March-April’s Monthly Experiment(s): Four Hour Work Week Comfort Challenges

So I’m re-reading the Four Hour Work Week, the book that started me on this path of entreprenomading that I’m still building and walking.

And…well, it’s excellent. After three years of trying to build businesses and still making less than 0.5K/month, I’m a little wary and weary of Tim’s claims of people building 40K/month businesses in a half year….yet I also know that people have done this.

Kinda pisses me off that he mislead me like this…until I remember that if I knew how difficult this would be I may not have had the energy to start. And that I have the potential to be making at least 10K/month copywriting within a few months of today, if I chose to drop all else and pursue it. And perhaps an automated 40K/month is within near grasp of me. I know I have at least one business that could potentially achieve this. Perhaps, this time around, I can use some of Tim’s advice and make it happen.

Anyway, back on point: this month’s experiment.

This month, I’ll be taking up the challenges that Tim throws my way in 4HWW. Most of them take 2 days. I’ll also be adding a bunch of my own that challenge my comfort zones.

Let’s begin.


The Eye Gazing Challenge (March 9 – 11, 2014)

The Challenge:

Simple. Make strong eye contact with everyone you meet. As a lower limit, never be the first one to break it.


This is one of those comfort zones that has tended to fluctuate for me. At times, I nearly challenge everyone I meet with an intense stare. At others, it is a curiosity. And, quite often, an inexplicable level of fear or discomfort finds me looking away quickly.

I suspect this will bring me somewhere between the first two. And I think I will enjoy it immensely.


It was awesome. A month later and I still have no problem catching and holding strong eye-contact with everyone. And I love doing it. I find that zoning in on someone’s eyes creates a great opportunity for connection, and helps to create a kind of bubble between you two.

And, each time I do it, I get a little thrill in my chest. Cool feeling.

Hugging (March 13th -March 16th)

The Challenge:

Every day I must hug at least two people, at least one of them a relative stranger. I’m doing this because I crave physical contact and yet am afraid to initiate it.


This is gonna be a bit scary. And it’s gonna feel great.


One cool thing that kept happening (especially in Ubud) was that I would be talking about the challenge and someone would come up and hug me. It was awesome!

Hugging people feels awesome. Especially when you hold it for 6+ seconds.

Getting In Touch With Mentors (April 9 – 16)

The Challenge:

Every day I will attempt to start an ongoing relationship with a hero of mine. I’ll ask them a question, take and implement their advice, and then come back at them with the results and another question.

At least 4 of these guys must be guys I have never talked to before. And at least 3 of them must be really high-level heros of mine.

People I’ll reach out to: Elon Musk, Richard Branson, Kevin Rose, Tim Ferriss, Ryan Holiday, Jason Mraz, Tynan.


This’ll be interesting. If I can create a loose yet recurring relationship with even one of these guys, that’d be absolutely amazing.

I’ve got no idea what to ask them though. I’m gonna take the approach of asking them a simple advice question, then taking their advice and implementing it, then re-contacting them to tell them the results. What to ask though…huh.

I’ve got Tanya (my VA) researching a 1-pager on all of them so I know what they’re up to and a bit of their history.


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