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HOW Design Live + Chicago


I can’t believe it’s been THREE months since I attended HOW Design Live in Chicago! For me the trip was a combination of the right conversations with the right people at the right time. It was epic.

The speakers were phenomenal. It was nearly impossible to narrow down my takeaways, but I did! Here are my tops.


1. Everything you do and say is auditioning you for leadership.
Sam Harrison, We’ve Got to Stop Meeting Like This

2. The quantitative stuff is easy! The warm and fuzzy stuff is hard.
-Glenn John Arnowitz, Bossypants: Making the Transition from Designer to Design Leader

3. Leaders cannot only see the dots, but connect them. People will want to work with you not just because of your ideas, but your ability to communicate in a powerful, effective way.
-Glenn John Arnowitz, Bossypants: Making the Transition from Designer to Design Leader

4. Micromanaging isn’t sustainable in a leadership role.
-Glenn John Arnowitz, Bossypants: Making the Transition from Designer to Design Leader

5. I’m a better boss because I’m a mom and a better mom because I’m a boss.
Tina Roth Eisenberg, The Best Way to Complain is to Make Things

There was so much swag. My favs were days of the week letterpress cards from moo and my Aaron Draplin signed Field Notes!


6. Creativity is not an answer, it is a process and needs to play out.
Stefan Mumaw, Anatomy of a Brainstorm

7. Design without objective is merely decoration. And we are not decorators.
Tim Cox, How to Get Taken Seriously


8. It’s harder to define your own goal than to take an assignment.
Cheryl Heller, Women, Money, Power: How to Be It, Have It, Get It

9. Problems arise when our job isn’t giving us chances to grow creatively. That’s when we need to create opportunities for ourselves.
Jim Krause, Sustainable Insanity

10. Do the work that feeds your soul, not your ego.
Jessica Walsh, Play By Your Own Rules

11. Discipline is the #1 factor of success. The more you do, the better you get.
Karim Rashid, The Future of Design

Tina Roth Eisenberg is amazing and was wonderful and kind when Jenni and I met her.


12. Relationships change the way we brainstorm.
Stefan Mumaw, Anatomy of a Brainstorm
(Putting this in life because I’d add that relationships change the way we do EVERYTHING.)

13. Don’t complain, make it better. You have two options: Do something about it or let it go.
Tina Roth Eisenberg, The Best Way to Complain is to Make Things

14. It doesn’t matter how much experience you have, you never get a free pass from the dark middle. The only thing you get is a little big of grace.
Brene Brown, Make. Believe, Courage and Connection.


I was also happy to enjoy the city…Chicago dogs, the bean, Sprinkles cupcake ATM, lunches and dinners with exceptional, talented friends and a river boat tour were all had in between sessions. Let’s just say I didn’t have much downtime because I was too busy packing everything in.





LITTLE GOAT DINER Worth the hype. In fact, I went twice.
CAFE IBERICO You can’t visit Chicago without a trip to Cafe Iberica, amiright?
SOUTH WATER KITCHEN The “Pb & J” Grilled Cheese is amazing!
CH Distillery When your friend says you need to try her fav cocktail in the city, you try it. Order the Cease and Desist, trust me.


EATALY Such a cool store. Plus, Nutella station.
GOOP The goop pop-up shop was up, so I had to go.
THE LAND OF NOD If you like to shop online, you must visit the store in person.


WENDELLA BOATS A river tour is hands down the best way to see the city.
SPRINKLES CUPCAKE ATM Cupcake. ATM. Need I say more?

Speaking of Chicago, these Chicago buildings above clouds photos are amazing.

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