Kaleigh Simmons
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A Tale of Two Cities

  • October 25, 2018
  • Personal thoughts

All week, I was looking forward to Saturday July 28th. Then it came. I woke up at 5am because I couldn’t sleep. In a few hours, we would be headed to a walking tour of a neighborhood well-known for gun violence and I was getting nervous. I didn’t want to back out, but I was […]

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A Meeting Ten Years in the Making

  • August 25, 2018
  • Personal thoughts

I was so nervous, I felt nauseous. It was Saturday August 11th at 9am and I was on my way downtown to see my mom for the first time in ten years. Would I remember what she looked like? Would she remember what I looked like? Do I look anything like I did at 22 […]

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About Journalism

  • August 15, 2018
  • Personal thoughts

I’ve been thinking a lot about a recent event I attended featuring Jennifer Brandel of Hearken. If you haven’t heard of Hearken, the best way I can explain it is to send you to Curious City, a WBEZ program she also founded that has served as Hearken’s inspiration. It’s a model of journalism rooted in […]

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Mom.

  • April 10, 2018
  • Personal thoughts

Several years ago, after not speaking to or seeing my mom in many many months, I got a text message asking me to meet her at the Starbucks at Eastview Mall. At the time, I thought the mall Starbucks to be such an odd choice of location, but I’d understand why she chose it later […]

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What I Learned From Several Years in Startups

  • March 15, 2018
  • Personal thoughts

You already know that after several years, I stepped off the startup hamster wheel. While I’m sure that separation will give me more and much better perspective, I’ve been itching to get some of my experiences down on paper. I’ve been given a wealth of opportunity in this community and am thankful for all it […]

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A tough lesson

  • January 14, 2018
  • Personal thoughts

Here’s a little story about a lot of screw-ups that finally pushed me to design my work around my life, instead of the other way around.

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Back to My Roots

  • October 30, 2017
  • Personal thoughts

It took writing the following into the card for a departing colleague to remind me of the kind of work that sets my heart ablaze: “I don’t know what to say other than thank you. You challenged me without even knowing it. You made me think bigger. Made me aspire to be something greater. Showed […]

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Where Did All My Posts Go?

  • May 3, 2015
  • Personal thoughts

Oof. So, when you get distracted and let your hosting lapse, turns out they do actually end up deleting all of your website content.

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The Rollercoaster of Emotions That is Startup Hiring

  • January 14, 2014
  • Personal thoughts

When you uproot your entire life and move across the country to chase a crazy dream, you gain a weird sort of notoriety back home. A mix of hope and cynicism. Wide-eyed encouragement with a dash of misanthropy. When you fly in the face of everything you’ve been cautioned against, your elders are sitting on […]

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Thanks, 2013

  • December 30, 2013
  • Personal thoughts

As I sit in my Chicago apartment, an official Startup Institute alumna, preparing for interviews for jobs I only dreamed about a couple months prior, I can’t help but to think about the year that got me here. What were some of the defining moments?

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Top Ten Startup Institute Chicago Moments

  • December 20, 2013
  • Personal thoughts

It’s hard to distill eight life-changing weeks down to ten top moments, but here’s my best shot:

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The Finish Line

  • December 11, 2013
  • Personal thoughts

It still doesn’t feel real yet, but I’m less than a week away from officially being a Startup Institute graduate.

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The Goods: Part Two

  • December 11, 2013
  • Personal thoughts

A continuation of some of my favorite learnings as a student of Startup Institute:

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The Goods: Part One

  • December 10, 2013
  • Personal thoughts

So many people have asked, “What are you actually learning there at Startup Institute? Do you feel like you’re coming away with worthwhile skills? Are you getting your money’s worth?” Here’s the short answer: yes.

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From Scratch

  • December 1, 2013
  • Personal thoughts

A good friend from home was in town last night and even just seeing his face reminded me of how much I miss about the network of friends and colleagues I left back in Rochester. Mostly, the pure existence of one.

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Don’t Be a Jerk

  • November 22, 2013
  • Personal thoughts

If there’s one theme that has been pretty consistent through the all-star lineup of Startup Institute fireside chat speakers, it’s this – don’t be an asshole.

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Drinking From the Fire Hose

  • November 12, 2013
  • Personal thoughts

One of the things I remember distinctly about the first day of Startup Institute came from Jenn, the director.

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Stop

  • October 24, 2013
  • Personal thoughts

Yesterday, we had a session on emotional intelligence. What it means, how it affects your relationships with your team and how you can be better at it.

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Drawing the Owl

  • October 22, 2013
  • Personal thoughts

I had read about this trademark Startup Institute phrase long before I walked in the doors, but it meant something today.

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Dream Makers

  • October 8, 2013
  • Personal thoughts

During my last week of work, I received an email in my inbox with the subject line, “for Kaleigh.”

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How it Feels

  • October 7, 2013
  • Personal thoughts

It’s Monday morning. For the past five years of my life, that has meant getting up at 6am and getting ready for work. Skirt and high heels, meetings and cubicles, 8 to 5, rinse and repeat. Today, Monday morning means the start of my two weeks journey packing up my life and everything I’ve known […]

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Recent Posts
  • A Tale of Two Cities
  • A Meeting Ten Years in the Making
  • About Journalism
  • Mom.
  • What I Learned From Several Years in Startups

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