100 Days of ‘Ukulele: What I Learned

One Hundred Days Later

One hundred days sounds like a long time when it’s still a goal.

Less so when it’s Tuesday and there’s another song to record.

When I launched my second 100 Days of ‘Ukulele project, I thought the challenge again would be consistency. Record a song. Edit a video. Publish it. Repeat 100 times.

What I didn’t realize was that the real challenge wasn’t consistency at all.

It was logistics.

This year, I knew I had a complication.

Actually, several.

There was a songwriting retreat in Costa Rica on the calendar. A trip to Disneyland. A house that needed painting. A trip to Hawaiʻi. A full schedule of gigs, open mics, and real life happening in between.

The first time I attempted a 100-day project, I faced it one day at a time.

This year, I decided to treat it differently.

If this project mattered to me, I needed to give it every reasonable chance to succeed.

My mantra became Leave No Rock Unturned.

So I started building systems.

Songs were grouped into albums. Days were color-coded. Recording days were batched. Editing days were batched. Publishing days were batched. I kept a running schedule nearby because I had an uncanny ability to say the wrong day in videos.

I still managed to do it at least twice.

Thankfully, that’s what editing is for.

Not everything went according to plan.

I forgot to hit record.

More than once.

I recorded videos without sound.

More than once.

And one of the biggest surprises was discovering that my carefully planned list of 100 songs wasn’t nearly as permanent as I thought it was.

When I started, I had all 100 songs mapped out. I planned them, but it never occurred to me that the project wouldn’t look the same as when I began.

Some songs turned out to be more difficult than I had time to devote to. Some never quite clicked. Some looked great on a spreadsheet but didn’t come alive when I picked up the ukulele. Others surprised me completely and demanded a different place in the project.

I deleted songs. Replaced songs. Rearranged albums. Moved songs between weeks. And more than once I discovered that a song I had carefully planned for one album belonged somewhere else entirely.

At first, I saw those changes as deviations from the plan.

Eventually, I realized they were part of the process.

I had to remember that the goal wasn’t to execute the original plan perfectly. The goal was to make the best musical decisions I could with the information I had at the time.

And somewhere along the way, something unexpected happened.

The project stopped feeling like a challenge and started feeling like part of my life.

My catalog grew.

My confidence grew.

The B minor chord stopped feeling impossible.

Songs that once felt intimidating became familiar. I started hearing arrangements differently. More than once I rearranged an entire week because a song revealed itself to be something other than what I originally expected.

The project became less about organizing songs.

And more about listening to what the songs wanted to become.

One of the biggest surprises came in Costa Rica.

I arrived expecting to spend a few days playing ukulele and learning from songwriters.

I left having written my first original song.

I didn’t see that coming.

Somewhere between coffee, creativity, and a lot of encouragement, a song called The Barista appeared.

Looking back, it feels fitting that an original song emerged from a project built around covers. The more songs I learned, the more I started asking questions about what kind of musician I wanted to become.

Not just what I wanted to play.

Who I wanted to be.

The project also gave me opportunities I never expected. I played open mics, community events, local gigs, and even found myself performing on a stage in Honolulu. Every performance taught me something different—not just about playing music, but about sharing it.

And that’s probably the biggest lesson from these 100 days.

I used to think becoming a better musician meant finding more discipline.

Now I think it means building a life that supports the things that matter.

A life where creativity has room to exist.

A life where goals are supported by systems.

A life where imperfection is expected and adaptation is part of the process.

The systems didn’t eliminate mistakes.

They made mistakes survivable.

That’s what allowed this project to succeed.

Leave No Rock Unturned wasn’t really about preparation.

It was about giving something important every reasonable chance to succeed.

Not perfection.

Preparation.

Not motivation.

Support.

Not rigid adherence to a plan.

The willingness to adjust while continuing to move forward.

One hundred days later, the videos are finished.

The project is complete.

And somehow, it feels like this chapter is just beginning.