5 Tips Form The World’s Best Business Coach…Bob Dylan.

Back in another lifetime, I was fortunate enough to have met and talked one on one with Bob Dylan for about half an hour. This was back in the 70s when he was just about the biggest thing out there.

The story of how this came to be is a long one, and would probably make a good post in and of itself. But the insights I gained from that conversation have helped shape my attitude towards writing going forward from there.

The most interesting things he said to me were in response to a question I asked him…we were talking about the higher purpose of writing, and I asked him what his higher purpose was. He told me two things:

1. That he never thought of himself as a poet or a prophet of any kind, but more as an entrepreneur whose product was songs.

2. That he hoped that people would read deeply enough into his writing to see that he was just giving them some pretty simple advice based in great part on his own experiences, but housed in metaphor to make it interesting.


Bob Dylan’s Business Advice, A Loose Translation

1. From “Shelter From The Storm”

The deputy walks on hobnails
The Preacher rides a mount
But nothing really matters much
It’s doom alone that counts
And the one eyed undertaker
He blows a futile horn…..

Now if you look at this from a business perspective, what it could very well mean is that you should always respect authority, never let religion influence your business decisions, and always be aware that if you’re not diligent, your competitors will eat you alive. Pretty solid advice.

2.  From Highway 61  Revisited

Well Mack the Finger said to Louie the King
“I got forty red white and blue shoe strings
And a thousand telephones that don’t ring
Do you know where I can get ride of these things?”
And Louie the King said .. “Let me think for a minute son.”
And he said, “Yes I think it can be easily done
Just take everything down to Highway 61.”

This is obviously a shrewd insight into targeting. Bob is saying that it’s critically important to understand your market and how best to reach them, and if you don’t know that, find some one who can help you with this very critical strategic challenge.

3. From “All AlongThe Watchtower”

“There must be some way out of here” said the joker to the thief
“There’s too much confusion”, I can’t get no relief
Businessmen, they drink my wine, plowmen dig my earth
None of them along the line know what any of it is worth.”

This tip has a lot to do understanding the true value of your business, and making sure that one of your goals should be to build your business into something solid that can can eventually become a saleable asset or passed down through your family. If you aren’t aware of this, a lot of people may offer you less than it’s actually worth. And what’s worse, you may sell it for that.

4. From “I Ain’t Gonna Work On Maggie’s Farm No More”

I ain’t gonna work on Maggie’s farm no more
No, I aint gonna work on Maggie’s farm no more
Well, I wake up in the morning
Fold my hands and pray for rain
I got a head full of ideas
That are drivin’ me insane
It’s a shame the way she makes me scrub the floor
I ain’t gonna work on Maggie’s farm no more

This advice is for those people who are working for a company and dying to get out there on their own. It sympathizes with the feelings of enslavement that are often the key motivator for taking the great leap into self-employment.

5. From “Memphis Blues Again”

Mona tried to tell me
To stay away from the train line
She said that all the railroad men
Just drink up your blood like wine
And I said “Oh I didn’t know that
But then again there’s only one I’ve met
And he just smoked my eyelids
And punched my cigarette”
(Oh, Mama, can this really be the end
To be stuck inside of Mobile
With The Memphis Blues again)

This advice states very clearly that not taking to the counsel of your trusted business advisors could get you into a situation with clients that may not be in your best interest. Running your own business, it’s always very important to have people who possess the kinds of knowledge that you don’t have, so that you can always make smart decisions and never get stuck in a bad place.


I hope that my translations of Bob’s metaphoric business advice were helpful to you. If you would like to read more of Bob’s wisdom you can find all his lyrics posted at http://www.azlyrics.com/d/dylan.html

Jim Murray is a communications strategist, blogger, writer,
blog editor, art director and producer. He creates and implements

for companies in the SME & B2B sectors who appreciate solid
creative thinking and value reasonable rates.

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Jim Murray, Creative Director

Direct Line: 416 463-3475
Email: jim@onandup.ca or onandup3@gmail.com
Web Site: http://www.onandup.ca
Portfolio Blog: https://onwordsupwords.wordpress.com
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