The Most Powerful Question You Can Ask Right Now, Transitions, Your Holy Shit Moment & Pirate (Scooby) Snacks
Welcome to The Different Newsletter.
Musings for entrepreneurs, marketing leaders, and creators with a different mind.
From Christopher Lochhead, co-author of of 14 number one bestsellers including Play Bigger, Snow Leopard & 22 Laws of Category Design
Sponsored by Bad Tuna Industries.
With content stolen from Category Pirates.
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This might be the most powerful question you can ask right now.
"If I were redesigning my career right now, with AI at its core, what would I build?"
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When the student is ready…
I was 14 the first time I read these words of the legendary Richard Bach. “When the student is ready, the teacher will appear.”
And I have found them to be (very) true.
If you pay attention you’ll notice. How often the right people show up at the right time for you. Cultivating an awareness of Richard’s words has served me well.
And I bet if you pay attention.
You’ll notice the power of this simple, profound insight in your life too.
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Transitions are tough.
Especially if you’re starting at the bottom.
I started my first business at 18. It was a desperate attempt to survive. Not some (made up personal brand bullshit) “journey”.
No glamorous display of polished posts detailing how I “built in public” in front of hundreds of thousands of adoring fans.
It was taking the bus
It was sweating the rent
It was cold calling the (fucking) yellow pages
(The yellow pages are an ancient book with a list of potential prospects & their phone numbers)
So the next time you’re feeling down.
Remember.
The vast majority of entrepreneurs, category designers, creators and innovators are regular people.
Who chose radical agency.
People who summon the courage to be different.
And make a big difference.
People just like you.
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Do not be confused.
But for our all volunteer military.
We’d all be dead.
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Katie Gatti Tassin was 23 years old when she had her “holy shit” career moment.
She was wobbling into her office job on pointy-toed heels, balancing an overpriced leather laptop bag, already sweating through her blazer. Six months into post-grad life, her dream job felt less like a dream and more like a never-ending loop.
She thought: "Is this it?"
She wasn’t burned out. She wasn’t underpaid. She was winning—on paper.
Katie had what most people spend decades chasing: a stable job doing marketing and user experience design for Southwest Airlines, Meta, and Dell, a growing salary, and a 401(k) that was technically “on track.”
But something didn’t sit right.
Her morning panic attack sparked a radical rethinking.
Instead of grinding for 40 years and hoping she could enjoy whatever time was left, Katie started building something different. She tracked her spending, calculated her “freedom number,” and started saving and creating like her life depended on it.
No surprise: it worked.
By age 26, Katie had gone from schlepping in corporate America to running a $1M+ creator business.
Not because she struck startup gold or hit the lottery. But because she built a financial runway—enough money to buy herself time. Here’s how she did it:
2017: Graduated with a full ride from the University of Alabama with a BA in Communication & Information Sciences, Public Relations.
2018: Started a simple personal blog with a few readers, mostly friends, while working at Southwest Airlines.
April 2020: Officially launched Money with Katie as a personal finance blog during the early stages of the pandemic.
Fall 2020: Expanded Money with Katie to Instagram and launched her first product, a digital wealth builder spreadsheet for $25, which made over $4,000.
February 2021: Started pitching her first sponsors, with brands willing to pay $2,000 for a blog post.
End of 2021: Left her full-time job at Southwest Airlines to focus on Money with Katie, which had generated over $250,000 in revenue that year.
2022: Money with Katie was “acqui-hired” by Morning Brew, expanding her audience and team.
2023-2025: Continued growing Money with Katie and launched a weekly podcast, The Money with Katie Show, which attracts 150,000 monthly listeners. She also created free personal finance courses and improved versions of the annual wealth planner.
March 2025 (present): Katie is working on her forthcoming book, "Rich Girl Nation," while continuing to lead Money with Katie as part of a team of three. Her weekly newsletter has nearly 200,000 subscribers, while her YouTube channel and Instagram following is over 300,000.
While Katie initially wanted to retire early, her mindset shifted after Money with Katiebecame her full-time career.
In a 2024 interview, Katie said she no longer views retirement as leaving work entirely. Instead, she plans to continue working on her business because she enjoys it.
She has set a "freedom number" of $3–4 million in investments, at which point she would have the financial flexibility to take sabbaticals or reduce her workload without needing income from her business.
Her goal (like any Creator Capitalist) is not to retire—it’s to build.
To create.
This was an excerpt from Category Pirates “Runway, Not Retirement: The Creator Capitalist’s Path To Financial Freedom”
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Thanks for reading.
Shalom my Pirate friend,
👊🏴☠️🙏
Here come the dis-credits.
Pirate Snacks ☠️
And Legal Warnings…..
People who subscribe on Substack get this Different newsletter first.
You should feel very little obligation to read from this point on.
Your time would be better spent watching re-runs of the original Wonder-woman show from the ‘70s.
Copyright Category Pirates, LLC
Category Pirates is our real newsletter.
And books.
And courses.
All Different newsletters contain nuts 🐿
The creator of this Different newsletter:
-can’t find his hat
-does not possess a GED
-was thrown out of school at 18
-was likely hangin’ out with Mary Jane
-is considered radically incompetent (by many)
-possess multiple learning differences (aka superpowers)
If you’re a regular reader, you will find repetitive content, rambling non-sense spell!ng anf gramer mistakes.
This is a feature not a bug.
You see Lochhead has Dysfucklia.
A nero-different condition that includes AD/HD, dyslexia, dyscalculia and AD/DC.
Plus Lochhead is too cheap to hire an editor.
And an editor would slow the roll.
Likely tell Lochhead he “shouldn’t write that”.
Or, suggest we “should tone that down.”
Enrollment is open for the 1st Creator Capitalist course.
Discover Your Superpower, Design Your Career, & Get Paid To Be You
Most people try to fit into a career. Not you.
You want to design one that’s uniquely yours.
Creator Capitalist is the step-by-step system that shows you how to break free from traditional paths and design a career that works for YOU—one that makes you irreplaceable, gives you agency over how you work, and pays you generously for the value you bring.
Bigfoot spotted in National Weather Service storm damage photo
“I need a little time off for bad behavior” - Whiskey Myers
Angry woman strips naked at airport in Philippines
Loch Ness Monster 'sighting' sparks public
Everything we value, we’ve been taught to value.
Ultrahuman thinks its 18-karat gold smart ring is worth $1,900
Don’t forget to tell 2 people you love, about 2 podcasts you love.
More proof that ideological racism is the fastest growing form of hate in the US (Both “sides” do it)
New bombshell study reveals 'assassination culture' spreading on the left
Amazon enters real-time AI voice race with Nova Sonic, a unified voice model that senses emotion
Queensland surgeon fined for sharing photo of patient’s swastika-tattooed penis
Trump Tariffs Hit Antarctic Islands Inhabited by Zero Humans and Many Penguins
Army Ants turn themselves "balls" during high water floods.
Creator Capital: A Proven Framework For Taking Control Of Your Career, Money, And Financial Freedom
Pentagon received hundreds of new UAP reports, but says no evidence of extraterrestrial activity
Why did they change the name of UFOs (perfectly great name) to UAP?
Ya!?
And what exactly is a UAP any way?
An Unidentified Apple Product?
Ha ha…
Where does he find all this pirate snack stuff at the end?
It seems very random.
He must have a AD/HD brain.
Is that why The Economist called him “off-putting to some”?
That’s just one of the reasons.
It turns out Lochhead’s not well liked in Silicon Valley.
Why am I not surprised.
Did you hear that Survivor has been airing for just over 24 years and 10 months. The show is currently in its 48th season.
Same guy hosting?
Ya.
Same guy.
I hear the Survivor guy is good friends with Dave Grohl.
That’s random.
Ya.
Apparently they vacation together.
How do you know that?
I read it on the Internet.
Do you know most Americans under 40 don’t know who Dave Grohl is?
Really?
And I bet they’ve never seen Survivor either!
Can you imagine spending 25 years of your life hosting that show!?
No.
And I also can’t imagine spending 25 years of my life watching it either.
Did you know the longest-running daytime soap opera in the US is General Hospital.
Really?
It premiered on April 1, 1963.
April 1st, eh?
A lot of weird shit goes down in that hospital.
Hey.
Who are we talking to?
We?
Why does this newsletter make us talk to each other in our own heads like this?
Each other?
Well, you’re talking to someone right now aren’t you?
No.
Pretty sure I’m just sitting reading this (never ending) newsletter.
Can a newsletter make you nuts?
This one can.
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Thanks for hanging out.