Jamie Gruber Blog/Newsletter/The ONLY Reason We Keep Our Jobs - My 7 Year Old Taught Me This!

Monday, March 20, 2023

The ONLY Reason We Keep Our Jobs - My 7 Year Old Taught Me This!

January 10, 2023 Newsletter.

This past weekend, my family and I decided to hit a resort locally to get some R&R. Amazing to me that we are 20 minutes from places many spend their whole year planning around! My 7 year old experienced a MAJOR lesson and simultaneously gave me the inspiration for this newsletter! I asked him and he gave permission for me to share!


There are two resort foo foo drinks people love getting. The Coco Loco (a creamy, milky frozen concoction that will clear you out if you have more than 1 💩💩) and the Banana Mama. My kids both love the latter and ask for it whenever we’re at a touristy place.

On Sunday morning, my 7 year old son was feeling the need to indulge. “I’m gonna get a Banana Mama”. I told him that’s great! The swim up bar was in our direct line of sight, right across the pool. “Go ahead and order one!”


What started as a light, easy morning chat under a palm tree umbrella pool-side while laying on lounge chairs quickly turned into shit-show.

Him: “Can you come with me?”
Me: “No bud - just go order one”
Him: “But you need to come”
Me: “Why?”
Him: “Because they’re going to ask where my parent is”
Me: “No they’re not - just go order it!”
Him: “What do I say?”
Me: “Just say ‘one banana mama please’ or you can say ‘por favor’”
Him: “No I can’t do it - just come with me”
Me: “Bud - why can’t you just go order it?”
Him: “They’re not going to let me have one without a parent. And what if they don’t understand me when I ask? They might not even be open right now so it’s too early to order one. It’s just…can you just come stand like over there where you can see me?”
Me: “I can see you from here - what is me moving going to change?”
Him: “It’ll just make me way more comfortable if you’re standing there instead of here”
Me: “But that’s the same distance from where you’ll be ordering, just another angle - and I can see you either way. But even if I couldn’t see you, what does that matter?”
Him: “I won’t feel safe - I don’t know what will happen if he doesn’t understand me. I’m just not comfortable”

At this point, I made a decision. He needed to do this on his own and I was going to use any parent leverage I could to get him to .. and maybe be a little bit of a dick.

“Bud, you want that game - I will get it for you if you go order your own banana mama. But … you have to do it within the next 2 minutes. I’m setting a timer on my phone now”


He was annoyed but he got up. He went into the pool and swam across to the pool bar. He sort of drifted left to right rather than go in a straight line, and when there, he went to the very corner of the pool bar to wait for the bartender. I couldn’t tell when he asked or how from where I was, but the next thing I saw was a drink in his hand. Here’s the zoomed in evidence!


Ohhhhh the smile on his face when he came back across the pool and sat next to me. It was that look of ‘ok ok - maybe that wasn’t so bad after all’.

My question for him and his response was something that immediately made me so proud of him AND made me ask if I could share this experience in my newsletter (thankfully he said ‘sure’).

Me: “What did you learn about all those fears you had?”
Him: “They’re not real”

(this is my visualization for ‘SUCCESS’ haha)


That entire experience with my son is no different than what we ‘mature adults’ experience when considering quitting a job we don’t love. We don’t want banana mamas, but we do want lifestyle freedom, control of our outcomes, to lean into our gifts, etc etc.

The universe says to us ‘well go ahead and do it then’ just like I told my son to order a Banana Mama.

Then the fears start coming up. The crazy thoughts in our monkey minds of these incredibly bad outcomes that COULD be if we take the action we truly desire. We ignore the fact that we MIGHT actually get what we want, without much or any resistance. But what we learn about those fears 92% of the time, is “they’re not real”!

That’s a literal number. Researchers have found that our fears come true 8% of the time. That’s less than 1 in 10 fears actually come true. Meanwhile, there’s a 100% chance that we’ll remain unfulfilled in a job. There’s a 100% chance that inaction will ensure you stay put.

We choose unhappiness over uncertainty. Or put another way, we would rather be miserable than to take a chance and dive into the unknown … even if only 8% of what we fear will come true!


Ok ok - for you left brained ‘practical’ types who are saying ‘yeah dude, getting a banana mama is way different than financial security for me and my family’. First off, I loathe that mindset. I ask you to unsubscribe if you can’t get past it. I’m working HARD on repelling as much as I attract in 2023, so that’s a real invitation.

But it’s a genuine thought and many may simply need help making this example more real for them. So here’s my 2023 playbook for you to get job free at a high level:

- Build Something to Run Toward - running AWAY from a bad job isn’t a good strategy and will increase the chance of you needing to get another job you don’t love. So run toward, don’t run away.
Buffer Your Savings - put 6-12 months of real expenses in the bank. Don’t overdo it and start adding in 50-80% more ‘just to be safe’. Just look at your expenses and say ‘ok, it’s around $10k a month for us to live comfortably - so I need $60k+)
Get Lines of Credit - use that W2 to get a HELOC, unsecured lines of credit from regional banks, etc. Have access to capital on top of savings.
Find a Community - this is not a shameless plug, but a true call to action. Emerge Supercharged is built for people to get around others that represent their future self. We’re launching sales for our February class TODAY - a bit ahead of schedule due to demand on our waitlist.


#1: Evidence vs. Emotion

The definition of Fear is ‘an unpleasant emotion caused by the threat of danger, pain or harm’. When you are in a place of fear, as the definition outlines, you are in emotion. Emotion is a powerful tool when used well. Embracing, understanding and dissecting why you feel what you feel is healthy and necessary. But succumbing or numbing those emotions by eating, drinking, or any other vice simply is a coping mechanism that keeps you at the job you don’t want. Instead, pivot from EMOTION to EVIDENCE. When you look back at what you’ve accomplished and how you have, you are harvesting your past to show you the path to your future. Evidence is powerful and can create positive emotion.

#2: Do This Exercise

I mentioned fears come true 8% of the time. That stat is compelling but it doesn’t define the fear you may have. Tim Ferriss has a great exercise called Fear Setting. Check out this Ted Talk he gave a few years back and simply google templates to do this for yourself. By outlining your fears - all of them - you get a chance to practically move through them and create a visual for worst case scenarios and even action items you can write down in case your worst fears come true.

#3: The Checklist

I intentionally gave 4 items as a checklist above for you to consider where you are. Go through and determine how many you check off. What’s scary is, many of you may be able to check all 4 which leaves really only one conclusion - that you’re able to quit your job! Here comes that fear again (go back to key takeaway 1 and 2 if so!). I’ll add one more consideration not in the checklist above. I didn’t include it because I don’t believe it to be essential for various reasons. If you have cash flow from your ‘run toward’ business to cover 50% of your monthly expenses or more, then it’s a lock. It’s time to go!

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
✯ My buddy Grant Warrington interviewed me on my own podcast. This is a 90 minute outline on quitting your job and becoming a Mid Life Entrepreneur. In fact, that’s the title of the episode. I highly encourage you to listen to it. Take it in chunks if you need to, or run it at 1.5 speed - but it’ll help you. Would love your feedback on it!

A Podcast/Book I Love
✯ Baseball fans will enjoy this. My friend Sean Casey has The Mayors Office podcast. Best if viewed on YouTube like this recent episode with Brett Boone. Sean was a 3x MLB All Star and career 300 hitter. His guests are legends and the format is essentially ballplayers telling stories. It’s like getting to be in the locker room listening to tales from the diamond. Epic!

Lesson from Living Abroad
✯ I’ve been working too much. Period. The relevance to living abroad is that I enjoy this environment and love that we accomplished it, but haven’t changed my behavior enough to experience it the way I want to. I love to work, but I love my wife and kids more. A major shift for me in 2023 is doing less and being more.

Shit I Find Funny
✯ This guy messes with his wife in the FUNNIEST and WORST way ever!! It's the Hall of Fame and Hall of Shame all at the same time!

Let me know your thoughts. Be sure to snag the key takeaway that resonated most and share to your story. Tag me so I can share your story too!

If you want to work with me and become a mid-life entrepreneur, here’s three ways you can do that!

1. Follow me on YouTube. We’re about to blow up that channel and have already put together great content to help you get unstuck. It’s totally free and will be tremendously valuable for you to learn the lessons of becoming a mid-life entrepreneur and avoid the same mistakes I made and continue to make!!

2. Join Emerge Supercharged. This is where I can help you get clarity, build confidence and leverage the community to get yourself out of your day job. It’s the exact cadence I followed and the exact process I learned to quit my $400,000/year job inside of 2 years! I had to fumble around to learn these processes and it still took me less than 24 months - so the possibilities for you are insane! We’ve had dozens quit their day job in the last 2 years and many more are on deck for 2023!! You can get into our 8 week Accelerator with full access to the community for that time for just $1500. Try us out and let us support you on your journey to lifestyle freedom!

3. Come to The Dominican Republic. Our January 2023 Mid-Life Entrepreneur Mastermind in Punta Cana is SOLD OUT! I am taking applications for a second event I plan to host in the late winter/early spring so fill out the form and get on the waitlist for the upcoming announcement! This is a fully immersive, in depth, luxury experience designed to push you beyond your limits and get you unstuck. If you’re feeling that sense of urgency to live your life purposefully before more time slips away, this is the best experience I offer and it will CHANGE YOUR LIFE!

Until next week

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