The Art of Brevity: How Bob Dylan cofounded my startup

“Less is More” is one of the hardest concepts to apply in business, but in the age of information overload, it is essential.


In 1962, Bob Dylan released his first important original song, Blowin’ in the Wind. It was released on his first album of all original songs, The Freewheelin’ Bob Dylan. It was a breakthrough song for so many reasons. First, it was a catchy pop song, pure and simple. Second, it had tremendous depth lyrically, well before it was common for pop songs to have any depth at all. But third, and the thing I want to talk about, was its stunning simplicity and brevity.

Years later when I started writing songs myself, in college, I heard the song again as if for the first time. Great songs reveal their depth more and more with each listen. And though I’d heard Blowin’ in the Wind dozens, if not hundreds, of times before, when I listened to it in college, it was the first time that I noticed how uniquely and simply the song was constructed.

Blowin’ in the Wind is nothing more than nine questions, each with the same answer.

Just nine straight-forward questions about life, war, love, happiness, and philosophy. No small, inconsequential issues. Very heavy stuff. Stuff that could take books to write about. Yet Dylan seemed to capture the core essence of these massive complex topics with a perfectly-written, incisive question.

How many roads must a man walk down before you call him a man?

How many seas must a white dove sail before she sleeps in the sand?

You can Google the rest of the lyrics, but here’s the big takeaway from this song, and the reason I’m citing it here. Brevity. The man did not waste a word. Not a sentence. Not a thought. He doesn’t meander through buckets of words in order to get his point across. His point came across in each syllable. He asks nine questions, and each question makes a stunningly poetic, deep and even obvious point about humankind. But he knew that in order to get these points across to the public, he had to be brief and efficient. He had to choose carefully. He could’ve asked these questions in any number of ways, but what he did was challenge himself to ask these deep, loaded questions with as few words as possible.

Because he succeeded in doing so, the song is perfect. And the answer to each of the nine questions — specifically that the answer is blowin’ in the wind — is also a perfect, crisply written answer to these truly unanswerable questions. There is no better way he could’ve answered these questions but the way he did. Brief and to the point. He had no doubt in his mind what the answer to these questions was. And yet, the content of the answer — that the answer is blowin’ in the wind — by its very definition, suggests doubt. Amazing.

So it is because of the efficiency and brevity of the words that this song has such impact, and will forever be known as one of the most perfect songs ever penned.

So what exactly does Blowin’ in the Wind’s brevity have to do with my startup, UpdateZen? Well the answer to that question, my friends, is… (nah, I won’t go there ☺.) The lesson I learned from Blowin’ in the Wind about the importance and impact of brevity is the reason I founded UpdateZen, and so I give an appreciative nod to Dylan as I launch my startup.

UpdateZen is about sharing information in as few words as possible. It’s about using brevity to cut through the ever-growing information overload we all face in our work-life today. UpdateZen is about updating your boss in as few words as possible. It’s about forcing yourself to distill the essence of an update down to only what is absolutely essential for your boss to know. Not only so you save them time reading your update, and not only so you save yourself time writing your update, but because by distilling your update down to the core essence of what needs to be shared, you are getting to the point more quickly and with greater impact… just like Dylan got to the point in each of his nine questions in Blowin’ in the Wind. Quickly and with great impact.

Yes, it can be difficult to be brief when getting your point across in your job. You want to make sure you cover everything when updating your boss, just in case you leave something important out. But by including everything, by definition you are diminishing the impact of each element of the update. Look, it’s surely difficult to be brief when writing a song about the essence of humanity. Brevity doesn’t always come naturally. If it did, everyone would embrace it and practice it. It takes a commitment to brevity, and UpdateZen provides a way for it to be as effortless as possible to update people briefly. At our core, we provide a framework that encourages and enables you to be brief and effective in communication. Updates limits you to 250 character updates. It’s similar to the way Twitter constrains people to make a worthy point in 140 characters. It can feel constraining. But it can also feel liberating when you don’t have to include a whole lotta fluff in your updates. And each of us has surely been amazed at the profound nature of a well-written 140-character tweet.

If we can help you achieve great brevity in your updates, while still getting your point across, the listener/reader will be all the more appreciative, and the effect of your words will be immediate, deep and more impactful.

It is our contention that any update can be written in 250 characters. Some people scoff at this. “It’s business, after all!” But hey, in the rare instances where your boss needs more information, he knows where to find you. And if Bob Dylan can ask the nine most poignant questions about humankind with one sentence each, inside of only one song, then why can’t we aspire to update our boss just as efficiently on each key project we’re working on. I guarantee you that he or she will appreciate it more than you could ever know.

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