The Price of Illusions – 16 Years Later
In 2010 I asked if you were living in an illusion. In 2026 that question is harder — the price of illusions, now that they have [...]
Are You The Best Version of Yourself? – Checking In After 16 Years
In 2010 the OS metaphor for self-improvement was an analogy. In 2026 it's literal — AI tools actually run as cognitive extensions. Here's what that changes.
The 2026 Definition of Success – 10 Years after I First Tried My First One
I had 9 definitions of success in 2016 and was split between all of them. 10 years later, here's what I actually learned about enough, alignment, [...]
Still Learning To Say No – 17 Years After First Writing About It
I wrote about saying no in 2009. The technique was right but incomplete. 17 years later, here's what I missed: the permission problem is harder than [...]
The Ancestor Syndrome – Revisiting Inherited Money Beliefs 10 Years After
I wrote about the ancestor syndrome in 2016. Ten years of crypto cycles and economic shocks have tested that thesis hard. Here's what held up and [...]
Life Has No Meaning – In 2026 I Still Think This Is Good News
In 2015 I argued that life's lack of inherent meaning is liberating. I still think so. But making that case in 2026 requires more honest scaffolding.
The Diamond Cutter, 12 Years Later — Buddhism as a Daily Practice
A 12-year test of The Diamond Cutter's Buddhist business principles. Which ones compounded into real results, and where the emptiness concept led me astray.
77 Reasons to Love Your Life — Why I’d Write This Differently After 17 Years
I wrote 77 reasons to love your life in 2009. The reasons haven't changed much. But the obstacle to actually enjoying them has, the world is [...]
7 Reasons to Enjoy Life More — 16 Years Later
In 2009 I gave 7 reasons to enjoy life. Sixteen years later: some held up, one needed honest revision, and one wasn't on the original list.
Living as a Digital Nomad: Revisiting a 16 Year Old Primer
I wrote a digital nomad primer in 2010. Here's what it got right, what COVID changed, and how AI expanded what one person can build — [...]
The Right Tool for the Job in 2026: What AI Changes About the Wrench Problem
In 2018 the wrong tool was obvious — you could see the mismatch. In 2026, AI made it invisible. Here's where the granularity problem actually went.
15 Years of Motivation: From Tiny, Genuine Sparks to Burnout
The "get and keep" model of motivation breaks down fast. After 15 years: what three methods actually lasted, what leads to burnout, and what actually works [...]
The First 6 Months of Blogging After 17 Years Of Blogging
I wrote a blogging retrospective after 6 months. Twenty years later: the advice held, the meaning changed, and the economics flipped completely.
Steadily Fluid after 10 Years: How Does it Feel to Live with the Paradox
Stability and fluidity aren't opposites — they're prerequisites for each other. Here's what 17 years of living that paradox actually looks like from the inside.
Technology, Ideology, and What Actually Happened Since 2018
In 2018 I bet that technology would outpace ideology as the force reshaping society. Eight years later — AI everywhere, authoritarianism still rising — time to [...]
100 Ways To Live A Better Life: 17 Years After – What Actually Worked
I wrote 100 ways to live a better life in 2009, then 100 subposts, then watched it float on the internet for 15 years. Here's what [...]
3 Lifestyle Design Blueprints I’ve Lived, Plus A 4th One That Works Best These Days
In 2009 I mapped 3 lifestyle design modes. After 17 years inside all of them, here's what held up, what broke, and the fourth mode the [...]
The Action versus Reaction Trap: Why I Had It Half Right in 2009
In 2009 I said acting is always better than reacting. 17 years later the picture is more complicated — and more useful. Here's what I got [...]
25 Things To Do In Your Life – Then and Now
I wrote 25 life goals in 2009 framed as alien advice. Sixteen years later — what happened, what I let go, and what the 2026 list [...]
Everything I Built That Fell Down (And What I Learned About Building Anyway)
In 2011 I wrote about keeping fragile structures standing. Since then several of mine have come down. Here's what the falling actually taught me about building.