October 20, 2026

I sold a to-do list

Six pages. They said yes. Then I had to deliver all six.

Oprah, arms out: you get a car!

My first $7,500 sale came on a six-page proposal.

Six. Pages.

I told them I'd build them an AI chatbot.

And help with their marketing.

And their brand positioning.

And build their website.

Oh, and take the headshots for the whole company.

AND teach them how to build a brand on social media.

And more. (If I could do it, I crammed it in that thing.)

Yes, for the fitting price of $7,500, I would be the EVERYTHING freelancer.

Why? Honestly, I was scared I wasn't giving them enough to charge them $7,500. So I figured I needed a giant list of value to justify a number that felt that big.

And it worked. They said yes!

Which was great. Right up until I realized I now had to deliver six pages of stuff I could BARELY keep track of.

I hadn't sold a result. I'd sold a to-do list. A very long one.

So why am I telling you this?

Because that same fear shows up in a lot of places that aren't six pages long.

You say your price really fast and keep talking so there's no awkward silence.

You hit send on the proposal, then sit there wondering if you should have gone lower.

They don't answer for a couple of days, so you think about knocking off a few hundred bucks before you follow up.

You add one more deliverable, just to be safe.

Every one of those feels like a pricing problem. (I know, I've lived it my friend...)

It's not. It's a positioning problem dressed up as a pricing problem.

Which is good news, honestly. You don't have to turn into the Wolf of Wall Street to fix it. You don't need a new Enneagram number either.

Leonardo DiCaprio yelling into a microphone in The Wolf of Wall Street

Sell what changes for the client, not all the things you can do for them.

These days I send a short written offer, usually two pages, after we've talked. It's built around the outcome they want, and everything else is gone. and its value to my new client is FAR more than the six pages ever did.
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Why? Because the offer is about them, not about me.

Because now I'm building it for their problem, not my anxiety, my insecurities.

So before your next proposal goes out, ask yourself one question. What's the one result this client really wants?

Then strip away everything that isn't helping them get there better and faster. Keep cutting until, if you took out one more thing, they'd definitely say no.

Hit reply and tell me how many pages your last proposal was. No judgment. Mine was six.

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Jonathan's signature

Jonathan "the everything person" Ray​
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​PS. To-do lists are great for grocery lists. TERRIBLE for proposals.


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Written by
Jonathan David Ray
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