The more I work with and use AI, the more convinced I am that AI is going to replace most jobs and make many skills obsolete. It got me thinking:
What should I do when AI is capable of doing 80% of what I used to do?
With AI, output is abundant. But clarity remains scarce.
The game isn’t just about doing more—it’s about doing what matters. And that requires distinctly human skills: pattern recognition, judgment, curiosity, and creativity.
These 25 skills aren’t trendy hacks. They’re durable capabilities that help you do what AI can’t. They are what I’ve learned from experience, research, and the people I study—founders, creatives, operators, and lifelong learners like you.
1. Ask Better Questions
Good questions beat good answers. When a startup asked how to grow faster, we paused and reframed the conversation: "What’s stopping current users from coming back?" That shift changed the roadmap. In A More Beautiful Question, Warren Berger shows how breakthrough ideas often begin with reframed questions—not clever answers. AI can generate thousands of ideas. The right question helps you choose the right one.
2. Make Decisions in Uncertainty
Uncertainty is part of every meaningful pursuit—building a product, launching a career shift, or making a hire. Simple rules like "what’s the downside?" or "what would I regret more?" help cut through the fog. Psychologist Gerd Gigerenzer found that simple heuristics often outperform complex models in uncertain environments. You don’t need certainty—you need a way to move forward.
3. Zoom Between Strategy and Tactic
Running a brand often means jumping between vision, strategy, and tactics. One hour, you’re shaping long-term vision. The next, you’re troubleshooting a landing page bug. Jeff Bezos called it "diving deep while thinking long-term." Those who can zoom in and out—without losing focus—gain an edge.
4. Get Clear on the End and the Now
Stephen Covey’s “begin with the end in mind” meets Eckhart Tolle’s “power of now.” Most people obsess over future goals or get lost in daily to-dos. The best operate in both. They stay rooted in present action while being pulled by a compelling long-term vision. Two questions I ask myself often: Does this move me closer to what I truly want? Can I give it my full presence now, regardless of the outcomes?
5. Get Close and Sit With the Real Problems
It’s tempting to build in isolation. But real traction starts with proximity. When running workshops, I learned more from hallway conversations than surveys. Clayton Christensen, in The Innovator’s Dilemma, emphasized the importance of understanding real customer struggles. AI can simulate personas. But nothing replaces direct connection.
6. Design For Leverage, Not Busyness
High-leverage thinking isn’t about doing more. It’s about doing the right thing once and letting it scale. That could mean shaping brand positioning that attracts ideal customers or making one hire who unlocks new capabilities. Naval Ravikant calls this "moving from labor to leverage." The question is: what moves create the most results with the least friction?
7. Hang Out Where New Things Begin
Breakthroughs often happen on the edges—in small communities, weird forums, niche meetups. Some of my best ideas came from being early in the right rooms. Peter Thiel said, "Look for secrets hidden in plain sight." AI has access to more data. But it can’t join underground scenes or read the room.
8. Tell Stories that Move People
Data informs. Story connects. When launching Wolo Yoga, telling the story of how yoga helped one customer feel strong again resonated more than technical specs. Yuval Noah Harari argues that humans run on fiction. People don’t buy the what—they buy the why.
9. Facilitate High-Level Conversations
Whether you’re leading or contributing, helping people see what matters is a superpower. Not by talking more—but by listening, reframing, and asking better. Great conversations shift direction, clarify thinking, and unlock alignment.
10. Create an Environment With Upward Spiral Loops
When I created a habit of reading first thing in the morning, everything else improved—ideas, focus, writing. BJ Fogg’s research at Stanford shows that behavior design beats willpower. Tiny cues lead to tiny actions, which lead to bigger ones. Design your environment to make doing what's good easier.
11. Make Things People Want
Paul Graham wrote this for startup founders, but it applies to creators, consultants, builders—anyone. AI can generate ideas, but it can’t feel what your audience deeply needs. Always ask: Would someone be disappointed if this disappeared tomorrow?
12. Unlearn Things That No Longer Work
The hardest part about growth isn’t learning—it’s unlearning. I had to unlearn strategies that worked at AppSumo when growing Wolo. I had to unlearn habits that served me in my 20s but drained me in my 30s. In Think Again, Adam Grant shows how success can make us rigid. In a fast world, flexibility beats expertise.
13. Write to Think Clearly
Writing is a thinking tool. When I write, I clarify what I believe, spot fuzzy logic, and discover gaps. Anne Lamott said, "Thoughts untangle themselves passing over the lips and through pencil tips." AI can generate text. But it can’t clarify your beliefs. Only you can do that.
14. Connect Ideas Across Worlds
Wolo Yoga came from mixing performance gear design, mindfulness culture, and DTC marketing. This blog does the same—pulling from business, psychology, personal growth, and systems thinking. Charlie Munger attributes his edge to a latticework of mental models. Innovation is often recombination.
15. Work Backward From the Truth
Start from what’s real—your beliefs, your market’s pains, your values. I’ve marketed things I didn’t fully believe in. It drained me, and I underperformed. Steve Jobs was famous for this. Don’t fake alignment. Begin with the truth. Then build.
16. Show Your Work Early
Every time I shared early drafts—blog posts, ideas, landing pages—I learned faster. In The Lean Startup, Eric Ries emphasizes launching Minimum Viable Products. It's not just for software. It applies to everything we create. Share before you feel done.
17. Turn Wins Into Systems
When something works—launches, hiring, onboarding—capture it. Create a process, template, or checklist. At first, it feels like extra work. Later, it saves time and builds momentum. James Clear wrote, "You do not rise to the level of your goals. You fall to the level of your systems."
18. Review, Reflect, and Recalibrate Often
Weekly reviews changed the way I work. Not because they add more tasks, but because they help me notice what drains or energizes me. Research on deliberate practice shows that reflection, not just repetition, drives growth. Think of it as mid-flight corrections.
19. Ship Before You're Ready
Every meaningful project—this blog, courses, Wolo Yoga—was launched before it felt perfect. Professionals ship. Seth Godin calls the delays “thrashing.” The market doesn’t reward potential. It rewards clarity through action. The internet made reaching your customers cheaper and faster. AI does the same to building and shipping your ideas. Start now, improve later.
20. Curate Your Inputs With Intention
Too much input = no room for insight. I started following a rule: create before you consume. Cal Newport’s digital minimalism isn’t about rejecting tech. It’s about choosing inputs that fuel your best work. Be intentional with what enters your mental space.
21. Stick With One Bet Long Enough to Compound
Compounding looks slow—until it doesn’t. Whether it’s writing, relationships, investing, or business, sticking with one thing unlocks nonlinear growth. Morgan Housel calls compounding the most powerful force in finance—and life. Don’t reset the clock too soon.
22. Build Conviction, Not Consensus
When we launched Wolo Yoga, no one knew if it would work, and not everyone agreed with our design choices. But we had a clear POV—and stuck with it. Peter Thiel suggests asking, "What do you believe that most people don’t?" Consensus feels safe. Conviction creates movement.
23. Develop Your Taste and Express It
Taste is what makes your work yours. I used to copy what worked for others. It's part of the process. Over time, I developed and learned to trust my instincts. Steve Jobs obsessed over details because he had taste. Sophia Amoruso built Nasty Gal, curating what she loved. Taste is the new signal.
24. Get Robust by Building Reserves
After moving on from AppSumo, I was grateful I had a 12-month runway fund. It gave me space to explore, recover, and build. The Stoics called it premeditatio malorum—prepare for the worst to act with courage. Nassim Taleb calls it antifragility. Reserves—money, time, energy—are what give you room to think and adapt, especially in times of chaos.
25. Protect Space to Think Deeply
AI floods us with both inputs and outputs. What’s rare now is stillness. I block time for walks, conversations with my wife, and writing to think (see #12). Paul Graham calls this "maker time." Without it, you’re stuck in reactive mode, responding to everyone else’s priorities.
