When you’re stuck second-guessing that email or text to oblivion

You know when you’re about to send an important text or email and you’re stuck in that phase of second-guessing yourself? Like, does this sound okay? Do I sound polite enough? Does it make sense? Am I forgetting something? Is this person going to think I’m rude or strange or stupid?

I completely understand you. I get like that all the time when I’m sending an email that is important career-wise or even an email to a new pen pal I’m just starting to get to know (Talkin’ to you, Nat!). What I end up doing is obsessively reviewing what I wrote over and over again, prolonging the suffering by refusing to click the send button until I feel ready. The longer it takes and the more I reread the message, the more insufferable it all gets.

I think part of this stems from guilt if I’m asking for something. Am I being annoying? Is this person going to want to say no to me? Even though I have the right to ask, like requesting a day off from work, I am racked with guilt for no reason. I’m just not the type that is used to asking for anything, which shows how I’m lacking in the area of self-worth and assertiveness.

When you're stuck second-guessing that email or text to oblivion

I think this is a sure sign that we are not sure of ourselves. We are scared of rejection, being an inconvenience, or hurting our chances when we are worth what we’re asking for. I’m pretty tired of it. This doesn’t align with my journey for achieving self-love, does it? And that’s what this blog is all about, so I wanted to tackle this topic. It’s debilitating. It’s frustrating to remain frozen over a method of communication with other human beings.

I’ve done this a few times before, but I think it’s a practice I need to implement much more often: just press send. Nothing is going to change by my rereading something and tweaking a word here and there for minutes and minutes on end. The outcome will be the same whether I ask, “May I take next Tuesday off?” or, “Hello! I am sorry to inconvenience you, but I was wondering if you could permit my absence the following Tuesday. I would be super grateful.” (Please don’t send that second one anywhere.)

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Reading what you wrote over and over again won’t even help because after a while, your eyes automatically skim through what you wrote without taking anything in. I’ve found that no matter how many times I reread something, I still miss or forget something after pressing send because my mind isn’t focused on the wording so much as worried about the possible outcome. My mind just loves to get ahead of itself.

Sometimes, I ask someone to read my message because I want a second opinion. It can be good to get an outside perspective, but in the end, you’re second-guessing yourself. You have to learn to trust in your voice and learn from mistakes. If I keep asking someone else to make sure I sound okay in this email or text, it shows a lack of trust in myself.

If there’s no rush, feel free to revisit the message at a later time when your mind is refreshed, but otherwise, reread it only a couple of times before forcing your hand on the mouse to press the dreaded send button. Click! You have to train your hand, and cut off your brain. This is a time when acting on impulse can be a good thing and something that you should aim for. Let yourself press send on impulse. It’ll feel much more freeing–once it’s out there, it’s out, so you really just need to let it get out there.

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There’s no need to torture yourself over something that you’re going to send anyway. And don’t let yourself back away from not sending something because you don’t think you have to when all your instincts are screaming at you that you should. Whether it’s asking a stranger for an informational interview or an administrator for information about a program, just go for it!

Eventually, you will get used to this. You will become more confident and more trusting in your voice and your decisions. The more practice you get, the better you get, right? The same applies here. Soon, you’ll be sending batches of email with no hesitation in no time–what a force to reckon with!

You have to do something a lot before you can get confident in it. The initial stages will be painful but think how brilliant you'll be later on. Go toward that light. Click To Tweet

Of course it’s easier said than done. I’m still working on pressing send without overthinking consequences or how I phrase things, but I think this is a good practice for asserting yourself. You have the right to ask something of someone or to express yourself.

Give yourself that power. You can’t guess how the other person will react or respond. They might indeed think you’re annoying, but why care? They might deny your request, so then what are the next steps you should take? It’s a natural process.

If you need more help silencing that voice within you that’s holding you down and keeping you from tapping send, feel free to listen to my latest podcast below. I wish you more luck on sending out all the emails and texts now! Stop second-guessing yourself! Feel that surge of power! Enable yourself to speak up! Go for it!


gallantly gal



  1. Bry Jaimea

    August 28, 2018 at 6:42 am

    Love this! Anxiety can manifest itself in so many ways xx

    1. gallantly gal

      August 28, 2018 at 10:37 am

      Yup! Thanks for reading ^^

      1. Bry Jaimea

        August 28, 2018 at 4:52 pm

        I always take the time to read your posts! ❤️

  2. Andrea

    August 28, 2018 at 3:19 pm

    I have a co-worker who’d send me emails at 3 in the night.
    He suddenly feels a lot of emotions or has a “great idea” for something and feels the need to write to me.
    Now I’m his manager, so I’m not sure if he is doing it to impress or something.
    I actually decided to tell him that I don’t want to see any email of him after 7 in the evening, unless it’s urgent.
    And as a little advice, also that maybe it’s better to wait with sending an emotional email.
    So, he has the opposite issue 😉

    When I see Jasper trying to send email, I get really annoyed because it takes ages!
    Personally, I don’t take long to send an email. I don’t have the patience, haha

    1. gallantly gal

      August 28, 2018 at 5:44 pm

      Haha he should find a program that lets him schedule his emails for a later time. You can ignore the emails til morning though right? It makes sense to wait for an emotional or important email but if all you’re doing is rereading it obsessively, it can be really unhealthy and unproductive and that’s what I end up doing xDD it’s good you don’t take that long sending an email. I think it’s bad to overthink so much! I hate it!

  3. Christy B

    August 29, 2018 at 1:09 pm

    When we’re overthinking things, it’s so easy for it to get out of perspective. Great words here!

    1. gallantly gal

      August 29, 2018 at 1:58 pm

      Yesss overthinking is the worst. Thank you 🙂

  4. Nat

    August 29, 2018 at 9:20 pm

    As your penpal, I definitely do struggle with some of the same things you mentioned in your blog post. XD I think I’m getting better at not staring at the screen for a lengthy period after I finished typing up a reply email and debating whether I should send it or not. Though I do have a tendency to reopen the email after it’s been sent just to reread it and think to myself, “Yep, it really went out. Now there’s no taking it back!!” I feel less stressed if it’s an email to a friend instead of someone who I am having a professional correspondence with, so if I have misspellings or weird sentence structures I don’t think about it as much.

    1. gallantly gal

      August 29, 2018 at 11:05 pm

      OMG haha sometimes I reread the email after I send it too xD it’s the worst when I see a mistake even though I reread it like 30x. See, after reading it so often, the words just blur and it doesn’t even matter anymore ahahaha. Yeah, when it’s for something more professional or important, I feel like every single word matters. And sometimes I’m like… is a smiley face appropriate here? But I want to smile. Otherwise I sound mad! Oh, the modern age.

  5. l'ambassadrice

    September 24, 2018 at 2:49 am

    I don’t usually feel like this, unless I’m writing a cover letter or something like that, and in that case I will read it at least 10 times haha. I love your message, and I think it makes a lot of sense to associate our need to reread and rewrite things so many times with our own insecurities. Thank you so much for sharing, I love your posts! 🙂

    1. gallantly gal

      September 24, 2018 at 11:10 am

      That’s awesome you don’t doubt yourself as much as I do! Thanks for reading and appreciating the message 🙂 Love the support!

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