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Making the Best of the Holidays –– and Dealing with the Worst

In the back of my mind, there’s been a little glimmer, a tiny place I’ve found solace the past few months. Sure, 2020 is a dumpster fire of a year. Sure, I’m a personal and professional basket case 90% of the time. Sure, my children have won the battle for control of daytime hours, and now they’re coming for my nights too.

But, for once in my adult life, I’ve been looking forward to this: a trip extending throughout the entire American holiday season. …


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Over and over, pundits have decried Trump’s outlandish, unprecedented, and uncouth behavior with some version of this headline:


Looking for the top #WFH tips to hashtag live your best life during the COVID-19 pandemic? This isn’t that article.

Halfway through Day 32 — or was it Day 3?

My wife and I are still “adjusting” to working from home with our 2.5 y/o daughter.

adjust: verb, to move regularly between anxiety, hysteria, acceptance, and optimism––preferably on a schedule alternating with a partner or housemate’s own “adjusting”

So, since things are going so well over here, going to share

Get started early

This one actually hasn’t been much of a problem. Not that we have any choice.

Adapt your exercise routine for #StayAtHome guidelines

If your first thought was “what exercise routine?” then congratulations––you’re either a fast learner or…


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It’s sunny in Chicago today, and the streets are nearly deserted. And not due to frigid weather––the high today is 45F. While not quite “warm” (even by Chicago’s warped standards) a March day like this usually prompts outdoor activity en masse. Not to mention, it’s St. Patrick’s Day––a holiday that I’ve found this city to take very, very seriously.

But of course, none of the typical jubilation is happening today. It’s also the first day of COVID-19 related-closures of schools, restaurants, bars, and most any other place designed for more than 4 people to congregate together. …


OR: What do The Wire, Freddie Grey, and the Iowa Caucuses have in common?

A friend and compelling writer in Chicago pens an engaging weekly newsletter — which I highly encourage reading. (As someone who’s practically disastrous with personal email or reading any given source consistently, I actually look forward to this weekly missive’s arrival in my inbox.) For 2020, she’s resolved, at the encouragement of a friend, to operate with “the confidence of a mediocre white guy.”

Weeks later, I’m still typing through tears of laughter at this phrase.

I’ve turned this line over in my mind repeatedly, and…


We’ll get back to you in a GIPHY 🙄

Bottom Line helps low-income and first-generation students get to and through college. Over the past year of working together on strategic student outreach, hundreds of students have re-connected to seek advising on financial aid, access career-related resources, and get assistance with complicated processes like transferring or re-enrolling in college.

We collaborated on re-engagement strategies for students from across Chicago, New York, and Massachusetts, utilizing Signal Vine’s texting platform. This service supports individualized, multi-media SMS campaigns, and allows mass-messaging to seamlessly transition into one-on-one conversations. …


July 2018 — eating treats with dad

Every week for the past year, I’ve spent at least one weekday at home with my daughter. Usually Wednesdays, but not always, because nothing in our life is consistent except chaos right now.

Next week, she starts “school” (a Montessori daycare nearby), and I’ll have a full 5-day workweek for the first time since she was born. …


The Glamours of Entrepreneurship

On the day I typed this, entrepreneurship tasted like cigarette butts.

Photo by Tyler Nix on Unsplash

More specifically, the Chitwood family’s morning coffee tasted distinctly of spent cigarettes. We switched, temporarily — thankfully — from locally-roasted sustainably-sourced beans to a massive pre-ground canister of Chock Full o’Nuts.

And yes, many fancy coffees, wines, and liquors proudly promise notes of tobacco in their flavor profiles. What goes without saying: they’re hoping to evoke the unsmoked variety.

Successful, post-exit or post-money entrepreneurs love to recount tales of barely-made rent payments, all-night coding sessions, bullshit-filled pitch meetings, and air mattresses (Why always air mattresses?).

What they’re less likely…


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Thanks to my mother, I have no memories of life without coffee.

A social coffee drinker married to a Dr. Pepper devotee, she just wanted someone to share a warm cup with (“devotee” is actually an understatement; my dad had nearly a 6-pack-a-day DP habit for the better part of my childhood). My mom and Gram (my dad’s mother) dubbed what they gave me “Cowboy Coffee,” because I guess cowboys were the inventors of the Frappuccino. My cup started heavy on the milk with a splash of coffee, and the ratio gradually inverted from there.

My earliest sleepovers were at…


The idea for my writing and storytelling business developed early in 2018, around the time my current job and program were threatening to implode underneath my feet. A long 12–15 months of unhealthy administrative culture had convinced me it was time to leave my job, but this conviction didn’t carry with it any convenient clarity about where to head next.

Photo by David Iskander on Unsplash

At the time, I was running a non-profit student outreach and enrichment program. Our work focused on college access, leadership development, and STEM enrichment, and we functioned as a semi-autonomous unit within a larger higher education institution. For years, we’d…

Luke Chitwood

Writer, Storyteller, Problem-Solver. Beginner-level Husband and Father. Coffee drinker since age 1. #CollegeAccess, #Writing, & #HigherEd.

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