The Other Side of Obvious
How Self-Investors Can Benefit From Subscribing
Welcome! Thanks for being here!
Obvious answers about investing are great. Their so obvious! You know, sayings like “Buy low, sell high!” Then you go to apply this advice in the real world with real money, and things become muddled.
During my 20+ years working in investments (with one of the greatest global investment managers in the world), I saw the outcomes of believing in the obvious. They aren’t pretty. More often than not, investors bought high and sold low. But why?
If much of the investment advice floating around is so “obvious” and the outcomes were so bad, that has to mean that obvious answers are obscuring something better.
That’s why The Other Side of Obvious (OSOO) exists. It’s where we poke at the usual advice, flip it over, and see what’s really underneath. Each week, we talk about things that quietly run many of our lives: Money & Mindset (Investing & the Psychology of Investing).
Why Investing?
Nearly 50% of adults don’t invest their money. Not because they’re lazy, but because money often feels like a foreign language. It’s 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 Psychology?
Because investing is a mind game that plays with your emotions—your psyche. There is no avoiding it, no wishing it away. We are creatures who become tied to our wealth, regardless of how much or little wealth we have.
Without understanding the psychology of investing, we are doing ourselves a disservice. Worse, we’re playing with financial fire. The mindset we adopt will have a much greater impact on our future wealth than any single stock we might own!
Who’s This For?
The Self 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 our wealth and what it means to us.
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.
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.
What to Expect
One or more thoughtful (and practical) posts each week.
Occasional subscriber extras (bonus content, Q&Rs, behind-the-scenes notes).
Trackable model portfolios that can serve as a compass.
Just clear, useful insights on money and honest, human conversations about the how we think about investing.
Why Subscribe?
Think of OSOO as a weekly pit stop: sometimes practical, usually reflective, always pushing past the obvious toward something truer and more helpful.
Because a successful investment portfolio doesn’t start or end with the right stock pick, but with the right mindset about investing.
Thanks for being here. I’m honored to think (and laugh, and sometimes cringe) through this with you.
Best,
Sean
Let’s get sociable! Hit me up at: LinkedIn | Facebook | Instagram | BlueSky
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.
Thank you, Primila! this is exactly why I started this. And thanks for spreading the word!
HI Sean this is exactly what I have been looking for the past 10 years and have been going in circles! Look forward to learning more from you and making a better future for my retirement, thank you for starting this and helping people like me who want to invest but don't have the knowledge.