Tim Cheadle
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timcheadle.com
Tim Cheadle
@timcheadle.com
VP of Agentic AI at Phaidra
I love to build products people love.
Here for hoops, music, food, friends, and mayhem.
Be kind. 💙
Thanks Mike!
September 14, 2025 at 7:19 PM
If you enjoy lessons like this, you might like my newsletter:
www.timcheadle.com#/portal/signup
September 14, 2025 at 6:49 PM
For months, I asked myself if I was wasting this time. Was I failing at my break? It finally hit me that time off isn’t about success or failure or productivity.

Letting go of that pressure gave me the space to rediscover myself and to rethink how I want work to fit into my life moving forward.
September 14, 2025 at 6:22 PM
I'm an idiot. Here ya go 😆

www.timcheadle.com/dont-let-cri...
Don't let crisis become a compass
Crunch time feels productive. It also reveals problems hiding in plain sight.
www.timcheadle.com
July 29, 2025 at 6:37 PM
Here's a working link! Hilariously I wrote this thread too fast 🤦‍♂️

www.timcheadle.com/dont-let-cri...
Don't let crisis become a compass
Crunch time feels productive. It also reveals problems hiding in plain sight.
www.timcheadle.com
July 29, 2025 at 6:36 PM
I write about engineering, product, and how to lead with skill and build with soul. No fluff, no hype, just hard-earned lessons, shared every week or two.
July 29, 2025 at 4:10 PM
I dove deep into why we get addicted to urgency and how to build sustainable productivity in my new newsletter "Built to Last."

Read the full piece and subscribe if you dig it.
timcheadle.com/dont…
https://timcheadle.com/dont…
July 29, 2025 at 4:10 PM
What you're actually seeing is a stress response that temporarily overwhelms the dysfunction that's always been there.

Crisis doesn't create great teamwork, it reveals what's been preventing it all along. If urgency is how you get focus, it's time to set a better course.
July 29, 2025 at 4:10 PM
In my experience, deep focus is already hard in offices. As companies push RTO while AI makes interruptions more expensive, it'll be interesting to see if office culture adjusts. I doubt it, as a return to office is really more about a sense of control.
May 22, 2025 at 6:06 PM
Also, I wound up prepping a 20 minute talk about the story of building Simple.org

It was a lovely walk down memory lane. We solved so many weird and interesting problems, work I’m quite proud of.

If you’d like to hear this story, let me know.
Simple.org
Fast, free software for clinicians to manage patients with hypertension & diabetes.
Simple.org
April 5, 2025 at 3:34 AM
Black excellence is the American dream.
Happy Black History Month ✊
February 10, 2025 at 5:06 PM
The larger story matters. It was for and by Black folks, a reminder of experience and community and power. It told white supremacy: you can lock us up but you can't trap our minds. He also reminds Drake he's a leach, forever an outsider to all of this.
February 10, 2025 at 5:06 PM
Same. Her mannerisms were off from the jump.
February 10, 2025 at 3:12 AM
My recent obsession is CrosswordJam+ on Apple Arcade. It gives you 5-7 letters and you find all the words you can. I turn all the sounds off and just space out.

It's SO calming.
February 9, 2025 at 5:54 PM
(No, my 8 year old doesn't have a phone. She uses her iPad)
February 9, 2025 at 5:41 PM