Dan Kennedy on life and the nature of success

Dan Kennedy is the author of American Spirit (a novel I adored), as well as a memoirs Rock On (which Elysha and I listened to and loved) and Loser Goes First (which is sitting on my desk, waiting to be read). He is the host of The Moth’s podcast and frequent host and storyteller for The Moth. I’ve gotten to know Dan over the years, and I adore this man. He is soulful and clever and lovely.

Dan posted a series of tweets (@DanKennedy_NYC) a few days ago on the nature of life and success, specifically speaking to those of us whose path through life was not predetermined or blessed by the financial support of parents, a traditional academic track, or employment in a family business.

The bootstrappers. The shiftless. The frightened. My people. 

These words spoke to me, and perhaps they will speak to you. Dan posted more than the four tweets I have transcribed here, but there were the four that meant the most to me. The four sentences that said so much about what it is like to maneuver through a complex, difficult, unyielding world while the people around you speak about college as if it’s a forgone conclusion, live happily with parents for extended periods of time in order to save money, furnish homes with tables and sofas that were bought in actual furniture stores, and land jobs in family businesses and with family friends when their creative dreams failed to materialize.

I do not begrudge these people. I just want to remind them that there are so many other people living outside that bubble of expectation, not because we wanted to but because there was no other choice. These are the people who have rented rooms from strangers, gone without heat or electricity for months at a time, wondered how they might eat tomorrow, and thought that their dreams would likely remain dreams forever, no matter how hard they worked.

This is what makes me love Dan’s words so much. They remind me and so many of us (the “cross between the pirates and the little kids”) that we are not alone in our ridiculous, impossible, oftentimes invisible struggle.

Dan’s words:    

That’s the thing: success takes risk. We go through straits… skate by w/o insurance… operate on cash…live where nobody else will…

If you don’t have a family break, automatic money, pre-destined academic track, you put it together any way you can.

When shit finally gets great, people applaud you. But all those other years (a decade, two, forever?) you’re the “problem.”

But for a long time you’re a cross between a pirate and a little kid. Breaking rules, full of heart, working your ass off.

— Dan Kennedy