About The Other Side of Obvious

✨ Clarity Over Cliché

This channel explores what lies on the other side of easy answers.

Each week, I share content on Money & Meaning that explore the ideas, clichés, assumptions and narratives that remain unquestioned.

It’s for people who feel like “obvious”… isn’t working.

For those of us who, for one reason or another, become too busy, distracted or settled to pause and ask…“Wait a second! What?!”.

This isn’t about being edgy. It’s not about being clever.

It’s about being curious enough to look again.

And, hopefully, it is a fun ride.

If you find a ‘thread’ that speaks to you, pull it. Let me and others know what you’re thinking.

Because sometimes what’s obvious is just what’s been repeated the loudest.

And clarity starts the moment we slow down and ask better questions.

📌 What to Expect

• Essays that offer thoughtful, honest reflection

• Videos that challenge surface-level thinking

• Occasional extras like behind-the-scenes notes, bonus clips, or Q&As

Most posts are free. Some will be available to paid or pledged subscribers who want to go deeper.

🔍 Who’s Behind This?

Hi,

I’m Sean. Recovering over-explainer. Excessive question-asker.

I explore what happens when we stop accepting the obvious and start asking better questions about Money & Meaning.

I’ve lived long enough to know that my assumptions don’t always serve me well.

So I started The Other Side of Obvious to explore ideas that are more reliable than impressive.

More practical than popular. And more generous than perfect.

I spent the majority of my career in technology (10+ yrs) and investments (25+ yrs). For the past 20 years I worked for one of the best investment advisors in the world (IMHO)!

But my real passion has always been exploring words and ideas.

So, 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 to consistently live by).

And that’s the catch. Ideas matter. They literally inform the way in which we live our lives - how we treat ourselves and others.

So, this is for people who still believe clarity is possible — if we’re willing to look again.

My goal is simply to point towards the best.

I value your time and input, and welcome the chance to go on this journey together.

👉 Subscribe here to get new posts each week.

Start wherever something tugs. And if it speaks to you, pull the thread.

Why subscribe?

Subscribe to get full access to the newsletter, videos, select publication archives and plenty of “aha!” moments.

👉 You can also choose to level-up to a Paid or Pledged Subscriber and in addition to receiving all articles, you will benefit from additional long-form articles, bonus content and videos, as well as special features and behind-the-scenes stuff.

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Important, Please Read.

We love exploring money, investing, and the ways people make (and lose) wealth. But let’s be clear: The Other Side of Obvious is for educational purposes only. Nothing here is tailored to your personal finances, nor should it be taken as investment, legal, or tax advice.

Think of us like financial tour guides—pointing out landmarks, sharing stories, and helping you see the landscape differently. But we’re not licensed financial advisors, and subscribing doesn’t make us your fiduciary. Your money deserves decisions based on your situation, so before making financial moves, talk to a qualified professional who knows your details.

Past performance? Not a guarantee. The future? Always uncertain. That’s part of the ride.

Finally, we’re completely independent—no strings attached. While one of us once worked at Fisher Investments, this newsletter isn’t connected to them (or any other financial firm) in any way. Nothing you read here comes from Fisher (unless otherwise publicly available and cited), and nothing here should be taken as promoting or aligning with them. OSOO is 100% our own voice.

Still unsure. Please read our full disclaimer here. Thanks!