Reflections from a “Think Week” Retreat
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Last week, I went on my first “Think Week” retreat.
Three days. Limited connectivity. No meetings. Just reading, deep conversations, journaling, and thinking.
I typically try to take a “Think Day” about once a month—but with the utter chaos of my book launch and tour over the last 12 months, I hadn’t been able to create the space necessary to zoom out and properly engage in this ritual.
If I’m being completely honest, I’d grown increasingly overwhelmed during that period. I'd felt the steady buildup of stress, anxiety, and tension that thrives in a reactive environment of constant stimulus and response.
So when my business partner proposed a “Think Week” retreat at his home in Cabo, I blocked my calendar and eagerly awaited its arrival.
The plan for the retreat was simple:
- 3 days
- Unstructured schedule
- Big questions as catalysts for reflection and discussion
(Note: For detail on specific question prompts, see here)
To say the experience was transformative would be an understatement.
Here are my most important reflections and learnings…
1. Urgency is the new oxygen.
I believe we’re entering a historically good period for those with hunger, high-agency, and bias for action.
But also a historically bad period for those without those traits.
AI has fundamentally disrupted the entire notion of an “average” knowledge worker. It’s no longer a viable option to simply punch the clock and go through the motions.
In a recent note, Axios CEO Jim VandeHei offered the following (emphasis mine):
“Employees need the hard truth that entire classes of jobs could be wiped away, especially if people don't quickly adapt…We tell most staff they should be spending 10% or more of their day using AI to discover ways to double their performance by the end of the year. Some, like coders, should shoot for 10x-ing productivity as AI improves.”
Urgency is no longer a nice to have—it's a necessity. A requirement for survival. The new oxygen.
P.S. The good news here: If you’re reading this, you’re self-signaling the traits of someone set to benefit from the tectonic shift that’s happening. Let’s keep learning, growing, and lifting others up along the way.
2. Distractions masquerading as opportunities are the greatest threat to progress.
The most damning distractions rarely look like distractions at all.
In fact, they usually look like opportunities. They might come with a stable paycheck, a shiny logo, or a promise for the future.
They’re a good thing—but they’re not the main thing.
The real threat to your progress isn’t failure—it’s lack of focus. There are plenty of opportunities out there that are clear, obvious, and entirely wrong. Just because you can do it, doesn’t mean you should do it.
Get comfortable saying no to the good so you can say yes to the great.
3. I am optimistically pessimistic about the future of AI.
Let me start by saying that I’m a default optimist—I tend to see the good in things. I have an easy time dreaming on potential and upside.
But I’ll be blunt—I’m struggling here.
During the retreat, I was reading an Axios AI newsletter about the new Anthropic release, when I got stopped in my tracks…

I posted on X that this seems…not good and got over 8 million views after the post was shared by Elon Musk.
To be clear: It’s not that I think this one release creates an immediate cause for concern—for all I know, this is a savvy marketing tactic by Anthropic to get more eyeballs on the new launch—but it did elevate a serious question in my mind.
Who has the incentive to think humanity-wide about AI governance and safety?
My answer: No one.
At the company level, the incentive is to move as fast as possible to make the biggest splash with the newest release and maximize profits.
At the national level, the incentive is to move as fast as possible to get the all-powerful AI before your geopolitical foes.
We will need global AI treaties in the same way we needed global nuclear treaties.
I worry that it might be the type of thing where no one thinks it’s necessary until the line is crossed. With rapid change, you have to act when it feels too early, otherwise it’s already too late.
So while I remain optimistic about the capacity of these new technologies to unlock human potential, health, creativity, and more—I am increasingly pessimistic about our ability to navigate the terrifying array of humanity-wide consequences of a lack of safety precautions and governance.
4. The worst decisions are made when you allow your head to talk you into something when your gut said no.
Reflecting on my biggest misses of the last few years, they follow a pattern:
- Scan opportunity and get excited (my natural optimism).
- Spend more time on it and develop some gut reservations.
- Talk myself into it on the basis of its potential upside.
- Delay removing myself even though I know it’s the right thing to do.
Put simply, my worst decisions were a result of allowing my head to outsmart my gut.
Well, no more. There are too many opportunities out there to chase things that give me pause.
New rule: If it doesn’t feel right, it’s not right.
5. There are basically two simple questions that cut through the noise on any new opportunity.
Those two questions are:
- Do I want the winning version of this thing?
- Am I willing to pay the price to get that winning version?
The first question forces you to think about whether you actually like what that thing looks like if you win. It’s another way of asking whether you like what the top of that mountain looks like.
So many of us spend our whole lives climbing a mountain without ever pausing to ask whether we want the view from the top.
The second question forces you to think about the energy necessary to get to that winning version. A lot of people like the idea of the winning version, but never consider the pain and sacrifice necessary to earn it.
The winning version is often unlocked through years of crawling through the mud on the losing version.
If you can’t find joy in that meaningful struggle, you probably shouldn’t take it on in the first place.
6. The value of long-term thinking peaks at the same moment as the temptation of short-term thinking.
The moment of maximum uncertainty is the moment of maximum upside.
But that’s exactly where most people falter. They jump at the easy out. They grab hold of the quick fix. They make the obvious play.
And unfortunately, short-term thinking at the testing point is not easily reversible—it’s hard to unwind the impact. The decisions linger. They act as blockers to future opportunity.
The most asymmetric rewards belong to those who are willing to confront the uncertainty and wait just a little bit longer.
7. Winning takes care of everything.
The journey will have a lot of noise.
There are hundreds of problems. Countless variables. Endless stakeholders.
But all of it—and I mean all of it—falls into place when you win.
It’s easy to get lost in the noise. You address every single problem individually. You try to weigh all of the different stakeholders and variables. You tie yourself into an unsolvable knot.
Just focus on winning. It’s the one thing that takes care of everything else.
You Need Space for Transformation
Psychologist Viktor Frankl is often quoted as having said:
“Between stimulus and response, there is a space. In that space is our power to choose our response.”
Our power is in the space that we can create between stimulus and response.
My “Think Week” was a transformative experience. It didn’t require I have any special talent or intelligence—just that I create the space for transformation.
Because here’s the truth:
The growth you asked for is found in the space you’ve been avoiding.
