Whatever You Do, Don’t Press Send

Credit: Robin Breeding


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A certain someone – now deceased – who served with me on the leadership team of a certain university, once went behind my back and said something very unkind about me. In the pecking order of power, he was second-in-command, just two notches above my position. I was furious, never once thinking this person would attempt to undermine my authority. In response, I wrote a long email that expressed my disappointment, anger, and absolute disgust over the matter. I was just about to press send when I decided to share the email with the president of the university. Not only was he my boss, but I knew he was a person I could trust.

He said, “Was this the first time that that someone had done something like this to you?”

I said, “Yes.”

He said, “No. It’s just the first time you heard about it.”

His insight hardly made me feel better, but then he asked me, “How do you feel now that you have written your email?”

I said, “I feel pretty good.”

He said, “Excellent. Delete it. And, whatever you do, don’t press send.”  

I’m not sure what would have happened if I sent the email, but I suspect it would not have been pretty. In the few years I’d been at the university, I’d seen heads roll for much lesser offenses to the hierarchical order.

Email has been around since the 1970s and, like it or hate it, it’s a very convenient way to communicate among peers, especially at work where communications are often transactional.

An email is eternal, it never goes away, even when it’s been deleted by the sender and the receiver. You may think it’s gone, but as someone who has been involved in more than a few litigations, trust me when I say your email is as everlasting as a Gobstopper from Willy Wonka’s Chocolate Factory.

The issue, therefore, is whether to send or not send. Or, as Hamlet might have said:

Whether ‘tis nobler, by the action of sending to suffer the unintentional slings and sorrows of our misfortune Or quill thy finger in a sea of judgement, and never send and save thyself.

Many years later, at a different university, another colleague of mine was sending an email to a high-ranking volunteer. The email was an unflattering characterization of an employee we all knew. When my colleague pressed send, he accidentally copied the employee whom he characterized in the email. OOPS! That was ugly.

I’ve authored more than a few angry emails to subordinates and superiors and feel fortunate to have exercised sound judgement and restraint. (By the way, this also applies to texting, since, for many, using email is yesterday’s news.) Nonetheless, each time I press the send button on my laptop, phone or tablet, I’m overwhelmed with just enough anxiety to churn my already churning stomach.

Now that I’m retired, the churn is of a different nature. I worry less about who I might offend and more about the content of the email and how it was perceived. As a writer, there is an expectation that I should have a fairly good grasp of grammar. Sometimes I do and sometimes I don’t. I’m grateful to have good editors but embarrassed by the occasional dangling participle.

And let’s not forget feedback. My aforementioned colleague got nearly instantaneous feedback upon criticizing a fellow employee. I’d like some feedback too, but not that kind.  An encouraging word would go a long way to calm my churning stomach.

Last month, I completed the novel I’d been working on for three years. I was so excited by my accomplishment that I wanted to send it out right away to begin to find a publisher. I knew, however, that before I press send, the novel needed to be proofed.

My proofreader wife, Paula, took a day and half to get the job done. I then took another ten days to dot my i’s, cross my t’s, and re-write the ending that she kindly described as “problematic.” Was I ready to press send? Maybe.

There are 84 keys on my laptop, but only one can send my manuscript to the critical eye of an agent or publisher. As my index finger hovered above the keyboard, nervous and afraid, I thought about all those emails (good and bad) that I never sent. There is something to be said for restraint, but restraint will never get me published. With absolute purpose (and very little confidence), I slowly lowered my finger and pressed the key, sending three years of work to a literary agent I barely knew.

Can you hear the churning in my stomach? Does my anxiety travel through space and time as quickly as my manuscript travelled between desks 200 miles apart? Only time will tell. The good news is that it’s been three weeks since I pressed send, and I haven’t been rejected. The bad news is that it’s been three weeks since I pressed send and I haven’t heard a word.

I feel confident that the response won’t be ugly, and I’m hopeful it will be kind. Mostly, I’m just happy that the only person whose ego might possibly get hurt from all of this is my own. Fortunately, for me, my skin is extra thick and I’m more than ready to press send again and again and again.