ASE Podcast

#25 Two Pockets

Trying, failing and trying again

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I spent this week wandering through Hue, the imperial capital of Vietnam. Full of hundred-year old pagodas, emperors’ tombs, and the imperial city, Hue has stunning architecture you can’t find anywhere else in the country. Yet more often than not, I was the only person visiting these historical sites. Few humans held so much power and built such structures; fewer people remember, or care.

This paradox reminded me of my favorite quote from Rabbi Simcha Bunim about how everyone must have two pockets:

“Everyone must have two pockets, with a note in each pocket, so that he or she can reach into one or the other, depending on the need. When feeling lowly and depressed, discouraged or disconsolate, one should reach into the right pocket, and, there, find the words: ‘The world was created for me.’ But when feeling high and mighty one should reach into the left pocket, and find the words: ‘I am but dust and ashes.'”

In this episode, I discuss how this paradox has helped me deal with trying, failing, and trying again. I also share a passage from my upcoming book, “Be a Nobody,” which shares how I deal with failure (below).

If you would like to be a first reader and help shape the final version of my book, join my Upstartist Facebook Group.

Be a Nobody

“Without desire there is stillness, and the world settles by itself.” 

-Tao Te Ching

Business rejections are tough, but I find personal rejections even tougher. Nothing hurts more than when someone who captures your heart is not interested in you. The denial can be outright and direct, or agonizingly slow and subtle, but when the dust falls, you end up alone, heart-broken.

I used to wallow in self-pity for weeks, sometimes months after a breakup. One time, as I told my best friend about the end of a relationship, I burst into tears, crying into a bowl of kimchi ji gae. That Korean restaurant became immortalized as “breakup cafe.”

There are a surprising number of parallels between business failures and break-ups. They both crush the spirit. Some part of you just can’t get over what should have been. We wallow in stubborn attachment to our desired alternative reality, complaining to our friends, and dragging out the drama by resenting and punishing those who turned us away.

What a waste of time. And what painful delusion.

The great American poet Maya Angelou had a rule, “When someone shows you who they are, listen.”

Our ego, desires and attachments muddy our ability to see and experience reality. They make us force something that’s simply not there for months – and sometimes years.

A tonic for failure – both business and personal – that has helped me is to remember Bruce Lee’s paradoxical advice to “Be a nobody.” One of the most iconic and ambitious movie stars, Lee wrote, “I must give up my desire to force, direct, strangle the world outside of me and the world within me in order to be completely open, responsible, aware, alive.”

Being a nobody gives you the superpower of heightened awareness. Being a nobody allows you to respond naturally and easily, without all the rigmarole required to caress your ego. Being a nobody allows you to accept reality and “move like water, rest like a mirror, respond like an echo.” Being a nobody puts you in your most fluid, unencumbered, effective state.

We need to stop fighting imaginary battles. Instead of fixating on what my ego craves and how someone or something should be, I can acknowledge what is:

She is sending clear signals about how she feels. You are not a priority for her. Time to let go and make room for women who value you. Thank her for her lessons. Drop the comfortable identity of being a victim. Wish her the best with her career and life.

As entrepreneurs we are tenacious – and stubborn. It’s difficult to know when to keep going and when to let go. But banging our head against the same wall serves no one. Being a nobody helps us see the wall that doesn’t need to be there. Yes, we must hold a strong vision for our lives. But equally important is remaining flexible and open to how we get there. The irony is that holding a view of our astounding insignificance is what allows us to achieve our limitless potential.


  • Hue (0:00)
  • Be a Nobody (1:40)
  • Two Pockets (7:36)

Show Notes


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