
I can’t leave disorder alone.I don’t mean dishes in the sink or clothes on the floor.1 I’m talking about behaviors that feel out of place, patterns that don’t line up, and other things that don’t make sense.This kind of disorder itches my brain in the best way. It draws me in. It makes it so I can’t put the puzzle down until I connect all the pieces.I’ve found the best way to scratch this particular itch is to ask questions because questions determine what you see.I thrive on unraveling the knots that feel too tangled to touch but too important to leave.I apply this compulsion to strategy at Point:Value, deep thinking at The Glaede, and my research, writing, and speaking at WTP.If you’ve found the easy answers aren’t working, let's connect.I promise, I’ll ask questions.
The Brain
Research, essays, and talks that provide a shortcut to deep thinking — without shortcutting the thinking.
The Community
A refuge to explore questions with other people who find deep thinking essential and fun.
Most people want neat answers. You want a totally different vantage point.Join the 300+ minds wrestling with better questions so they can make sense of things in a gray world.WTP is the only newsletter that gives you a shortcut to deep thinking — without shortcutting the thinking.

Knots I'm Unraveling
What is strategy, really? And what does that mean?
Book forthcoming.
What are the effects of prizing "changing the world"?
Article forthcoming.
What's causing runaway costs at independant schools?
Original research forthcoming.
I am committed to engaging in transparent and ethical practices. This AI Usage Policy details which Artificial Intelligence systems I use and how I use those systems. While I remain committed to adopting new technologies to aid my work when possible, and encourage my clients to do the same, I also understand the risks and limitations of various AI systems.Last Updated: February 6, 2026
This policy applies to the use of all AI systems. For the purposes of this policy, the term “AI system” means an engineered or machine-based system or functionality that is designed to generate outputs such as text and images, make predictions, or create recommendations influencing human action in real or virtual environments. This includes software products licensed by me or my companies for use in projects and activities and any other external AI tool I may use in the course of performing my work.
Based on the AI tools I currently use, I understand AI as a “bag of words.” This metaphor, coined by Adam Mastroianni, compares AI to a bag of words that contains all the words that could be scraped off the internet or scanned out of a book. When users send words into the bag, the AI system sends back the most relevant words it has. There are so many words in the bag that the most relevant ones are often correct and helpful.
I use AI for things that a bag of words can do well. Specifically, I use AI tools to conduct research, analyze unstructured text data, create LinkedIn posts based on articles I’ve written, generate meta-data for articles, draft emails, and search the web.
I do not outsource my thinking or relationships to AI. AI systems can support and enhance output, but they are not a substitute for original human thinking or genuine human connection.
Moreover, I advise my clients not to use AI for thinking or decision-making. Research shows that AI use in this context weakens cognitive abilities, which undermines much of the value I strive to deliver. While steps can be taken to mitigate this damage, the effort required suggests these steps will not be consistently taken. Therefore, I advise against adopting this practice.
I evaluate all AI output. I acknowledge that AI systems can generate authoritative-sounding output that is incorrect, incomplete, or biased. I review everything an AI system generates and am solely responsible for the quality, integrity, and accuracy of such content, regardless of whether AI systems were used in the production of that output. I also acknowledge the limitations and biases inherent in the AI systems I use and I take appropriate steps to mitigate these limitations.
I treat all information gathered from my clients as strictly confidential. I ensure that nothing is stored by the AI system or used for AI training purposes.
I continue to learn and adapt. I recognize that AI is a rapidly evolving field. I am committed to reviewing and updating this policy as needed.
I disclose my use of AI systems whenever requested. My use of AI systems is limited to the following tools and purposes:
Notebook LM. I use Notebook LM to analyze unstructured text data. | Generative AI, Natural Language Processing (NLP), Expert Systems
I use Gemini as a research assistant. Specifically, I use Deep Research to gather information and create reports. I then use Gemini to analyze those reports, compile and analyze datasets, proof documents, and red-team arguments and results. I also use it to create LinkedIn posts, search the web, as a dictionary/thesaurus, and as a calculator.Generative AI, Multi-Agent Systems, Natural Language Processing (NLP)
System Spellcheck
I use built-in spell checker tools to correct grammatical, spelling, and formatting errors.Narrow AI, Algorithmic AI, Natural Language Processing (NLP)
I use Riverside.fm to transcribe audio and video content.Algorithmic AI (audio/video processing), Computer Vision (transcription)
I’ve taken steps to turn off AI functionality in the other tools I use but I recognize that product updates can result in changes. Here are the tools that may be affected:
Calendly. I use Calendly to schedule appointments.
Gmail. I use Gmail to send and respond to email communications.
Google Slides. I use Google Slides to create reports, guides, presentations and facilitation decks.
Google Docs. I use Google Docs to create and edit documents.
Google Sheets. I use Google Sheets to capture data and create and edit spreadsheets.
Google Forms. I use forms to create and deploy surveys.
Brave. I use Brave to access other tools.
Walling. I use Walling to capture and reference notes and ideas.
Airtable. U use Airtable as our CRM, project manger, financial manger, publication database, and to build tools for clients.
Microsoft Excel. I use Microsoft Excel to open and edit CSV files.
Microsoft PowerPoint. I use Microsoft PowerPoint to build presentations.
Coda. I use Coda to manage our company and build the same kind of tool for clients.
Zoom. I use Zoom to host facilitated sessions and to capture screenshare videos.
Google Meet. I use Google Meet for brief one-on-one meetings.
I reserve the right to change this AI Usage Policy at any time. If I decide to change it, I will post the changes on this page to ensure transparency regarding my use of AI systems.
If you have any questions regarding this AI Usage Policy, please contact me by email at [email protected].

She works with teams at Point:Value and hosts a space for questioning at The Glaede. Through WTP, she shares her research, writing, and talks so you can discern what’s valuable — and ignore what isn’t.As a sought-after expert who provokes deeper thinking, Katie has delivered keynotes, talks, and workshops for curious teams and communities — including those at Babson and the Ascent Conference. She's also appeared on numerous podcasts like On Brand with Nick Westergaard, Leadovation with Dean Newlund, and Soloist Women with Rochelle Moulton. Her work has been published in Entrepreneur, The Startup, UX Collective, and Social Media Examiner.Katie is a city dweller who walks everywhere she needs to go. She’s direct and meticulous and thought the first day of school was the best day of the year. She doesn’t understand small talk, loathes having her time wasted, and does her best to never waste yours. Her grandparents still read her newsletter.