Before you Press “Send”

One of the most famous books ever written was “How to Win Friends and Influence People” by Dale Carnegie in 1936.

The book sold 30 million copies and is considered one of the most influential books of all time.  It was so popular that it became the subject of seminars all over the world and is still used today to teach people how to deal with others successfully.

One of the insights from the book that stands out to me is that no sound is more pleasing to an individual then the sound of his or her own voice.  Each of us has that natural inclination to believe that the sweetest sound to the human ear is the sound of our own voices, especially when we are speaking about ourselves and our opinions.

In today’s world—our internet crazed techno nerdy world of 2017—the sound of our own voices has been replaced by seemingly endless streams of emails, text messages, blogs, instagrams, snapchats, etc.  Unlike the way that the world operated a generation or two ago, there is no sight more pleasing to many  than the sight of their own written words. And for reasons that have yet to be adequately explained to this writer, we have a need to express ourselves even if our opinions don’t matter or even if our opinions concern something about which we know little or nothing.

In my world of taxation, these expressions are incredibly important.

Our federal government has undertaken an extensive program to make sure that it has digital access to our emails and text messages, including and especially those emails you send to business associates, accountants and lawyers which may not be privileged.  The people who govern us intend to take advantage of our need to express ourselves in written word and then use it against us.

That’s right, friends, in a legal proceeding the words that you send to others can and will be used against you—not only to create tax liabilities or aid in collection of those tax liabilities, but also to put you in jail.

The national news in recent months is filled with examples.  Anthony Weiner is in jail, Hillary Clinton famously deleted 33,000 emails which damaged her election campaign, and Congress has ongoing investigations of FBI text messages to colleagues and girlfriends.  These are but a few examples on the national news level, and I don’t expect this trend to slow down.  People’s lives are being impacted in powerful ways by their own written words which they send.

So today I am dedicating this article to a very simple concept, and I am asking each of you to carefully consider it.  We live in a new world.  That world includes an electronic record of our personal expressions, and these personal expressions are permanently available on the internet. The federal government knows this and is developing tools that will allow it to store those transmissions.  In legal proceedings, the government will obtain those personal expressions and use them to punish us in civil and criminal proceedings.

I strongly urge each of you to consider what my father told me years ago when I first went into law practice.  Review everything that you write as if a grand jury was reviewing it.  If you just cannot restrain yourself from pressing “Send”, then at least consider how a grand jury might view your words if later re-discovered in a legal proceeding.

In my law practice, I am constantly required to defend the written expressions that my clients have given to the IRS prior to my involvement.  These expressions are often misstated in the client’s written history, and I then have to do my best to defend, disavow and/or explain them.

It’s sad but true that we find few things more pleasing than expressing our feelings and opinions to others.  I suppose it’s the need that each of us has to feel significant, and one of the ways that we do so is by expressing ourselves to others.  In the business and legal world, however, I strongly encourage you to be very careful in your written expressions and to consider whether those expressions should be tempered by the legal and financial risks in making them.

This is one of the reasons that I don’t often give out my email address, and I almost never send emails to my clients or to other lawyers or accountants.

Also, other than routine transmittal letters, I have a practice of allowing my letters to go unsigned and unsent overnight- so that if I am certain the following morning then I sign and send them.  I have written many letters over my career, and there are more than a few which upon reflection have been discarded and never sent.

David Leeper is a Board Certified federal tax attorney with 38 years of experience.  He can be reached at 915-581-8748, by email at, or visit