The planning trap most side hustlers fall into (and how to avoid it)


Hi Reader,

Here's a phrase I’ve been thinking about a lot lately:

Don’t let planning get in the way of progress.

It reminds me of when I was in high school. Anytime I had a big assignment or an exam to study for, I would suddenly decide my desk absolutely had to be cleaned first. Or my entire room.

Not because it really mattered, but because it felt productive.

I could tell myself I was “getting ready” to do the work, without actually doing the work.

Starting a side hustle often triggers the exact same behaviour.

You finally decide what you want to do. You’re motivated. You’re excited. And then your brain immediately starts listing everything you “need” first.

A website.
A business name.
A logo.
More research.

None of those things is wrong. But they’re often just modern versions of cleaning your desk before you start studying.

They keep you busy. They keep you comfortable. And they keep you from doing the one thing that actually moves the needle: putting your idea in front of real people.

Planning feels productive. Progress feels uncomfortable.

That’s the difference.

When you choose progress, you risk being ignored or unqualified. Maybe you'll discover that you picked the wrong side hustle.

It's much easier to hide in planning and call it being responsible. I know because I've been there.

In my experience, most people don’t quit their side hustle ideas. They just keep “getting ready” for them until the motivation fades.

Here's a simple filter you can use to avoid falling into the "planning trap":

If my next step doesn’t involve another human being, I’m probably still avoiding progress.

You don’t need to feel ready. You need to take a step that forces feedback.

Here are some examples of what that might look like:

  • Message someone you already know and ask about a problem they’re dealing with.
  • Reply to a post in a Facebook group with a thoughtful, helpful comment.
  • Asking a potential customer if they’d be open to a quick 10-minute chat.
  • Post a rough version of your idea and see what people respond to.
  • Offer to help someone for free just to learn what actually matters. (I do this every single day on Reddit)
  • Sending a simple “Hey, I’m thinking about starting something around ___ — does this sound useful?” message.

I'll leave you with this simple question:

What’s your version of cleaning the desk?

And what’s the actual homework you’ve been avoiding? Do that part instead. Even if it’s messy or imperfect.

That’s how side hustles actually start.

Have a great week!

Colin


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9-5 Escape by Colin Graves

I built a six-figure remote business and walked away from the 9 to 5 at age 46. Every Tuesday, I email a story, tip, or idea to help you climb down the corporate ladder and live life on your terms.

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