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Alan Watts and Designing Work to Fit Our Lives

Updated: Dec 22, 2022

Have you heard of Alan Watts before?


He's a British Episcopal priest turned counterculture icon and "philosophical entertainer" after moving to California—known for bringing Eastern philosophy to the West. Years ago, I was mesmerized by his recordings on a local Berkeley radio station, and later, I started reading his books in gulps and eventually spent a birthday at the Esalen retreat center in Big Sur, staying in a cabin named after him. (Can you tell when I get into something... I get really into something?)


One of my all-time favorite talks by Watts starts with a question that seems simple, but as we all know, the simple questions about life tend to be the most complex.

What do you desire? What makes you itch? What sort of a situation would you like?

He then ends on a real zinger:

But it’s absolutely stupid to spend your time doing things you don’t like, in order to go on spending things you don’t like, doing things you don’t like and to teach our children to follow in the same track. See what we are doing, is we’re bringing up children and educating to live the same sort of lifes we are living. In order that they may justify themselves and find satisfaction in life by bringing up their children to bring up their children to do the same thing, so it’s all retch and no vomit. It never gets there. And so, therefore, it’s so important to consider this question: What do I desire?

In essence, Alan Watts points to a universal truth: How we live our days is how we live our lives. And, given I'm a remote work advocate, I'll take it a step further: how we work is how we spend our lives.


It's estimated that we'll spend 13 years and two months at work. The only activity that will capture more of our time is sleep. When compared to other things that we say make life meaningful, like friendship and romance, work always wins. (Together, friendship and romance only account for two years of life.)


Therefore, if we'll likely spend much of our lives working, how can we make those years as fruitful and fulfilling as possible?


Here at Remote Works, we believe it starts by structuring work to meet your needs, which we've distilled into four basic needs:

  1. Security: You can bring your full self to work without punishment, and the organization will fulfill its promises.

  2. Autonomy: You can determine how, where, and when you work.

  3. Mastery: You can showcase your expertise and grow skills.

  4. Connection: You understand how you fit into the team and organization

When work meets your needs, you're beginning to itch towards Alan Watts' provocation: What do you desire? What sort of a situation would you like?


As Noah Gale, the co-founder of Tribe.ai, aptly said during an interview for our book:

“The last 40 to 50 years in mainstream American culture, our entire life has been about work, which is sad if you really think about it. It's just been your identity. People built their life around work. Now, I think people are building work around their life. That's a beautiful thing.”

Reflection Questions:

  1. What are three things that you desire in life?

  2. Which of the four needs (security, autonomy, mastery, and connection) do you feel are lacking?

  3. How can you design your work week to make sure those desires are met and that you feed the need that is lacking?

PS - If you have an extra four minutes, listen to Alan Watts' full talk for inspiration.


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