Getting out of my "Comfort Zone"

I am a 40 year old male that grew up in a north-west Iowa town. A small town where everyone knew you or thought they did. I wasn't an athlete... strike one. I wasn't a brain... strike two. And my family weren't farmers... you're out. Evidently I have some hang ups about that place.

I currently live in one of Phoenix, Arizonas' fast growing outskirt towns, Surprise 55000+. I am self-employed thanks to my dad that talked me into buying a semi. It is a JOB. The construction market is very competitive and that keeps the rates down. I have been around this business for 30 years (since my stepdad married my mom). I was never the charismatic type like my stepdad, he loved his business and was a workaholic. Evidently his constant question/statement "Mike... Why don't you think of some way to make some money!" sunk in because that is how I spend most of my days.

I discovered Nightingale-Conants materials back in 1986. I was drawn to the idea that commission sales was the greatest way to make large amounts of money and provide yourself with a great living. I bought all the books... Ziglar, Hopkins, Betger, I have even discovered recently Jay Abraham and Dan Kennedy.

I have a problem though...

I am afraid to talk to people about products. Fear of failure? Fear of Success? Fear of "No!" Something, I don't know exactly.

My brother-in-law said the other day that "So-and-so is outspoken like Mike(me?)" I do reach a certain level of comfort around people I know or are in the same field as I am.

I was given a little bit of hope recently when I read somewhere that many top-level sales people are actually quite shy and don't have a gift of gab. What? They are talking about me.

Anyway what I would like from this forum is your advice, what would be a great way of getting out of my comfort zone? How should I go about stretching my ask muscles? Could it be as easy as "Ask someone each day for something that you know might get you a "No!"?" Nothing ventured...

I feel like Gordon Alexander's "information junkie" I know a ton of this stuff. I can usually "Walk the talk" with others in this field, but you aren't going to buy from me and I probably wont buy from you. I don't want to be an info junkie, please help if you can.

P.S. Gordon, your "Crossroads" and your "Do you want to Know Your Future" articles are talking to me. I am going to try to figure out what I want my future to look like. I do believe in goal setting, I recently made a "Wish-List" of 28 things I wanted, the very first item was for a vacation, a real vacation. (In the trucking business in AZ. you get time off, but it isn't planned and you don't want much of it because it doesn't pay.) Anyhow I had wrote "I want a vacation, not a no-work period, an honest to goodness vacation, a trip somewhere because I am ready to go. Because I can. 3 days later out of the blue my 70 year old mother called me up and wondered if I would like to go to Alaska? I did not even hesitate when I said, "Absolutely!" She would call back with the details. She had wanted to go for a long time, her emphysema wasn't getting any better and she wanted to leave her kids with a GREAT memory. She paid for herself, her sister and brother-in-law, a half sister, my four older sisters and two of my brother-in-laws, and my wife and I (13). We flew in to Anchorage, took a train to Denali National Park, then on to Fairbanks, flew back to Anchorage, took a motorcoach to Seward and boarded the Ocean Princess cruise ship for a 7 day cruise on the "Inside Passage". It was Heaven, my mom was a Saint before all this. Goals... there is magic in the written word.

In the beginning was the Word, the Word was with God, the Word was God...