Trash Can on Fire!!!

(August 10, 2010) Trash can fully engulfed in flames on a busy Chicago street... Nobody seems to mind or care, too busy texting on phone(s) to stop. I love city life!

Much Room for Improvement

(August 9, 2010) A wonderful, small-business owner enlightened me to how much time I waste throughout the day. This woman not only runs her own company... but also finds the time to manage two not-for-profits and stay ridiculously involved in community efforts.

Why Can't We Be Friends...?

(July 16, 2010) Unintentionally, had coffee with a guy who worked for a direct competitor of one of my company's business unit. After carefully dancing around the "what do you do" conversation we settled into a nice conversation about family and travel. Can't we all be friends...?

It's Been Too Long...

(July 1, 2010) Because of my work schedule, this is the first Random Cup of Coffee in about a month. It's made me realize how much I appreciate these mini-encounters. I need to get back into the swing. And, met a director from the Make-A-Wish foundation. Talk about an amazing person. Dedicated to making a difference.So many amazing people out there.

My First On-Air Personality

(May 3, 2010) Lovely cup of coffee with a woman who was an on-air anchorwoman out west. She gave me lots of insight on what goes on behind the camera to put together a daily production. I managed to internalized all the quotes running through my head from "Anchorman" the movie. I think it was a good move on my part.

ILL-INI...

(April 30, 2010) Always good to talk to a fellow U of I alum...

The Changing Face of Business...

(April 29, 2010) Spoke with the owner of a not-for-profit focused independent graphic designer. He mentioned that he hasn't actually met most of his clients face-to-face... even clients he has worked with for over 5 years. Interesting...

What a Find!

(April 23, 2010) So… Met the founder and editor of a fantastic, Chicago-centric online publication. One thing led to another and we found ourselves down the street from the café furniture shopping in an antique shop together. Not exactly how I expected the meeting to go… but it was a great conversation and I think I found a bench.

I'll Take Two Companies Please

(April 23, 2010) Single mom of two… started her own consulting company five years ago and is starting a new company this summer. Lots of hardworking, talented people in this city.

Floral Wallpaper

(April 15, 2010) Girl next to me is psychic and apparently can visualize the type of wallpaper you have in your house – just through casual conversation. I don’t have wallpaper, wonder how that works.

Scientific Explanation of Heaven

(April 15, 2010) Coffee with the owner and founder of an ad agency. Told me the next time we meet, he'll share a "scientific explanation of heaven". Need I say more? I like to think that I'm not easily impressed, but this guy impressed me. Really impressed me.

Prom Night

(April 8, 2010) Stood up for the first time today. Coffee for one please. Sniffle. This social experiment is not without pain...

If Anyone Asks...

(April 1, 2010) When the conversation starts, "if anyone asks, we're buddies from college" you know it’s going to be an interesting conversation. Met a guy from a transportation company that was unhappy with his current employer and looking for a new gig. Nice guy. We talked about what he’s looking for and maybe I can connect him with some people. But, couldn't stop thinking about how people will be more honest and forthcoming with a stranger than with people they interact with on a daily basis.

Sometimes Tea is Better

(March 26, 2010) When the crowd zigs, sometimes it's best to zag. I met a young, extremely professional senior associate for a cup of coffee. Unfortunately, about seventy-five other people showed up as well. The line was long and the milk wasn't frothing fast enough, so we jetted across the street to a quieter tea shop and enjoyed a relaxing cup of tea. I’m not usually a tea drinker but it was delicious. She worked for a “turnaround” consulting company and told horror stories of companies in decline. Extra motivation to work a couple extra hours on Sunday… Time to zag again.

The Restaurant Business

(March 25, 2010) Another book-cover lesson. Made arrangements to meet at a train station for coffee. Train station? Was expecting the worst and some interesting odors. Escalator up, escalator down and I found myself in a hidden wing with a gourmet market place and one kick-ass cup of coffee. Also learned a little bit about the restaurant industry (and an investment tip) from the president of a restaurant management company.

World Design

(March 23, 2010) Most interesting conversation yet. Coffee with the owner of a product design company. Given his line of work, I could tell he viewed the world a little different than most people. Always dissecting things in his head and putting them back together. Making things stronger, faster, better. Making me realize that I need a new coffee maker and that we all have to make things stronger, faster, better.

Life Plans

(March 25, 2010) A financial advisor surprised me today. Thinking that his job revolved around numbers and 401ks, I was surprised to learn how involved he gets with his clients. Long-life dreams, marital problems, and family planning are all, very personal, yet very common conversations for him on a daily basis. Great guy. Great conversation.

Trip to Israel

(March 19, 2010) Coffee with a commercial real estate broker who just won a big deal. Years of work finally paid off for him. Obviously, he was in a good mood. Conversation migrated to the topic of travel and he told me about his trip to Israel and how he initially didn't want to go and how it turned into his "best" trip ever. Good reminder to always try new things and good things happen.

Bathroom Emergency

(March 19, 2010) While I was waiting... some poor guy locked himself in the coffee shop bathroom. Firemen just showed up with axes. Thought this was worth a post...

Kindness Returned

(March 16, 2010) It was a cold Chicago morning and my guest was the owner of a small business real estate financing company. We met at an incredibly crowded coffee shop and did introductions in the middle of a caffeine starved mob. Slow to the wallet, my guest beat me to the draw and paid for our drinks before I could react. Not sure why this had a impact on me but it did... Kindness returned.

You Always Remember Your First

(March 11, 2010) With fears of rejection and awkward conversation close at hand, my adventure began with a smile and a cup of black tea. My guest was a successful lawyer who recently switched careers in order to achieve a better work-life-balance. Getting past the "So, what's your angle?" question, we quickly settled into a pleasant conversation. Surprising open, she shared her story - complete with accomplishments, challenges, and even some regrets. A remarkable woman, a strong cup of tea, and a simple conversation that has changed the way I look at "strangers".