Jamie Gruber Blog/Newsletter/The Crippling Effects of Side-Eye

Monday, March 13, 2023

The Crippling Effects of Side-Eye

December 20, 2022 Newsletter.

As I lean more into lifestyle entrepreneurship, I made the decision to document the journey so I can be more effective and efficient in sharing. This led to a decision to hire a videographer to follow me at an event. This week's edition shares the learnings and an epiphany that resulted!


My friend Marcos hosted an event in Orlando of mostly W2 employees looking to get free from the rat race leveraging Tax Liens and Deeds. He is one of if not THE foremost expert on the topic in the country. He asked me to speak about lifestyle freedom and how to quit an unfulfilling job. I repurposed some of my prior content into a speech called ‘The 3 C’s to Get Job Free in 2023’. This took place at a large hotel and convention center.

Marcos actually gave three exclusive trainings on tax liens and deeds to Emerge Supercharged and even added a bonus session where he purchased deeds live - all in our library. That along with training on making 7 figures on YouTube, buying businesses, how to optimize your health, understanding dynamics of masculine and feminine energy in relationships and much more is just some of the value. As a reminder you can join now for just $1500 and get our 8 week Accelerator and access to EVERYTHING for our January 2 launch but we’ll be closing out enrollment soon!


I saw this as a great opportunity to capture the experience of speaking at an event as well as the questions I anticipated from attendees. I found a cameraman and shared my vision. He spent 5 hours with me and I paid $750 for his time and transfer of the videos. My editor will then cut it up and my Social Media Manager will schedule the posts and add the captions.


Inside a conference center with a stage and a speaker, there is a clear expectation that there will be cameras and lights and all of that. But when you’re walking down a corridor from the cavernous hotel lobby to the large convention center part, you pass by a lot of people! They’re walking around, in line at Starbucks, sitting down to eat at the various restaurants along the way, and so on.

When you see a bald white dude with a TV news style camera, giant white light and microphone coming through (see below), naturally there’s curiosity.

For me though, I could see and feel the ‘side eye’ that I was getting. Here’s the definition if unclear…

a sidelong glance expressing disapproval or contempt.
"after we complained of being ignored she kept giving me the side-eye"

‘Who does this dude think he is?’
‘Another freaking ‘influencer’ trying to be big time 🙄’
‘Mr. Big Shot .. how big can he be .. never saw or heard of him before’
‘Gimme a break baldy

1 png


Those glances were exactly what held me in place for so long. They’re the external manifestation of internal dialogue and fear of judgment. Not a word was spoken to me but I had already decided that the above was what was going through all of those people’s minds. And because of that, I almost didn’t have this guy record me. I almost swallowed the $750 and said ‘thanks for your time’. I almost caved to pressure that I perceived was upon me from these prying eyes.

When I had my job, inaction ruled in large part because of ‘side-eye’. That fear of failure we all have I truly believe is really fear of judgment. If you could fail without being seen, I don’t think the fear is as real. When you’re walking down the street and trip, the first thing we all do is look around to see who saw it. If someone observed, you make the silly face, self-deprecate, make sure they know that YOU know how stupid that was. You want to preempt their judgment with self-judgment. Show that you belong.

But if no one saw it, you dust yourself off and are on your way.


#1: No One Cares

After this experience I really thought about all those side-eye people. My imagination created a narrative where these people were all seeing me, double taking and then tapping the person next to them and pointing at me - whispering something that makes the other person giggle until uproarious laughter emerges with fingers pointing as a mob surrounds me taking photos and uttering phrases I could hear amongst the laughter like ‘what an idiot’, ‘dweeb’, and so on. It’s something out of an 80’s teen movie. I was Daniel Russo dressed like a shower and these people were all Cobra Kai.

Sounds ridiculous, I know. But can you relate?

The reality is .. these people are staring at their phone, glance up at me and maybe think ‘wonder what that’s all about’ and then look back to see which latte do they want .. pumpkin spiced or chai? They don’t care about you the way we imagine. They have their own lives and worries. In fact, most would probably simply be curious and supportive if they thought to stop and ask me.

#2: I Don’t Care Either

I’m a lifestyle entrepreneur. That category includes Gary Vee, Ryan Serhant, Lewis Howes and others that always have a camera on them. At some point though, they were unknown guys walking through hotels with a giant camera following them and getting side-eye. The difference between me and them? When we decided we don’t care.
They did this early. Before the TV shows, podcasts and the explosion of social media. They decided to be true to their brand, ambition and build an audience early.

#3: It’s All About Service

Society determines the norms of service. If someone is working a soup kitchen or an animal shelter, you’re in service and there’s nothing abnormal about it from everyone else’s perspective. Providing a product that solves a problem is also a service most accept and see as normal. For me to hire someone to document my journey is the same. Many would see it as ego, vanity, crying for attention. But what those lifestyle entrepreneurs above know that I’m learning is their ability to communicate, motivate and inspire others is a gift that is put to work when broadcast. Whatever your endeavor, when you create side-eye but are in service to others, then it’s irresponsible not to take the action required.

CALL TO ACTION: Screenshot the key takeaway that landed for you and tag me in a story on Instagram so I can see what’s working for you.


Tribe of Millionaires Podcast Episode
✯ Imagine the side-eye Daniel Perez got in high school when he started driving team busses of his peers to their games! But, because he knew no one cared, he didn’t care, and he was in service to his gifts, he’s built an 8 figure company at the age of 33!! Check out this inspiring and jam packed episode with one of my best Gobundance friends!!

A Podcast/Book I Love
✯ Going into 2023, this may be the most incredibly timely episode of the Ed Mylett show I’ve heard with guest Rob Dyrdek. He has amazing advice on time, systems and more. Highly recommend it!

Lesson from Living Abroad
✯ I continue to be amazed by the people of the Dominican Republic. What they lack in resources they make up for in spades in resourcefulness. This is a reel I did a little while back that really summarizes what I mean! Check it out (and give me a follow if you’re willing 😉)

Shit I Find Funny
✯ DON’T WATCH if you’re easily grossed out or offended .. but I can’t stop laughing at this reel. Gross, but points for creativity!

If you’re not already in Emerge and Ascend and want to be part of our Emerge Supercharged relaunch in 2023, join the waitlist here!! The objective is to get you unstuck, clear on vision and goals, and provide a concierge level experience to introduce you to your future self!

Until next week

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