iiinova — where your digital self keeps evolving

Capt. Jack Sharrow @sharrows.bsky.social · 03/10/2026

I had no doubt the Legend was involved 👏🏽👏🏽

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Capt. Jack Sharrow @sharrows.bsky.social · 19/09/2026

Deeeeetroit style dish deep on bikes is a match made on 8 mile, really doe 💯

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Capt. Jack Sharrow @sharrows.bsky.social · 18/09/2026

I worked in prisons for 10yrs all over Indiana and I can tell you they have a more respectful entrance experience.

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Capt. Jack Sharrow @sharrows.bsky.social · 18/09/2026

I ordered my impossible burger at Sox park from the Fyre Fest menu. From the urbanism, bike valet, entrance experience, and concessions, the Cubs really are better in every way. Except tix prices. Shoutout to the best part of the Sox: @chicagobikesox.com

The saddest impossible burger, one sad tomato slice, no other toppings

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Capt. Jack Sharrow @sharrows.bsky.social · 16/09/2026

Breaking generational curses but it’s just me not leaving events early to beat traffic to drive back to the suburbs bc we park our bike out front and ride home peacefully.

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Capt. Jack Sharrow @sharrows.bsky.social · 16/09/2026

They are super chill about it which I greatly appreciate.

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Capt. Jack Sharrow @sharrows.bsky.social · 15/09/2026

My 1yr work anniversary is at the end of this month and I’ve been in the PTO negative most of that time. Currently at -8hrs. My high (low) was -26hrs.

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Capt. Jack Sharrow @sharrows.bsky.social · 12/09/2026

What’s your favorite part of Cubs games? Baseball. Definitely the baseball that’s happening on the field.

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Capt. Jack Sharrow @sharrows.bsky.social · 12/09/2026

Lit Fest blocking the bike lane bc the whole street is pedestrianized??? APPROVED.

Bike lane blocked by beautiful book people

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Capt. Jack Sharrow @sharrows.bsky.social · 11/09/2026

Birthday dinner means I called the most expensive chauffeur I could think of 💃🕺🏽 🚍

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Capt. Jack Sharrow @sharrows.bsky.social · 11/09/2026

Seeing my bike shop owner in the wild is like running into your drug dealer like oh I’ve given you thousands of dollars for my vice 😈

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Capt. Jack Sharrow @sharrows.bsky.social · 10/09/2026

Get that guy an ebike. It looks like he’s struggling. 🥵

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Capt. Jack Sharrow @sharrows.bsky.social · 10/09/2026

When I’m elected mayor, all buses will be treated as emergency vehicles where cars will be forced by law to heed the right of way. Buses will also be equipped with snow plow scoops to assist with car removal.

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Capt. Jack Sharrow @sharrows.bsky.social · 09/09/2026

Hell yea. Just got tix to Dead Girl's Quinceañera. Same venue but probably different vibes 💀💃

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Capt. Jack Sharrow @sharrows.bsky.social · 06/09/2026

Puppy and wife were very illegal. I classified them as precious cargo.

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Capt. Jack Sharrow @sharrows.bsky.social · 06/09/2026

Not me trying desperately to create core memories by handing stickers to kids on the back of cargo bikes at BTD. Several successful distributions.

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Capt. Jack Sharrow @sharrows.bsky.social · 01/09/2026

They’ve been trying to go out of business for a few years now so this makes sense.

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Capt. Jack Sharrow @sharrows.bsky.social · 01/09/2026

Every. Day. Whether it’s a lost taxi, drunk driver, or yes, even a driver with a permit from the Parks, our “car free” lakefront trail is anything but. But go off about fast e-bikes and scooters while these 2 tons living rooms roam our trails unimpeded.

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Capt. Jack Sharrow @sharrows.bsky.social · 28/08/2026

Believe me when I tell you, if the people in power gave a shit about our safety, we’d be talking about the cars I see on the lakefront trail every day and every night. Follow the money.

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Capt. Jack Sharrow @sharrows.bsky.social · 27/08/2026

Are cars allowed on trails and bike paths? Exactly. 🙄

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Capt. Jack Sharrow @sharrows.bsky.social · 27/08/2026

I applied for the “bike director” position and didn’t even get a call back. The city is so unserious about hiring people actively in the community doing the work. They could never handle the honesty and courage it would take to make meaningful change.

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Capt. Jack Sharrow @sharrows.bsky.social · 26/08/2026

Nah, we have our street vendor ride that wipes me out

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Capt. Jack Sharrow @sharrows.bsky.social · 26/08/2026

While I wait for my local bike shop to work on my bike, I’m eating this, drinking a horchata while Chicago house music plays. I’m never leaving this city.

Enchiladas with sweet plantains smothered with sour cream and mole, side of rice and beans

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Capt. Jack Sharrow @sharrows.bsky.social · 23/08/2026

When the in-laws needed seating and refreshments to watch their son in the tri and all roads are closed - #BikeIsBest

Cargo bike being the chairs and blanket with cooler, watching cyclists in the Chicago chi, city in the background

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Capt. Jack Sharrow @sharrows.bsky.social · 22/08/2026

But how fast was the scooter going and was it on the sidewalk?

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Capt. Jack Sharrow @sharrows.bsky.social · 22/08/2026

Sky - 15min walk Bears - 15min walk Sox - 15min bike ride Bulls - 20min bike ride Cubs - 35min bike ride

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Capt. Jack Sharrow @sharrows.bsky.social · 22/08/2026

Omg first Sky game and it was top 5 Chicago sporting events. Game winning 3 with .6 seconds left holy cow. My fav part had to be the Metra race! 2nd fav part was the 3 block walk to the arena.

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Capt. Jack Sharrow @sharrows.bsky.social · 21/08/2026

I’ll be at the Sky game too!! 👋🏽

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Capt. Jack Sharrow @sharrows.bsky.social · 20/08/2026

Parks can’t keep cars off the lakefront trail but they have surveillance money for people who need housing. Cool cool cool

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Capt. Jack Sharrow @sharrows.bsky.social · 15/08/2026

Doing a rain dance to wash out the air and water show but not our party 💃🌧️ who am I kidding, we ride in any weather

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Capt. Jack Sharrow @sharrows.bsky.social · 13/08/2026

Front loaders? Yes! Full suspension? Absolutely incredible.

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Capt. Jack Sharrow @sharrows.bsky.social · 13/08/2026

Have you seen the DIY at-home fountain setup? It’s thousands of dollars and zero savings and don’t think the wife hasn’t considered it.

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Capt. Jack Sharrow @sharrows.bsky.social · 13/08/2026

Was it my most difficult haul? Not even close. Was it my heaviest? By far. 1 case of water, 2 cases of soda, 1 case of energy drinks plus more. The lower center of gravity and geometry of the bike made riding a breeze. 🦾 #OneLessCar #BikeIsBest

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Capt. Jack Sharrow @sharrows.bsky.social · 12/08/2026

And the fact that means people can’t hang out in the seating areas outside is ridiculous

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Capt. Jack Sharrow @sharrows.bsky.social · 12/08/2026

That’s what people were saying. He didn’t wanna hear any of that and kept saying this is private property, yall need to leave.

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Capt. Jack Sharrow @sharrows.bsky.social · 12/08/2026

It was at 10:13p. His message wasn’t this space was “closed,” it was that it was private property and we could go across the street if we wanted to hang out.

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Capt. Jack Sharrow @sharrows.bsky.social · 12/08/2026

We tried to hang out in the grassy area of the Obama Center and this nice cop said this is private property and we had to leave. At least they didn’t drone strike us??? 🫠

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Capt. Jack Sharrow @sharrows.bsky.social · 12/08/2026

If you asked me to design what I think the prison from The Platform would look like from the outside, this is what I would show you.

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Capt. Jack Sharrow @sharrows.bsky.social · 09/08/2026

Fly the Co-Op, I missed it last year so I was determined.

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Capt. Jack Sharrow @sharrows.bsky.social · 09/08/2026

Saw 2 bike friends on the LFT today!! Surprised I’m still alive after yesterday’s ride! 💀

Screenshot of a long ass bike ride around Chicago

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