June 11th Newsletter
A thought: What emotions are holding you back from your next big adventure?
You know that Sunday evening feeling? When you're thinking about the week ahead and a little voice in your head asks, "Is this really what I want to be doing?"
I know that voice well. For years, I felt like I was on a path that didn't quite feel like my own. That feeling is exactly what pushed me to make a huge change a while back, pivoting my entire career from the world of higher education into the deep end of data, analytics, and AI.
It was a challenging, rewarding, and eye-opening process. Along the way, I realized I was essentially creating a "playbook" for myself—first on how to change careers, and then on how to make sense of all this new technology in a practical, human way.
Well, I decided to use my notes and turn those playbooks into something real.
I've been working on this for a while, and I'm excited (and, honestly, a little nervous) to share them with you. I've collected all of my guides on my digital bookshelf over on Gumroad.
If you're curious, you can browse everything here:
»Take a look at my updated Gumroad page <<
I've tried to tackle a few of the big challenges I see people facing today:
* If you're feeling that career itch I mentioned, The Career Pivot is my story and my framework for finding what you're good at and making a change with confidence. It's the guide I wish I'd had.
* If you're in business and tired of all the AI hype, The AI Employee Handbook is my simple, practical take on how to actually use AI like a new teammate to make your life easier.
* If you're in sales, The Digital Advantage is about how to use all these new tech tools without losing the human connection that actually closes deals.
* And if you're ready to get your hands dirty with data, The Data Analyst's Jumpstart is my start-from-scratch guide to learning the exact tools (R and Power BI) that I used to build my new career.
I also bundled them up in case more than one sounds interesting.
My hope is that maybe these guides can help too.
No pressure at all, but I wanted to share with this community first. Feel free to just have a look around.
I’ve been working my way (as my employer will cover it, don’t get it twisted) through the Digital Transformation certificate with Stanford Online. I took the course on Human Centered Design last year and I’m working on the one for AI Enabled Organizations right now.

Last year I did the course "Human-Centered Design for Digital Transformation", a course that focused on developing solutions that solve customer needs through user research, rapid experimentation and building stakeholder buy-in.
Honestly, I was pretty stunned by how fantastic the content was in that first course, one of the better ones that I have ever taken. Well worth the cost of admission, I think about and apply those principles at least once a week.
I’ve written before about the value of digital thinking. I think it has the potential to change your career, your company and your life if you can buy in to this way of solving problems.
I know so many of us can get caught up in paralysis by analysis, or, worse, over invest in ideas that don’t work. Digital thinking is a way to help you manage that risk but keep moving.
I find the process thrilling.
I would love for my next career pivot to be emphasizing this way of working.
I've been following with great interest the American president’s forays into cryptocurrency and the genius act now making its way through Congress.
The world is getting more open to crypto and the US in particular.
People like to grade good things and bad and crypto, more often than not, is considered bad. I find this grading system to be flawed regarding technology. Technology is just a tool, it's not only good or only bad.
For the unfamiliar, what we're talking about when we say crypto is the token generated when a new record is recorded in a Blockchain. That token is basically a receipt, a log, that the record occurred.
There are many different iterations of this basic setup. But essentially a Blockchain is a fancy database and the tokens are records of what's being logged in the database.
What most people are talking about when they talk about crypto is transacting these tokens, likely buying and selling them like commodities.
There's some debate about whether crypto can be currency. Theoretically anything can be currency. Currency is assigned social value through what it's backed by. Seashells could be a currency if we agreed on value. The crypto market has a marketplace where these coins are bought and sold and they are benchmarked to global currency markets.
The issue with using crypto as actual currency is that often the transaction costs are very high. That being said, we are seeing more businesses charge a transaction fee on using a credit card so maybe transaction fees are just becoming a new normal if you don't use the US dollar.
The other big knock has been that crypto isn't backed by anything. I'm not sure that's accurate, I believe the backing is anti government and anti state. It's backed by the Internet and belief that the state can be worked around. I am skeptical of this belief as crypto gets more integrated into our financial system and is being pushed by the US president.
The genius bill in congress will open up the door to companies like Facebook and X and Amazon creating their own cryptocurrency. Do you want to own Facebook money? Do you have full faith in Mark Zuckerberg like you do the US government?
This arrangement will tie users closer to their platform and allow companies to operate with less oversight as they venture into “banking”.
My take for a while has been that crypto has the potential to cause a major global financial meltdown. Facebook money feels like a good match to start the fire with.
AI has managed to turn otherwise reasonable people into shrieking lunatics. I can’t help but hear a comment from Twitter - “when people say things used to be better, they are saying they used to be younger”.
I get there are a lot of critiques of AI and they’re all fair and reasonable.
But the outrage from some is so far past what’s even close to reasonable that it starts to take on the sound of Abe Simpson screaming at the clouds.
New things scare people and often older people struggle to understand real things. We all get comfortable and scared to adapt. Totally normal.
But progress continues. Things change. Best to go along and recognize the tendency to yell at clouds might be just signs of you losing touch.
An example of AI turning people insane, I saw a billionaire investor saying that AI was going to create massive demand for in person events because people won't know if things are real.
Man, no.
The question isn't whether it's real but whether it's valuable and solves a problem. Social media made it easy for connection to be made online rather than in person, Ai will make it easier to have online interactions with a human like entity. I don't see massive pent up demand for more human experiences now and I'm skeptical that they will materialize when there's a way to make a connection with something that feels like a human.
To put this in a different frame, social media allowing people to publish fake news, so people will want to go out and buy real news. How much more evidence do you need that isn't true?!??
People are looking for information about their world. People are looking to feel less lonely. That doesn't mean they'll buy subscriptions to the la times or they'll start going to more face to face events. . Do you notice the commonality? Subscriptions cost money. Face to face costs money. If you can get good enough, cheaper and easier, you will.
The other funny thing about this argument is that it assumes that face to face is always better. Anyone who's been to a professional conference can tell you that face to face interactions are often dull and inconvenient. Human systems are complicated.
An actually interesting question that people should be asking is when is getting a problem solved by an in person interaction actually better.
I would argue a crappy answer from your neighbor is better than a good answer from someone who lives 500 miles away and better than an answer from a computer, but maybe the new best will be my neighbor and I not needing the person 500 miles away when we can work with the help of the computer.
I've had this theory for awhile that technology is actually making our world more hyper local. If I can harness the wisdom of the Internet, via ai, to figure out some ideas for my life off the computer, maybe I should be focusing on making connections where I actually live rather than in the computer. Maybe I don't need that person 500 miles away if I can figure out my world with a little chat bot.