Hey 👋,
I’ve gotten a few questions about the 3.5 to 4.0 challenge, so I wanted to send out this email to everyone to answer some of the most common ones:
Q: When does the challenge start?
A: Monday, February 2nd, 2026.
We're kicking off with a FREE live webinar that day where I'll walk you through exactly how the challenge works, what to expect each week, and how to get the most out of it.
Even if you're not a member yet, you can join the webinar to see if it's right for you. (We’ll email the link out)
Q: How much time does this take each day?
A: Here is what you’ll do each day:
📅 Schedule: Set aside just 10 minutes a day in your calendar to log in, complete the lesson, and do the assignment. Consistency is everything!
🎥 Film: Make sure you have or go record a match, we will ask you to do this weekly so we can use the film to self assess and track our progress.
📖 Notebook: Take notes and journal your progress. Writing things down will help you absorb the lessons and track your improvement over time.
💬 Engage: Ask questions, share your work, and encourage others. Push yourself outside your comfort zone and eliminate FOPO (Fear of People’s Opinions). The more you engage, the more you’ll grow—both in this challenge and in your Pickleball game.
Drill: Yes, we're asking you to commit just 45 minutes just 1x a week to drill with intent. This is a requirement to ensure you level up. Find a partner ideally, or get a ball machine and put it on your schedule.
If you want to see the full plan, you can check out this Google doc:
(Just please don’t share it, it’s for internal purposes only)
Q: What if I miss a day?
A: No problem.
All the content stays available inside your ThatPickleballSchool classroom, so you can catch up whenever you need to. This isn't a "fall behind and fail" situation. It's structured so you can move at your own pace.
That said, the magic happens when you show up consistently. Even 3 days a week is better than zero.
Q: Do I need a partner to do the drills?
A: Nope.
Some drills work better with a partner, but most can be done solo or adapted to whatever you have available. We'll give you options for each one.
Q: What's the actual structure? What am I learning?
A: Great question. Here's the week-by-week breakdown:
Week 1: Automate Your Openings
Stop thinking on the first four shots. Learn to automate your serve opening and return target so your brain is free to read the game. Plus: how to study your own film using the Shot Scale.
Week 2: Pick ONE Thing
You can't improve everything at once. Identify your ONE development focus using the Skill Map, learn the 3 Stages of Development (Recognize → Decide → Execute), and connect to the right classroom content.
Week 3: How to Drill
Most drilling doesn't transfer to games. Learn deliberate practice methods that actually work, build a 30-minute drill session for your ONE thing, and bridge the gap between practice and play.
Week 4: Set Your Intent
Make every week of pickleball intentional. Build your weekly intent system, celebrate your progress, and discover what's next on your path to 4.0+.
Want the full day-by-day roadmap?
👉 View the Complete 30-Day Program Here (Google Doc Link)
Q: Is this just for 3.5 players?
A: Not exactly.
This challenge is designed for anyone who:
Feels stuck and wants to break through to 4.0+
Struggles with consistency under pressure
Knows what to do but doesn't always execute when it matters
Wants to stop overthinking and start playing with confidence
If that sounds like you, you're in the right place.
In fact, we had many players last year who weren’t at the 3.5 level, and they told us they got as much out of it as anyone else.
Q: How much does it cost?
A: The challenge is FREE for all ThatPickleballSchool members.
If you're not a member yet, you can join for $49/month or $499/year and get immediate access to:
The 3.5 to 4.0 Challenge (starting Feb 2nd)
197+ on-demand training videos
Monthly live Q&A sessions
Private community with 1,300+ serious players
Access to me (Kyle) to help you overcome your biggest pickleball challenges
You can try it risk-free with a 7-day free trial.
Q: What if I join but don't like it?
A: You have 7 days to try ThatPickleballSchool completely free.
If it's not for you, cancel before the trial ends, and you won't be charged. No hard feelings.
Q: What if I can't make the live webinar on February 2nd?
A: No problem.
The webinar will be recorded and available inside TPS. But if you can make it live, I highly recommend it. You'll be able to ask questions in real-time and get clarity on anything that's confusing.
Q: Will this actually help me break through to 4.0?
A: Here's what I can tell you:
We ran this challenge last year. Over 330 people participated. 67% of them stuck around after the challenge ended (which tells you it worked).
And here's what they said:
"The game slowed down"
"I finally knew what to focus on"
"I stopped second-guessing my shot selection"
"I won my first 3.5 tournament"
"I got asked to sub in the 4.0+ group"
I can't guarantee you'll go from 3.5 to 4.0 in 30 days.
That depends on how much you play, how consistently you show up, and how quickly you apply what you learn.
But I can guarantee this: If you commit to this challenge for 30 days, your game will change.
You'll stop overthinking. You'll see patterns. And you'll play with more confidence.
Still have questions?
Reply to this email, and I'll answer them.
Or just join the FREE webinar tomorrow on Monday, February 2nd and ask me live.
See you inside,
Kyle
P.S. The challenge begins tomorrow. If you're still on the fence, now's the time to decide. You can cancel at any time during the 7-day trial if it's not for you.
But if you wait too long, you'll miss the first few days of the challenge, and that's when everyone's energy and accountability are at their peak.