Today is deeply meaningful for me: it marks seven years since my sister Kristin passed away and is my son Theo’s 3rd birthday. Today I reflect on how committing to values over comfort leads to a meaningful life. During Kristin’s illness, there were several months she spent intubated and on life support at Mass General…
All posts in Blog Posts
![[11] Reflecting Greatness – Gratitude as Insight](https://kdlibby.com/wp-content/uploads/2025/11/20230920_083552-scaled.jpg)
[11] Reflecting Greatness – Gratitude as Insight
When I decided to leave New York Life, I struggled with how to craft meaningful individual farewell messages for my closest colleagues. I wanted to express my gratitude in a way that matched the deep impact they had on me. Gratitude is often seen as a small gesture of connection. It’s also a way to…
![[10] A Life-Changing Product – My Whoop Experience](https://kdlibby.com/wp-content/uploads/2025/05/whoop-scaled.jpg)
[10] A Life-Changing Product – My Whoop Experience
How many products truly change your life? And of those, how many continue to deliver year after year? I joined WHOOP in 2019 on my brother Ken Libby‘s recommendation. At the time, we were still grappling with the loss of our sister Kristin, a tragedy that brought our health into sharper focus. It began as…
![[9] Purple Tuesday – How rituals can transform loss into inspiration](https://kdlibby.com/wp-content/uploads/2024/12/IMG_0539.jpeg)
[9] Purple Tuesday – How rituals can transform loss into inspiration
Today is deeply meaningful for me: it marks six years since my sister Kristin passed away and celebrates my son Theo’s second birthday. In this post, I reflect on the transformative power of rituals in honoring those I’ve lost. After college, my first role at NYL was in the Sleepy Hollow office. Like many of…
![[8] Becoming a Cyborg – How to Adopt Gen AI](https://kdlibby.com/wp-content/uploads/2024/10/IMG_0516.jpeg)
[8] Becoming a Cyborg – How to Adopt Gen AI
Amongst the flood of information on Chat GPT and similar tools, I initially struggled to engaged with Generative Artificial Intelligence (Gen AI) effectively. After months of research and trial and error, I’ve developed a practical guide for integrating these tools into daily work and life. This isn’t a collection of quirky use cases or speculative…
[7] Seed Collecting – How to capture and enable great ideas
Since moving the suburbs I set up a compost bin behind my garage. In addition to food scraps, I compost brown paper and even the decorative pumpkins at the end of the fall. Each spring, I empty the bin of mostly composted materials and bury it behind my patio for future use around the yard.…
[6] The Lemon Tree – How to use grief to make the world a better place
Today is a very special day for me: it’s the five year anniversary of the passing of my sister Kristin and my son Theo’s first birthday. This post is a reflection on growing anew following loss. When I was 13, I grew a lemon plant from seed, which over the years blossomed into an eight-foot-tall…
[5] The Last Drop of Toothpaste – How to appreciate the status quo before making changes
Every few months when I near the end of a tube of toothpaste, I flatten and crimp the end hoping to make it last a couple more days. Surprisingly, I routinely find that I get at least a couple of weeks out of it. The broader application here is we often underappreciate how much we…
[4] All Green Lights – How late night cab rides emulate the optimal customer experience
I recently discovered a business-applicable secret during my time living in Manhattan and staying out way too late: the cab ride home experience. Ride up or down a long avenue deep in the night and you’ll experience the optimal timing of traffic lights. Each light will turn green as you approach and you can often…
[3] Shredding the Veil of Difficulty – How to overcome a prerequisite mindset
Growing up, I was always fascinated by people who could accomplish hard to replicate feats; as a 10 year old, solving a Rubik’s cube fell in this category. With the help of a library book (if only YouTube had existed back then!) I taught myself the solving algorithms which are still committed to memory. I’m…