have a terrible block when it comes to writing (back to) people. I get very anxious about writing the “right thing” in different situations — when I need to say no (even for a trivial reason like “I don’t have time this week for a call”), when I’m not exactly sure how to answer, when I need to give a critique, or when I need to ask someone for something — and I put it off. Then the longer I wait, the more guilty I feel.

In general, I don’t do this with my own colleagues or clients or partners. It tends to happen with others. For example:

* When I left a previous job (voluntarily – they didn’t want me to leave) I didn’t let my broader contacts know, only my direct clients, as I was embarrassed that the job hadn’t worked out.
* I promised to check around for a contact with any ideas for possible funders of a documentary she was working on, and never did.
* I was informally offered a role as a consultant with a network whose work I greatly admire and instead of directly saying, “I’m probably going to be joining another org, but thank you so much,” I said “sounds great!” and never got back in touch.

Often I’m not quite sure how to respond and I don’t want to send a less-than-fully considered answer (this is where my perfectionism plays out at its worst, although I am managing it okay in most other ways), but then end up never writing, e.g. I don’t know the answer to a question that’s being asked, I’m unsure of the right words to phrase an email that I’m worried the other person may not like, or even I’m feeling so happy about a piece of good news that an email seems inadequate and I think I should send a card instead but then end up not getting in touch at all, etc.

Or I’m avoiding discomfort, e.g. I don’t want to say no to someone asking for funding, I don’t want to say that I don’t have time in the near future to talk with someone who’s asking for a short call, I am reluctant to reach out to someone I haven’t talked with in a while to ask them for a favor, I don’t want to ask someone to do something, I’m not ready to think about whether or not to take on someone who’s asking for an internship for a summer that’s still eight months away…

There seems to be a short window of a day or two or three within which, if i could respond, I would be able to do so in a non-anxious way. After that, the guilt at not having responded in a more timely manner kicks in, I then feel like I need to make up for my delay by writing “an even better” note, but since nothing has changed that would make that more likely, I still don’t do it and it spirals from there.

Despite this habit, I’ve done well in my career so far, thanks to many advantages, lots of luck, and a good work ethic (other than this bad habit). I currently work on the management team at an NGO working for a cause I care deeply about, and was recruited into my last three jobs based on my reputation or their past experience of working with me.

But writing the above out, I’m ashamed. I would be shocked if I heard of anyone else in a senior role in an organization — or indeed anyone who had managed to make it to middle age – acting like this. It’s absolutely not who I want to be either as a professional or as a friend. And yet I can’t seem to shake this habit.

First, fundamentally: How can I change this? Can others relate or am I alone in this neurosis? Any advice on helping to get past this block of my own making?

Second, for this situation overall: Is it too late? Is there anything I can do to make up for my (lack of) response? I’m fully prepared that many of my relationships will never be the same, but is it still better to reach out anyway? Is there anything I can do to at least partly make amends?

Third, practically speaking: What should I say? How much should I try to apologize / explain? There is no good excuse for my (lack of) action. The problem is that my good intentions aren’t translating into actions. Yet it sounds insincere to say, “I’m sorry, please know i’ve been thinking of you” (“if you were thinking of me why didn’t you get in touch?”) And I don’t want the focus to be on me. Yet I feel like I should say something that indicates how sorry I am because I don’t want them to think I didn’t care.

What else should I say? Respond to their request even if it’s no longer needed? Say that I was thinking of them and wanted to say hello? Update them on what I’m doing? Offer to be of help in general? Send along an interesting article? Etc.

Any advice would be so much appreciated. Thank you so much.

You can change this! Can we make this your new year’s resolution? I really do think you can change this, and it will probably be easier than you think once you try it.

Some things that I think you’re not accounting for:

1. People are aware that other people are busy! If you respond a few weeks late and say something like, “I’m so sorry for my delay in responding to this — I’ve been swamped and in triage mode, but I wanted to get back to you even though it may be too late,” most people will understand. They’ll appreciate the response, they’ll get that you’ve been busy, and they’re unlikely to think negative things about you. Busy-ness is a known state. If you don’t reply at all, that’s when you’ll seem unreliable. If you don’t respond at all, people will be more likely to think “There’s no point in emailing Jane about this because she didn’t respond last time” or even “Huh, Jane never got back to me, that feels kind of rude.” But responding late — even very late — changes that, as long as you acknowledge the delay and include some kind of explanation or apology.

2. People understand no’s. Really, they do. When someone asks you a favor, 99% of the time they’re aware that the answer might end up being no. As long as you’re nice about it, it’s really pretty normal to say no to things. I suspect you just need the wording to do it, so here are your new form letters:

  • “Thanks so much for thinking of me for this! I’d love to say yes, but my workload is crazy right now, and I’m trying to be disciplined about not taking on anything new. So I need to pass, but the project sounds great and I wish you luck with it! I’d love to hear how it went when you’re done with it.”
  • “I’m in triage mode with my schedule this week and next, to the point that scheduling a call would be hard. I can answer a quick question or two over email if that would help — but if not, I understand and hope you can find the answers you need some other way.”
  • “Thanks for contacting me about this. I’d love to say yes, but I’m fully booked for the next couple of weeks. I’m sorry I can’t help!”

3. Put yourself in the other person’s shoes: If you ask someone for a favor, would you rather hear a “no, I’m sorry I can’t” up-front, or would you rather hear “yes” and then spend weeks/months wondering why it’s not happening and why the other person ghosted you? It sounds like you are putting way too much weight on satisfying people with an immediate “yes” and way too little weight on what happens after that. People care about what actually happens, not what you say will happen. So by saying yes and then disappearing, you are setting people up to be confused/frustrated/hurt/disappointed/angry. It’s like in your quest to avoid a mild flick on someone’s arm (the immediate “no, sorry”), you’re punching them in the gut a month later instead. It’s not a logical trade-off.

4. You cannot go through life ensuring that all interactions with other humans are free of discomfort. You are going to sometimes have to deliver uncomfortable news, or say no, or ask someone for a favor. In your quest to avoid doing that stuff, you’re actually just signing yourself up for a whole different (and worse) type of discomfort — the discomfort you’re feeling now about being someone who flakes out on people. So there’s really no discomfort-free path. It’s just a question of which kind you want. If I asked you to choose between (1) mild, up-front discomfort of saying no/delivering bad news/etc. or (2) long, lingering discomfort of knowing that you let someone down/flaked on a commitment/stopped responding, and now need to feel awkward for months/years about contacting them, would you really choose #2? I don’t think you would, but you’re picking it now by default because you’re so focused on avoiding #1 that you’re not being clear-eyed that #2 is the price.

Assuming you want to interact with other humans, you’ve got to pick #1 or #2. There are no other options.

Okay, now some concrete recommendations of what to do going forward:

1. First, no, it’s not too late to respond to some of these people. Even if it’s been months, you can email and say, “I’m so sorry I never got back to you about X over the summer. My schedule got overwhelming, and I should have reached out to update you sooner. I’m sorry I wasn’t able to help with this, and I hope the project ended up going well.” (You do not need to then do the work you promised; in most cases, it’s going to be too late to be useful. Although if you’re still willing to, you can say, “Would it still be helpful for me to do X now? If so, I’d be glad to, although I realize the window may have closed.” But don’t offer this unless you’re 100% committed to doing it this time. If there’s any chance you won’t, it’s better not to include that offer.)

2. It sounds like you’re not just declining to say no, but that you’re also saying yes to things you don’t necessarily want to do, like that contact who wanted ideas for documentary funders or the offer for consulting work. I very much know that feeling in the moment of “sure, of course I can do this!” and then realizing later that you can’t or don’t want to. Obviously, you want to get better at thinking things through before you commit to them, but if you do find yourself in that position, in some cases it’s okay to write back and say, “I know I said yes to this, but I’ve realized that my schedule is making it impossible to do it justice. I will definitely let you know if I think of contacts for you, but for now it probably doesn’t make sense to count on me for this.” Obviously you can’t do this when it’s the week before someone’s wedding and you agreed to make the cake for them, but if it’s more like “Bob asked six people, including me, to read his screenplay,” it can be an option.

But ideally, you’d head that off by being more realistic right from the start. Some things you can try:

  • Don’t say yes to anything unless you are willing to put time on your calendar right now to do it in the next week. If you’re saying yes thinking you’ll do it at some hazy future point, say no because what you’ve learned is that it’s not likely to happen. (This won’t work for everything, but it’ll work for some things.)
  • If you don’t feel equipped to figure out if your answer is yes or no right now, say that and ask for more time. That person who wants an internship eight months from now? Write back and say, “I won’t be able to start planning for fall interns until June. Can you reach out then and we’ll talk more then?” That job offer you accepted that you didn’t actually follow through on? It might have been better to have said, “Thanks for this offer! I’d like to take a few days to think it over, but I’ll get back to you by Friday.”

3. Stop waiting for perfect. In most cases, people like timely responses more than they like “perfect” responses written several weeks too late. Effectively immediately, take “perfect” off the table as a goal or at least redefine it. For you, “perfect” is “I respond within two days,” regardless of how flawless the content is. In your case, “flawless” ends up meaning “never happens,” so it can’t be in the equation.

4. Set aside 30-60 minutes a day to deal with emails that you’re avoiding. Every day between 9 and 10 a.m. (or whatever you choose), you’re going to sit down and respond to the emails that you’ve been putting off. If you don’t know an answer or don’t have time to fully consider a question, in most cases you can say that. It’s okay to say “sorry, but I don’t actually know” or “I’d need to take more time to think about this — do you want to give me a call so we can talk it through?”

And since you sometimes put off emails thinking you’d rather send a card, and the card never happens, permanently take cards off the table as an option. You no longer send cards in this context. You send emails. That’s it. The emails have the big advantage, in that they will actually arrive.

5. You can take a similar approach with non-email stuff that you’re avoiding. I once read about something called “guilt hour,” where a bunch of office mates would meet in a conference room and take turns announcing the undone task they felt guilty about putting off, and then they’d each spend the rest of the hour tackling that task. Have your own guilt hour.

This is already a long answer and we haven’t even covered everything, but start here. If you really do these things, it’s going to solve a big chunk of the problem. And I think this stuff has its own momentum — once you get into these habits and see how frickin’ nice it feels not to be walking around with tasks and guilt hanging over you all the time, it becomes self-reinforcing. It’s easier to keep making these choices when you see that they leave you feeling good, not bad like the previous methods did.

Try it and tell us how it goes?

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{ 187 comments }

{ 187 comments… read them below }

  1. Mel*

    This is all fantastic stuff! One small thing that helps me personally with regular requests I have to make is to have a few me-approved boilerplates saved away as a starting point. Nothing clams you up quite like a blank email sometimes…

    1. Beth*

      Same! If I’m really stressed about an email that I don’t have a template for, I’ll also write a draft while telling myself I don’t need to send it yet, it’s just a draft and it can sit overnight before I hit send. That takes some of the pressure off of tackling the blank white screen.

      I also really relate to this: “There seems to be a short window of a day or two or three within which, if i could respond, I would be able to do so in a non-anxious way. After that, the guilt at not having responded in a more timely manner kicks in, I then feel like I need to make up for my delay by writing “an even better” note, but since nothing has changed that would make that more likely, I still don’t do it and it spirals from there.” I have the same experience, and I actually find that it’s great motivation to do things right away. I LOVE dodging that anxiety spiral–that’s hugely motivating–and the joy of knowing I’m escaping it helps me reply right away. Almost nothing sits in my inbox for longer than a day or two.

      1. Corey*

        I use a very similar trick – I’ll put “Draft email to X proposing Tuesday afternoon meeting” in my to-do list instead of “Email X about meeting.” Calling it a draft takes some pressure off and including some basic details of what I want the email to say makes it easier to get started. Plus sometimes it reveals that the real block is that I need to do something else before I can draft the message, like figuring out what meeting time to to propose.

        1. Marillenbaum*

          In the same way, I draft most documents in Comic Sans–it feels sufficiently silly that I feel like I can write whatever. And once the draft exists, I’m just editing, which is much lower-stress.

    2. tinaturner*

      The DECLINE: Sorry but I just won’t have time, etc.

      Then the COMPLIMENT: But thanks for asking. I know how detail oriented you are and know this will turn out great, etc.

      Leave a sweet taste in her mouth.

      1. The Rural Juror*

        I’ve always also liked the advice to thank someone for their patience rather than saying, “I’m sorry I’m just now responding” or “Sorry I’m late!” Maybe they had patience or maybe they didn’t, but it implies something nice about them instead of something negative about you.

        The ol’ kill ‘‘em with kindness :)

    3. Grumpy Elder Millennial*

      Came here to say the same thing. One of the things I love about AAM (and Captain Awkward) is the scripts. Rather than having to start from nothing, I can take their wording and tweak it so it works for me. Having a few options saved somewhere easy to find, then tailoring a little, will probably make this all way less daunting.

      1. Slow Gin Lizz*

        Yes! I was thinking scripts are the way to go here! And also, OP, remember that “perfect is the enemy of good.” (I’m sure others have said this in other comments but I haven’t time to read through all of them.)

        I’m not great at thinking on my feet and I’m really not good at saying no in person (getting better though), so many years ago I decided that if I was actually certain I didn’t want to do a thing but I was afraid I would agree to it anyway because the other person was pressuring me to do it, I would say, “Ooh, let me think about that and get back to you!” and then I would give it at least overnight or a few days and then email or text them to say, “Actually, no, I decided I can’t do the Thing, sorry.” Because the other thing that would happen is that someone would ask me to do a Thing (usually a music gig, my second job), I would immediately look at my calendar and see that I was free at the times they needed me, accept the gig, and then the next day I would have regrets about accepting the gig. Maybe it was a long drive, maybe it was some piece of music I’ve played a hundred times and am sick of, maybe the conductor was a jerk I don’t like working with; all of these are things I used to not take into account when accepting gigs. So now I definitely give myself overnight before accepting a gig unless it’s something I’m really excited about. Sometimes I will at first think that I am NOT interested but then with the benefit of a good night’s sleep would realize that I actually was interested.

        The other thing to think about is that if the other person really needs the Thing and you have not responded, they will likely ask you again. If you don’t respond and then you don’t hear from them again, well, that’s also partly on them for not following up on their original request.

        Would it help, OP, to realize that it isn’t necessary to perfect the wording of your emails? Emails are not meant to be novels, history text books, or peer-reviewed scientific papers. They are a quick way for people to communicate, and no one is going to closely scrutinize what you write in them. (Side note: maybe in your past you’ve had some terrible boss or coworker who DID scrutinize the wording of your emails? Maybe this is part of what holds you up when writing them?) And not only is no one going to scrutinize your wording, half the time people don’t even really read the email very closely, they just skim it to see what your answer to their question is. If the answer is no, they just file that information away and don’t even think about the email again. So just a quick “Oh, sorry, I can’t do that, too swamped with current projects!” is all you need to write. And remember that No is a full sentence.

        Best of luck, OP!

    4. Frankie*

      Same, I keep a word doc with all different wording suggestions for all kinds of scenarios and add to it regularly, I’m adding some of these from today!

  2. A.P.*

    Sending out replies to people is the kind of thing that ChatGPT is great at. Even the free version works pretty well. Just give it a prompt like, “Write a polite email turning down a consulting gig,” and it will come up with something pretty good.

    It’s a lot easier to make some light edits to an already existing note compared to sitting down at a blank screen and trying to come up with something on the fly.

    1. yvve*

      that’s a really good idea! I’ve also found that often when i start writing down the prompt of what i want, and context for the bot, i end up with 90% of the email done anyway. But it’s easier because it doesn’t feel like I’m “writing an email”. This is very useful if you’re struggling with specifically the “perfection/creating the perfect opening” aspect, i think

      1. Elle*

        I was about to say exactly this! I like using AI to generate a response and then heavily editing it.

        1. Wendy Darling*

          I feel like a lot of the time the hardest part is just starting writing, and using something like chatGPT kind of gets started for you. Once there’s actually something on the page you’re either like “oh god no not like THAT” and fix whatever it said, or actually what it said is basically fine.

      2. Kes*

        Yes, this is similar to what I do, which is “just start writing a draft at least, you have some thoughts about what you’re going to say even if you’re not sure exactly” and then once I make it through the draft, a lot of the time it is pretty much ready and I can just do whatever tweaking is needed and then go “yeah, okay, just send it”. But generally the hard part is writing it out to start with. I also often write it in notepad++ and then copy to wherever it’s needed.

    3. Throwaway Account*

      I came here to say this! Ask ChatGPT to write a draft for you. Once you get the hang of asking it questions, you can tell it the tone you want, tell it how to update a version to change the tone, add more details, etc.

      It can really help to have a draft to work with and tweak as you like.

  3. Victoria, Please*

    Oh, OP, you are SO NOT ALONE. I do this too. All the damn time. For lots of the same reasons you do. I haven’t read Alison’s answer in full yet, but will, and hope it helps me too.

    I’m a successful person in my org and in my field, maybe not at the top but certainly a positive influence in my little corner of the world. So, it’s not like this habit stops a person from being a great professional. It’s just an area to get better at. Please try to let go of the shame. <3

      2. Wendy Darling*

        I had to reschedule an appointment for another week because when the person texted me all “Is Thursday at 10:30 good for you?” instead of responding “Great, see you then!” I just did not respond until Thursday afternoon even though that time was fine. Literally all I had to do was text some kind of affirmative, a thumbs up emoji probably would have sufficed, but I simply could not last week.

        I’m in my 40s and by most measures a reasonably well-functioning adult, but being a human who has to communicate with other humans can just be tough.

    2. Generic Name*

      Yep, same. I’m a middle aged manager, and I was also recruited into my current job. It sounds like we are very similar. I also sometimes put off responding to stuff out of either perfectionism or people-pleasing. For me I know that those tendencies come from a background where people who were important to me made it very difficult for me to say no to anything. It might be worthwhile unpacking why the thought of saying no to someone is something you feel like you can’t do. Or why doing something imperfectly is worse than not doing something at all.

    3. ampersand*

      Yes, I also do this and hate it. These suggestions look very helpful and I’ll be implementing them.

      LW, lest you feel alone, just know that I’ve ignored a couple of emails regarding a research study for several months now. A study I happily, voluntarily signed up for, and then reneged on. This is especially terrible because I work in research administration and know better. It kills me to have this problem—I’m hoping Alison’s suggestions help!

    4. One Of Us*

      I am in a senior role and, if not actually middle-aged, close enough to it to feel middle-aged. And I, too, could have written this letter! I still have this problem, but I have gotten better. Here’s a random list of things that have helped me.

      1. Figuring out why I didn’t want to respond. Often, for me, it’s just plain shyness. Other times, it’s wanting to have said no, but having felt I should have said yes. Or even not having been good at understanding that no one was what I wanted. But often, being able to honestly assess the situation really helps me say to myself, “OK, you don’t want to do this, but you can BE BRAVE.”

      2. I once got an email from someone responding to an email my predecessor had sent him nearly two years previously. The emailer responded exactly the same as if it were to an email from the day before. I was astounded and realized that I apologize far too much.

      3. Someone on a message board I frequented said something along the lines that her version of “The perfect is the enemy is the good” is “The good is the enemy of the done.” I find it helpful to ask myself, “Would it be better for the recipient to have this done, or to wait until I can get it to be good?” Sometimes just done today is far better than achieving the right tone or other tweaks you might make.

      4. When I get procrastinate-y in any aspect of my life, thinking about what I MOST am avoiding is useful. Often it’s one thing I REALLY don’t want to do that causes other tasks to gather around it. If I can face that getting that one thing done is going to be unpleasant and just do it, it can get me over the hump.

      1. One of Us*

        In the second paragraph, the third sentence should be, “Or even not having been good at understanding that no was what I wanted.” Even I had trouble understanding that sentence, and I wrote it!

      2. Slow Gin Lizz*

        Oooh, I like your #3! I need to remember that one!

        Another thought occurred to me when reading OOU’s comment, which is that no response is still a response. I think it’s Captain Awkward who says that no decision is still a decision. Not sure if this is particularly helpful to OP but I just wanted to throw it out there.

    5. Teekanne aus Schokolade*

      I froze like this about sending out wedding thank-you’s. it’s been six years and at least three guests have passed away but I realized in many cases continuing the relationship, professional or personal, is enough to let that person know you’re not totally flaky, just a human. I thanked most people in person and Believe that my reputation as a friend (in OP’s case, professional colleague) was strong enough to withstand that momentary lapse.

      1. Miss Manners was right*

        it’s never too late to send thank you notes for wedding gifts. you can use Alison’s script and say I’m so sorry for the delay but we really loved your XY and z. you may think that everyone has forgiven you but many won’t forget. if you have kids, you can expect to possibly not get presents from people to whom you have not expressed your gratitude, in writing, on paper. all the effort and expense that goes into buying a wedding present deserves a note. yay for Alison’s Scripts! they apply all across life. having done something similar, I can assure you you will not regret it. and it is likely that the relief you will feel when you don’t even know you need relief will be huge! you can do this even if you’re already divorced! a friend of mine did and all those notes were really appreciated! hers went something like I’m so sorry for the delay in writing this. Joe and I really loved your x y&z. I’ve been meaning to tell you forever. now Joe got the x, but I wanted to let you know how much we loved it during our time together.

        1. MaineCat*

          As someone who has had large amounts of both outgoing and inbound USPS mail vanish into thin air, my suggestion is don’t be that person who holds a grudge over never receiving a thank you note. I had wedding congratulations cards never arrive (thankfully this person inquired, but it made me wonder who else sent stuff that never arrived). I’ve had cards with checks in both directions disappear, probably stolen. I received a thank you note that had been postmarked 6 months earlier with an apology from USPS about it being dropped behind something. Think how you would feel if you behaved punitively towards someone or even nurtured hard feelings not knowing they HAD sent you a beautiful thank you note.

          1. Waiting for perfection*

            My aunt gave me a crockpot for a wedding gift 35+ years ago. She specifically said “don’t send me a thank you note. You’re too busy with a wedding and all the rest. Don’t waste a stamp.” I have no idea what I was given by most everyone else, but I remember aunt Joan every time I use the crock pot.
            Also I found my thank you notes MANY years later and was too embarrassed to send them.

          2. Miss Manners was right*

            So true! I’ve had so many things disappear in the mail. Once a check I sent to a doctor actually was cashed by someone completely different! Stolen right out of the mail by someone, and they walked into a bank in another town of the same branch and cashed it in person! That was a whole fight with the bank, because they cashed it even though the person who did the cashing, in person, in the bank, spelled the doctor’s name wrong when endorsing the check!

            Twice I had some info to send to a government agency, and I ultimately had to send it UPS, because both initial mailings got lost in the mail, and the agency never received them. and that was certified mail, return receipt requested!

            What I was saying though, was that the relief I experienced in finally sending my thank you notes was so much worth giving up the energy expended in making justifications to myself like this:

            “I realized in many cases continuing the relationship, professional or personal, is enough to let that person know you’re not totally flaky, just a human. I thanked most people in person and Believe that my reputation as a friend (in OP’s case, professional colleague) was strong enough to withstand that momentary lapse”

            Continuing to say similar things to myself turned out to be taking up way more mental energy than I realized. And way more energy than just sending the notes! and I felt so much better about myself after sending them. Being someone who has trouble like the OP.

            It’s not about holding a grudge or being friends with people who hold grudges. It’s about doing what you know is right, instead of spending all the effort and time internally trying to justify not doing it.

            And it’s also, according to Miss Manners, about people knowing that their efforts were appreciated. Perhaps feeling that they don’t want to bother trying again with a handmade baby quilt, when the expensive $200 rice cooker for the wedding gift was never even acknowledged.

            True that people can always inquire and say did you get my $200 rice cooker? I’m very concerned that the store may not have sent it, and I didn’t want you to ever think that I didn’t send it! But it’s also true, in my experience, that just sitting down and doing it takes away so much internal energy spent justifying not having done it, that it’s completely worth it! Whether or not the other people are holding grudges, or simply thinking that their gifts weren’t really appreciated and that they should put their effort elsewhere, doesn’t really matter. What matters is I cleaned up my side of the street, and didn’t even realize how much energy having all that justification stuff in the back of my head swirling around actually took. ymmv.

        2. Usurper Cranberries*

          Wow, I could never even imagine being so petty as to refuse to buy someone’s kids gifts because their parent didn’t send me a thank you card for a wedding gift. I’m honestly shocked that anyone thinks that way.

          There’s absolutely something to be said for sending late notes if you feel guilty about them being unsent, but personally I wouldn’t waste a moment feeling guilty in case some people in my life were that petty about it – I don’t want to be friends with someone who’d hold my thank you writing timeline over innocent children’s heads!

          1. Miss Manners was Right*

            Gosh I don’t think it’s petty at all to think that if you fail to please someone with one large gift, that you simply might have a bad idea of what they like, and best to put your efforts where they are better spent. Certainly it’s not taking it out on innocent children to fail to give a baby gift, because the baby isn’t going to know it. Baby gifts are for the parents.

            And one doesn’t have to feel guilty about not sending thank you notes for wedding gifts in order to wish they had done so. But if someone spends their time justifying it in their own head, they might, like me, feel a sense of relief at just doing the right thing and quitting all the mental gymnastics.

            I guess I read Miss Manners as much as I read aam, and I think she’s correct on this point. If you put a lot of effort into a present, such as a wedding present, and you get no reply, or only a casual thank you verbally, it’s reasonable to assume it did not please the recipient.

            But in any event, that completely isn’t the point. The point is, the original poster had difficulty taking care of certain basic things even when she wanted to. The scripts given, and advice given, was for ways to manage to take care of those things, not find further excuses to not take care of those things. Because it feels much better to take care of those things. This is just another example of that.

            It follows right along the lines of advice saying weeks or months later you can send an email saying oh I’m so sorry for the delay, I just got swamped. But I can’t do that, or I still can do that if you’re interested, but not until july. Or what have you.

            All I’ve pointed out is that it is perfectly possible to send thank you notes for wedding gifts 6 years late. And that in my case, I didn’t realize until after I had sent them quite late, how good it felt to have it over with, and know I had done the right thing, instead of constantly having this little justification loop in the back of my head, which took up way more energy than I expected.

            Whether or not one thinks that people who don’t get a thank you note for an expensive wedding present are being petty by assuming that their largesse was not well received, and putting their efforts elsewhere in future, or whether it’s understood that while people give presents for the sake of giving presents, knowing that the present was well received because they are the recipient of some gratitude is quite reasonable, is really irrelevant to the point. To all of those who have no interest in sending thank you notes even for their wedding presents, don’t! And if you then don’t get further presents for further life events, such as the birth of a child, and you wish to consider those people petty, by all means, please do.

            My point is that like the op, it can really feel much better to just get it done, and like the advice given, one can do it down the road with a simple line or two at the beginning of the note saying so sorry for the delay. Anyone who does not wish to do this is obviously not obliged to do so! I simply found that it was in the end, much more of a relief to write the notes, and took a lot less energy, than the energy I didn’t realize I was spending justifying my behavior to myself. I’m just human after all, not a flake, on repeat in the back of my head, takes a lot more energy than sitting down and writing the notes, in my experience. But by all means, please feel free to not write wedding thank you notes, and then to consider your friends petty if you don’t wind up getting any more presents for life events! Like I said, your mileage may vary.

    6. KC*

      I am another person with this problem! What helped me the most was like Allison said –setting routine times to do this. For me, Monday and Thursday mornings were what I called Biggest Frog days (if you have to eat a bucket of frogs, start with the biggest one). I’d have a checklist with all the tasks I didn’t want to do and I’d go down the list before starting any other work those days. Checking off items feels so great, doing it 2x per week didn’t allow them to sit too long, and the rest of the day feels so easy once that weight is lifted. Good luck OP! I hope you find something that works for you!

      2. Slow Gin Lizz*

        This is good, or there’s the converse of this. I have a really hard time getting started on some tasks that I really hate but if I start with the easiest part of the task or a related task that I don’t hate as much, sometimes that’ll kick-start my task brain (or give me a quick dopamine hit) such that I am then in a better mood to do the more hated tasks. Or, you know, eat dessert first. Or even intersperse dessert (or less hated task) with eating healthy, less appetizing food (hated task).

    7. Elle*

      Chiming in to say me, too! On paper I’m extremely successful (multiple Ivy League degrees, prestigious job, top performer, etc etc etc) and I feel so ashamed that like… I can do all this, but I can’t answer an email from an old mentor in a timely manner, and then I can’t answer it at all because I feel so guilty, and how am I just *so bad* at this thing that seems to be so easy for other people?

      One reframing that’s helped me is Alison’s advice: “Effectively immediately, take “perfect” off the table as a goal or at least redefine it. For you, “perfect” is “I respond within two days,” regardless of how flawless the content is. In your case, “flawless” ends up meaning “never happens,” so it can’t be in the equation.” — basically, reminding myself that the most important thing is that I send *a* reply, even if it’s not perfect. I know my tendency is to say “oh well I’ll just wait until tomorrow and then I can spend more time and it will be perfect”, so when I catch myself saying this, I can counter with “nope, you know that’s how you end up in a delay -> guilt spiral, just send the dang thing now” and do it.

    8. Sleve*

      You can add another email procrastinator to your list. As I read this letter I started to wonder, did I email Alison in my sleep?

      It happens when I’m overwhelmed with juggling too much crap in my life and my brain is trying to preserve my last vestiges of energy by avoiding things that make me feel bad. The only solution I’ve found is to never, ever, ever allow a reply to go unsent. What that amounts to in practice is writing a brief reply the minute I get the email and scheduling it to send in two days time. Either I get back to it and edit the email into something I like better or I don’t, but something is guaranteed to get sent. Nothing else works. Not scheduling reminders, not ’email hour’, not beating myself up for my lack of conscientiousness. They just make me feel bad and so my brain will try and protect me from them by more avoidance; which is a great response to things like snakes or rotting food, not so useful for modern emails. The good thing is, the threat of having 2 mediocre lines sent out in my name tomorrow morning spurs me on to write a proper timely reply in a way that nothing else can, because the only way to avoid that danger is to properly finish the email – and SOON.

    9. Cheesesteak in Paradise*

      Me too! Early 40s professional in health care. Same reasons as OP basically. Shame hour (has to be in the morning, my motivation evaporates after lunch) works well for me.

    10. Ruth Anne*

      This is one of the most relatable letters (to me) yet. I could share so many anecdotes. I’m printing Alison’s response and some of the comment suggestions!

  4. Alton Brown's Evil Twin*

    No advice to add, OP, but you are not alone! I took me years to get into the habit of doing this kind of correspondence and I still sometimes end up with things buried in my to-do list.

    1. SBT*

      I know we cannot armchair diagnose, and my experience with anxiety is in no way the same as someone else’s, but agree that this is a possibility. I’d say if you try to implement Alison’s suggestions and STILL find you can’t do it, it’s worth exploring why that might be and some deeper root causes.

      1. Jade*

        I have done things like this in the past. Even the simplest task seemed overwhelming. It’s worse when under stress.

    2. Anonymoose*

      I think it’s less about anxiety and more a part of being human.
      I have several friends with diagnosed anxiety who like to spend time with me because I’m known for being the calm, non-anxious person. Yet I do this too. Much less often now that I’ve worked for people who avoided making any decisions and I saw how badly it impacted me (Alison is right – saying no early is a million times better than saying yes and then not doing anything), but I can name a few people that I haven’t responded to last year and I feel guilty about it.

      I’m not excluding it as a possibility with OP, but I wouldn’t assume anything.

      1. Caramel & Cheddar*

        I want to be clear that I’m not armchair diagnosing here because that’s against the site rules, but I do want to say that part of any kind of mental health diagnosis is about frequency and severity. A lot of people miss out on important diagnoses because when they talk about their symptoms with people, they get dismissed with “This happens to everyone!” reactions. As the joke goes, everyone goes to the bathroom, but if you’re doing it 100 times a day, you might want to see a doctor about it.

    3. Beth*

      Even if it’s not clinical anxiety, a therapist may have concrete strategies for managing the situation and working through stress and shame productively. If you can access a few sessions, OP, it might not be a bad idea!

      2. zaracat*

        yeah, I’d frame this approach as being “coaching” rather than “therapy” if that makes it easier to accept this idea

    4. Sparkle llama*

      Agreed! My therapist helped me to rework the negative thought patterns around similar things so I can recognize anxiety brain is being irrational and how to move forward from there. You might be able to get a few sessions covered by an EAP!

    5. Lily*

      I agree with the rule about not armchair diagnosing but I do think it’s worth leaving this suggestion up for the OP to consider. I had a LOT of problems like this in the past year – people suggested anxiety but it just didn’t feel like anxiety, it felt like paralysis. I’d always had procrastinatory tendencies and there were a lot of exacerbating factors going on at my new workplace (no systems, poor management, no culture of getting things done etc). But fast forward to an overdue check up and it turns out my thyroid meds were way out of whack, and the doctor asking about any anxiety symptoms (I was so over ‘normal’ that she was worried about panic attacks). Getting my meds on track is not the whole solution (I’ve invested in some really good support for self-management at work, I will be implementing everything Alison suggests above PLUS trying to work out my next career move to find a better workplace) but it’s part of the picture that I hadn’t worked out for myself.

  6. Sola Lingua Bona Lingua Mortua Est*

    Echo #3 on the suggestions. Forgive your imperfections and yourself for sending an imperfect email.

    Nothing’s really perfect, anyway.

    1. GreenShoes*

      One of my favorite boss’ had a saying… “Don’t let perfect get in the way of good enough”

      I thought that was a really good way of conveying that not everything needs to be perfect (or even good, for that matter) and a lot of times ‘done’ is all that is needed.

      I can guarantee that the recipients of these emails aren’t evaluating the OP’s (or anyone’s) responses on a scale starting with “Perfect”. Really they are using them as intended… did I get a response and did the response give me the needed/requested information. That’s it.

      Sadly the OP’s ‘Perfect’ responses aren’t even ‘Good Enough’ because they aren’t actually being sent to the recipients – And I say that not to stick the boot in, but to point out that the OP is spending a lot of time and effort with worse results than if they used less time and effort in the first place :(

    2. The Prettiest Curse*

      Hands up anyone who would much prefer to get an imperfect response than not get one at all! I don’t do this with emails, but would definitely get frozen by perfectionism earlier in my career.

      One technique I use when I’m avoiding doing something apparently non-urgent but still vital is to tell myself to imagine how good it will feel to have finally done that thing. It doesn’t always work, but it often does. Best of luck getting around this mental block, OP.

      1. allathian*

        Yes, absolutely.

        “Don’t let perfect get in the way of good enough.” Sometimes you can even go further than that, it doesn’t even have to be “good enough,” however you define that. Sometimes simply “done” is all that’s necessary.

        For people with perfectionist tendencies, there’s a quote that’s been attributed to Leonardo da Vinci: “Art is never finished, only abandoned.” Granted, most people don’t work with art, but if you have trouble finishing a job and keep fiddling with it, at some point you’ll only get ever diminishing returns for your efforts. Ideally you should be able to decide that your work is done before you get to that point.

        I don’t have this problem with emails, but I’m sometimes guilty of procrastinating with things that I really don’t want to do but that need to be done. My biggest is our mandatory trainings, because I find video trainings so unpleasant to do (I’d much rather simply read the script than watch talking heads on a video). But they have to be done and won’t be any more pleasant to do later.

        I have a friend, and before the pandemic lockdowns I saw her about once a week at our tai chi class. Now I haven’t seen her for more than a year. I sent her a virtual Christmas card and she responded, but we haven’t talked after that. I really should at least text her and ask if she wants to talk, but I keep putting it off… I admit that I’m often bad at maintaining friendships when I have to do most of the work, but she has enough troubles as it is that it’s unrealistic of me to expect her to do much, and I don’t want her to think that I’ve abandoned her because I don’t know what to say to her.

        1. Philosophia*

          “I’d much rather simply read the script than watch talking heads on a video.”

          Then there’s a pair of us! — Don’t tell.
          They’d banish us, you know.

    3. Yorick*

      For perfectionism, I think it helps to remember that never doing a task or doing it really late is just as imperfect (or more!) as getting the wording a little wrong.

  7. That Snake Wrangler*

    These are all fantastic points that I’m going to apply to my own response blockages. One other thing/idea to add: I tag my emails that need a response with “Needs Follow-Up”. I set aside two hours a week to go through the “Needs Follow-Up” email category. Sometimes it takes longer, but just having that time blocked off on my calendar helps immensely. It also means that I don’t feel as much pressure to respond Right Now to emails that I just don’t know how to respond to in the moment. It is also really satisfying to watch the number of emails with the yellow flag slowly decrease during those hour blocks.

  8. Evelyn Karnate*

    I struggle with this too! I find it helpful to remember that timeliness is one element of a thoughtful response, and that “good and on time” is (usually) better than “perfect and late.”

  9. Flora_poste*

    I have the same issue, OP, and I am bookmarking this page! Let’s both make it our new years’ resolution!

  10. Objection*

    Oof, I feel this so hard, OP. And like you, I’ve done fairly well in my career. I’ve been in a somewhat senior management position in my organization for about 18 months, and as my responsibilities and the demands on my time increase, I feel like my “non-responses” get worse and worse. And I beat myself up and tell myself that the outside stakeholders I work with think I suck compared to my predecessor. I’m glad you asked the question, and I’m glad Alison answered it with some good suggestions. When I do finally write the emails I’m putting off, I tend to do it after 5:00. I’ve realized that’s when I get the least interruptions because emails stop coming in and adding to the pile. I’m most productive from 5:00-7:00 on my in-office days because of that.

  11. Charley*

    Oooh, this resonates! I’ve been getting better since I decided to make email management more of a priority in the past few months, but in the past I have absolutely felt of that yucky guilt/dread amalgam every time I opened my inbox and remembered some fairly mundane email that was weeks to months overdue. I can still make myself cringe thinking about some of my worst offenses. Things got a lot better when I stopped believing myself that I would respond ‘later,’ and started responding whenever I saw the message, even with something brief or noncommittal.

    1. Charley*

      In reassuring news, I just dug up and responded to an email from an old professor whom I’d left dangling for months after using them as a reference for a professional opportunity. They just responded to me and were perfectly gracious and glad for the update. All my fears of what they’d say (‘why didn’t you answer my email? You’re so entitled! Never ask me for anything ever again’) were totally unfounded, we are on good terms, and I feel a lot more confident in our relationship going forward. I’m sure it will be the same for you in many cases once you do follow up with your contacts.

      1. Elle*

        I love it when my worst fears about a totally low-risk situation are shown to be absurd and everything works out fine.

  12. Heather*

    Yes to all of this advice!

    I am very good with email. I sometimes encounter people like the OP— someone I know is kind and thoughtful, but who seems to just ignore my emails. Honestly, it’s awful to be on the receiving end. I *think* the OP knows this, but maybe not fully.

    I feel humiliated when I’ve reached out to someone (especially if they’ve said “Please get in touch”) and then they just flatly ignore me. It doesn’t make me feel so much upset AT them, but rather embarrassed and awkward— “I guess I misunderstood; they said they wanted me to write them; now they’ve made it clear that they actually do not want to hear from me.”

    And the relief I get if they finally do write— even if it is months later, as Alison said! An email that says “I am so sorry I never replied to this. I realize the date for that project is long since past, and I’m sorry I wasn’t able to help. All the best.” allows me to relax and sleep soundly (and makes me feel much more fond of the sender!).

    1. Ghostess*

      Thank you for sharing this perspective, it is really insightful and reinforces that in many cases, any response is better than no response.

    2. Ruth Anne*

      This is so important, to hear it from the other side: I am putting someone’s mind at ease when I reply, not upsetting them further!

    3. Nonprofit writer*

      Yes, I am the same—email is not a problem for me; in fact, I often spend time emailing as a way of procrastinating other things! And I have to remind myself sometimes not to reply to people too quickly, especially on group chains when it can be better to let the rest of them work something out rather than jumping in.

      I feel for people who have anxiety about this (I have lots of anxiety about other things!) but yes, it does feel crappy to feel ignored. I am the same with thank-yous. I’m not Miss Manners & I don’t care if it’s a handwritten note on paper or if it comes quickly or a few months after the fact—but it stings not to be thanked at all for a gift.

  13. English Rose*

    I love the idea of the ‘guilt hour’! OP you are definitely not alone.

    Around reluctance to say ‘No’, it may help you to google “Ask and Guess Culture”.

    Basically if someone is an “Ask culture” person, they will ask directly for favours, projects etc., entirely expecting to be turned down some of the time. They are direct communicators who don’t have an emotional investment in what is actually transactional stuff.

    A “Guess culture” person will rarely ask directly for favours, they will hint. And when asked for a favour they will either respond in the affirmative then regret it, or make up all kinds of convoluted reasons they can’t do something to avoid saying a direct no.

    Ask -v- Guess people really struggle to understand each other.

    1. Willow Pillow*

      I was going to suggest the same thing about Ask Culture vs. Guess Culture. Searching online for “reformed people pleaser” might help as well.

    2. The Unspeakable Queen Lisa*

      Guess v Guess people also struggle to understand each other! Communication failures are inherent in hinting and lying and making excuses to avoid a direct yes or no. Since no humans can actually read others’ minds, Guess culture people inevitably get it wrong most of the time.

      I was raised Guess culture and it’s a terrible way to be – constantly either being offended or worrying you are offending the other person. Totally exhausting.

  14. Rachel*

    DID I WRITE INTO ASK A MANAGER AND THEN FORGET?? LW you are so not alone, I struggle with this all the time. AAM’s advice seems really helpful, especially having a dedicated ‘hard email time’.

    A thing I find helps is to decide just to draft the email, without commiting to send it. It’s less anxiety inducing to say to myself ‘I’m writing this and will send it later” and then I usually end up sending it anyway

    1. Wendy Darling*

      I feel like I have started writing this letter to Ask A Manager about five times and then not sent it because I couldn’t get it quite right and didn’t want to be a bother.

  15. KK*

    I’ve never related harder to anything in my life. Solidarity, LW.

    In my case (not advice, just sharing) I’m setting up calls with an ADHD coach this week to try to work on it—I’m borderline, but this is one of the behaviors where it shows most. Also, switching up my antidepressants has helped. You are in my thoughts, you’re not alone, and while the shame is very real, it doesn’t serve us. If it did, we’d be fixed! Let go of it to the extent you can and be kind to yourself.

  16. The Anonymoose Mouse*

    Dear OP: I feel like it was me writing this letter. You are not alone. I’ve worked through a lot of these issues already, but I’m 47 years old and still have trouble cold-calling friends, let alone business contacts! It might be the introvert in me, or that I don’t feel like I’m worthy of someone else’s time, and I’ve been pondering whether I should really tackle those issues with a therapist, now that they’ve clearly become AN ISSUE – and an issue that I can actually point to, as opposed to when I was younger and just wondered what was wrong with me without being able to see myself clearly.

    Alison’s advice is spot on: don’t wait for perfection when answering those emails. Ask for more time, or say no. Or say YES and put it on your calendar – because you think you will remember, but if you’re as busy as all of us are, you never will…

    But also, if you’re so moved, maybe it’s time for both of us to visit our friendly neighborhood therapist and work through some of what’s holding us back. Good luck!

  17. Elle*

    This is all great advice. You’re SO not alone, LW. I especially enjoy point 4- I’ve staked out a half hour in the morning and one in the evening to deal with emails that require more than a quick response.

    A lot of this also sounds familiar to me as a person with ADHD. I assume LW would know if that were a factor for them, but then again, I wasn’t diagnosed until I was nearly 30. So who knows!

  18. office hobbit*

    OP, I do this all the time (mostly in my personal life), and I’m trying to fix it too. I’m grateful you asked so that we can all get advice!

    One tip that might help you to say no to favors: if I am in the position of asking someone for a favor, I WANT that person to feel comfortable saying no. If I think that person will say yes regardless, then I feel that I have to make the decision for them before I even ask. “I’d love to have Jane help with this, but I know she’ll agree to even if she’s swamped, and I saw her logging so much overtime last week. I won’t ask.” vs “I’d love to have Jane help with this. She always manages her obligations well so I know she’ll turn me down if she’s too busy. Even though I saw her working late last week, I’ll ask just in case.”

  19. COHikerGirl*

    Also joining the “no advice but solidarity” train. Bookmarking this for another read later. And taking the ChatGPT advice. My No replies come out a bit short, so I’m going to try using that to help me tweak…maybe help me figure out how to not be short. (NeuroSpicy so I know that’s part of it…and apparently autocorrect needs the capital S…!).

  20. cldlz*

    Get checked for ADHD and/or anxiety. I have the same issue, and turns out that this is a pretty good sign that you might have something that goes beyond just perfectionnism, and into executive function borkage (for lack of the scientific word).

    I have been reduced to tears in the past by not being able to answer to one frikking email, even knowing that I was letting down people, and with the fear that not anwering would have extreme negative consequences on my future. Just couldn’t do it.

    It requires a lot of courage to answer a couple of weeks later to an email, and I hate it, but things tend to work out anyway.

    1. jrab*

      Seconding this – I think this is really really common for people with ADHD!

      I have always struggled with this, but have got better over time. Firstly, it has happened so often now that I’ve started to realise it generally hasn’t ended in a total catastrophe of some kind, even if it isn’t good and I feel bad about it. Secondly, having tried to get better at replying even when it was late and when I felt guilty, I’ve really realised that people are generally much more understanding about it than I expect them to be. Also, I’ve got into the habit of sometimes sending quickfire emails as soon as requests come in, or catching up during a ‘guilt hour’ type session every week or two.

      Finally – try not to see this as a reflection of your worth as a professional. Everyone has stuff that they’re not good at, and this feels stupid and annoying and weirdly frustrating when you’re in it (why can’t I just do it, it shouldn’t be this hard?!), but it doesn’t define you as a person and you wouldn’t have achieved what you have without having lots of other good qualities that your colleagues value!

    2. ampersand*

      For me this is definitely related to my diagnosed, medicated ADHD. The fact that I still have this problem is a reminder that medication isn’t a panacea for solving executive function problems! It’s equally important to have systems in place to deal with this stuff, and to work on strategies and behavioral changes, etc.

      I’m amused that LW was like, “can’t imagine anyone else has these problems…” and then almost all the comments prove LW wrong (in the best way–they’re not alone, and sounds like many of us could benefit from the strategies listed). :)

    3. The Unspeakable Queen Lisa*

      ADHD seems unlikely since LW indicated, “I don’t do this with my own colleagues or clients or partners.” If it’s executive dysfunction, it should be dysfunctional all the time.

      However, anxiety is not executive dysfunction and is often paired with perfectionism and catastrophizing, so that seems more likely.

      1. RD*

        just gonna throw it out there that this might not be true. I was just diagnosed with ADHD and I could have written this letter. sometimes I push through when I “have” to and then let the rest slide. It’s absolutely ADHD for me.

      2. jrab*

        Well, executive dysfunction will manifest differently in different contexts, depending on how interesting a task is, the level of urgency it holds, what else is going on, etc.

        I have ADHD and I completely recognise this issue as something I do, and I know several others with a diagnosis who do the same thing – always exacerbated when dealing with broader contacts or a wider professional network rather than close colleagues. But of course, as you say, it could also be anxiety.

    4. I Have RBF*

      I have unmedicated ADHD, and I do this when my stress level is too high. When my executive functioning breaks hard, I can stare at an email I need to respond to, and … not be able to answer it. I can have all the intention in the world of writing it, and just not be able to start.

      Usually, I respond when I get it – them it is just part of “read and reply”. But if I get interrupted, or have to do something before I reply, I may end up dropping it on the ground, so to speak.

      Even now, I have very important stuff I need to follow up on, and all it does is crank up my anxiety about it, because I. Just. Can’t. Start.

      I know there are all sorts of techniques and tricks to doing this. Sometimes they work for me. Most of the time they don’t.

      If I can get started, I can usually complete the thing and send it off. But starting a task involving apologies and/or refusal? I’ll be over here under my blanket fort.

      I don’t have much advice, other than make it a habit of composing at least a draft response when you first get the email. That makes it easier to pick up later – you already have a draft, you just need to finish it and send it, not start from a blank. If you make drafting the reply a part of reading the email, it’s a little easier. You can sit on it while figuring out words, but an existing first draft is the best place to pick it up later. Hope this helps.

    5. Wendy Darling*

      I have both ADHD and anxiety and this stuff is my kryptonite.

      I forget to respond to things and then when I remember I procrastinate because I’m anxious about doing it. And half the time I’ll be like “I am going to get off the sofa and answer that email!” and then by the time I get to my desk I’ve forgotten what I was going to do.

      It’s… a lot. I’m working on it.

  21. Colette*

    One thing I would suggest is that, the first time you think of it, you write a response, but don’t send it. Come back to it in a day or two and wordsmith it, but having a start will make it easier (and will solidify in your mind that you’ve made a decision.)

  22. Lenora Rose*

    As an additional note, sometimes completing the task, instead of feeling good to have it off your plate, can start a *new* guilt spiral; “Look, I didn’t do this for two weeks, and now that I did it, it took five minutes. How horrible I must be.” This can lead right back to task avoidance, since it turns out there’s no reward for a job well done.

    Anyone have suggestions for heading off guilt spiral #2, or mitigating it? I find it happens less if it’s a to-do-list task I can cross off or if I make a sticker chart (yes, really, pretty stickers! I had one at home for a while. I can’t think of a way to make one look professional for keeping at work but you can always hide it inside your notebook/binder).

    1. English Rose*

      This is an excellent point around the guilt spiral. It’s like beating ourselves up over anything that isn’t perfect. Don’t think I have any advice except to say I’ve always found that anything I think is going to take ages turns out to be a five minute job, and anything I think will be a five minute job takes five hours!!

    2. acoustic-alchemy*

      I’d love an answer to spiral #2 as well, as I haven’t found a strategy that mitigates this feeling completely.

      Something that helps sometimes is to remember to give myself some credit in this moment and not “should” on myself – sure, the task itself might have been 5 minutes, but it wasn’t “so easy”, exactly because I had been moving with the baggage of anxiety, shame, etc that started the avoidance in the first place. That work isn’t always visible, but it is as real as physically walking 5 minutes with 50 lb weights on. The goal then, isn’t to just crush immediately and forever after, it’s to make the gap between spiral and hard thing a little smaller each time. This is a difficult task *for me*, and I am moving in the direction I want to be in despite that. I’d say that makes me (and you) the opposite of horrible.

    3. ampersand*

      The only strategy that’s worked for me regarding the secondary guilt spiral is to be aware of it and try to head it off once it starts. What this means for me is recognizing when I’m doing the thing I don’t want to be doing (in this case, more guilt) and telling myself to stop. Sometimes it’s literally: OMG you’re doing the thing again, STOP IT! And also not taking yourself too seriously, if possible. Brains are weird and sometimes we’re at odds with them. I internally roll my eyes at mine and tell it to cut it out. It helps, assuming I’m not already too far down into the shame/guilt spiral. You’ve got to catch it early!

      1. YoureNotAlone*

        The only thing that’s help *somewhat* for me is to just be kind to myself like I would be to my kid. “This is something I struggle with, it actually wasn’t that easy because the task initiation part is what was hard, so it is what it is. Well done self for one less item on the guilt list!”

    4. Little Blue*

      Something that my therapist did today that might relate to your struggles was confront my critical inner voice with the fact that it’s actually making it HARDER to do the stuff, because of the added guilt/shame/layers of criticism. My inner critic’s goal is for me to be successfull/happy but what they are doing is actively hindering me being successfull/happy. I can’t really say whether this will help in the long run because my inner critic either disappears or deflects when this comes up, but maybe it will help you to get out of feeling ashamed and believing everything the critical voice says and connect to your inner grown up who knows shame and guilt lead nowhere and can have compassion and kindness for yourself.

    5. Jiminy Cricket*

      Oh, gawd, the secondary guilt spiral. I have so been there.

      I don’t know what “works,” but here’s what I do: I name it. Sometimes even out loud. “I am feeling guilty about getting this done so late. But instead I will feel proud of myself for getting it done.” Or I’ll go full-on cheerleader for myself, out loud, until I feel ridiculous.

      1. Lenora Rose*

        I keep thinking just naming it never helps, but you know what, this may be me overthinking it. I tell myself, It can’t be as simple as saying “Oh, look, this is what’s happening” but sometimes, it is.

        I like your addendum about piling on the counterweight until it’s ridiculous.

    6. Not that Jane*

      When I procrastinate on something that seems small, I try to recognize the invisible parts of the task & honor myself for doing them. For example – and I know this isn’t an email, but it’s a real example that just finally got solved today – setting up a hummingbird feeder for my daughter. My brain weasels might want to TELL me it was just a five-minute task and why did it take me six weeks to get it done, but my brain weasels are not seeing the invisible parts of the task: searching in the (stress-inducingly crammed) garage to find the old feeder, failing to find the old feeder, ordering a new feeder, looking up a sugar syrup recipe, making sugar syrup, etc.

      It works prospectively too. If there’s something on my to do list that I just can’t seem to get done & I notice that I keep putting it off from day to day, I’ll ask myself what the components or sub parts or steps of the task are. And usually the reason I’m not getting to it is that I’m stuck emotionally or logistically on a sub task that I wasn’t taking into account.

      In other words, the “five-minute task” that your jerk brain wants to send you into a guilt spiral about probably isn’t just a “five-minute task” for you. Maybe it requires more preparation, mental energy, planning, etc, and that’s OK.

      1. Lenora Rose*

        This is definitely a good one! Breaking down tasks even smaller has worked elsewhere, but this specific application never occurred to me!

  23. allhailtheboi*

    No advice to share but I want to let OP know that they aren’t alone! Although I’m in a very different stage of my career, this is also my Achilles’ heel.

  24. Kimb*

    A weird trick I have for writing emails that perfectionism is delaying, is to start writing them in a word document. This just gives me a mental shift from the goal being to write and send a perfect reply to starting my first draft of an email. Once it’s started they tend to come together quickly, but the pressure to finish and my reply immediately is off.

  25. AMT*

    As a therapist who treats anxiety (and who has raging ADHD that makes efficiency doubly important), I’m a huge fan of Merlin Mann’s Inbox Zero method: https://www.43folders.com/43-folders-series-inbox-zero

    At its core, it’s existential philosophy disguised as productivity advice. The basic idea is that your time in life is limited, you will inevitably fail to do some things you wanted to do, and you will disappoint some people. Inbox Zero just helps you do that more efficiently and with an eye toward what’s actually important to you, not what makes you feel the most guilty. In other words, it’s not so much a productivity system as it is a process of owning your decisions about what you choose to spend your time on.

  26. Ann Onymous*

    I think all of Alison’s advice is great, but there’s one thing I’d add. Please try to let go of the idea that you should already be better at these things at your age or at your point in your career. Different things come more easily to different people. You’ve clearly got many other strengths to be where you are in your career. You can shame yourself over and over again for struggling with email responses, but at the end of the day it’s much kinder to yourself and much more productive to accept that your current level of skill is your current level of skill and then invest your energy in improving it. As a champion self-shamer and guilt-feeler, I realize this is easier said than done, but believe me, it’s worth the effort.

  27. ConstantlyComic*

    Joining the “I could’ve written this letter” crowd and wanted to add that I’ve fallen past the point of even trying to hit perfection and instead worrying that there’s some glaring mistake that I’m unaware of in any non-routine email I’m writing

  28. Viki*

    Years ago, my Director told us all to book either half hour at the beginning or end of the day, or 15 minutes at both start and end of day and just clear the inbox. Reply to who you had to, file and move what you didn’t.

    It’s always been the best advice, eventually you get the knack of writing business emails, especially the hard stuff, but the worse is just an email in limbo from all ends.

  29. JulieK*

    This website (https://goblin.tools/) has some great tools that might also help!

    The “Formalizer” looks at what you’ve written and can help change it into something more (or less) professional. So if you want to say “No way, buddy, I don’t have time for that!” you can type that in and it will change it to “I’m sorry, but I currently don’t have the availability for that.”

    The “Judge” will tell you how your text could be perceived. So if you say “No way, buddy, I don’t have time for that!”, it will tell you:
    “Based on the given text, “No way, buddy, I don’t have time for that!”, the emotional tone of the sentence appears to be dismissive and somewhat impatient. The use of phrases like “no way” and “I don’t have time for that” indicates a strong lack of interest or unwillingness to engage in whatever activity or conversation is being referenced.”

    This may help alleviate some of your anxiety. Good luck!

  30. Anon (and on and on)*

    I’m also middle-aged and reasonably successful in my career, and I relate to the shame-spiral you described a great deal! One thing that helped me was learning to be more compassionate with myself. When I read your letter, I hear someone who desperately wants to do the right thing, so much that they’re crippled by that need to do well by other people, and who could really use some understanding and a hug! And yet, this was your own reaction: “But writing the above out, I’m ashamed.” There is nothing here to be ashamed of! You’re having a really difficult time and experiencing very unpleasant emotions. Not only are you not alone in how you feel, I think a lot of what you experience is universal! The self-imposed pressure to perform can be incredibly stressful. Of the flight, fight, or freeze response, your natural inclination is to the latter, which is pretty common (especially among women!). I highly recommend Kristen Neff’s book Self-Compassion: The Proven Power of Being Kind to Yourself. The first step in changing your actions is to believe that you deserve better and finding ways to cut yourself some slack. This is the great paradox of perfectionism, which often makes us feel like we should be doing MORE and not LESS. Good luck!

  31. Dawn*

    Please understand that you are absolutely really normal for this, into middle age. It’s something an awful lot of us struggle with, every day.

    The goal is not to not struggle with it (broadly speaking, which neuroses you have/experience are not within your control) but to develop effective strategies for dealing with it.

    Alison already outlined a ton of those. Here’s one that works for me: I have smart speakers (think like the Amazon Echo with Alexa if you’re not familiar) and I use them to set reminders for myself for everything because it is so much easier for me to do that by speaking out loud at the time that it happens. And when a reminder pops up? I have to complete the task then. No delays.

    It’s made a massive difference in my personal and professional life. The trick for me was always recognizing and accepting that I’ve got issues and stopping getting so embarrassed about, you know, being human that I was paralyzed by it.

  32. anononon*

    This is all very good advice, but I’d question the guidance to say ‘sorry…’

    As a woman I have learned that ‘thank you for…’ is a more empowering and less gendered way of gaining respect. So instead of ‘I’m so sorry for the delay, my schedule has been crazy…’ I use ‘My schedule has been crazy these last few weeks – thanks so much for you patience!’ and so on.

    1. Sparkles McFadden*

      Yes, 100%. “Thank you” instead of “Sorry” frames the email in a much better way for both parties.

    2. JDiva*

      I was going to chime in on this as well, and it also sometimes feels less insincere and less like an excuse if you are thanking someone for being patient. I also rarely make an excuse for the delay in that instance unless it’s very relevant to the people involved because when I put myself in their shoes, I often don’t need to know the reason for the delay, I just need the answer I was looking for (and where I’m working for at the moment, “I’m very busy” is kind of status quo for everyone, so that can feel off-putting).

  33. Former Gremlin Herder*

    I need to bookmark this and come back to it when I get a backlog of things that are hanging over my head. It’s so, so human to be overwhelmed and let things slip, and also very human to feel bad about it! If you can swing it, I highly recommend doing a collaborative session with trusted friends or co-workers that is specifically for this kind of thing. My former roommate/former co-worker/bestie and I used to sit down for an hour or two every week to plow through unpleasant life admin tasks. When there’s someone else holding you accountable, it makes a big difference. Thank you, Alison, for compiling such kind and practical advice in one place!

    1. Kotow*

      I printed it out so I could re-read it! So grateful to the OP for writing in (and incidentally, I was just beating myself up for having the same issue come up in my own life lately, so this couldn’t be more timely).

  34. daeranilen*

    I have this EXACT problem, OP; you are not alone; in my case it does impact my personal life too, so kudos to you for managing to keep it contained!!! And to build on the “guilt hour” concept – I have found it is so, SO vital to me to have COMPANY while I do tasks that I get mentally roadblocked on. Frequently the person present doesn’t need to do anything to help me with the task at all – I just need someone to validate that the thing I’m doing is in fact hard for me and to reassure me that IF something were to go horribly wrong somehow, I’m not going to be on my own to deal with it.

    I realize this might be trickier to do in a work setting, but being honest with someone you trust that this is challenging for you, that you’re self-conscious about it, and that you’d appreciate some moral support while you work on this habit might go a long way.

    1. Grumpy Elder Millennial*

      In the last year of my PhD, I set up work dates with colleagues / friends, on weekend days. We would just go somewhere and work next to each other. The whole point was to create a situation where we would work, even though we didn’t really want to.

      1. Ann Onymous*

        A friend and I did this in college – every Sunday afternoon we’d grab a snack from our favorite local coffee shop and then spend the afternoon at the library doing homework.

  35. BubbleTea*

    I get a lot of emails. Many of them contain errors, spelling mistakes, weird phrasing, or just not perfect wording.

    I have never thought less of the person who emailed me because of that kind of totally normal human trait. I only even started noticing once I began writing my own email newsletter and analysed some of my inbox to see what I could learn from more experienced people.

    I promise that no one else is looking for perfection from your emails.

  36. Kotow*

    No additional advice, just sending my sympathies because I literally had to do this on Friday for an email I have been avoiding responding to (due to not having a good answer). This advice is wonderful and I will print it out to refer back to. I have nothing to add except that it isn’t just you!

  37. Constable George Crabtree*

    I am like this!! I am extremely familiar with the hanging dread and anxiety and it’s paralyzing. I eventually ended my habit when I picked up something similar to the 60-second rule of chores (if you see something that needs to be done and it’ll take less than 60 seconds to complete, do it now) Basically I resolved that when I see an email/text/missed call that I’m going to need to respond to, I handle it right now (or as soon as possible). Even if it’s a pretty generic response or I’ll want to add something later, it just totally removes that sense of constant dread because I have Done My Duty and gotten back to the person, even if not fully. I don’t know how practical that would be for someone in a senior role, but getting this stuff off my plate and out of my mind ASAP, and having that be the bar of success, has been amazing.

  39. Anon in Canada*

    Being told yes then seeing the person disappear, or never following through on their yes, or just being treated evasively in general, hurts A LOT more than being told no up-front.

    If you don’t feel comfortable saying no up-front, saying maybe and then turning the maybe into a no is also a reasonable option. Just don’t leave the “maybe” hanging though – you have to actually turn it into a no.

    Turning a yes into a no is also acceptable, but 1) you have to actually communicate the change – don’t just leave a yes hanging without following through! and 2) this should be a rare occurrence, otherwise people will stop taking you seriously.

    Take Nancy Reagan’s advice for once. Just Say No. Stop trying to please people when you can’t or don’t want to!

    It should be noted that some cultures (chiefly in Northern Europe, e.g. Germany, Austria, Netherlands, Norway) are extremely direct about saying no. Feeling bad about saying no is a cultural thing. Everyone would be better off if people adopted more direct manners and just said no when they mean no.

    1. Willow Pillow*

      It’s just confusing sometimes – a family member and I share a common interest and they don’t seem to like parts of it. Let’s say we’re both into birding and they don’t like going to the best local birding spot – I want to include them and I’ve tried to figure out that does that with zero direct context from them. They never say no, nor have they every said why they don’t like going. Sample conversation:

      Me: “hey, there’s a birding event at (this other birding spot)! Want to go?
      Them: “cool!”

      Also them, commenting in response to someone else: “I love going to birding events! I go to all of them, especially (birding event they didn’t actually attend)!”

      I’ve had a very negative reaction from them in response to my being direct in the past, so I don’t believe it’ll help. I’ve also said “just let me know if you don’t want my suggestions, I don’t mind if you say no”. I just don’t interact with them much.

  40. Ellis Bell*

    OP you’re certainly not an anomaly, because most of us have done what you’re describing, but yeah it’s definitely worth coming up with strategies to avoid this very human failing of wishing we could be all things to all people. I think the key point of your letter is you don’t send anything that’s a “less-than-fully considered answer”. But you probably don’t expect anything like that from other people, right? When you send a message to people, you just want to know whatever answer they’ve honestly got to hand. So I propose a two-ingredient response which is a) acknowledgement that you haven’t got the prophecy of everyone’s future in your pocket just yet, and just say whatever you do know for sure: “At this point in time I’m not really sure about the possibility of this happening; What I do know is that it’s typically a very busy period but we may have extra hands by then” (or whatever is true). b) Propose a point in time for you both to be responsible for checking in on this again: “Can we speak about this in a month’s time? If I don’t come back to you by then please feel free to ask again at that point” or (possibly easier) just say you don’t think it’s a likely possibility (People want the word no! They can make other plans after ruling something out!)”but if this changes for any reason, I will come back to you then”. Oh and definitely dispense with waiting on written out cards to say something appreciative and joyful! Just do it straight away when you feel it!

  41. Melissa*

    I’m someone who is quick to respond to all emails and, from that position, I can tell you that you are being way too hard on yourself! I understand the perfectionism-procrastinate-shame cycle, but your letter reads like this is some huge personal failing and it’s only by chance that it hasn’t tanked your career. You wrote that you only do this with some people in some situations, so you already possess the skills to overcome this because you reply quicker at times. Please be gentle with yourself, lots of the commenters are saying you’re not the only person who does this.

  42. Lady Sally*

    I get a large volume of client email, some of which is easy and some of which involves hard or unpleasant responses (delivering bad news, saying no, etc.). I am often tempted to delay those unpleasant responses. Two idioms that I tell myself daily: eat the damn frog, and worst first. They have the same meaning to me – if you don’t do it, it will hang over your head and blow up worse in your mind. If you do it right away, it’s off your back and the weight goes away.

    1. The Unspeakable Queen Lisa*

      Dan, please don’t diagnose the LW through the internet. Also, you are projecting things that nobody here is saying (will and commitment) because of your experience. Nobody said they aren’t doing their best. Nobody is blaming them. In fact, I see everyone being really compassionate.

      It is not obvious to me that this is ADHD, especially because LW said they do not struggle with this all the time, but only in some contexts. I see anxiety and/or perfectionism as possibilities. Or none. People don’t have to have mental health problems to struggle with bad habits and negative self talk. Therapy is always a good idea though.

  44. lunchtime caller*

    I have definitely been guilty of this as well! Here are a few techniques that have helped me beat this habit.

    1. Write shorter and less “perfect” emails in general. It takes the pressure off replies overall, including the ones you’re putting off, if you get used to firing off a quick response without giving more than a quick glance for accuracy/etc. This isn’t applicable to all emails or industries, of course.

    2. Try replying verbally and see if that gets past your block. By that I mean, use voice to text features to draft an email, or see if you can trade off with a friend and dictate a few things to each other that you’ve been putting off.

    3. Draft email templates. There are some great starts here with how to say no to things, so make your own versions and just use that same language every time.

    4. Don’t explain (this goes back to tip 1). “My apologies for the delayed response” is sufficient if you really want to apologize, but no need to go into why (I’ve been so busy, etc etc). “Unfortunately I won’t be able to join in this time, but best of luck.”

    5. Once a week (or more, depending on the backlog), assign yourself one of these lingering emails that you HAVE to get done that day. Even if it’s right before bed and you write the shittiest email imaginable, you have to cross it off your list. Then hey, at least it’s done!

    1. The Prettiest Curse*

      This is all great advice! This year, I’m going to try and go through my inbox on Fridays to make sure that I’ve responded to all of the week’s email that needs a response.

      A former colleague of mine had the phrase “Start before you’re ready. Just start” pinned up at his desk. I try to bear this in mind when I’m trying to psych myself up to do something difficult.

    2. Rainy*

      I received a piece of wisdom in grad school that I have since repeated to others many times: Nothing is ever done, only due.

      If you wait for it to be perfect, it’s never going to happen. Imperfect but done is better than perfect and late any day of the week.

    3. londonedit*

      Yes, totally agree with the not explaining. I used to feel awful about saying no to things if I didn’t have what I felt to be a ‘good enough’ excuse, so I’d fall over myself trying to explain why I couldn’t do the thing or go to the event or whatever. Then I learnt that you don’t need any of that. It’s perfectly polite and reasonable to say ‘Unfortunately I won’t be able to attend, but I wish you every success with the event’ – or if it’s a non-work thing, just ‘Sorry, I can’t make Thursday – hope you have a fab time!’. People really don’t mind. No one asks why you can’t make it. It’s totally fine.

  45. Ink*

    I do this! It’s a bit silly, but do you have a spouse/friend/whoever you’d trust to help if you’re really stuck? I do better at fixing someone else doing it “wrong” than creating my own “perfect” response from scratch. Basically, describe what you need to say in the broad stroke and whoever’s helping you spends two minutes tops bashing out a response written as if they’re you and emails it to you. Either it’s serviceable, an you copy it into an email for whoever you need to answer, or it’s Horribly Wrong and you can basically write your response by elimination fixing it. Similar to what people have suggested with chatgpt, but for me the human element helps because it creates obstacles inherent to procrastinating. If leaving it be means a conversation with someone face to face etc, for simple messages and times I’m not fried from stress just doing it becomes the easier alternative.

  46. Ms. Norbury*

    Just joining the chorus of “Oh, I do that too”! I have a strong tendency to fall into perfectionism-based procrastination, and emails used to be the worst. I’ve got much, much better at it by paying more attention to the emails I received and noticing how the sender clearly did NOT spend much time crafting their message.

    One other thing that can help (though might not be an option for a variety of reasons): when I do need to answer a truly sensitive email, that requires thought and carefully chosen wording, I usually get a colleague (or depending on what’s at stake, my boss) to give it a once-over.

  47. YoureNotAlone*

    Oh, yes, I do this too. Alison’s answer is spot on but what helps me most is getting to the bottom of that perfectionism. Give yourself a break, the perfectionism has probably gotten you very far in your career so it’s a double edged sword for sure. I like to tag all those emails that would ideally take less than 5 min to answer into their own folder, let them simmer for a day or two max and then take an hour to tackle as many of them as I can. For me the delay is key to get at least 75% of what I want to say. Then, I just psych myself up and do a ton of them. I invariably feel great relief at the end of that hour. The stoic principle that states that suffering is inevitable, but you get to pick the type of suffering you prefer, somehow, helps a lot. Good luck!

  48. CS*

    No tips, just letting you know I am often in a similar boat. I have clinically diagnosed OCD, ADHD, and anxiety. I find my OCD prevents me from responding to emails if I don’t have the perfect answer, or I don’t know how to word it. The anxiety plays on that, and the ADHD helps me get distracted which drags out the timeline. Let’s throw in some Catholic Guilt for feeling bad I never responded… ugh!

  49. FormerProducer*

    I could have written this entire question for myself! Letter writer, you are not alone or even that unusual, not even a little bit.

    Alison, I can’t thank you enough for this answer, I know I’m going to re-read it many times!

  50. Sparkles McFadden*

    I am actually good with responding to emails and I can tell you from the receiving end: I just want a response. If the answer is “no” I’d rather hear that sooner rather than later so I can figure out where to go from there. It sounds to me as if you are worried about explaining things “well enough” so the person will understand and won’t be upset. Well, someone *may* get upset because people get upset about all sorts of things, but it’s not on you to manage that for everyone.

    Please be kinder to yourself about this! There are no “perfect” emails. I have a whole bunch of generic “thanks but I can’t” or “I have a lot of hard deadlines this week, so I will get back to you by [insert date here]” phrases saved as email starters. It gets easier with practice.

    1. Adultier Adult*

      I agree! I am an inbox zero person- and as long as an email is floating out there waiting for a response- I feel like it is still on my to do list- Respond- no that I know now is fine!

  51. CanadianPublicServant*

    I FEEL THIS ALL SO HARD!

    OP, thanks for writing in – my issues aren’t exactly the same as yours, but I have the same shame and guilt and fear (especially as an otherwise professional, successful, competent person who sometimes just can’t do that supposedly easy thing).

    And Alison thank you for the kind, conpassionate and practical answer.

  52. Sarah*

    OP, also if you’re struggling what to say, then consider using ChatGPT, even if just for ideas. I’m not great with wording and it helps me immensely with stuff for my local club.

  53. KathyG*

    OP, are you me?

    I have lost friends because people think I’ve ghosted them, when I am just too embarrassed to write.

  55. Name*

    You are so not alone in this! It happens to me in both my personal and my professional life, especially the part where I avoid things because I think that I need to be perfect which means I postpone them which means I’m late and am so ashamed that I should have already done them, that I don’t do them at all, which in turn, makes me feel flaky and undisciplined and inept. And I’m in my mid thirties.
    In fact, I will take this letter as a bump to finally write an invoice to a client who mailed me in January because they (!) had a bad conscience about not having payed me yet for a service they received in October last year. I knew I should write it but now that I’ve been called out it seemed pretty much impossible to do. But I’ll use some of Alison’s wording (thank you!) and write it in celebration of admitting to ones’ struggles and trying to do better.
    In addition to Alison’s advice, I want to add the following: this does not make you (or me) a bad person. It makes us people who struggle with following through sometimes. But we’re not fundamentally flawed and we’re not bad colleagues or friends or professional people because of it (look at your amazing career and successes as proof!). And I do still have friends and people who actually enjoy my company despite me forgetting their birthdays. I’m working on that, but in the meantime, we’re not unworthy just because we are humans with human flaws and struggles.
    If you take anything from this, I hope you see that you are not alone in this and that you helped someone else to get one of those things of their “guilt list”.

  56. Tsankawi37*

    Just wanted to jump in and say (as others have) that you’re not alone — I could have written your email (or not, as the case may be!).

  57. SometimesSomewhereSomeFolks*

    I feel this letter. Really outstanding feedback & thoughts from Alison on the emotional, behavior, psychological side of things.

    On the “but literally, though, what words should I say & in what order?” side of things…this seems like a perfect, ethical use of AI. Plug in the situation,including any relationship history that matters, and ask, ‘write an email to explain this situation (don’t have time, joining another org, etc etc) and express my thanks for thinking of me, in an upbeat, friendly tone.” Or whatever.

  58. Jiminy Cricket*

    I struggle with procrastination, and one thing that helps with some tasks is that I schedule a meeting. So, let’s say I owe a report to someone. I’ll schedule a meeting to review a draft at some reasonable point in the future, but before the actual due date.

    That gives me a hard-and-fast deadline and a person whose face I will be looking directly at if I don’t have a solid draft.

    Obviously, this doesn’t work in all workplaces or for all tasks, but it keeps me on track with key things.

  59. LG*

    I remember hearing someone suggest that every time you decide whether or not to say yes to something you pretend it is tomorrow. Would you want to go/help/do the thing tomorrow? If not, then you are a no. It doesn’t work for everything but it helps me be realistic instead of optimistic.

  61. Friendly Office Bisexual*

    I struggle with this exact same issue. Thank you OP for writing in about it and Alison for these suggestions! I’m going to try the “guilt hour” strategy for emails and tasks I’ve been putting off.

  62. Morning Reading*

    Loving all the advice and sympathy here. But can I ask… it’s too late to send Christmas cards, right?

    3. zaracat*

      Not too late, but maybe it’s a good excuse to switch to Happy New Year cards for the next round, because any time is a good time to wish that

  63. Procedure Publisher*

    I feel for this OP. My problem is that I will be rewriting while I am trying to write an email. When I write, I found that looking away from the screen has helped reduce rewriting. I think it is because I am concern about how my message in my writing comes across.

  64. Nik*

    I always put a reminder flag on an email that I need to respond to. That at least makes it easier to see all the things I need to respond to.

  65. Antigone Funn*

    I do this too. For me, I think it’s connected to social anxiety that also pops up in other ways. But from a scan of the comments, it seems like there are lots of different reasons! You are very, very not alone, LW.

  66. Molly Millions*

    I could have written this letter.
    OP, these tricks don’t make a lot of sense, but I find they help by reducing distractions and taking the pressure off.

    1. Type your email drafts into a Word document rather than the email program itself.
    2. Use the speech-to-text function on your phone to draft the email aloud, then just make minor edits for grammar and formatting.

    Also, give yourself permission to tell white lies in your delayed responses. “I didn’t see this until just now,” “This must have went into my spam,” “I thought I’d responded to this earlier,” “My internet was on the fritz last week,” etc.
    (Note: this is mainly for self-soothing, as the recipient may not actually believe their message went into your spam folder. But if the illusion of saving face is what it takes to hit send, do what you have to do.)
    (Note II: this only works for non-urgent matters or situations where you weren’t egregiously slow to respond, not for situations where you inconvenienced someone and owe an actual apology)

  67. Brevity*

    All of the advice, especially Alison’s, is already here and valuable, so here’s a meta-question:

    What, exactly, is going to happen if you disappoint people?

    That’s at the heart of it, I think, for a lot of us who have the same problem. There is this vague but powerful fear of disappointing others for whatever reason: saying no, not being perfect, not having a “good enough” reason to not do something. That’s why I especially like Alison’s last point. It’s worth thinking about in depth, as it may help you come up with a solution beyond the many excellent suggestions here.

  69. Office Plant Queen*

    Both the problems in the question and a lot of the answer feel like they could’ve come straight out of The Anti-Planner by Dani Donovan. Would highly recommend checking it out (or at least, the chapter on being overcommitted/overwhelmed) for anyone who struggles with this kind of thing, especially if the cause for you is ADHD! Obviously ADHD doesn’t have exclusive claim on people pleasing perfectionism, but it’s a really common problem among those who have it

  70. Miss Ann Thropy*

    I want to say that the letter was extremely relatable, and the advice is so helpful! Thank you both.

  71. Glen Cocoa*

    I appreciate Ask A Manager for simply treating the OP as a person with a struggle they can improve on and for focusing on how we can improve the impacts our actions have on people! Judgment-free and constructive — truly helpful. Thank you!

  72. Lucy Van Pelt*

    Joining the long list of people who feel like I could have written this letter. My personal experience:
    – The “just do it” advice doesn’t work for me. Setting aside an hour to answer quick emails would be like setting aside an hour to stress about emails and wonder why I have such a hard time answering “quick” emails.
    – Having boilerplate text that I can reuse definitely helps me. So does looking back at previous successful emails. Reading an email that I sent late that didn’t make anybody get mad at me, or reading a reply from someone who said “It’s so nice to hear from you” can reassure me and give me the energy I need to write the next one.
    – Somebody mentioned trying to figure out exactly what is holding you back from sending that particular message. This helped me. For example, I hate feeling like I don’t have enough information and am always worried about looking stupid or uninformed. If I could boil my fears down to, “I need to get the correct budget numbers for X before I send this email,” it was a lot easier to deal with than the free-floating anxiety.
    – Having someone stay on the phone with me–a coach, a friend–got me through the scariest emails.

  73. John Slow*

    I wish we could be best friends. Word for word I have the same issue. Largely successful, Nonprofit, senior leader, I even had a documentary project I never responded to! Only difference is my manager has noticed and really wants me to get a handle on it. Sadly, him noticing has made the fear all the worse, especially since he already strongly dislikes me.

    Lately, I’ve started keeping track of all the emails I haven’t answered yet in a notebook to keep the pressure on (or at least the awareness). I’ve also tried not allowing myself to close an email until I respond to it which works half the time just about. AAM’s advice about acknowledging also super helps.

    I have faith in you! Even if I don’t have it in myself yet. Haha

  74. Melisande*

    LW – you are not alone! Anxious perfectionism is a common curse. Thank you Alison for this great advice.

  75. Mad_Bear_Lady*

    To whomever wrote this in – thank you! It’s like looking in a mirror, honestly.
    Thank you Alison for the kind and useful advice, I’m putting this into practise as of tomorrow.

  76. Sam*

    This is so common, the podcast Reply All even created a holiday for it, Email Debt Forgiveness Day. That’s the day you’re allowed to send all those emails you haven’t been able to and not feel any guilt. And it’s coming up on January 31st!

    If it helps you to use that date as an impetus to catch up on those emails you could, and if you feel like you need to acknowledge the lateness, you could even include a link to the explainer they made for the holiday (https://gimletmedia.com/shows/reply-all/posts/edfd)

  77. jemanuel@gmail.com*

    I struggle with this as well. One thing that has worked for me is to write a quick email response at the end of the day, but queue is up in my email software so that is doesn’t get sent until the morning. Then, I can push my anxiety/procrastination aside and usually totally forget that is is going to be sent. I don’t know why, but the psychology of doing this puts me at ease.

    And yeah, I’m senior enough I should know better, but yet this is an issue.

  78. Another Procrastinator's Two Cents*

    LW, I have this problem, too, and one thing that helps is to have a few templates on my laptop — for thank-you notes (to a friend for a gift, to a friend for a home-cooked meal), for sympathy notes, for situations like this. ****Please note**** that I always personalize each note — but having the basic template helps me get started.

    One other important thing: For many people, procrastination is a manifestation of the (usually unconscious) belief that they don’t deserve anything good and that instead they deserve to be tied up in anxious knots all the time, or a manifestation of a desire to undercut all relationships by making (or trying to make) other people annoyed with them when they drop the ball. I’m not saying that this is the case for you — only that it’s worth asking yourself whether this could be. If so, then a therapist who combines a psychodynamic (explore the family-of-origin patterns that shaped you) + cognitive-behavioral (learn new ways of interacting with self and others) approach could help.

  79. Hashtag Destigmatize Therapy*

    You are very definitely not alone, LW. One thing I’ll say is that if your experience is like mine, the shame isn’t helping you (although it’s very normal to feel it). Shame tends to frame this as “either it isn’t important to get back to people reliably, or I’m a bad person,” and that doesn’t motivate you to get better; it just discourages you. The framing that helps me is to tell myself “I’m responsible for getting better about this, which includes picking myself up and trying again when I inevitably have setbacks.”

    Brendan Mahan has a concept called the “wall of awful” for this, where the negative emotions around doing something pile up into a barrier that prevents you from doing it. Sometimes that means you have to allow yourself time to process those emotions (instead of running away from them) before you do the thing. I’ve found this really helpful too.

  80. OrigCassandra*

    Hi, OP. One thing I’ve been doing this month (since it’s between semesters) is cleaning out my email inbox.

    Lo and behold, I found two pieces of fairly important email from last October that I do not remember reading and certainly didn’t respond to, seeing as how I was in the hospital at the time.

    I replied with apologies and an explanation, and you know what? Nobody was mad or anything like mad. I even have a new talk scheduled for April, which is cool.

    I was pleasantly surprised at how forgiving people were. I bet they’ll be forgiving to you too.

  82. SkyBlueSam*

    Just wanted to add my name to the list of people who identify so, so much with this LW! Thank you for taking the time to verbalise this (as I’m not sure I would have been able to!) and thank you to Alison for the strategies. I’ll definitely be trying to implement them too – if only we could set up a ‘Guilt Hour’ among ourselves!
    Also – apologies if this has been mentioned already but ReplyAll did a podcast episode about ’email debt forgiveness day’… I enjoyed it and it’s also reassuring that there are many, many people like us.

  83. JustaTech*

    Hey OP, I want to let you know that even responding long after the request to made moot can still be nice for the recipient.
    One time I emailed a city department to ask some questions for a grad school class. The next day I saw in the newspaper that this department was in the middle of a GIANT practice run of disaster response for our whole region, so I wasn’t surprised that I didn’t hear back.
    But then I did! It was after the semester was over and I didn’t need the information anymore, but someone had taken the time to dig through all the emails they missed during the disaster practice and responded to a random student. It gave me a lot of warm fuzzy feelings and I’ve had a lot of goodwill for that office ever since.

  84. mcm*

    I feel this so much! There’s a semi-common internet joke that actually has helped me frame this better for myself. The joke is around college students, in particular, writing and re-writing very formal emails, ie “Dear Professor so-and-so, I am writing to request…”, re-reading and stressing over it, and then getting a response five minutes after sending that’s just “Sure. – Bob [Sent from my iphone]”
    I have received those emails 100%, and while it’s a joke, it does remind me that the majority of busy professionals live in the world of “Sure. – Bob”. If that’s all you need to say, that’s all you have to say! It’s normal to send emails with the occasional typo, with short answers, etc. Given the number of emails most of us send and receive in a day, the likelihood that someone is worried about the specifics, length, detail, writing of your response is low. I literally think “Sure. – Bob” when I’m trying to make myself answer someone and I can tell I’m overthinking it.
    I agree with all of Alison’s suggestions as well, but keeping this in mind has been helpful for me as well and might be for you!

  85. MCMonkeyBean*

    There’s one other big thing I would add–try to get comfortable saying “I don’t know!”

    It seems like you’re feeling pressured to say yes or no, defaulting to yes and then often regretting it later. Or else giving no response because you’re not sure which you want to say, or are afraid of letting them down. Any time you genuinely don’t feel ready to make a decision or a commitment one way or the other–it’s 100% okay to say “I’m not sure, let me think about that and get back to you.”

    Then ideally you would indeed get back to them, and if the answer is no you can just send a short “sorry, after looking at my schedule I don’t think I’ll have time for that but best of luck!” message. And if the answer is yes you can make sure you’ve really checked that you have the availability and desire to back that yes up.

    And then if you accidentally ghost on them entirely, that’s at least mildly better after an “I’m not sure” than it is after a “sure, sounds great.”

  86. Joelle*

    I also struggle with this, and AI has helped me a ton. If I don’t know how to word a response, I plug it into ChatGPT. Something like “A professional response to [question, request, situation] that communicates [I am unwilling to do so, I don’t have time, I’m not sure when I can get this done, I need more information, etc.]”. I find the generated responses can be redundant, so I pick out a few key phrases and customize. If it doesn’t fit the bill, you can tweak. Eg. “This, but more firm” or “Communicate more agreement”.

  87. TakingNotes*

    Just noting that this challenge could be related to a task initiation/ working memory/ executive function neurodifference! I always used to wonder “why do i keep doing this?” and had all kinds of answers: perfectionism, anxiety, procrastination, an insufficient education, etc etc… it really helped me to (finally) receive a learning disability diagnosis in middle age. I can benefit from tips like Alison’s here, but with a little more context on the specific reasons why “send a quick reply” is so difficult for a smarty-pants like me. Good luck!

  88. CWL*

    OP you are not along, and all of Alison’s points are spot on. I just want to reiterate that I’d much much much rather hear a No than a Yes and need to bug and follow up with you 100 times. And then I’m apparently not a Normal and don’t necessarily understand the subtext of saying one thing but meaning the opposite, so I might either bug you about it, not getting the hint that you won’t do it, or assume you’re taking care of it, or assume you never want to talk to me again because I bugged you so much.

    It’s confusing. “Politeness” is SO CONFUSING!

    So I’d rather a quick, abrupt No than a polite, lying Yes.

  89. Ellen Ripley*

    If I heard someone I respected at work say this, I would feel relieved/compassionate, not judgemental! It is very normal to not be perfect in every way. Your track record shows your success so you clearly are competent at your work and doing a lot right.

    Seconding the recommendation to talk to a therapist. I think Allison’s advice is good but at least for me the cause goes so much deeper than surface level and I needed to change my thinking/perspective before I could change my behavior, and therapy is really helpful with this. Sending positive vibes! Hope you’ll send an update one day and let us know how you’re doing.

  90. Pinniped*

    I’ve struggled with this my entire career, and like others in this thread, I feel I could have written your message myself. I am pretty successful, and it always astonishes me that I can be so competent in some aspects of my job and so completely incompetent in others. (Also, I am a professional writer! It makes no sense to me that I struggle so much with emails!)

    I have tried multiple things in order to get better at this. Almost nothing works. I can tell you that what hasn’t worked for me is:
    – therapy for anxiety. I’ve had a ton of therapy for anxiety. I don’t think that’s the problem for me. – listing emails to reply to on a paper to-do list and ticking them off
    – writing “draft an email” on my to-do list in order to take the pressure off writing the email
    – inbox zero, because any organisational system I always inevitably get behind in, and after that 3-day window, I feel too guilty to reset the system
    – putting myself in the other person’s shoes isn’t motivating at all for me; I feel too guilty in myself to be able to empathise with them

    What does work for me is:
    – having 5 minutes before I go out to do something and forcing myself to “just write and send this email before I go”, the time pressure unlocks me somehow

    What I’m trying this year is:
    – addressing my self-esteem, which I think might be the root cause (in cahoots with perfectionism)

    I would love to hear about ANYTHING you find that works for you, even if you think it’s super weird. This is the biggest challenge of my career, and I feel demoralised because I’ve tried for years to sort it out and haven’t succeeded.

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