Every December I find myself doing the same ritual: closing dozens of tabs, scrolling back through months of bookmarks, and asking the same question—which pieces actually changed how I think about money this year?
2025 was weird. We had a sharp spring sell-off that felt like 2022 all over again, then an AI-fueled melt-up that made people question reality itself. Somewhere in that chaos, a handful of writers cut through the noise with ideas that have already outlasted the headlines.
These aren’t the most viral posts. They’re the ones I emailed to friends, quoted in client letters, and still think about when markets get stupid. In no particular order, here are my favorite investment reads of 2025.
The Reads That Shaped 2025
The Bubble Conversation Nobody Could Ignore
Early in the year, one memo landed in inboxes and instantly became the reference point for every valuation debate that followed. The author didn’t scream “bubble!” from the rooftops. Instead, he calmly laid out psychological, technical, and historical markers—then let readers connect the dots.
What made it brilliant wasn’t the conclusion (there wasn’t a hard one). It was the framework. Seasoned pros told me they printed it out and keep it in their top drawer. When clients ask me if “everything is in a bubble,” I still point to this piece first. It’s that good.
Private Markets Finally Got Called Out (Politely)
While public markets obsessed over AI multiples, something quieter—but potentially bigger—was happening in private equity and venture. Fees crept higher, liquidity terms got worse, and suddenly your dentist had access to the same “exclusive” deals as Yale’s endowment.
One writer, known for sharp humor, asked the question everybody was thinking: Why be a limited partner when being a general partner pays so much better? The post was equal parts funny and brutal, exposing how Wall Street repackaged mediocre funds for retail investors hungry for “alternatives.” I laughed, winced, and immediately reviewed my own allocations.
The democratization of private markets is wonderful—until the moment it isn’t.
The Housing Article That Broke My Brain
I read a lot about real estate. Most of it rehashes the same stats. Then one deep-dive came along that stitched together zoning laws, institutional ownership data, construction labor trends, and demographic shifts into a single, depressing picture.
The paradox? America has never built more housing units in raw terms—yet affordability has never been worse for the median buyer. The research was exhaustive, the charts were gorgeous, and the conclusion was sobering: don’t hold your breath for a crash that makes homes “affordable” again. This one piece shifted how I advise younger clients about buying versus renting more than anything else in years.
“When Will Prices Fall?” — The Eternal Question, Answered Honestly
Every cycle breeds the same hopeful headline. One veteran writer, who probably has the best long-term housing track record in the blogosphere, tackled it head-on with fresh data. His answer wasn’t the cathartic crash porn people wanted. It was better: a clear explanation of the feedback loops keeping shelter costs elevated for the foreseeable future.
If you only read one housing piece before making a real estate decision in the next five years, make it this one.
The Quiet Power of True Independence
Mid-year, a post appeared that had nothing to do with P/E ratios or GDP forecasts. Instead, it explored different flavors of independence—financial, temporal, creative—and why the rarest (and most valuable) form is the ability to say no when everyone else is saying yes.
I’ve reread it three times. Each pass hits harder. If you’ve ever felt trapped by golden handcuffs or lifestyle creep, this one will feel like a cold glass of water on a hot day.
Building a High-Leverage Career in a Low-Leverage World
Most career advice is fluffy. This wasn’t. A newer voice dropped an exhaustive guide to creating asymmetric upside in your work life—audience building, equity ownership, skill stacking, niche authority, the works.
- How to turn expertise into digital assets
- Why most people accidentally choose the lowest-leverage path
- Concrete plays that compound faster than a 401(k)
It’s long, tactical, and zero-BS. I sent it to every mentee I have.
April’s Crash Reading List (That Aged Beautifully)
When markets dropped 15% in three weeks, panic porn dominated feeds. Three pieces stood out for their calm:
- One historian walked through every major bottom since 1929 and spotlighted the emotional markers that appear right before capitulation.
- A veteran planner published a simple checklist titled “What smart investors do when everything feels broken.”
- Another analyst reminded readers that volatility is the tuition for long-term equity returns—then proved it with data going back to 1871.
Together they were the emotional ballast I needed. Still are.
Investing Lessons from a Legend’s Farewell
When news broke that the greatest capital allocator of our era was stepping back, markets paused. One young analyst wrote a love letter disguised as an investment primer: simplicity, margin of safety, temperament over intellect.
The timing made it poignant, but the lessons timeless. New investors should bookmark it; old investors should reread it.
The UBI Experiment Results Nobody Wanted to Hear
Few topics polarize like universal basic income. A rigorous, evidence-obsessed writer followed several large-scale trials and reported back: the effects on happiness and health were real but modest; the effects on work ethic and entrepreneurship were… complicated.
It wasn’t the victory lap supporters hoped for, nor the disaster critics predicted. Just honest data. That’s why it stuck with me.
Who Really Profits from Your Attention
One economics writer took a flamethrower to the attention economy, mapping how platforms, advertisers, creators monetize eyeballs—and how the pie has shifted dramatically in five years.
Depressing but essential. Once you see the machinery, you can’t unsee it.
A Crypto Piece Even Skeptics Loved
I usually skip crypto writing. Then “long degeneracy” showed up—part philosophy, part anthropology, zero shilling. It explained why speculative manias persist across centuries and why trying to outlaw them is futile.
Whether you own bitcoin or think it’s tulips 2.0, the historical parallels are chillingly good.
Two Goodbyes That Hit Hard
2025 took two giants from the personal-finance world. One reflected on a Nobel laureate’s final decision with grace and depth. The other wrote his own farewell at 78, simple and generous as everything he ever published.
Both reminded me why we do this—not for Lambos or leaderboard rankings, but to live richer lives with the people we love.
That’s the list. Fifteen pieces, thousands of words, one consistent thread: the best writing doesn’t predict the future. It changes how you see the present.
Here’s to sharper thinking in 2026.
