Push, Push, Push: Expanding Your Comfort Zone

Push, Push, Push: Expanding Your Comfort Zone

What scares you? Entrepreneur Derek Sivers explains how that question has guided his adventures and challenged his comfort zone.

Photo by hji

I’m 40 metres underwater. It’s getting cold and dark. It’s only the third dive in my life, but I’m taking the advanced training course, and the Caribbean teacher was a little reckless, dashing ahead, leaving me alone.

The next day I’m in a government office, answering an interview, raising my right hand, becoming a citizen of Dominica.

I’m in a Muslim Indian family’s house in Staten Island, washing my feet, with the Imam waiting for my conversion ceremony. Next week they will be my family in-law. The Muslim wedding will make her extended family happy. I’ve memorised the syllables I need to say. “Ash hadu alla ilaha illallah. Ash hadu anna muhammadar rasulullah.”

We’re on a rooftop in Rio de Janiero on New Year’s Eve, celebrating with some Brazilians we met the day before. Down below on the beach, a million people are wearing all white.

I’m alone on a bicycle in a forest in Sweden. I left from Stockholm six hours ago, headed south, with only 50 Krona, and I’m getting hungry. I don’t know the way back.

We’re in a filthy dorm-room apartment in Guilin, China, studying at the local university. At the local grocery store, we choose from a bin of live frogs.

The India Embassy official hands me a pseudo-passport that says I am now officially a “Person of Indian Origin” — a pseudo-citizen of India.

I’m the back of a truck in Cambodia, soaking wet, hitching a ride back to Phnom Penh after an all0day bike ride. The roads were flooded but we rode our bikes through anyway, Mekong River water chest-high.

That week I speak at four conferences in Cambodia, Singapore, Brunei and Indonesia. By the fourth one, my American accent has started to morph into something kind of Asian.

We’re in a hospital in Singapore, having a baby. It’s a boy, which means he’ll serve two years in the Singapore military in 2030. The birth certificate says his race is Eurasian, a word I’ve never heard.

I’m on a diplomatic mission in Mongolia, with the Singapore Business Federation, talking with the Mongolian government’s head of business development, walking with the next mayor of Ulaanbaatar.

I suppress a laugh at the ridiculousless of this situation. I’m just a musician from California! What the hell am I doing here? But that feeling lets me know I’m on the right track. This is exactly what I wanted.

Some people push themselves physically, to see how far they can go. I’ve been doing the same thing culturally, trying to expand my California-boy perspective.

I love that when we push push push, we expand our comfort zone. Things that used to feel intimidating now are as comfortable as home.

I remember how scary New York City felt when I moved there in 1990, just 20 years old. Two years later it was “my” city — my comfort zone.

Now previously-exotic Singapore is my long-term comfortable home, while I push myself into exploring foreign places, new businesses, and different perspectives.

After years of stage fright, performing over 1,000 shows, I have a strong case of “stage comfort”. Being the lead singer or speaker on stage is now my comfort zone.

A lot of my musician friends feel this when playing on stage with their legendary heroes. You push push push, then one day find yourself on the very stage you used to dream about. And it feels so natural — almost relaxing. It’s your new comfort zone.

The question is — what scares you now? What’s intimidating? What’s the great unknown?

I keep using that question to guide my next move.

Push, Push, Push. Expanding Your Comfort Zone. [Derek Sivers]

Derek Sivers is an entrepreneur, programmer, musician, and creator of CD Baby. His latest book is Anything You Want. Read his blog here.


  • I read this article expecting serious advice no how to push your comfort zone, I found none. Just a strangely written story of a California boy, the heck?

  • It’s a window into Derek Sivers’ inner workings (trolls). He has a good series over on AppSumo. I have to ask, why do people need things spelt out for them? Try observing for once. Here’s a nugget for you, memorize it (works for me) “KNOW and UNDERSTAND, HOW and WHY SUCESSFUL people THINK and ACT the WAY THEY DO.” Now go back and read the article again, you might learn something rather than just absorbing it. Are you a person or a sponge?

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