Last week I was prepping for a Escape The City career change workshop on “Intelligent Transition.” Which basically means – if you want to quit a job or chase a dream (or even play with a half-formed dream), how can you make it work financially?

Simultaneously, I heard Brandon Stanton’s story on how and why he started the photography project Humans of New York eight years ago. Which has since become THE most popular photography project to-date, with over 25 million fans globally and a New York Times bestselling book to boot.

In 2008, Stanton was a happy bond trader in Chicago. He took pleasure in the game, learning how to earn and multiply money. But something was missing. On weekends, he started photographing strangers on the streets:

“The whole reason I started taking photos was because I was trying to create some space in my mind away from work. I was desperate for something to do on the weekends that would give me…a sense of purpose and sense of identity outside of how the markets were doing every day.”

Soon after, during the 2008 financial crisis, Stanton lost his bond trading job. (After watching The Big Short for a second time last night, I imagine moral guilt contributed to that pull toward purpose – although I’m speculating here.)

Looking for something to hold onto, he kept up the photography project and moved to New York – despite the endless rejection, lack of cash, and no clear business or life plan behind it:

“[I decided] instead of spending my time trying to make money, I’m going to try to make just enough money to where I can control my time. And just do something I enjoy doing for no other reason other than it is nourishing in the moment.”

Photo: Amazon/ Twitter/ Brandon Stanton

Stanton’s story reminds me of what’s true of most stories of transition (mine included).

FIRST — before worrying about the nuts & bolts of finances, savings, earnings, blah blah blah – a different kind of transition typically takes place: a new relationship with money and work.

With money, usually it’s a switch in priority from money-wealth time-wealth. Like Brandon says, “enough money” to control your time. And spending the luxury of that newfound time to do your work.

Not the full-time, nose-to-the-grindstone employment – that busy-ness, non-essential, toiling activity so many of us have come to think associate with work.

Most meaningful career and life transitions detach from that definition and reframe work in a fresh and blasphemous new way:

Exploring that which is “nourishing in the moment.”

* * * * *

More Resources:

  • Listen: The Full Story of Humans of New York. Listen to the full conversation between Stanton and Tim Ferriss. It’s a great case study on someone moving from a salaried corporate job to launching an artistic endeavour. Includes stories on facing endless rejection, learning a new craft on the fly, and seeking identity outside of “what you do” for work job. Listen here.
  • Rolf Potts: Time = Wealth. From the author of Vagabonding (one of my favorite books on travel), Rolf Potts speaks on why “time wealth” is the only wealth that truly matters. Potts’s core belief: “anyone armed with an independent spirit can achieve the dream of extended overseas travel – without spending lots of money.” Watch: Time = Wealth.


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