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[Day 3] 💡Is My Newsletter Idea Any Good???
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[Day 3] 💡Is My Newsletter Idea Any Good???

How to Use a Newsletter to Change Careers, Rebrand Yourself & Strut Into an All-New Industry With *Swagger*

Ash Ambirge's avatar
Ash Ambirge
Feb 27, 2025
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[Day 3] 💡Is My Newsletter Idea Any Good???
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Hi! Welcome to Day 3 of our brand-new career training series, “How to Use a Newsletter to Change Careers, Rebrand Yourself & Strut Into an All-New Industry With *Swagger*”—muahahahahaha.

-Ash


Table of Contents

Day One: What’s Your Newsletter’s Job?
Day Two: What’s Your Newsletter’s
Big Idea?
Day Three: Is My Newsletter Idea Any Good???
Day Four: Which Newsletter Software Do I Use?
Day Five: What (The Hell) Should I Write About in My Newsletter?
Day Six: How Do I Make My Newsletter Fascinating, Sticky, Memorable &
Sellable?
Day Seven: Write a Hook That’s Stickier Than a Jam Packet
Day Eight:
Own Your Voice & Dare to Take Up Space

Let’s dive into today’s lesson! ⬇️


Day Three: Is My Newsletter Idea Any Good???

Something I know from experience to be true:

You won’t start the damn newsletter until you (think) you’ve GOT IT ALL FIGURED OUT IN YOUR HEAD. 🤣 And, do you know when you’re going to have it all figured out in your head?

HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAAAAHAHAHAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA.

No, darling. This is not a thing. There is cruel and then there is cruel, and operating under the guise that any of us will have anything “figured out” someday is the latter.

The truth—Big Truth, with all sorts of capital letters to convey importance—is that it’s never (I promise) going to feel finished. You’re never going to feel ready. Never, ever will you ever feel like it’s ‘good enough,’ or ‘smart enough,’ or ‘cool enough,’ or ‘wow-enough’ or ‘pretty enough,’ or ‘special enough.’

But, take heart! This is a great thing. This gives you permission to let go and try.

And, once you let go, you can (somehow) make it over the hump that is that complete and utter *cringe* feeling, and learn how to push publish on your own ideas anyway—especially if the whole goal of this is to help you expand into a new industry and get over the inevitable hairy, gray-toothed imposter syndrome that comes with that.

We’ve all got the syndrome, lads. You must treat it like it’s your crazy Aunt Barbara with the tin hat, always hootin’ and hollerin’ about conspiracy theories.

Your imposter syndrome is a FLAT EARTHER. Please treat with the same regard.

(Side note: home improvement contractor was walking through farmhouse the other day and saw my huge collection of THE MIDDLE FINGER PROJECT books on my shelf—my book—whose tagline reads: Trash Your Imposter Syndrome and Live the Unf*ckwithable Life You Deserve. And he was like, what’s imposter syndrome, a disease? I think he was very concerned about me. Or he thought I was a doctor, which we all know would be terrifying. So then I was like, hahahahah, no Richard, it’s that feeling you get if you, as a home improvement contractor, suddenly found yourself on stage in New York City, made to perform a ballet. You’d feel really out of place, right? To which he nodded solemnly and said, Ah. Like when a client asks me to install wallpaper. AND IN THAT MOMENT I WAS SO HAPPY I WASN’T ASKING HIM TO DO ANY WALLPAPER, I AM THE WALLPAPER MASTER, THIS IS MY NEW DOMAIN, BOW TO ME, RICHARD!

Anyway, I learned this whole you-gotta-go-go-go-and-cover-your-eyes thing after 15 years writing this newsletter, after 15 years having a super fun unconventional online business, after 15 years of having to fight my perfectionistic bozo brain and just do the damn thing anyway.

Do you know how hard that is when you’re someone who can’t even leave a dirty dish in the sink without having OCD about it? Especially if there are eggs. Do not fuck with me and a plate of sticky yolks. Ditto if you think you’re going to put that yogurt cup in my garbage without rinsing it out first. WHO AM I? WHO HURT ME? I don’t know, but don’t you dare.

I remember once, in the long-lost ancient year of 2009, emailing with Danielle LaPorte and we were talking about how to know when your work is good enough to ship. And she was like, dude, there is no such thing. And, now that I am an internet grandmother, I agree. Declaring that you are ready is a decision, not a place you can actually arrive. You can either decide to be generous with what you do know, or to be scared of showing what you don’t.

But, I can tell you what: the people who are generous are also the ones who get rich. Convenient, right?

Okay, so yes, we’re on the same page: building your body of work is always going to be an work in progress, and you’ve gotta make peace that it’s going to be B+ work.

B+ work is still the work.


You’re Not Trying to Be ‘Right,’ You’re Trying to Start Conversations

Alright, so what kind of kick-ass, B+ material are you going to commit to writing?

It can be hard, in a new industry, because you aren’t an expert at it. But, omg, what a fucking blessing! I would kill to have my same naiveté that I did when I first started writing online. I know that sounds backwards, we’re supposed to want to be wise. But, do you know how much KNOWING EVERYTHING THAT CAN GO WRONG can hold you back? It’s a curse, in its own way.

So, look at this as a chance to experiment, to play, to test new ideas—without the pressure of having to be right all the time. Fresh ideas are valuable in and of themselves, even if they aren’t proven.

I want you to think of your new newsletter as an idea bank.

A place where you’re going to store all of your ideas related to this new industry.

They don’t have to be perfectly formed ideas. They don’t have to even be right, necessarily. They just have to be thoughtful, interesting, smart, considered. That is how you break into a new industry: by taking the time to care about the industry.

You do that with contributing your ideas, however cringeworthy they might be. You are not trying to be right, you’re trying to start conversations.


Specifically, you’re trying to start conversations around one big idea.

Your hypothesis.

And now, your newsletter is going to serve as a vehicle to test that hypothesis. There are a lot of ways we can use content to do that. But, in order to see how this works, let’s first consider an example.

Let’s say you want to break into the food industry.

And, let’s say you want to write a newsletter about burgers. 🍔 (I love that there’s a burger emoji, and that it actually looks delicious. Unlike this one: 🍥. Do you know what that one is? “Fish cake with swirl design.” That’s what it actually says when I hover over it. How many times have you actually used that emoji? I declare martial law.)

OKAY, so first, you’re going to need a strong POV; one big idea that holds it all together; one single hypothesis to structure all of your burger content around.

Here are a few examples of what that might look like.

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