Letter to the Editor—The Little 🚂 That COULD — Sometimes You Need a Little Help Up the Hill

13 hours ago

4 min read

Susan,

When we met over coffee this morning, I didn't expect our conversation to end with me writing something this personal a few hours later.

But you listened. You understood what I was trying to do. And instead of simply wishing me luck, you gave me something practical: a place to ask.

You told me to write something that might help me find the trade I'm looking for.

So I went home and wrote it.

There's something fitting about the timing. Today's playlist was already about a little engine, a workbench, mistakes, repairs, and making it up the hill.

Then I met you.

Maybe this morning was already a little push up the hill.

If you think this belongs in Sunnyside Common Sense, I'd be grateful if you'd publish it. I've included today's playlist and the artwork that goes with it.

Whatever comes from this, thank you for helping me make the ask.

Warmly,

Michael

The Little Train That COULD — Sometimes You Need a Little Help Up the Hill

I grew up in Bonita. And today, I find myself on a hill I can't quite climb alone.

That's not an easy sentence for me to write.

My name is Michael Darius.

I'm a designer, engineer, and builder.

I've spent much of my adult life making things.

At Apple, I worked on the iTunes Music Store and with the team that became iCloud. Since then, I've continued building products, businesses, systems, and ideas of my own.

I'm still doing that work.

I'm still dreaming.

I'm still building.

And right now, I am doing it without stable housing.

I'm not going to turn this article into an explanation of everything that brought me here. A human life rarely fits neatly into a paragraph, and I don't believe someone should have to put every difficult part of their life on public display before they're allowed to ask their community for help.

So I'll simply tell you where I am.

I need a safe, stable place to live in the South Bay.

A room.

A guest house.

A casita.

A studio.

An ADU.

Somewhere I can close a door, put my computer on a desk, wake up in the morning, and keep building.

I'm not asking someone to give me something for nothing.

I'm asking for the chance to make an exchange.

I have something valuable to trade.

I've spent a career learning how to see what isn't working and make it work better.

Give me a small business and I'll study the experience through the eyes of the person walking through its door for the first time.

Give me an organization with an important mission and I'll help make that mission understandable.

Give me a complicated process and I'll work to make it simple.

Give me an idea scribbled on a napkin and I'll sit beside you and figure out what it wants to become.

Products. Services. Software. Websites. Customer experiences. Community projects. New ideas that don't have names yet.

This is what I know how to do.

So perhaps somewhere in Bonita, Chula Vista, Imperial Beach, National City, or elsewhere in the South Bay, there's someone reading this who has a little more space than they need—and something they've always wanted to make better.

If that's you, let's talk.

Maybe there's a fair trade here.

Maybe the value of an unused room isn't rent.

Maybe its value is finally building the thing you've wanted to build.

And if you don't have a room, you can still help.

This appeal doesn't need to reach everyone.

It needs to reach one person.

One homeowner.

One business owner.

One family.

One person with an ADU that's sitting empty.

One person who knows someone else.

One person who reads this and thinks: I should call Michael.

That's why I'm writing this publicly.

Because I've spent my career believing that difficult problems become more manageable when you stop hiding them and start designing a way through them.

This is me doing that now.

There is vulnerability in telling your hometown that you need somewhere to live.

I know that.

But there is also dignity in being clear about what you can contribute.

I have a great deal left to contribute.

I have things I'm building.

I have work I care deeply about.

I have experience that took decades to acquire.

I have ideas I haven't built yet.

And I intend to build them.

What I need right now is some solid ground beneath that work.

Sometimes you need a little help up the hill.

That's the part of The Little Engine That Could that means something different to me today.

We remember the little engine saying, I think I can.

But before the climb, somebody had to ask for help.

That's where I am.

I'm doing the work.

I'm pulling.

I'm climbing.

And I'm asking for a little help up the hill.

If you have a safe place that might work, write to me at michael@smallstep.ventures.

If you're a business owner and the idea of trading space for serious design and engineering work makes you curious, write to me.

If you know someone with a room, casita, studio, guest house, or ADU, send them this article.

If you know somebody who knows somebody, make the introduction.

You don't need to solve everything.

You just need to help this reach the person who can open one door.

Today's playlist: The Little That COULD

I make playlists the same way I make other things: as little stories.

A fairy tale with a workbench in it. Turn the pages from the first wish through making, mistakes, repairs, and the climb. Somewhere along the way, “I think I can” becomes “Look what we made.”

Listen on Apple Music:

https://music.apple.com/us/playlist/the-little-that-could/pl.u-BNA6jDJTP444m

I'm still climbing.

I'm still making.

And I still believe in what can happen when somebody says:

Let's see what we can build.

I grew up here.

Bonita helped give me my beginning.

Today, I'm asking the community that helped give me that beginning for a little help getting up this particular hill.

Not to carry me.

Just to help me find some solid ground from which I can keep climbing.

And when I get there?