Bob Weir, Scott Adams, and the Courage to Think Clearly

This past week has had me sitting quietly with gratitude, loss, and reflection.

We said goodbye to Scott Adams, the creator of Dilbert—a man who, to me, was far more than a cartoonist. And we also lost Bob Weir, whose music and presence shaped not just a band, but an entire slice of Americana.

Two very different men on the surface.
Yet together, they leave behind a shared lesson about thinking, humility, and how to live awake.

What Bob Weir Meant to Me

I’ve been a follower of the Grateful Dead since 1989. And if you know that world, you know it isn’t just about music. It’s a living culture—roads traveled, friendships forged, stories told, and something ineffable passed hand to hand.

Bob Weir was a sculptor inside that ecosystem.

He wasn’t always the loudest voice, but he shaped the edges—turning folk into fire, blues into prayer, rhythm into a current you could step into. Over the years, I’ve found myself looking backward, studying the early Grateful Dead years of the 1960s that I never got to witness firsthand. And somehow, they’re still alive. Still teaching. Still moving.

Bob helped build a world where the music wasn’t the product.
It was the doorway.

A doorway into community.
Into experimentation.
Into a kind of freedom that didn’t need to be explained.

That’s Americana at its best.

What Scott Adams Taught Me About Thinking

Scott Adams fascinated me because he understood something most people never slow down enough to study: influence.

He spoke openly about his background in hypnosis and persuasion, and how that trained him to observe human behavior—especially under emotional pressure.

I first encountered Scott during the 2016 presidential election. At the time, he described himself as “far left of left,” yet he publicly predicted—and argued for—Donald Trump’s win. Not as a political endorsement, but as an analysis of persuasion unfolding in real time.

That stance cost him friendships and standing in his own circles.

Still, he held his ground—not emotionally, but analytically.

What mattered to Scott wasn’t who you voted for.
It was how you think.

Humility in Real Time

That same quality showed up again during COVID.

Scott looked at the early data and concluded that vaccination made sense on a benefit–risk basis, and he got vaccinated. Later, as more information emerged, he publicly admitted that he believed he had been wrong.

No defensiveness.
No doubling down.
Just recalibration.

That kind of intellectual humility is rare—especially in a world where identity and opinion are so tightly fused.

Connection Until the Very End

In his final days, even while facing paralysis and hospice care, Scott continued to go live—sometimes from his hospital bed—connecting with his audience.

It was clear that connection and community weren’t optional for him; they were nourishment.

One of the last things he shared struck me deeply. When followers told him, “It’s not too late,” he responded with something like:

If you’re asking me to do it, I’ll do it.

Not from fear.
Not from doctrine.
But from openness.

Not emotional reactivity—relational presence.

Mortal Trappings and the Next Adventure

Years before his passing, Bob Weir once said something that has been echoing for me this week:

“Death is a liberation… the last and best reward for a life well lived.
That’s where the adventure starts—when you leave behind your mortal trappings.”

Taken together, these two men—very different in expression—point toward the same deeper truth.

A life well lived isn’t about certainty.
It’s about clarity without rigidity.
Conviction without contempt.
Thinking deeply without being owned by emotion.

Scott Adams stayed engaged with life until the very end—curious, connected, willing to revise, willing to listen.

Bob Weir, in his own way, modeled that same wisdom—holding life lightly enough to speak of death not as an ending, but as a doorway.

What I’m Carrying Forward

So here’s what this week leaves me with:

Live engaged.
Think clearly.
Stay humble.
Stay connected.

And loosen your grip on your mortal trappings—just enough to remember what actually matters.

If this reflection gave you a sense of an exhale, you’re not alone. That’s the direction I’m moving—personally, professionally, and with everything I’m building going forward.

— Rob