Why Learning a New Skill Feels Like Going Backward (And Why That's Normal)

The first time I drove through a mountain pass, I thought my GPS was broken.

The destination was 30 miles away. But the road kept curving back on itself—switchbacks that pointed me temporarily in the opposite direction of where I was going. My arrival time kept jumping. I felt like I was getting further away even as I climbed.

I've felt that same disorientation every time I've tried to learn something new.

You read the books. You do the exercises. You practice. And then one Tuesday, you're worse than you were the week before. The thing that worked stops working. The insight you thought you had dissolves.

Your mental GPS says you're going backward.

But here's what I've learned: the switchbacks are the road.

Progress doesn't move in a straight line. It loops. It spirals. It doubles back so it can climb higher.

Where Else This Shows Up

• In writing: Your second draft is often worse than your first—messier, more confused. That's not failure. That's the road curving back so you can see the story from a new angle. Draft three climbs higher than draft one ever could, but only because draft two went "backward."
• In business: The strategy that worked for your first ten customers often breaks at fifty. You feel like you've regressed. You haven't. You've hit a switchback. The skills that got you here aren't the skills that get you there.
• In learning any skill: Plateaus aren't flat. They're coiled. You're not stuck—you're circling the same territory at a slightly higher elevation, seeing things you couldn't see the first time around.

Why This Matters

Because if you expect a straight road, every curve feels like a wrong turn. You start questioning yourself at exactly the moment you should keep driving.

I don't have a clean framework for knowing when you're on a switchback versus genuinely lost. I'm still figuring that out.

But I've noticed a few things.

Switchbacks feel frustrating but not hopeless. You're confused, but you're still moving. Lost feels like standing still.

Switchbacks often follow a breakthrough. You learned something new and now you're integrating it. That integration temporarily makes things messier.

And switchbacks usually point you—eventually—back toward the destination. Even when you're facing the wrong direction, the road keeps climbing.

Try This Today

What if the place where you feel like you're regressing is actually the turn you needed to reach the next level?

I'm still not sure. But I'm learning to trust the switchbacks more.

The straight path up the mountain doesn't exist. The only way up is through curves that sometimes point you backward.