Time for me to go into diary-mode. Dig it. 🙂


Tell me something. Have you ever asked a stranger for a dollar?


Background of the Exercise
Here’s a bit of background. Recently I joined a group, a learning cohort, a pact, a posse, a “secret (not really) crew” of sorts, that’s pushing me to grow. 

Not sure what to make of it, but the first mission was basically to go out and embarrass the hell out of myself by getting waaaayyy uncomfortable. I kept thinking to myself, “Maybe I should just stop being a wuss. It’s not like I’m stealing candy from babies or anything.”

It’s so strange that the whole challenge behind this first mission really just involved swallowing your pride. Arghhh, not an easy task. Ya see. If you pondered for a minute every chat about work, working, and earning that you’ve ever had with your fam, you’d probably instantly recall certain phrases that were probably deeply ingrained into your psychological make-up which help shape your feelings about responsibility, honor, and respect. 

Internal Scripts
If your fam is like my fam, you can probably instantly remember hearing things like, “No pain, no gain,” or “No free lunch,” or “Early bird gets the worm.” Or you might’ve heard stuff like, “Everybody pulls their weight here,” “No beggars in this family,” “Work before play,” “Hard work pays off,” “Work hard to play hard,” etc.

So my entire life I’ve learned that you cannot EVER, under any circumstances, ever just ASK for something. Work first, then rewards. RULES. These are the rules. Those are the rules. Everywhere are rules. Be a good Catholic boy. Be a good son. Be a good team player. Nothing’s guaranteed. This is how you work. Work hard. Never ask for anything. Earn first, play later, but do NOT ASK for anything. Okay, got it.

So now that I’ve joined this learning cohort of entrepreneurs who are asking me to do stuff that feels “unnatural,” I recognize that there’s real fear there. It’s weird. There’s this lingering verbiage, “No beggars in this family,” that somehow still echoes.

The other day I was asked do a simple thing, something I could’ve probably done in five minutes if I really wanted to. But I stalled. I stalled for almost a week if we’re really being honest here. Why? Because it felt stupid. At least, that’s what I told myself at first.

Then I started really thinking about it. The challenge itself wasn’t difficult. The task was easy, if I were a robot. But I’m human. The truth is that the challenge went against everything I’d ever learned about work ethic. Stuff like ‘never ask,’ ‘hard work pays the bills,’ and on and on and on. I was afraid. That was it. No excuses. It was just plain fear and guilt, especially guilt. I actually rationalized a dozen different ways to get around this challenge by thinking up different things I could sell or do or exchange instead of having to just ASK anyone for anything.


A Critical Lesson On Dreaming and Doing
Wanna know what my first lesson about entrepreneurship was? Forget everything you’ve ever been taught by 99% of the business gurus and professors. Being an entrepreneur isn’t all that different from having a profession, having a day job, having a hobby, or anything else you do with your time. The shift is only mental.

The first lesson I discovered was that NO ONE is going to walk up to you and hand you money. You HAVE to ask. If you want to sell something, anything, even if it’s just your pretty face and charm, if you want to earn, if you want to apply for a job, if you want to build something worthwhile, anything, and especially something that helps make the world a better place, YOU-HAVE-TO-SELL-IT. You HAVE TO ASK for the damn dollar!

At this point, let me just send a special shoutout to an awesome female named Arielle who witnessed me do this surprisingly eye-opening challenge live on Facebook. I’m sure I made it waaaayyy harder than it had to be, but let me just say that SHE-IS-AMAZING. Honestly, she was so supportive I feel like I should hug her; and I’ve never even met her in person!

Sure, in the past I’ve sold products and services. To some extent, we all do that. Heck, I’ve even played the tough guy and collected on people for not playing fair and walking out on agreements, but NEVER in my life have I EVER just asked someone for a dollar. Even when I was a kid earning an allowance for work completed, I never just asked anyone for something. That was a huge no-no in my family. “Work first, then rewards.” This exercise was completely outside my comfort zone. Even with some prewritten scripts made up for my own comfort, I still couldn’t initially verbalize what this exercise was really about in order to go out and ask someone for a dollar because everything, and I mean EVERYTHING, about this step went entirely against all of my social programming. Arielle probably had a good laugh over my man-tears (ha!) as I’m sure she could probably tell you how much I agonized over this.


Overcoming Fear and …Guilt?
At first I stalled, then I dismissed the exercise, then I realized that I was actually just rationalizing the fact that I was in the process of overcoming a little bit of fear and especially some strange sense of guilt about asking someone, anyone, for something so random for no particular reason. While the task was just to ask for a single dollar, the mental exercise was infinitely more complex. If I were a robot, I could’ve done the exercise in about five minutes flat without thinking or learning anything. But I’m not, I’m human. And I’ll be the first one to admit that I stalled for almost a damn week! 

Then I just did it. I JUST DID IT. Jeez, this was like a spiritual cleansing. Lol. I realized that it wasn’t like I was doing something morally wrong, or like I was chopping heads off live chickens or something weird. I was just asking for a freaking dollar. 


Surprised By Love Unspoken
Here’s the funny thing too. Right after I asked, I received more love in the form of text messages, phone calls, and emails than I ever could’ve anticipated for such a simple exercise. I even received love from people who weren’t contributing. In fact, a girl I dated literally years ago even messaged me right afterwards to tell me what a “breakthrough” it was that I would actually ask for anything. Huh? So to summarize, do not underestimate the value of this seemingly minor exercise. You may just inadvertently discover some things holding you back that you never even realized. 

And if you really want to know what moved me the most, it was the fact that my brother, my own flesh and blood brother, gave me a dollar and I never really even had to ask. This is the same guy who used to “steal” money from me when we were kids. Sure, I mentioned that I was doing an exercise, but I didn’t give him all the details. In fact, I told him not to give me a dollar, and that it was the thought that counted most. Still he was there. He knew I didn’t need the dollar, but he knew that the challenge was what I needed. He saw me throw out an embarrassing public request, and he was there. And I think his dollar, his sincere sentiment meant the most for me.


So maybe it’s just a dollar, and maybe I never would’ve thought about doing a seemingly simple mission like this if I hadn’t been challenged in the form of a competition, but the meaning and life value that takes place when you actually step outside your comfort zone to do something difficult cannot be understated. So if you get a chance, try this exercise. Maybe you’ll learn something too.

More to come. 

Peace,
Daniel