The Comfort Challenge

life begins at the end of your comfort zone quote

On my quest for having more discipline in my daily life, reducing my work hours, and having more free time, all while making MORE money, I picked up the book, “4-Hour Work Week” by Timothy Ferriss. This book is supposedly a guide to how I can possibly do all of the things I really WANT to do – travel, yoga, songwriting, learn a 2nd language and learn to dance, spend time on the beach, meet awesome people, etc. – all while earning a decent living (and potentially beyond).

And the book is helping, I think, so far. I’m on the 6th Chapter of 16.

The book has helped me to design a plan, at least, for what I want to have, be, and do in 6 months time and in one year’s time. I also priced out all of these things I want to have, and be and do, so I can see how much it will all cost me. I haven’t gotten to the part where I figure out how to PAY for it all yet 😉  However, I am just now beginning to eliminate things in my life that I don’t really need to be doing, stuff that hinders my ability to do what IS productive and provides a profit. Stuff like checking my email every 5 seconds. Tweeting. No, compulsively tweeting. Re-organizing files. Re-organizing the apps on my iPhone. Checking my email, again. Checking my Facebook account 10 times a day. You get the point. Stuff that makes me feel like I’m busy and productive, when really…I’m not adding any value to my life or, more importantly, my purse.

I’m ready to move on to the 7th chapter which is “Interrupting interruption and the Art of Refusal”. But I’m stuck on the 6th chapter. Let me tell you why.

At the end of each chapter there is a little exercise, none of which have been a problem for me, though some of them are tough to think through, since it requires planning and elimination. But at the end of the 6th Chapter there is a “Comfort Challenge”.

The basis of the Comfort Challenge is to obtain two phone numbers of the opposite sex over a two day period. So, four phone numbers from four members of the opposite sex. How I go about getting the phone numbers isn’t all that important, but Tim suggests walking up to person and saying:

“Excuse me. I know this is going to sound strange, but if I don’t ask you now, I’ll be kicking myself for the rest of the day. I’m running to meet a friend [i.e., I have friends and am not a stalker], but I think you’re really cute. Could I have your phone number? I’m not a psycho – I promise. You can give me a fake one if you’re not interested.”

My first instinct, was “That sounds like fun”. Which is probably not a typical first instinct. But a few weeks ago, while I was in Asheville, NC imbibing the good life, I walked right up to a cute man in a bar, who I had been exchanging glances with for some time, and blurted out, “Hi. My name is Jami.” We hit it off from there. Soooo….easy.

It’s called “liquid courage”, my friends. Life is so simple after 2 glasses of wine and 2 or 3 beers.

But now I’m completely sober. It’s 1 pm on a Saturday afternoon and I’ve just read the end of the 6th Chapter. I’m at a cafe sitting outside enjoying a jazz band. It’s a perfect location to get out of my comfort zone. The Challenge is ON.

overcoming shyness

But as I started thinking about actually physically walking up to someone and asking for their phone number, my stomach started doing butterflies. I looked around at who I could request a phone number from. I’m not only sober, but I’m also not in a foreign town anymore where I don’t know a soul. I’m in Pittsburgh, where 90% of the time when I meet someone new and strike up a conversation we soon discover we have several mutual acquaintances. Pittsburgh is not that big.

That makes me think, “Uh, this could be weird. I don’t think I can do this”. And the butterflies are getting really anxious now.

Next thing I know, a cute boy walks in the cafe. I said to myself, well if he lands anywhere near me after he gets his latte, I’ll target him. And then he did exactly that and sat right next to me.


So, now I need some courage. Here’s where I start texting a girlfriend, who I had discussed the “4-Hour Work Week” with the previous evening. The text exchange went something like this:

Me: “In 4 hour work week, a “comfort challenge” is to get phone #s of opposite sex. YIKES.”

Her: “Remember we kind of did something like that. We should have written a book like that.”

Me: “I don’t think I can do it sober.”

Her: “Come on. Does it say anyone or someone you have to might like?”

Me: “Anyone. Ugh. I get nauseated even thinking about it. Cute guy just sat next to me at cafe…i’m such a chicken!!!”

Her: “Do it!”

Her: “Ya got nothin to lose!”

So, while cute boy sat silently staring at the park behind me and sipping his latte, I began to memorize the above paragraph of what I should say to get his number. And then I tried to imagine myself actually doing it (which, by the way – not helpful). I thought about the old folks in front of me and how they might think it was funny to hear what I was about to say. I thought about the fact that this cute boy was probably a good 5-7 years YOUNGER than me. And then I started to imagine the boy’s face as I began to sputter out what I had just memorized. None of this was helpful. I advise against this type of precognition if you are ever up for taking the Comfort Challenge!!

And I thought to myself, “Jami. You have about 2 minutes before he gets up and leaves.”

And I sat there. For about 2 minutes.

He got up and left.

SUCH A CHICKEN. I couldn’t do it.

But it made me realize something kind of sad about myself in that I (still) heavily rely upon alcohol to get me through certain situations. It was very easy for me to walk up and introduce myself to a stranger after a few drinks, but now, clear-headed, the thought of it made me ill. I hardly ever drink anymore, but I used to use it as a crutch to socialize. In fact, I would say that it was nearly impossible for me to socialize when I was younger without alcohol.

That is not the case anymore. I own my own business. I speak in front of groups of business people and executives all the time. I should be able to walk up to someone and ask for their phone number, especially if they’re a total stranger and there is no real risk involved.

Why is it so hard for people to step outside of their comfort zone? What is the big deal? The WORST case scenario is that he would say, “I’m seeing someone right now” or “I’m not interested, but thanks.” Big deal. The only reason I would have been asking him for his number in the first place was because some stupid book told me to!

But how LIBERATED would I have felt had I been able to muster up the courage in those last two minutes. Now I just feel like a big wimp. And like I can’t move on to the next chapter, not just of the book, but of my life.

I’m not going to make any promises to myself that I can’t keep, but I will say that I am going to seriously TRY this activity again and see if I can break through these invisible and self-wrought chains. And if you have any advice on how I could get over this fear, I’d love to hear it!





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