How to Avoid Email Regret

“Resentment is like drinking poison and then hoping it will kill your enemies.”
– Nelson Mandela
Have you ever received some news via email, voicemail, word of mouth, etc, that has made you so angry that not only did you have physiological responses (increased heart rate, knot in your stomach, rise in body temperature, etc.), but you obsessed on this perceived or actual way in which you were wronged that you could think of nothing else but reacting as soon as possible?
If so, what did you do?  Did you take out your phone and bang away ferociously on your iPhone’s screen (good thing it’s made of Gorilla Glass) typing faster on your phone than you ever had before?  Maybe you only took some notes capturing the bullet points.  Maybe you waited till you were at your computer (assuming you weren’t at the time and “unleashed hell” like in “Gladiator” but in the form of email.

Perhaps you showed some “restraint” and decided to deal with it later and were actually able to re-engage in your life for the remainder of the day.  For many, this “restraint” lasts until that night, when laying in bed, you can think of nothing else.  So, you become more and more angry / upset / resentful until you “can’t take it” and write that Manifesto to the individual or institution that has “wronged you.”  If you’ve ever done the latter, you’ll know that this action always takes longer than expected.  You read your email.  You re-read it.  You realize you forgot yet another dagger to throw because as you write and review more and more ways in which you were screwed as well as your increasing disgust with how the other party handled themselves you realized you must capture ALL of the ways the dared to screw with you!  They must be fully aware of their actions and what a horrible person they are (or so you thought, irrationally, at the time).

If you invested the time and emotional energy in writing that email, you know it was a waste of time and likely caused more harm than good.  Worst off, it perpetuated stress and needless drama.  Why?  Because, it’s now the next morning and not only did you take time out of last night’s sleep, but you feel a nagging anxiety about the email.  Maybe before you were even fully awake, you grabbed for your phone to see if there was a response.  Amazingly, often the lack of response is a relief.  It’s a short lived paradoxical relief, because it’s only a short-term delay.
This may not hit you immediately.  Perhaps you’re in the shower and are reassuring yourself you did the “right” thing.  That’s your defense system advocating to you that you stood up for yourself and not only should you not feel anxious about it, damnit, you should be proud for taking a stand.  The unconscious, however, is far more powerful and in that lies the anxiety that your inner cheerleader can’t compete with.
Dread.  Anxiety.  “WTF?  WHY DID I DO THAT?  OMG, I MUST RE-READ WHAT I WROTE IMMEDIATELY.”  Here’s paradoxical consequences.  Those same feelings of urgency in which drove you to obsess on and address the issue are back except the urgent matter is damage control, possibly remorse, and definitely anxiety in some form.  People often forget that anxiety has many forms.  Knowing that you have to deal with this confrontation and “gearing up for battle” to do so, is anxiety even if it’s not panic in nature.  It’s lining up all your ducks in a row, anticipating every kind of response you may receive and how you will have an immediate retort.  Ultimately, it’s a distraction from the important things and it’s exhausting!  These days, only few email systems have a means of retracting sent emails.  These are most often seen within a company’s internal network.  So what are your options?  If this was 1986, you might consider breaking and entering to steal the tape out of the answering machine a la George Costanza.

There are a number of alternative ways in which you can deal with this issue BEFORE you set the above cycle of shit in motion and they all involve some sort of self-intervention:
Disarming our scathing impulse before it turns into an action is the number one way to avoid sending an email and suffering from “email regret.”  Take the precipitating email (or write / type whatever the precipitant was) on paper or in a word processing program.  If it’s an email, the easiest thing to do is copy and paste the the text in a new document:
READ: Read the precipitating text
IDENTIFY:  Identify the key triggers for your negative feelings (use a highlighter or the highlighting function in your word processing program”
SIMPLIFY:  Boil these down to  bullet points.  This may require you to insert a few lines in between some of the sentences of the text so you can better identify the key triggers.
WHY?: Take each of  each of the “offenses” and ask yourself why such a powerful emotional response was illicited.
WALK AWAY:  Do something else for at least a few minutes, then come back to it.
Once you identify what pissed you off and why, you can make bullet points as to how you respond to the “offense.” You may feel after reading the offense and the whys you’ve identified, you don’t feel like you need to address this issue.  Be careful here, because if it’s someone you’re close with, or important in your career, you may not want to address a particular aspect for various reasons including the worry that you’ll come off as offensive.  If you’re feeling that way, then you’ve already proven that self-intervention has at least started to disarm your quest for justice and need to show them!  That said, if it’s something that does bother you, note that you wish to address and think about you you can do so without causing a contentious situation.  Don’t reply yet.  Wait till the next day if possible and then you can respond (see below regarding ways in which you can effectively respond).
I think you’ll find that after this exercise and by waiting, you are not nearly as angry, you are thinking clearly, and therefore will have the ability to address the situation logically, with practicality and without it being steeped in reactive emotion.
A. Let’s Get Ready To Get Ready:
If you tried to reflect and delay responding (better to try method number one) and still find yourself ready to shread your newly sworn enemy, it’s time to write the scathing email.  READ THE REST OF THIS PARAGRAPH FIRST.
Rip them a new a-hole.  Don’t hold back…..let’s see what you got!  WAIT, WAIT, WAIT – BEFORE YOU START DISMEMBERING THEM WITH YOUR WORDS, HIT COMPOSE NEW MESSAGE, AND COPY THE SUBJECT OF THEIR MESSAGE INTO THE SUBJECT OF YOUR NEW EMAIL.  Put “re:” in front of the subject AND FOR GOODNESS SAKE, DO NOT ADDRESS THIS TO ANYONE.  I recommend a new message, because if you hit “reply” and accidentally fail to remove their address or hit “send” effectively sending them a blank response, you won’t be happy.  Remember you’re anxious, mad, and you may even be shaking a little, because you’re not gonna take this sh#t.  Don’t read it, just get it OUT AND DON’T READ IT.
After making this suggestion, the typical response is, “why type it out in my email program, why not type it in word.”  Slow down, young grasshopper, we are not finished with our training.
Pai Mei
ASSOCIATIONS (They’re Not Professional Clubs / Organizations):
The answer is simple.  Our brains make powerful associations.  Whether I’m helping someone in their efforts to stop a maladaptive behavior, or increase their self-awareness, breaking associations is a great place to start.  First off, these associations that contribute to a negative behavior are known as “triggers.”  A great example is quitting smoking.  If you are a smoker or a former smoker, how often do you light up after a big meal, after sex, while having your morning coffee, or just leaving work, putting on some tunes in the car, and lighting up a cigarette (or something else!)?  Triggers can be tricky as well as we’re not always aware of them on a conscious level.  These can include “Anniversary Syndrome” where we find our self in a foul or sad mood for no particular reason (assuming this experience is out of the ordinary for you), but it happens to be on the “anniversary” of a negative event from your past.  This deserves its own post, but you get the idea and by replying to an email with one that won’t be sent within your email program, your gain the satisfaction of feeling as though you are responding.
So, you took the time, and wrote the email.  You either felt some level of satisfaction or dirty and shameful with your hateful onslaught you monster!  Just kidding.  Relax.  It wasn’t about them and most likely doesn’t reflect your true feelings.  It was a means of appropriate coping because you just couldn’t shake it.  Congratulations, assuming you only wrote the email that won’t be sent, you made a huge step because you didn’t rely on maladaptive behaviors (drinking, drugs, binge eating, online-retail-therapy), and in reality you just engaged in catharsis.  GO TO SLEEP!
I can pretty much guarantee that when you read the email you were going to send fueled by anger, rage, resentment, and the need to let your inner-warrior out, that you’ll have a reaction in the realm of ‘I must be nuts to have even considered sending this.’   If you didn’t go to sleep and just HAD to read what you wrote, I hope you at least took 10 minutes between writing and reading, stood up, walk around, had a cup of tea, or did some f’n thing for a few minutes which you should have been able to after purging yourself of these all consuming negative emotions.
In reading what you wrote the night before, you may laugh uncontrollably (mostly due to the extraordinarily quick change in your emotions and the physiological effects of this change).  You may wonder why you’re not hosting the Comedy Central Roasts, or selling out MSG because you are the funniest, and most raw comic who can say what others only dare to occasionally think.   Karma wise, you might be thinking that this is wrong.  I should not even do this to my fellow human, you need to reframe this thought.  Like I said, you are not doing this to them.  Instead you are doing this for yourself and by doing so, you’ve removed the irrational hatred and negativity that was never going to be sustained anyway (come on, I know you said ‘F them, I don’t need them in my life’) but that was your defense system.
You now must decide how you want to secure this email.  You can delete this unaddressed ‘draft’, save it to drafts, export it, or copy / paste into another format.  If you wish to save it and personal security and privacy is an issue or if this is a work email account, get that text out of your email account and somewhere else.  Again, you may wish to delete.  You can also email it to yourself after making edits that remove the individual’s name – the specific offense, and anything else identifying and save your hot comedic material.  Seriously, you may want to save it as a reminder of what can happen if you don’t intervene and unburden yourself of an intense emotional response.  Just remember if you email yourself, you’ll have a copy in your sent mail and it traveled through a myriad of servers.
Regardless of what you decide to do with the file, text, etc., you got the poison out so to speak (for the Howard Stern fans, not THAT kind of poison).
Sometimes when one is feeling resentment, anger, or even feelings of being overwhelmed, taking only a couple of minutes to do the following exercise can yield huge results.  What you do is make a “gratitude list.”  You can write it, type it, or even just make a mental list of some of the things you are grateful for.  Often, we’ll identify the most basic blessings that are often taken for granted in as we are consumed with our day to day.  On your way to a job that makes you miserable, you can intervene and be thankful you have a job to go to and/or that you are physically able to get to this job.
If you’ve lived in a major city as I have, I know there were many times I was unhappy going to a job that stressed me out, just to step in or out of the subway and see a physically disabled homeless individual.  A more extreme and specific instance comes to mind when I was walking cross town in NYC, taking my typical 8 foot strides to get to work on time, and saw a homeless woman who had lost her legs at some point in her life with a huge smile on her face.  She said “good morning” and I did the same, smiling back and putting some money in the jar she was holding out which said “Have a Grateful Day.”  Immediately, I was taken out of my self-absorbed thoughts, and the pity party that was going on in my head (amazing how that pity party was raging and hadn’t been shut down by the authorities is beyond me….I mean that party was bumpin’!).   Immediately, I got outside of myself and my negative thoughts in a positive way.   When I arrived at work, I felt empowered.  Not because I was any better than that woman, but because her attitude was inspiring and her smile infectious.  Often, it’s all about perspective, and when that perspective is rooted in what “truly matters,” as it was for me you may feel as I felt that morning.  I was feeling true euphoria just to be alive.  It didn’t matter that my boss was going to yell at me about something.  That’s his problem and personality disorder (classic Borderline Personality Disorder – I’ll leave that for another time).
Is it worth it?  The question of is it worth it, is a difficult one to answer when you’re fired up and pissed off.  It’s human nature to want to prove to someone that they are wrong in their offense.  Especially if said offense is taken as a personal attack, criticism, or illicits feelings of being taken advantage of.  If the person is very important to you, and you were able to reflect and delay sending that email, it’s still important to address how you were affected.  What is worth consideration is where your efforts in proving them them wrong actually get you.  If this person is important to you either personally or professionally, the better route is to try and look at things from their point of view once it is clarified that there is no misunderstanding.  If the action or communication offended you, perhaps listening to that voicemail again or re-reading that email they wrote you was done so while they were going through their own stuff.  This doesn’t excuse disrespect, but for selfish reasons, this realization might take the wind out of your indigent or incredulously angry response.  More on this below.
Many years ago, I was driving while seething about someone who offended me in such a terrible way, I can’t remember what it was they did or said.  I do remember the physical response and that it lasted a few days (associations / triggers here again).  This was someone who I later realized and came to understand that I really didn’t care what they thought.  I was probably avoiding thinking about something truly important and was actually procrastinating about addressing the important issue at hand which was not what this person said or did.  I drove past one of those Churches that have those marquee signs on the lawn out front usually with some schedule and often with a quote (missing a letter or two – think movie theatre marquee).  Often I notice that space is reserved for a biblical quote.  Not that day.  It read, “He Who Angers You Controls You.”  Immediately, my resentment was gone.  This was because my mind reframed my anger into the attitude of, “Holy shit (no pun intended), I can’t believe I’ve been letting [insert name here] control me for the past 2 days.  They didn’t know they were controlling me and odds are they didn’t know that they had any affect on me or my mood.  I remember thinking I’ll be damned if I’m gonna let this person rent space in my head.  Actually I wasn’t just letting them rent space in my head because i received no rent check, I was letting them squat.  WTF!?
First, forgive yourself for having a normal reaction.  I could have beaten myself up for twice as long as I obsessed over this great and monumental offense, so horrific and I have no clue what it was that offended me.  Those who know me, know I’m a nice guy and wouldn’t treat anyone else 10% as bad as I used to treat myself.  When I remember that, delay my response, tap into my gratitude and or look at the situation from both sides, I know that not only will I not have to experience email regret, but that I will be free of the bondage of resentment and move on to what’s truly important, like my daughter or even something I like to do for myself (workout, make music, read, watch some tv, etc).
Once you’ve considered the angles, tapped into your gratitude and feel strongly about addressing this issue, I would encourage you to do so face-to-face.  It’s normal to have anxiety about this meeting, or fear that you are either going to have difficulty expressing yourself in a controlled manner (or conversely not express yourself strongly enough), again I’ll go out on a limb here and say that if you are able to be calm, ask questions to clarify, and not attack or defend, odds are the anticipation of the meeting was far worse than the actual meeting.
You’re gonna regret it and prolong the agony.  One misunderstood statement in either way will lead to pressing on that glass, fast and with stiff thumbs, cursing auto correct for f’n up your ability to send your comeback.  Let’s not forget the potential for even more intense negative emotions one will experience after sending something (possibly aggressive) just to see the dots that the other party is responding and then need an air sickness bag once those dots disappear and no response is received. That MF’er bailed on what they were writing, leaving you to speculate what horrendous and vile things they were going to say.  Come one, let’s face it, odds are they weren’t going to write anything that bad, they’re just second guessing how to deal with your volatility should you not take the above measures to disarm your emotional reactivity.
Oh, the horror!
text remorse
Sometimes, we don’t have the luxury of face-to-face or by setting up such a meeting, our need to “resolve this immediately” becomes delayed, than consider the phone (they still make ones that allow you to make phone calls as well as text).  By calling, you’ll have a much better chance at quick resolution and be able to use some key tactics or approaches to avoid both a contentious situation as well as unnecessary back-and-forth of emails or texts.
By calling them, you have the chance to find out that you very well may have misinterpretted their intentions.  A good way to start such a conversation is by saying you were confused by their email, the news you heard, etc, and this will clarify if you misunderstood or were misinformed.  If it was an email or a means not communicated directly by that person, then they may have no idea how what they wrote or got passed along actually came across in the few minutes they took to create the communication in the first place.  Perhaps more importantly, you’ve saved hours of agonizing over this.  The sooner you make this call (assuming you at the very least re-read and identified what bothered you, thus disarming your impulsive reaction to crush this party, the better you’ll feel, and you’re body will actually provide you a jolt of endorphines and hormonal balance that energizes and makes you productive in getting back to your life.
If you are able to take even one thing away from this, you’re ahead of the game.  Often we lose a disagreement  the minute we lose control of our emotions.  If you really can’t shake it but know it’s not smart to try and address it as you know you’re emotional, there are so many other positive outlets to channel negative stress into positive stress.  Sure there are some similarities in the two (elevated heart rate, dilated pupils, etc), but the hormones realeased into our brains are different and we have the chance to make lemonade out of lemons rather than find ourselves unable to focus, sleep or worse.
At the end of the day, sending out an emotional response without processing it (hopefully with the help of a trusted party or professional), is to perpetuate the misery and not only a form of sabotage but very disrespectful to yourself.  How weird is that?  Feeling disrespected so let’s react by disrespecting ourselves too!  Let’s invite a line of others to just beat us up as seen in “Airplane.”
airplane nun
With the exception of some companies that have exchange servers that allow for recinding sent email (and let’s be honest if you do that on company email, at the least you have an IT team member reading it and laughing at you), you can’t unsend an email.  Well you can’t un-send an email, and George Costanza can’t help ya.
Show yourself some love and respect.  Not only will you be glad that you did, you may even get some momentum going and intuitively know how to handle these situations in the future.  Because let’s face it, someone’s gonna piss you off again soon.  If they step across the line (aka habitual line steppers – “Chapelle Show” reference) then your best bet may be acceptance.  You won’t be able to change them, but you sure as hell can change how you react to them!
habitual line stepper
Contact me if you would like some more clarity, because I’m sure as hell not gonna sleep on this and re-read before posting – just kidding.
Got an idea or suggestion.  Feel free to share it below, but don’t hate because after all, I don’t want to have to write an unposted posted comment {^_^}.
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