iiinova — where your digital self keeps evolving

Jake Schoolman @jake.school · 10/10/2026

I love strapping my taco bell into the divvy basket.

A Taco Bell paper bag sitting inside a blue bicycle basket at night, illuminated by the bike's front light.

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Jake Schoolman @jake.school · 21/09/2026

Went to a wedding this weekend. It was really nice to dress up and see so many friends

A man in a blue suit and patterned tie taking a mirror selfie in a hotel room.

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Jake Schoolman @jake.school · 19/09/2026

Here is an alligator named broccoli.

Broccoli the mini Aussie looking like an alligator

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Jake Schoolman @jake.school · 11/09/2026

One more day until Robyn concert, Broccoli and I both woke up very excited. He doesn’t know he can’t go yet.

Brown mini Aussie named broccoli and me with big excited faces laying in bed.

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Jake Schoolman @jake.school · 19/08/2026

After nearly three years of wearing my whoop everyday I’ve cancelled my subscription. Just need a sale on garmin watches to show up now.

Screen shot of whoop dashboard screen showing 1087 consecutive days logged.

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Jake Schoolman @jake.school · 05/08/2026

What a bummer! Green Machine helped me build my Gunnar during the pandemic. Sad news.

A blue Gunnar bicycle leaning against the green machine bicycles shop window

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Jake Schoolman @jake.school · 01/08/2026

This gentleman named broccoli requests my snacks.

Australian shepherd named broccoli politely asking for my cheese snacks. Paws crossed.

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Jake Schoolman @jake.school · 25/07/2026

Also love not owning a jet ski 😬

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Jake Schoolman @jake.school · 25/07/2026

Never want to own a boat, but it sure is great to have friends that do!

Me on a boat, selfie, Chicago skyline in the background

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Jake Schoolman @jake.school · 12/07/2026

Broccoli is upset we keep him behind this cage

Mini Aussie broccoli staring out from behind a fence

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Jake Schoolman @jake.school · 02/07/2026

I agree and it is why I named my dog Broccoli

Mini Aussie named broccoli. Sometimes called broccolini.

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Jake Schoolman @jake.school · 02/07/2026

Broccoli is the best hangover cure

Broccoli the mini Aussie snuggles with me while hungover in bed.

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Jake Schoolman @jake.school · 14/05/2026

Broccoli heard me yelling at my computer today, since work is awful, and immediately crawled into my lap. Face on mine. Either trying to calm me down or shut me up.

Broccoli the brown and black Australian shepherd with a concerned look out his face over my mouth. I have a black Timberwolves hat on sitting in my office chair.

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Jake Schoolman @jake.school · 13/05/2026

New scorpion! Needles on the Achilles were an… interesting feeling

A new black and white scorpion tattoo, done by @kelsey_moore_tattoo (on instagram). Tattoo on my lower calf

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Jake Schoolman @jake.school · 08/05/2026

Broccoli is always looking like a gentleman, even if he doesn’t always act it.

The broccoli dog is a mini Australian shepherd. Black and brow, crossing his front paws while laying on the floor.

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Jake Schoolman @jake.school · 23/04/2026

There’s a small lizard in my hotel in Puerto Rico but he’s being cute so I guess he can hang out.

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Jake Schoolman @jake.school · 15/04/2026

Broccoli has been keeping me sane while working way too much the past 6 weeks. He shares my pillow in the morning and sleeps next to me while I work. He’s a good dog.

Photo of my black and brown miniature Aussie sleeping next to me in bed, he is sharing my pillow. Half of my face is in frame as well. I just woke up.

Broccoli the mini Aussie laying down next to me while I work, he’s sleeping on his back with his fuzzy belly showing. Paws folded up real cute as well.

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Jake Schoolman @jake.school · 23/03/2026

National puppy day. Both of mine as babies.

Broccoli the brown and black mini Aussie in the snow. Blue eye is looking bright

Tilly the black and white mini Aussie doing a play bow and showing off her booty

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Jake Schoolman @jake.school · 17/03/2026

I could mail in my ballot, but there’s something about going to the polling place on voting day.

Selfie of myself sitting at my desk with an I voted sticker. Not sure why I look so fucking tired. Maybe it’s stress. Maybe it’s being 40. Wearing a grey flannel and Timberwolves hat.

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Jake Schoolman @jake.school · 13/03/2026

Work has been very busy this week. Painfully so. But I did just get back from telluride gay ski week and that was so fun, so I will not complain.

Me sitting at a mountain top restaurant in the sun in telluride. Gay flag and mountain behind me. Hat says Handys. Gorgeous sunny day.

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Jake Schoolman @jake.school · 02/03/2026

My mustache looks crazy from the lighting here, but i kind of like the picture. Had way too much fun DJing last weekend!

Dj Schooolman behind the decks at a party in Chicago called Factory.

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Jake Schoolman @jake.school · 01/03/2026

What a fun night getting to play house music in Chicago.

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Jake Schoolman @jake.school · 26/02/2026

Look at this dog. Sleeping dangerous under my chair since he was a puppy.

Broccoli the mini Aussie sleeping on my rolling desk chair as an old boy.

Broccoli the mini Aussie sleeping on my rolling desk chair as a puppy.

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Jake Schoolman @jake.school · 21/02/2026

Woah whoop, it was just a game of of basketball. Sure it’s a gay rec league, but chill out…

Screen shot of whoop fitness review that says, “you pushed a big basketball load into a body that woke up in the yellow with 42% recovery an a resting heart rate of 65…”

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Jake Schoolman @jake.school · 05/12/2025

Tilly in her advanced age is starting to love wearing my hoodies ☺️

Tilly the white and black mini Aussie wearing a hoodie. Lookin a lil like a Jedi.

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Jake Schoolman @jake.school · 03/12/2025

Oh hey, look at this happy broccoli! 🥦

Smiling happy miniature Aussie named broccoli. He is black brown and white with his paws in the side of the couch.

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Jake Schoolman @jake.school · 26/11/2025

Since I finally have a job and decent health insurance, I felt comfortable going back to CrossFit again. My first snatches in about 8 months! Not the best form or heaviest load, but I’m very happy to be back.

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Jake Schoolman @jake.school · 15/11/2025

My dad painted a watercolor of a crow for my birthday card this year and I love it so much!

Water color of a crow perched on a log, done by my father

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Jake Schoolman @jake.school · 08/11/2025

In Palm Springs for pride and this is gonna be me all weekend.

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Jake Schoolman @jake.school · 04/11/2025

It’s Broccoli’s birthday! He’s such a sweet snuggly (5 year old) baby!

Broccoli the miniature Australian shepherd: begging

Broccoli the miniature Australian shepherd: swimming in Lake Michigan

Broccoli the miniature Australian shepherd: as a puppy with in the snow

Broccoli the miniature Australian shepherd: snuggling on the couch

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Jake Schoolman @jake.school · 01/11/2025

Yikes what a super weird and gross thing to have on your license plate.

A fancy car with a vanity license place that reads “LNDLORD”

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Jake Schoolman @jake.school · 27/10/2025

Did a thing tonight. DJed a party. Was a vampire.

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Jake Schoolman @jake.school · 17/10/2025

I have two very fuzzy dogs and I’ve just come to terms with the fact that I’m definitely regularly eating their hair.

Two miniature Australian shepherds. White one is Tilly and the other is broccoli. They are standing at the dog beach on Lake Michigan.

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Jake Schoolman @jake.school · 16/10/2025

Start my new job on Monday, so I chopped off my long hair!

Selfie with a fresh new haircut, walking down the street in Chicago.

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Jake Schoolman @jake.school · 12/10/2025

DJ gig went great last night but wow I am tired.

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Jake Schoolman @jake.school · 15/09/2025

On a boat today, did a cruise on the river. Beautiful end of summer.

Selfie on Lake Michigan with navy pier in the background.

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Jake Schoolman @jake.school · 06/09/2025

I haven’t done as many long bike rides this year, but today was perfect weather. 56 miles complete, with a stop at a brewery in the middle.

Me riding my bike on the des plaines river trail, blue helmet, sun glasses and a mustache that needs to be trimmed.

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Jake Schoolman @jake.school · 15/08/2025

Spending time camping with friends, good way to ignore the world’s problems for a couple days.

Camping trailer with a roof top tent in front of a red rock cliff face

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Jake Schoolman @jake.school · 04/08/2025

Got to spend Saturday on a boat, and while the air quality was bad, it did make for a great sunset.

A sunset selfie of me with the Chicago skyline, a sailboat, and a light house. Taken from a boat on Lake Michigan.

A hazy view of the Chicago skyline taken during sunset from a boat on Lake Michigan.

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Jake Schoolman @jake.school · 01/08/2025

Stopped for a little lakeside beer on the bike ride to a friends birthday. Hard to beat this city amenity

Picture of the concrete beach and Lake Michigan. Coast guard ship is entering frame right. Blue skies and blue water.

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Jake Schoolman @jake.school · 28/07/2025

I biked to a concert in the suburbs last week. Meant to take more photos along the way as it was mostly nice bike paths. I forgot because I was having fun! I did come across a deer on the way home though, casually crossing in front of me. Ya don’t get that close when driving a car.

A deer next to a picnic table, taken at night. It had just crossed my path 3 feet in front of me.

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Jake Schoolman @jake.school · 23/07/2025

Here’s a funny looking broccoli! That’s a big yawn 😁

Black brown and white mini Australian shepherd named broccoli. He’s doing a big yawn with his eyes closed.

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Jake Schoolman @jake.school · 18/07/2025

Tilly and broccoli are the phone wallpaper of course.

Cellphone Lock Screen with two mini Australian shepherds. A black and white one named Tilly, and a black and brown one named Broccoli.

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Jake Schoolman @jake.school · 12/07/2025

Chicago summer has been a 10/10 so far as expected.

Me smiling with a beer on a rooftop in Chicago on a beautiful day.

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Jake Schoolman @jake.school · 11/07/2025

What a good sign for my Friday, my friend just sent me a video of the new baby opossum that’s moved in under her chicken coop! They will have to get her to move homes because apparently they will harass the chickens. But so cute!

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Jake Schoolman @jake.school · 10/07/2025

Same! I’ve heard there is an insect asylum near me that has a resident opossum, that I must go check out. I even have a tattoo of one!

A tattoo of an opossum on the calf of the leg

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