The Laptop Hobo Manifesto

Tyler Alterman is a 2014 CIW Co-op member and the Co-Founder and Operations Director at The Think Tank at the University of Chicago. Here, he invites us all to join the Chicago laptop hobo brigade, hopping from cafe to cafe in search of delicious coffee, comfortable seating and inspirational work mates.

We are the Chicago laptop hobos, and we are proud. We live in the crannies of your corner cafes, with one hand on our mochas and the other answering emails. Pity the office dwellers, confined to their cubicles, stuck to the schedule of a 9 to 5. We, the hobos, know no timetables; the opening and closing of coffee shops are our only clocks. We are students, starters, graphic designers, web developers, directors of nonprofits, poets, hackers and artists. The heirs to cafe intelligensia of 1890s Vienna, we turn caffeine into culture. Behold our manifesto.


Having recently moved The Think Tank from NYC to Chicago, my first task as a newcomer was to find the top coffee shops for hobo-ing. I present my four favorites below.


Filter (1373-1375 North Milwaukee Ave.)

The mecca of laptop hobos in Wicker Park, Filter is replete with outlets, funky lighting and people of all types united by a single god: the softly glowing rectangle.


Wormhole (1462 North Milwaukee Ave.)

Wormhole is yet another Wicker Park classic. The music can get a bit grating, but outlets are as plenty as the hip-bourgeoisie occupants. A fun feature of Wormhole are large tables for co-working with fellow hobos.



New Wave (2557 North Milwaukee Ave.)

You’re probably not cool enough for New Wave, but on the off-chance you are, there is a nice array of seating arrangements for all manners of hobo-ing in this spacious, Logan Square haunt.

Dollop (4181 North Clarendon Ave.)

“This is a chain???” is what you’ll think upon entering this cozy cafe near Montrose Beach. Then you’ll sip their Mexican Mocha as you slip quickly into hobo-tude.


Any coffee shops I missed? Add them to the list.


The laptop hobo must stay the path to productivity without pressure from bosses and managers. My solution: the Pomodoro Technique. This simple method requires that you commit to 25 minute chunks of utter focus, interweaved with five-minute breaks for all your BuzzFeed and cat video needs.


The life of the laptop hobo can be a lonely one without office mates. Find fellow laptop hobos. Work together. Sit proximally. Motivate one another in between Pomodori. The way colleagues and I achieve solidarity is through a competitive Pomodoro spreadsheet, in which we all battle for the highest weekly total of Pomodori. If you’d like to join us, carve out your space on our collective Google Doc.


As a laptop hobo, you must be prepared for all the potential pitfalls of cafe life. Shoddy wifi? Purchase a personal hotspot. Limited outlets? Bring a power strip. Crappy music? Download Coffitivity to reinstate the white murmur of background chats.


With great hobotude comes great responsibility. We must not bankrupt our coffeeshops, for they are our homes. Purchase a pastry, refill, or sandwich every one to two hours. Let the resulting warm-fuzzy protect you from Chiberia temperatures.

Are there any tenets missing from this manifesto? Email the author at

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