Progression vs Regression in Training New Skills

Welcome to the Habit Chess newsletter where I talk about training the strength & conditioning of skills. So you can use fitness as a mental model for learning new skills, faster.

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The one guarantee we have over the next several years and decades? We'll need to learn new things faster.

Whether it's building an agent for your team, speaking on camera, mastering new software, etc. Learning new skills quickly is no longer optional.

Here's the problem: most people try to jump straight to the finish line. They want to nail the perfect presentation without practice. They want to code an app without understanding the basics. And that approach leads to frustration, giving up, or worse–injury.

Instead of this haphazard approach, I want to show you a systematic mental model from fitness that I've used with executives, athletes, and high performers for over 10 years.

The Push-Up Problem

Think about a push-up. Seems simple, right? But it's easier said than done.

If you've ever worked with new or deconditioned clients just starting to work out again after months or years, you know they can't just jump into sets of 10 perfect push-ups.

So how do you build this skill systematically?

Start with a forearm plank - just getting comfortable in a static position
Progress to a straight arm plank - developing wrist stability and core control
Move to knee push-up negatives - practicing the eccentric (lowering) phase
If that's too challenging, try incline box push-ups - the higher the box, the easier
Gradually lower the box height as strength develops
Return to push-up negatives on the floor when ready
Finally, attempt full push-ups

Along this journey, you'll discover limiters - like when someone's back looks "broken" after a few reps. This isn't failure; it's data. Their core stability is the limiter, not upper body strength.

Beyond The Linear Path

Progression and regression isn't just a linear staircase you climb. It's cyclical.

When I competed in Olympic weightlifting, I discovered I could get weight overhead but my core would wiggle because I couldn't support the load. My speed was fine, but stability was my limiter.

Another great example is the Single Leg Romanian deadlift. Standing on one leg, hinging over to touch the floor, and standing back up. Most people can't even stand on one leg without losing balance after a few seconds, let alone perform the full movement with control.

So I'm presented with two options: train the balance, or remove the element of balance. Long-term, I want to train the balance because that's needed for the full movement. But I also want to remove the balance temporarily so we can train the full movement pattern without that limiter.

You can do this several ways:

Hand-assisted: Hold onto something with one hand while performing the movement
Double leg RDL: Keep both feet on the floor and master that first
Staggered stance: Place one foot half a foot in front of the other

To specifically develop balance, add holds in the positions where you're most unstable. When fully standing up before you hinge, or at the bottom of the movement, try holding for 10 seconds and just breathe through it to find control.

The real growth happens when you find your "sweet spot of struggle." If you're just doing perfect repetitions of forearm planks without challenging yourself, you're not growing. But if you immediately try the most advanced variation and fail completely, that's not productive either.

Why This Mental Model Matters

What makes this approach powerful is that it works for ANY skill acquisition, not just fitness.

If you're learning presentation skills and find yourself blanking during practice, that's your limiter. Now you can address it specifically. Maybe with memory exercises or by simplifying your content structure.

The real magic happens when you cycle through progressions and regressions. Some days, that forearm plank will feel just as challenging as it did in week one, even though you're now doing much more advanced variations. That's normal, and it's part of the process.

Your 4-Week Skill Development Framework

Pick ONE skill to focus on. Then:

Week 1: Master the most basic version of this skill
Week 2: Slightly increase difficulty while maintaining control
Week 3: Identify your main limiter and create specific drills to address it
Week 4: Attempt more advanced variations, then reassess

Remember that progressing too quickly will sideline you, in fitness and in skill development. Sustainable progress compounds over time, while rushing leads to frustration and quitting.

Just think of how Kobe Bryant spent an entire summer in his teens solely focused on his jump shot. Then dribbling with his non-dominant hand, and so forth. Attack the limiters one phase at a time.

This isn't a one-and-done approach. Look at progressions and regressions as cyclical. The fundamentals always matter. And you’ll have seasons where it’s time to return to those basics.

In your corner,

Misbah Haque
Founder & Consultant at Pod Mahal
Writer & Host of Habit Chess

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