An Intro to The Other Side of Obvious

Money & Meaning: Minus the Myths.

🙏🏽 Welcome! Thanks for being here!

Sometimes the “obvious” answer about money or meaning sounds great… until you try it. Then you realize the obvious isn’t always right—it’s often what blocks us from finding something better.

That’s why The Other Side of Obvious exists. It’s where we poke at the usual advice, flip it over, and see what’s really underneath.

Each week, we talk about two things that quietly run most of our lives: Money and Meaning.

Money keeps the lights on. Meaning makes flipping the switch worth it. They might feel like separate conversations, but let’s be real—they’re tangled together more than we’d like to admit.

💵 Why Money?

Nearly 50% of adults don’t invest their money. Not because they’re lazy, but because money often feels like a foreign language—complicated, intimidating, even a little embarrassing.

We’re here to change that. Not with hot stock tips or “get rich quick” nonsense, but with clarity, humor, and the kind of basics that make you wonder: why didn’t anyone explain it this way before?

🌱 Why Meaning?

Because even if you “win” the investing game and build your wealth, you can still feel like you’re losing the point. We live in a noisy world full of obvious clichés:

• “Money makes the world go around.”

• “Just be yourself!”

• “Never stop searching.”

Sometimes those ideas help. Sometimes they just keep us stuck. Here, we pause, flip those assumptions over, and ask the better questions hiding underneath.

❓Who’s This For?

The Emerging Investor. Those of us who see the need to be invested, but don’t know where to start. Maybe you’ve dipped a toe and froze. Maybe you’re stuck, circling the “what’s next?” question. Or maybe you’ve invested, but without a real foundation.

Whether you are un-invested or under-invested, OSOO is here to help you cut through the noise, skip the jargon, and actually enjoy building investing confidence, while discovering the deeper connection between wealth and meaning.

⏱️ Why Now?

Because the world is noisy. And the “obvious” answers don’t always solve the real problems.

We’re overloaded with information and still starving for wisdom. That’s not a content problem—it’s a depth problem. We scroll, we nod, we move on. But nothing shifts.

This is a space for pause. For questioning. For honesty. Not to tear things down, but to sit with what we’ve built—and ask: Is this still true? Is this still helpful?

🤔 Why Me?

Because I have been in your shoes. I know what it’s like to stop and say “Wait a second…that doesn’t sound right!” or “Why isn’t this working?!”

After 10+ years in technology and over 25+ in the investment world, I’ve learned a lot about successful investing and even more about deep meaning.

I’m totally obsessed with the thing-behind-the-thing and I get quickly bored with the surface answers.

Recovering over-explainer. Excessive question-asker. I explore what happens when we stop accepting the obvious and start asking better questions.

The Other Side of Obvious is as much an outlet for me (a place for ideas to live), as it is a confessional - every topic covered is one which I failed miserably to understand and/or consistently live by).

👉 What to Expect

• One or more thoughtful (and practical) posts each week.

• Short videos with actionable takeaways.

• Occasional subscriber extras (bonus content, Q&Rs, behind-the-scenes notes).

• No hype. No yelling. No Wall Street buzzwords.

Just clear, useful insights on money—and honest, human conversations about meaning.

✨ Why Subscribe?

Because if you’ve ever thought, “I should be investing… but I don’t know where to start” or “I want more purpose, not just more productivity,” this is your corner of the internet.

Think of it as a weekly pit stop: sometimes practical, sometimes reflective, always pushing past the obvious toward something truer—and way more helpful.

Thanks for being here. I’m honored to think (and laugh, and sometimes cringe) through this with you.

Best,

Sean

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Let’s get sociable! Hit me up at: LinkedIn | Facebook | Instagram | BlueSky | YouTube

And one important note:

This publication is for brains, not bets. The Other Side of Obvious shares ideas, stories, and general financial information—not personalized investment, tax, or legal advice. Investing comes with risk (including losing money). Talk to a pro before you act. Please take time to read these important disclosures before you get started.