(Doing my best Anthony Bourdain impression today)

I spend most of my time behind my desk and computer screen at home. But whenever I get the chance — outside of Zoom calls or things that require me to be at my command center — I try to work from a coffee shop.

It’s one of my little joys in life, to have a 3-hour window that I can walk down to one of my favorite coffee shops and simply type away to my heart’s content (today I rode my bike through Lincoln Park up to Intelligensia Coffee in Lakeview, and as I sit here I am just reminded how much I love it, there’s nothing like it)

And that’s the thing, what’s not to like? The beautiful brown noise, the ungodly good smells, the usually great lighting, the plenty of caffeine to keep me going, and above all — the excuse to get out of the damn house.

One of the things I’ve loved most about moving to Chicago is the sheer volume and variety of coffee shops here. I could try a couple new ones each week and never hit them all.

Naturally over these past few months I now have a short list of favorites, places that I frequent, even one or two where the baristas and I are on a first-name basis (nothing cooler). As I zoom out I’m realizing there is a bit of an implicit art form to picking a really good coffee shop to work from.

Perhaps it can be systemized a bit, I think I will try. So, without further ado, here is my definitive guide to finding the perfect coffee shop to work from.

The 4 Factors to Consider

These are the four things you should consider when picking a coffee shop to work from: Accessibility, Atmosphere, Menu Quality, The People 

Of course I’ve listed these in order of my personal preference, which I think are objectively correct. But before you begin looking for yourself, it’s good to take a quick mental inventory of how important each of these factors is to you; and there may be other factors as well (ex: my wife would probably say number of dogs).

1) Accessibility

How easy is it to get to and find a seat? In a denser upper Midwest city with many coffee options and many chilly winter days, this is the number one thing to consider. If I lived somewhere like San Diego I might feel differently, but quite frankly traveling more than 30min in <30 degree weather to get to a coffee shop just for every seat to be filled is a sunken cost I cannot afford.

Once you are in, how easy is it to connect to wifi, use the bathroom, etc.? I’d say 90% of my coffee shop visits are to locations within 8 blocks of my apartment. For me my personal fav in this department is the Foxtrot Coffee on North and Wells in Old Town Chicago — a quick 14 min walk, plenty of open seating, not too busy, great WiFI.

2) Atmosphere

Simply put, how are the vibes? Smells, sounds, lights, temperature, all are at play here. You must realize that primary product a good coffee shop sells is not the coffee, it’s the atmosphere. Starbucks built an entire American institution on this notion throughout the 90s and 00s (though many of their locations these days are not cozy and vibey as the days of old).

My favorite place in this department is Elaine’s Coffee on Clark, located inside of the Lincoln Hotel just off of Lincoln Park. Not too bright, quiet, comfy leather booths, chalkboard walls, great plants, awesome aromas. It’s a bit further away than some of my staples, but whenever I’m in need of some extra boost to focus down deep I go there.

3) Menu Quality

Coffee, believe it or not, is the 3rd most important factor to consider of the 4. Part of it might be that these days most coffee shops uphold a minimum threshold of good quality coffee — the hipsters have won. On top of the coffee you might also consider - do they have orange juice? breakfast burritos? candles or off-sale liquor?

Of all the coffee shops in Chicago, my favorite coffee is Dark Matter’s Osmium Coffee Bar in Lakeview. Their beans are like alien X-men strength, last time I went and got a cortado I almost got heart palpitations. I go up there on the train once every couple months and buy a few bags to bring home. The vibes are fine, but I go for the coffee.

4) The People

Last but not least, beyond the location, vibes, and coffee itself: how are the people? Do other interesting people hang out there? Some coffee shops are filled with commuters and tourists, others with students and startup founders, others with old people catching up. You overhear the other conversations, and they can either fuel you or deplete you. This is not the most important factor, but it can make a big difference.

For example, whenever I go back to Minneapolis I love to work from FRGMT Coffee on Washington in the North Loop. Not because the coffee or vibes are anything to write home about, but because of the people who work from there — every time I go it’s filled with other startup founders and people I know, and I love to bump into people and sit and chat for a minute.

Common Questions

What if there are 6+ great shops in the area to choose from? Sometimes it can feel like splitting hairs if there are a lot of great options in a 2-3 block radius. When this is the case I like to utilize the Secretary Problem from my college optimization class - simply review a subset of the shops (~3) on Google Maps, pick your favorite, then continue searching until you find one that’s slightly better than the best of the 3 you reviewed.

What about lunch? I should say that all of my optimization here is for places to work from, and it’s important to note that. If you are looking for a coffee shop for different reasons — a place to eat, a place to go on a date, and please to meet someone for the first time, then the optimization strategy is probably different. We could write more about that in a different post.

What are your all-time favorite coffee shops? I’ve briefly mentioned a few of my favorites above with respect to individual aspects. If I have to choose my absolute favorite places all things considered, my Mt Rushmore would probably be something like this: Archetype Coffee in Millwork Commons (Omaha), The Briar (Northeast Minneapolis), Foxtrot Coffee (Old Town, Chicago), and Cafe Steam (Rochester, MN)

IF you have any favorite coffee shops in your neck of the woods or you think I missed something, let me know. I’d like to probably come back and update this a bit in the future, for now I hope this helps you find a good place to escape to :-)

Peace,
Ramsey