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Founder, The Cage Free Life
Take back the wheel of your life while there’s still time to drive.
↓ The Way Back To Yourself Starts Here. ↓
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I’m back after a little break. 

How was your summer? by @garetfree
1
5 days ago
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We’ve been trained to never say no.

It shows up in that 12:30am email that you catch because you check your messages one more time before bed. 

“Pls fix. Thx.”

Your heart sinks as you see the board member’s name in the ‘From’ line. 

The phone drops on your chest as you justify why now is the moment, when most of the world is asleep, to check one more box for the day. 

Your compulsion to keep the peace has you reach for your laptop and commit to another 30 minutes of work for someone else. 

It’s only Tuesday. 

You know that the email can wait but you keep opening that fucking laptop, night after night. 

▪️▪️▪️▪️🟪

Building success can feel like you’re building yourself into a cage. The free assessment on my profile page will show you the door. taken in Chicago, Illinois by @garetfree
0
13 days ago
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Ⓢ Ⓔ Ⓟ Ⓣ Ⓔ Ⓜ︎ Ⓑ Ⓔ Ⓡ taken in Fire Island Pines by @garetfree
15
17 days ago
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Microdosing masterclass coming soon, IRL, to river north. DM me “MD” and I’ll send you the details when everything is finalized. taken in River North by @garetfree
0
17 days ago
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All the feels this week. 🌚💫🫧 taken in Chicago, Illinois by @garetfree
6
18 days ago
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A coach once told me, in front of 300 people, that I’m a little bit of a weirdo. And she’s right. 

For a second my chest went tight. Then I remembered — I spent two decades doing it the “right” way. The straight lane. The politically correct meeting notes. The fat bonus checks that cost me a chest full of tension every damn day.

The weirdo is the one who doesn’t flinch when a client’s mid-breakdown. Who shoots the elephant in the room because a comfortable truth doesn’t move anybody. Who’s watched twenty years of grief leave a body that’s been carrying it like cinderblocks.

The part of you you’ve been told to tone down isn’t the liability. It’s the floor everything else gets built on.

Stop editing it out.

Save this for the next time someone tells you you’re “too much.” taken in First Ascent Uptown by @garetfree
1
a month ago
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Feeling numb is physiology, not a character flaw. 

What part of your foundation is sending you a signal? taken in Chicago, Illinois by @garetfree
4
a month ago
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75 Hard, or 75 STRONG as I like to say, is in the books. 

What kept you going if you’ve been on this journey? taken in Chicago, Illinois by @garetfree
3
a month ago
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Right before asking a friend to record this video yesterday, I was standing there thinking: I feel too skinny fat to put this on the internet.

Then I handed them my phone anyway. Because that thought is the whole reason I need this next 75 days more than my body does.

I’m not doing 75 Hard.

I’m doing 75 STRONG.

Same discipline underneath it with the diet, the two workouts, the water, the reading, the daily photo. I’m not discounting any of that.

But the program stops short, so I’m adding 10 minutes of meditation a day, morning pages, 33 minutes and 33 seconds of writing, no matter what shows up on the page.

Ten years as a paramedic taught me the body’s rarely the actual emergency. It’s just the part people can see.

This video’s from yesterday. My starting point, and the thought I almost didn’t share of being “too skinny fat” is part of the starting point too.

Save this if working out isn’t your issue… if the real nudge you need is to sit with yourself when it’s time to be quiet and create instead of consume and dissociate. taken in Fire Island Pines by @garetfree
0
a month ago
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Welcome to The Cage Free Life. Where your reality becomes a life you enjoy waking up to. taken in Chicago, Illinois by @garetfree
6
2 months ago
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ᗩᑌᘜᑌᔕT ᖇᗴᑕᗩᑭ taken in Chicago, Illinois by @garetfree
5
2 months ago
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Someone comes to you and tells you they’re stuck. Specifically with a business idea.

Your first instinct is to jump to asking “𝙒𝙝𝙖𝙩’𝙨 𝙬𝙧𝙤𝙣𝙜?”

Stop right there. Don’t do it.

Ask about what they’re not worried about first.

This has become a staple for my coaching work. Before we dig into the thing they think is broken, I ask two questions back to back:

𝙒𝙝𝙖𝙩’𝙨 𝙮𝙤𝙪𝙧 𝙗𝙞𝙜𝙜𝙚𝙨𝙩 𝙬𝙤𝙧𝙧𝙮 𝙝𝙚𝙧𝙚?

𝙒𝙝𝙖𝙩 𝙖𝙧𝙚 𝙮𝙤𝙪 𝙣𝙤𝙩 𝙬𝙤𝙧𝙧𝙞𝙚𝙙 𝙖𝙗𝙤𝙪𝙩 𝙖𝙩 𝙖𝙡𝙡?

The first question is usually answered in less than 10 seconds. Legal risk. Money. Getting the messaging right. It’s the answer that they obsess over like me when I’m trying to book the perfect hotel.

The second question is the one that does the work. 

When someone says, “I’m not worried about my ability to do this. I’m good at what I do,” that’s not a throwaway line. That data tells me the block isn’t skill. It’s not readiness or a flimsy plan.

It’s something else entirely.

Next, I ask:

𝙒𝙝𝙖𝙩 𝙙𝙤 𝙮𝙤𝙪 𝙛𝙚𝙚𝙡 𝙡𝙞𝙠𝙚 𝙮𝙤𝙪 𝙙𝙤𝙣𝙩’𝙩 𝙠𝙣𝙤𝙬?

This is where the person in front of me stops giving the answer they’ve been giving everyone else and starts telling me the real one. Something they haven’t said out loud yet.

Here’s what I’ve learned…

The business logistics are almost never the real problem. Contracts, pricing, and positioning are all check boxes on a to-do list. 

The real problem is always upstream of the plan. It’s the thing insight alone doesn’t touch. 

You can gain thousands of insights about your business and still not move, because insight was never the block. Integration was. 

That’s the work. Not finding the next answer, but finding which question you’ve been avoiding asking yourself.

Answer that question and then get your ass in gear to move forward. taken in Chicago, Illinois by @garetfree
1
2 months ago
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