How to do “First Times” Properly so you Actually Proceed and Dominate

by / ⠀Entrepreneurship / August 21, 2014


We all kind of get uncomfortable when we think about doing something new for the first time. 

A lot of that discomfort really comes from fear of failure and the fear of the unknown.  We think we will suck at it.  We don’t know how it will go and those kinds of thoughts can be really paralyzing.

In fact, that’s the reason that most people never even try to do something for the first time, even if they know that, eventually, they might love it and it could change their life for the better and forever.  Isn’t that nuts?

We would rather stay comfortable and in complete certainty, than to actually branch out and do something that could be amazing and life changing.  It’s kind of hard wired into us for a means of survival, but at this point, we must be strong with our logical minds and override these primitive fears.  We WILL live through it.

I am no different than you.

I have had plenty of fears through my life and entrepreneurial career that have definitely held me back, even though I knew that they were very necessary for growth and success.

After some time, I figured out a way to approach “firsts” of things so that I would actually do them and actually start doing them more often and consistently.  That’s when a lot of things in my business and personal life really took off.

I am a real estate entrepreneur and house flipper and I can remember one specific thing, years ago, that I was afraid to do, even though I knew it would drastically help me grow.  I knew that I needed to connect with more attorneys in my local area so that I could land more deals and get more referrals.  It was more of an “outside of the box” strategy that isn’t that common, but I knew it was a great source of deals and I really wanted to pursue it.  I was really afraid to call these attorneys on the phone though.  I couldn’t stand the thought of calling them.  I thought they were going to answer and act all cocky and think “how dare you interrupt my big ‘attorney’ day to bother me with this stuff.” 

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I really didn’t even have a legitimate reason to think that.  I’ve never heard of that happening to one other person, but somehow my mind imagined this little story and completely sold me on it.  I was sick of letting this little mind get to me like that.

Here’s what I did (and it’s extremely simple).

1.)   I said to myself, “I’m going to call one of these guys, and I expect they are going to reject me completely, but I’ll live through it.

It’s not gonna kill me.  I will smile and just say ‘thanks’ and realize that it’s the cost of doing something for the first time.”

 2.) I adjusted my psychology to be okay with full blown rejection and actually accept it.

I also said to myself that I wasn’t going to just make one call and then try again tomorrow.  I knew that I had to commit to a certain amount and not let myself off the hook.  I told myself that I would make 10 calls.  PERIOD!  No exceptions.  I did this on purpose because I knew that my mind would be starting from scratch if I waited to make that first call again tomorrow. 

I’m sure you know what happened.  In fact, I’m sure you know most of this already, but hearing it a certain way with a certain little story attached to it may hit you differently and help you out.

Anyways, as the calls progressed, it got way easier and by the 10th call, I was sounding much more confident over the phone, which lead to a greater success rate of getting what I wanted out of the call.  When we force ourselves to do uncomfortable things consistently, connections in our brain actually change and we automatically become more comfortable and confident with it.  It just works that way.  You don’t have to think too hard about it, just force yourself to do it back-to-back and watch what happens.

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The bottom line here, is that I approach all of my “firsts” in business and life with an open mind and a mindset that totally accepts a sucky scenario in the beginning.  Then as I actually proceed and do them, I visualize these “firsts” happening in the “10th call” psychology, and it has revolutionized my life and business and allows me to get through the beginning with much more ease.  These days, when I call attorneys, they offer to buy me lunch by the end of the call EVERY TIME (just kidding) 🙂

Please let me know in the comments how you are with “firsts” in your business or life…

This is a guest post from Nick Ruiz.  He is a TWICE self-made real estate entrepreneur that started in his late teens and built a multi-million dollar business from scratch and AGAIN from bankruptcy after the big real estate crash in 2008…He blogs about his journey and strategies for real estate entrepreneurship at

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About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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