Inside Out Leadership

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"Why do you work?"

Welcome Entrepreneurs, I'm so glad you're here. And special welcome to those new subscribers who joined us after reading the last issue, a story about the ancient process of "dying before you die". I'm grateful for the emails from so many of you. I hadn't realized that would touch such a chord. 

I was listening to an old Ram Dass recording (recommend) and heard him tell the story of Zumbach the Tailor. I can't honestly remember the context, because in my mind the parable is clearly about nothing but the startup journey, and how easy it is for founders to build the company others want them to build, rather than the one that lights them up.

Hope you enjoy.

Why do you work?

Ask a group of first time founders this question, and I almost invariably get one of two refrains: 

  1. To make a dent in the universe. To build a unicorn.

  2. To become a billionaire. To create generational wealth.

There’s nothing wrong with those answers. It’s just that they’re not yours (even if you think they are). They belong to our culture. They’re in the water you’re drinking. 

Chasing someone else’s dream is problematic enough, but on top of that, these startup dreams also lead to very specific places that, like your favorite Monet, tend to look much more appealing from far away.

It reminds me of Zumbach the Tailor, a parable that to me speaks to the startup journey. 

There once lived a tailor named Zumbach who had a reputation for making the finest clothing. He used only the best fabrics, and he was especially known for his impeccable suits. One day a man named Sam walked into his shop and plopped down a bundle of money in front of the famous tailor.

"I've always wanted to own one of your suits, and I've been saving up for years. Is this enough money for you to make me a suit?" 

After carefully counting the money, Zumbach replied. "Yes, I could make you a suit." 

"Wonderful!" said Sam, clapping his hands and smiling with delight. 

"First," said Zumbach, "I need to take your measurements." The nimble tailor took out his tape measure and proceeded to measure Sam from neck to toe, carefully recording every detail in a small notebook. Then together they picked out an elegant cloth from Zumbach's fine selection.

"Come back in two weeks," Zumbach said, "and the suit will be ready for you." 

When the promised day came, Sam could barely contain his excitement. He arrived at the tailor's shop before it even opened. "Is my suit ready?" Sam asked Zumbach when the tailor finally opened the door. 

"Yes, of course," said the tailor, "Come in. Here it is. Try it on."

"It looks beautiful!" said Sam as he stepped into the suit. There was however, one problem. The suit didn't fit. One leg was four inches shorter than the other, the sleeves were different lengths, and the shoulders were several sizes too small. Sam was disappointed and angry. "Zumbach, what have you done? You've ruined it!"

"Nonsense" said Zumbach. "There's nothing wrong with the suit. You're just not wearing it properly." 

"Not wearing it properly?" asked Sam incredulously. "What are you talking about?"

"Here," said Zumbach, "just bend your left knee a little more. Yes! That's good. Now pull your right arm up two inches and bend your elbow. Perfect! Now one more thing; raise your shoulders so that they're almost touching your ears. Beautiful! You see? The suit fits you perfectly! Look in the mirror. You look like a million bucks!"

Sam took a look. He had to admit that the suit did seem to fit better now that he was wearing it properly although somehow it still didn’t feel quite right. He paid Zumbach, shook his hand, and left the shop to catch a bus back to his apartment. 

As he stepped on the bus, the driver smiled at him and said, "That must be a Zumbach suit that you're wearing." 

"Yes," said Sam, smiling with pride. "How did you know?”

"Because," said the driver, "only the gifted Zumbach could make a suit for a man whose body is as crippled and misshapen as yours."

Zumbach’s suit is tailored to those who chase dreams of unicorns and stacks-on-stacks. And, what’s worse, the world applauds as you contort yourself to make the suit fit. It cheers as you build the most powerful, influential organism of your life steering with your eyes closed, navigating using a map someone else created. 

The affirmation is intoxicating. All the bus drivers in the world telling you that you look great with your shoulders hunched. It almost makes you want to Quazimodo yourself a bit more. Zumbach’s appreciation almost satisfies in lieu of your own. But success at someone else’s life is the most expensive form of failure. The one you don’t realize until after you’ve sacrificed everything. 

“I  wish everyone could get rich and famous and everything they ever dreamed of so they can see that's not the answer.” 

– Jim Carrey

What people don’t tell you is that you can build an amazing company dressed however you want. You don’t have to wear Zumbach’s suit to play the game. In fact, an outfit tailored to your natural measurements – what you really want out of your one wild and precious life – might even let you run just that much faster. 

“I’ll tell you one thing, I’m definitely not trying to build a unicorn any more.” 

– Founder, two years into his second startup, one year prior to life-changing exit after his A-round

Whatever you’re chasing, recognize that you’re spending your life to do it. Make sure the destination is worth the sacrifice it’ll take to get there. 

If you’re game for some field work on this topic, I’d offer these questions for your reflection. 

You’ve likely been asked the first question before – it’s worthwhile to answer again. If you’re satisfied with your answers to the first two, you can stop there. But if your answers sound like Zumbach’s, I invite you to dig deeper with questions three and four:

  1. Why are you building your company? 

  2. What would success look like, and how will you know when you have it? 

  3. How did you first learn to want that? 

  4. What will having that do for you?


Things I read this week

One: I demand deep okayness for everyone (Sasha's Newsletter)

This was a wonderful deep dive into a person's first hand experience in going from "I must achieve to earn the right to live" to learning to feel legitimately, deeply, just ultimately okay about himself. As he is. Interesting to notice that the process (which mirrors my own in many ways) runs predominantly outside the mainstream therapy world.

LINK >>

Two: The Dark Retreat Dopamine Fast

We spend our lives, most of us, chasing dopamine hits. And some of us (presumably many reading this newsletter) get most of the dopamine hits that we chase. Enter the Dark Retreat, which sounds equal parts terrifying and compelling, and for the same reason. Maybe it's just me :)

LINK >>

Three: Alan Watts on life

"We thought of life by analogy with a journey, a pilgrimage, which had a serious purpose at the end, and the thing was to get to that end, success or whatever it is, maybe heaven after you're dead. But we missed the point the whole way along. It was a musical thing and you were supposed to sing or to dance while the music was being played."

-- Alan Watts

Four: The Goal Setting Guide (Sahil Bloom)

Investor Sahil Bloom created a pretty neat guide to goal setting, which jives with my previous work Goal Setting for Momentum so I like it.
LINK >>

Five: CEOs are forced to embrace uncertainty (NYT)

"CEOs swapped some of their favorite tropes -- timelines, confidence, strategic plans -- for something new: saying "I don't know." Or even: "I changed my mind."

Let's consider that it's the New York Times that printed this. If you're still pretending to your team that you know what to do, you're behind.

LINK >>


Want to dive deeper?

If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.

Here are a few of my favorites:


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I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency supporting founders to rapidly scale themselves as leaders, so they can thrive professionally and personally as their company changes the world. Leveraging 15-years as a founder/CEO, a decade of meditation & mindfulness training, and deep training in Neurolinguistic Programming (NLP), I have helped leaders from companies across the world, funded by some of the world’s top venture funds, to design a more conscious life and make key changes to improve their performance and satisfaction.

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