Issue #005: The New (Old) Job Skill Nobody Taught You
The future will belong to those who think about their thinking, and how to make it as wise as possible.
I’m convinced of that after a couple of events in recent weeks.
The first was hearing Ryan Holiday, author of The Daily Stoic, speak in Seattle about Stoicism.
Two thousand years later, wisdom from ancient Greece is still steadying our nervous systems in the middle of modern chaos.
The other event was meeting with Paresh Rajwat, VP at Google, for a Zoom meeting following Seattle AI week.
I shared with him that at Seattle AI Week, I kept hearing a variation of the same line:
“AI isn’t coming for your job — but someone who knows how to use AI well probably is.
We discussed how important critical thinking is/will be in terms of using AI expertly.
Both perspectives landed in the same place from different angles:
Thinking well — and thinking about your thinking — has become one of the most important job skills of our time.
Here’s why.
As AI becomes more capable, the differentiator won’t be who has the most information (AI can produce that instantly).
The differentiator will be:
- the quality of your questions
- how you frame problems
- how you weigh options
- how you integrate emotion and logic
- how well you orient yourself in uncertainty
In other words:
AI won’t replace thinking. It will expose, and build on, the quality of your thinking.
Critical thinking is foundational and perhaps the most important job skill is…judgment.
Judgment is thinking about your thinking.
It’s the ability to orient yourself wisely when there is no clear answer. And it’s the skill almost no one was taught.
Let’s walk through what that actually means.
What Critical Thinking Actually Is
Critical thinking is the ability to slow down, examine assumptions, weigh evidence, and make judgments that fit the situation.
It includes:
- curiosity
- perspective-taking
- reflection
- emotional awareness
- ethical consideration
As Paresh reminded me, AI is only as good as the prompts you give it.
If we think better, we prompt better.
Were We Ever Really Taught This?
Most schools focus on content, compliance, correct answers, and speed.
Much less time goes into:
- framing questions
- revising beliefs
- tolerating uncertainty
- integrating emotion and logic
Right answers are often valued over good questions.
So if you feel unpracticed at critical thinking, it’s not a personal flaw — it’s a systemic gap.
How Critical Thinking Is Actually Learned
You don’t learn thinking by memorizing facts. You learn it through:
- real decisions
- feedback
- reflection
- perspective shifts
- safe spaces to be wrong
And AI now gives us something school rarely did:
- a place to externalize thinking
- a way to test assumptions
- room to iterate without embarrassment
Used well, AI becomes a thinking gym. That’s what I love about it!
3 Core Thinking Skills for Better Living
What thinking skills will actually help us exercise better judgment so we can enjoy better health, work and life? See a quick list below.
Problem Framing
Ask yourself: “What problem am I actually solving?”
Most errors happen before solutions begin.
As the saying goes: “A problem well stated is a problem half solved.” -Charles Kettering
Try This:
Before prompting AI, write one sentence: “I am deciding about ______.”
It will sharpen everything that comes next.
Intellectual Humility + Confidence
Be coachable. We are constantly iterating. “I don’t know — and I can learn.”
Be humble about constantly updating your knowledge without shame.
The goal is thoughtful confidence.
Probability Thinking
Uncertainty can be very unsettling, and in the absence of concrete answers, we can become anxious.
But practicing probability thinking can help. Ask: “How likely is this — not is it true or false?”
Life isn’t binary. There are ranges, likelihoods, and tradeoffs.
A wonderful book on this subject is Thinking in Bets by Annie Duke.
Probability thinking reduces anxiety and improves outcomes.
So What Is the Skill We’re Actually After?
I’m going to be honest and say that the skill I’m working on most is:
Judgment under uncertainty.
The ability to orient yourself wisely when outcomes are unclear.
I have felt this in business and in making health decisions for my neurodivergent family
Judgment is knowing what matters, what doesn’t, when to wait, and when to act.
And it’s the skill almost no one has been taught — until now.
The 5 Judgment Skills You Can Practice Daily
1. Decision Clarity
Start with:
“I am deciding about ______.”
If no decision exists, you’re not thinking — you’re spinning.
2. Naming the Type of Problem
Is this primarily a:
- knowledge problem?
- emotional problem?
- values tradeoff?
- timing issue?
- systems issue?
Wrong type = wrong solution.
3. Assumption Surfacing
I learned a great question from Michael Hyatt:
“What must be true for this plan to make sense?”
Then: “Which assumption might be wrong?”
This is where blind spots hide. The fewer blind spots you have, the better your thinking is.
4. Think Like a Poker Player: Probability Over Certainty
Replace “Is this right?” with:
- How likely is this?
- What’s the range of outcomes?
- What would increase or decrease my confidence?
Pro Tip: It’s great to challenge anxious thoughts or worries with questions like these. Seek evidence to see if what you’re worried about has a low or high probability of actually happening.
5. Take Time to Reflect: Post-Decision Review
After outcomes:
- Was it a bad outcome or a bad bet? A good outcome or a good bet?
- Did emotion lead the process?
- What early signs did I miss?
I could tell you about so many wrong turns and failed experiments, but I’m buoyed by the Edison quote:
“I haven’t failed. I’ve just tried 10,000 ways that won’t work.” Thomas Edison
Why This Matters in the Age of AI
This practice won’t eliminate risk.
But it will:
- reduce regret
- improve clarity
- shorten wrong paths
- increase confidence
- strengthen decision-making
- make you harder to fool
- help you use AI without losing yourself
Better thinking doesn’t guarantee a perfect life, but it dramatically improves the odds.
Thinking About a Workshop…
I’m thinking about holding a workshop to help us all think better with AI — applying everything above to your health decisions, work decisions, and life decisions.
If you’re interested, SEND ME AN EMAIL and let me know.
Your feedback helps me shape what I should teach.
All my best,
Debbie Steinberg, LMFT