Ever feel like you should be improving faster—but life keeps getting in the way?
Maybe in pickleball. Maybe in your career. Maybe in that one hobby you swore you’d get good at–
two years ago.
Yeah, same.
Between filming YouTube videos, editing content, and trying to find my future wife 😂, I catch myself frustrated.
Why haven’t I found her yet? Shoot, I mean–
Why am I not improving faster? (Stay focused, Kyle.)
See, five years ago, I got obsessed—not just with learning, but with how to learn faster.
Why?
Well… Covid.
Like everyone else, I found myself stuck at home.
So, I went deep into studying writing. Then I got into filming. Then editing. Then comedy. (Although, I wasn’t mad that Covid ended my stand-up career because my career stats were:
3 open mics
0 laughs
Not the best start for an aspiring comedian. But I digress.
As I studied how to learn, I realized something obvious—but still worth repeating:
High performers don’t learn like the rest of us.
They take a different approach. They have systems. And when you follow those systems, you see progress more quickly.
So today, let’s steal some ideas from four people who’ve mastered skill-building:
Jerry Seinfeld – Legendary comedian
Tim Ferriss – Bestselling author & life hacker
Josh Waitzkin – Chess prodigy & martial arts champion
Magnus Carlsen – World Chess Champion
Let’s start with Jerry.
Jerry Seinfeld – The Power of Daily Reps
One of the greatest comedians of all time, Seinfeld, swears by this system!
Commit to Daily Practice – Pick one skill & work on it every single day (e.g., writing jokes).
Track Progress Visually – Use a big calendar & mark a red X after he wrote jokes each day.
Never Break the Chain – Keep the streak alive, even if the effort is small. And if you do miss a day, don’t miss twice. Gosh I love this one!
Let Momentum Do the Work – The longer the streak, the easier it gets to keep going.
Tim Ferriss – Learning Faster with D.S.S.S.
Ferriss is a master at picking up new skills in record time. His method?
Deconstruct – Break the skill into smaller, manageable parts.
Select – Identify the 20% of actions that produce 80% of the results.
Sequence – Learn things in the most effective order for rapid improvement.
Stakes – Add accountability, rewards, or consequences to stay motivated.
Josh Waitzkin – Mastery Starts with Fundamentals
A chess prodigy turned world-class martial artist, Waitzkin’s approach is all about deep mastery.
Master the Basics First – Drill core techniques until they feel automatic.
Increase Complexity Gradually – Layer in more advanced skills as you improve.
Train Under Pressure – Practice in real-world, high-stakes situations.
Let Intuition Take Over – Once the basics are ingrained, creativity and instinct drive performance.
Magnus Carlsen – Success equals Recognizing Patterns Faster
Carlsen isn’t great at chess because he memorizes everything. He’s great because he sees patterns faster than anyone else.
♟ Immerse Yourself in Data – Study past games, strategies, and real-world cases.
♟ Spot Key Patterns – Train yourself to recognize recurring structures instantly.
♟ Develop Automatic Decision-Making – React quickly by internalizing common scenarios.
♟ Refine Through Experience – The more you play, the more instinctive your decisions become.
For the record, this is THE exact reason I started the Pattern Recognition library inside ThatPickleballSchool (available for annual members).
So, What Do All These Approaches Have in Common?
Show Up Every Day – Improvement isn’t about massive breakthroughs. It’s about small, consistent effort.
Keep It Simple – The best learners don’t overcomplicate things. They break skills down, focus on the essentials, and build from there.
Pressure-Test Your Skills – Growth happens when you challenge yourself in real conditions—whether that’s in chess, comedy, or pickleball.
That’s exactly why I’m running a 30-day challenge inside THATPickleballSchool.
In order take a group of players from 3.5 to 4.0 (or better) in just 30 days.
By applying principles like these— strategic learning, pattern recognition, and real-world testing—you’ll have the opportunity to experience the breakthrough you’ve been wanting, but haven’t committed to make happen.
Until now 🙂
So…
If you've been feeling stuck or like progress is slower than you'd like, maybe it’s not about working harder.
Maybe it’s about learning smarter.
30 days.
Focused effort.
Let’s see what happens.
Are you in?
-Kyle
P.S. If you’re already a member of ThatPickleballSchool and you want to join the 30-Day Challenge, you can sign up directly right here:
🎉 EXCLUSIVE OFFERS FOR YOU 🎉
1️⃣ Join ThatPickleballSchool before March 28th at 1PM ET to participate in the ‘3.5 to 4.0+ 30-Day Challenge.’
2️⃣ USE CODE: INF-thatpickleballguy to get a digital gift card when you shop all things Selkirk.
3️⃣ Use THIS LINK to get 15 credits (that’s 15 FREE AI Match Analysis) with PB VISION.
Thanks for reading! Reply any time.