Man in a Chicago Cubs cap, sunglasses, and navy suit.

Into the Weekend 11.6.26

  • Brad Lippitz
  • November 6, 2026

Into the weekend!

Man in a navy suit, sunglasses, and a blue-and-red baseball cap

If you’ve been smart and diligent and keeping up with your weekly “Into the Weekends,” then you’ll know that a couple of weeks ago, I announced the first-ever annual global worldwide “Into the Weekend" contest. For those of you who have slacked, we’ve taken the necessary steps and included a hyperlink for your convenience.


Soon thereafter, amid much anticipation, the judges concluded their deliberations, emerged from sequestration, and announced a tie - for the first time ever in the history of the contest!


With the first winner’s submission having been heretofore - but not hereinafter - published, this week we end the anticipation, subdue the murmur, quash the street buzz, and publish the entry of the second contest winner: Josh Paley. So, without further ado, my friends, in his words…


Let me begin with a confession. Unlike some devoted followers of this internationally acclaimed publication, I haven’t been a subscriber for years. However, after conducting what I consider an entirely adequate amount of research (did you know there is a book), I feel more than qualified to contribute. But let’s be honest, isn’t confidence half the battle?


So, I’ve settled on five things I’ve learned from the wisdom of Brad Lippitz. 


1. Food is serious business, treat yourself. Afternoon tea is delightful, dinner with friends and family is a must, Italian beef deserves landmark status, candy corn is an insult to humanity, and the tuna at Gemini? Worth its own newsletter. Brad knows what he likes and he won’t shy away from it for anyone. Much like his real estate career, he’s earned the right to tell us and make those recommendations. 


2. Patience is a virtue. Especially when someone takes a second too long at an intersection and there’s a loudly colored (slightly older model) Porsche honking behind them. Still awaiting confirmation this lesson has been learned.


3. Behind every great success is a great team. From bringing “Into the Weekend” to life to keeping the real estate empire running, the people behind the scenes deserve some time in the spotlight, too. 


4. Progress doesn’t happen by accident. A boy choosing another boy at a Snowball Dance represents years of people like Brad working to make those moments possible. There’s more to do, but it’s worth recognizing those who helped get us here (https://www.youtube.com/watch?v=qqVfkJHjVD8&t=163s).


5. Be unapologetically yourself. From his red and blue Cubs hat to his unwavering refusal to entertain mustard (seriously, put some ketchup on that man’s hot dog!), Brad has made an entire brand out of being himself. Perhaps that’s the real secret to his success. Sure, there’s experience, market knowledge, and presumably actual work involved (Brad, please fact-check), but people remember authenticity.


After all, the world already has one Brad Lippitz. I’m fairly certain that’s all it can handle. JUST BE YOU.


6. I know I said five, but in true Brad fashion, I’m doing what I want and adding one more (rofl x551). For all your buying or selling needs, contact the Lippitz Group. Apparently, being unapologetically yourself is also excellent marketing.


Have a great weekend!


Best,

Josh

Things to do this weekend...

Theater auditorium with seated audience facing a blue-lit stage and Chicago Humanities screen.

Chicago Humanities Fall Festival

Date: November 7

Time: Times Vary

Location: Locations Vary

Chicago’s biggest ideas take the stage at the Chicago Humanities Fall Festival, a series of nearly 50 talks, performances, and conversations with authors, actors, comedians, and thinkers. The fall event is centered around Hyde Park with events at the University of Chicago.

People share a meal around a wooden table, with a burger and assorted dishes.

Andersonville Restaurant Weeks

Dates: November 1 - 15

Time: Times Vary

Location: Locations Vary

Explore a diverse cornucopia of cozy fall cuisines with specialty prix fixe menus curated by our local chefs. Participating restaurants will offer multi-course brunch, lunch, and dinner options ranging from $35 to $60 (prices vary by location). Participating restaurants updated daily!

312 Comedy Festival event graphic over a packed theater audience.

312 Comedy Fest

Dates: November 6 - 8

Time: Times Vary

Location: Locations Vary

Chicago’s premier comedy festival brings big laughs and big names to venues across the city. The 312 Comedy Festival is a celebration of stand-up, sketch, and improv that draws nationally recognized comics (think Nikki Glaser and Ali Siddiq) and rising stars to stages throughout Chicago for one unforgettable event.

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Dozin' with the Dinos

Date: November 6

Time: 6:00 PM - 9:00 AM

Location: Field Museum

Pack your sleeping bag for one of Chicago’s most unusual overnight experiences, a night spent surrounded by dinosaurs at the Field Museum. Dozin’ with the Dinos is a family sleepover event filled with games, challenges, and stories among some of the world’s most iconic prehistoric fossils.

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Check out previous "Into the Weekends" on our website here.


Into The Weekend! — Brad Lippitz’s Musings, 2020–2026

Check out our new flipbook containing the past 6 years of Brad's musings here!

Compass
Compass RE is a licensed real estate broker. All material is intended for informational purposes only and is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to the accuracy of any description or measurements (including square footage). This is not intended to solicit property already listed. No financial or legal advice provided. Equal Housing Opportunity. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions.

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