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Start When No One Is Watching
That's when it's safest to fail - and smartest to begin.

Lately, my Garmin running watch has been nudging me toward longer and longer runs. And honestly, I am trying to keep up with it — mostly because I want to see my (low) VO2Max climb again. (Hello, running nerds 👋)
Anyways, it also gives me time to catch up on audiobooks. And so I recently queued up Malcolm Gladwell’s Outliers.
I’ve heard his general concepts before, but since I saw it on Jensen Huang’s top 6 must-reads list, it went straight into my Spotify playlist.
A few weeks back, I posted about The Career Framework that Changed How I Think — how catching the right tech wave inside the right company can reshape your career trajectory.
Listening to Outliers expanded on these thoughts, and I truly believe, now reinforced through the book, no matter what industry you are in, our generation will see massive shifts invoked by AI. These shifts will bring opportunities.
Gladwell talks about how talent doesn’t matter as much as timing. And timing my friends is on our side.
So let’s talk about what Outliers can teach us about catching this moment.
(Plus: a short take on Ray Dalio’s post about tariffs and why the global order is changing, no matter if tariffs are walked back or not.)
Timing Beats Talent
In Outliers Gladwell explores the hidden advantages behind extraordinary success. One key insight: being born at the right time matters just as much as what you do.
He directly points out how Bill Gates, Steve Jobs, Steve Ballmer, Vinod Khosla and many other names you will connect with success in the early computer world were born in the mid-1950s. They hit that computer tech wave at just the right age. Old enough to understand it, young enough to fully ride the wave.
Start When No One is Watching
Gladwell goes deep on Bill Joy in Outliers. Joy, also born in the mid-1950s by the way, is a co-founder of Sun Microsystems and a key early contributor to BSD Unix - software that still influences systems today. In fact, rumors say, some of his code can still be found on a Mac.
Gladwell describes that it wasn’t just talent that helped him.
In the early 1970s, computers still relied on punch cards — a super slow process. You write code, hand in the punch cards, and wait for hours (or sometimes days) to get the results.
But at the University of Michigan, Joy got access to a cutting-edge system. It allowed multiple users to interact with a terminal in real-time. Decades ahead and leaps faster to see if your code worked or not. And Joy spent almost all his time there.
This is where Gladwell introduces his now famous “10,000 hours needed to become a master in any skill” rule. Bill Joy had the opportunity to get comfortable and proficient much faster than almost anyone else. And when no one was watching. But just having access wasn’t the reason. Putting in the hours and gaining hands-on experience did it for him.
When personal computing took off, Joy was already a master.
Pattern Recognition
The historical pattern of tech waves goes like this: Industrial Revolution, Computers, the Internet, Mobile, and now, AI.
Before the era is established, there is a small time window where it’s the wild west. No rules, nobody is watching, free roam. And that’s the best time to start.
What matters during these windows is access and effort.
It’s not hard to see where I am going with this. Doesn’t AI feel like that window again?
Even if all our newsfeeds are full of AI headlines… Most people (or companies) have no idea what they're doing. Not how to apply it, not how to control it, not how to improve it.
People who build, apply, and experiment with AI now will reap the advantages later. They’ll have the edge.
What Would Bill Joy Do in 2025?
He’d dive into AI. Not wait for AI to come to him. We all need to start putting in the hours. But we’ve all got full-time jobs, so what can we do to get started? How can we build AI skills and get our practice hours in right now?
In my post 'The Career Framework that Changed How I Think,' I talk about which companies to look for. But in case you don’t want to switch, you could still start racking up necessary hours and get deliberate practice with AI:
Learn how AI is affecting your industry.
What are competitors doing with AI? What startups are emerging that will disrupt your business? What will your company need in 12-18 months, and who builds AI that can help with that?
Approach Tech Incubators
Silicon Valley Incubators, like Plug and Play, usually work closely across industries. They match disruptive startups with enterprises and their problems. Reach out to attend demo days or let them help you explore case studies.
Shadow an exec for a day
Observe how they work and where they spend time. Document everything that could be supported or enhanced by AI. Then build a “what-if” or “how might we…” deck that lays out an AI strategy. Once you have collected all the pain points, ChatGPT can help with solutions and content—no need to come up with them yourself.
Offer “AI Curiosity Office Hours” (trademark pending 🙂)
Set up a recurring time for coworkers to drop in and ask AI-related questions, brainstorm ideas, and use cases. Great way to build visibility and establish yourself as “The AI Person”.
Automate painful tasks in your job
Look for anything repetitive, manual, or dead boring.
If nothing comes to mind, start talking about other people
Find coworkers across teams. Offer help to automate their workflows. I am sure they’ll be able to call out some painful things they’d like automated
And here is the best part, this is not mandated by anyone. So no one is watching. The best time to fail! And from failing, we learn. And we learned before anyone else.
Outliers Show Up Early
We don’t need to be geniuses. We just need to show up early.
There is no playbook just yet. And while we are still in the wild west of AI. And that’s the perfect time to learn. We’ve got the freedom to experiment, learn, and fail forward.
And later, when it matters? It will look like we always knew what we were doing. 🙂
📖 Good read
Ray Dalio - It’s Too Late: The Changes are Coming
My take from his post: Big shifts are happening. The US role as top consumer and debt engine is going to end. There are current trade and capital imbalances that are just not sustainable. A complete realignment of the global order will follow. Less US involvement in global trade is happening.
This is not something caused by tariffs. But tariffs accelerated it. US consumption, financed with massive debt and made possible by US influence, is facing limits. Tariffs were like a kick in the face to everyone who hadn’t realized it. Now this situation can’t be ignored, no matter if tariffs are dropped or not.
x.com/i/article/1916…
— Ray Dalio (@RayDalio)
9:28 PM • Apr 28, 2025
Did you already rack up serious AI hours or maybe you want to host “AI Curiosity Office Hours” (trademark still pending)? Hit reply and let me know.
Have a great rest of the week,

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