The Ride-Along Phase Nobody Talks About

November 10, 2025 by MiKaah

I worked at a delivery company one summer during college.

Day one was training. Classroom stuff. How to read the routing system. Safety protocols. Package handling.

Day two, they put me in a truck with Marcus, a driver who'd been there eight years.

"You're riding with me for two weeks," he said.

I thought I was already trained. I wasn't.

What Actually Happens After Training

Marcus didn't just let me watch. He narrated everything.

"See that driveway? Ice in winter. Park on the street instead."

"This customer? Never rings the bell. Dogs go crazy. Knock twice, step back."

"Rush hour hits at 4:15 on this route. Adjust your sequence or you'll sit in traffic for an hour."

None of that was in the training manual.

The company knew something I didn't: initial training teaches you the system. The ride-along teaches you how to actually do the job.

By week two, I was driving. Marcus was just correcting me. By week three, I was on my own—but the habits stuck.

I could do the route without thinking because I'd practiced it enough times with someone who knew what they were doing.

The Pattern I Keep Missing

I do the same thing with creative skills that I did before Marcus: I think one training session is enough.

I take a weekend workshop on story structure. Read a book about business strategy. Watch a YouTube tutorial on a new tool.

Then I wonder why it doesn't stick. Why I freeze when I try to apply it. Why my writing still feels clunky or my business decisions still feel uncertain.

I skipped the ride-along phase.

Where This Shows Up

Writers learning new vocabulary:

You can't read one craft book and expect sophisticated prose. You have to write badly using those new techniques dozens of times before they flow naturally.

I learned about "showing vs. telling" five years before I could actually do it without thinking. The concept clicked in a class. The skill developed through repetition.

I had to ride along with my own bad attempts until it became automatic.

Builders learning new tools:

Watching a tutorial on power tools doesn't make you competent with them.

My friend bought a table saw and watched 10 hours of YouTube videos. First cut? Disaster. The wood kicked back. He nearly broke his thumb.

He needed the ride-along phase: slower speeds, simpler cuts, repetition with supervision (even if that supervision is just extreme caution and deliberate practice).

Tools become extensions of your hands only after you've used them wrong enough times to learn what right feels like.

Painters learning new techniques:

You can't watch one demonstration on glazing and nail it in your next painting.

My sister took a watercolor class. Learned wet-on-wet technique. Her first 20 attempts looked muddy and out of control.

She wanted to quit. I told her about Marcus and the delivery route.

"You're still in the ride-along phase," I said. "Keep going."

By attempt 30, it started clicking. By attempt 50, it was in her bag of tricks.

Why We Skip the Ride-Along

We treat skills like light switches. Off or on. Trained or not trained.

But that's not how learning works.

Initial training gives you the framework. The vocabulary. The concept.

The ride-along phase—the repetition, the correcting, the doing it badly until you can do it right—that's where the skill actually develops.

Most people quit during the ride-along. They take the class, try it twice, decide they're "not good at it," and move on.

But they're not bad at the skill. They just didn't finish training themselves.

The Real Pattern

Companies understand this. That's why they don't send new employees out alone after a one-day training.

They know the gap between "I understand the concept" and "I can do this without thinking" is big. And that gap is filled with repetition.

The ride-along phase is where understanding becomes competence.

And here's the thing: when you're training yourself, you have to be both Marcus and the rookie driver.

You have to create your own ride-along phase.

What This Looks Like in Practice

For writers learning new techniques:

  • Don't just read the craft book—rewrite 10 of your own scenes using the technique
  • Practice badly. Let yourself write clunky versions while the skill develops
  • Go back to the lesson after you've tried it. The second read-through clicks differently.

For builders learning new tools:

  • Start with practice materials, not your actual project
  • Repeat the same cut, the same joint, the same technique until your hands know it
  • Give yourself 10-20 "throwaway" attempts before expecting good results

For anyone learning anything:

  • Plan for the ride-along phase: "I'll practice this 30 times before judging if I'm good at it"
  • Create repetition deliberately—don't just wing it and hope
  • Expect the first attempts to feel awkward. That's not failure. That's training.

The Permission Slip You Need

You're not bad at the skill. You just haven't finished the ride-along phase yet.

One class doesn't make you trained. Neither does one book, one tutorial, one attempt.

The ride-along—the repetition after initial learning—is where skills move from your head to your hands.

Marcus knew I couldn't drive the route after one day of training. He didn't expect me to. He gave me two weeks to practice while he corrected me.

Give yourself the same two weeks. Or two months. Or 50 attempts.

That's not slowness. That's how skills are built.

Try this: Pick one skill you recently learned but haven't mastered.

Commit to your own ride-along phase: 10 practice attempts. 20. 30. Whatever it takes to stop thinking about the steps and just do them.

Track your attempts. Notice when it starts to feel automatic.

That's training. That's how new skills get added to your bag of tricks.

What skill are you still in the ride-along phase with?