Good morning,

October’s off to a strong start! Warm days, Jays on a win streak, and markets doing what they always do when politics meet policy: restless.

The headlines are familiar, another potential U.S. government shutdown, short-term volatility, long-term déjà vu. The economy will absorb it, as it always does. But the reaction says something deeper about how we live: we move fast, we panic fast, and we forget fast.

The irony is that the noise in the markets mirrors the noise in our minds. Every alert, every headline, every metric demands attention. We live in a world that rewards reaction over reflection, where the goal is to move quickly, not necessarily wisely.

We’ve mistaken busyness for progress, and goals for guidance.

And maybe that’s why the story I was thinking about over the weekend, of a young wild writer from Kentucky, still lands today. Long before we had government shutdowns, stock tickers on our phones or KPIs on our dashboards, he saw the same trap we’re still seemingly falling into…..

Late One Night in 1958

Before the chaos or the cult following, a young Hunter S. Thompson sat at his typewriter in a rented room in Louisville. He was twenty-two. Broke, brilliant, and restless. The kind of restless that only comes from knowing you’re meant for something more but not yet knowing what.

He wasn’t writing an article that night, no, he was writing a letter to a friend named Hume Logan, a man equally adrift. In that letter, Thompson wrote something that could’ve been written this morning:

“If you let your life be guided by goals,
you’ll be forever running to the next one.
The trick is to choose a way of life, and let the goals happen to you as a natural by-product of that way.”

What a fantastic line…..it was raw, unpolished, and honest, the kind of wisdom that feels obvious only once you’ve lived it. Thompson wasn’t yet the outlaw journalist of Fear and Loathing in Las Vegas. He was still a kid with a typewriter, a whiskey habit, and a growing suspicion that chasing someone else’s definition of success was the fastest route to losing yourself.

The letter is worth a read, I can send along to those interested…it’s like a quiet manifesto, not one about ambition, but about alignment. It was about living with direction instead of velocity, about trading the illusion of control for the discipline of awareness.

We’ve Mistaken Goals for Guidance

If Thompson were alive today, he’d laugh at how obsessed we’ve become with goal-setting. We celebrate targets and milestones like they’re maps, while most are just motion.

We don’t live our lives anymore. We manage them.

We set objectives, track metrics, and measure progress against dashboards that rarely ask the only question that matters: Where are these goals actually leading me?

We treat our lives like portfolios, chasing growth without asking: growth toward what? We rebalance constantly, but rarely toward meaning.

Don’t get me wrong, I think goals are important. Goals give you something to aim at. But Intention, Intention gives your goals something to stand on.

Goals don’t create meaning. Intention does.

The Greatest Leverage Isn’t Goals

In finance, leverage magnifies results.
In life, alignment does the same.
It’s the quiet force multiplier of a life lived in sync with your values.

Markets reward patience, diversification, and disciplined allocation. Lives reward presence, perspective, and deliberate direction. Both demand the same skill….the courage to stay still when everyone else is reacting.

Yale psychologist Laurie Santos calls it the miswanting gap - the space between what we think will make us happy and what actually fulfills us. Drawing on the work of Kahneman and Gilbert, she shows how often we misprice our desires.

We chase wealth but long for worth.
We chase recognition but hunger for contentment.
We chase goals but ache for grounding.

Thompson understood that contradiction better than most.
He lived fast (sometimes too fast) but he saw clearly. His rebellion wasn’t against the world; it was against illusion.

The Investment of a Lifetime

We do this in money, and in life. We set targets, build forecasts, and race to hit them. But most goals are just motion, not meaning.

An investor chasing returns can feel productive while drifting from purpose. A person chasing promotions can feel successful while trading contentment for pace.

Hunter’s advice reads like an investor’s parable: Don’t build your life around targets. Build it around principles. When your principles are clear, your performance follows.

In my investment world, markets reward patience, discipline, and alignment….so does life. In both, compounding happens when you stop forcing the outcome and start refining the process. The point isn’t to abandon goals. It’s to make sure they grow out of your way of life, not the other way around

Five Lessons from Hunter S. Thompson

1. Principles outperform goals.

2. Clarity compounds faster than speed.

3. Process drives performance.

4. Alignment is the real alpha.

5. Awareness is your greatest edge.

Return on Intention

ROI once meant Return on Investment.
But the new economy - of life, not money - runs on Return on Intention.

It’s not a metric.
It’s a mirror.

Return on Intention asks:

• How much meaning do you draw from the minutes you spend?
• How aligned are your choices with the life you claim to want?

The world used to reward those who moved quickly, I suggest now it rewards those who move clearly.

Because? clarity compounds.

In the markets of life, awareness is your greatest edge – the ability to sense change before it arrives,
to stay grounded when others are swept away by noise.

Thompson once said he wasn’t afraid of death…only of “not being alive when I die.” It sounds wild until you realize what he meant. He wasn’t chasing chaos, he was chasing consciousness – the rare, lucid awareness that comes from living on purpose.

You can’t outperform the world until you stop being outpaced by your own goals.

The Quiet Dividend

The Return on Intention is the dividend of alignment.

It’s the calm that comes when your goals serve your values. It’s the satisfaction that arises from moving deliberately, not reactively. It’s what happens when ambition finally meets awareness.

Thompson once wrote, “Freedom is something that dies unless it’s used.”
He was right.

But freedom without intention isn’t freedom, it’s drift, and it’s this drift that I consider the illness of our time.

We were taught to measure progress in numbers, but I would suggest the truest measure of wealth is resonance – how closely your outer world reflects your inner one.

So, as we head into the week…… slow down.
Clarify your goals through the lens of intention.
Invest your time, energy, and attention in what aligns.

Because whether you’re managing projects, portfolios or priorities, clarity compounds.

The richest lives aren’t the ones that achieve the most, they’re the ones that aim with meaning.

The greatest freedom is moving deliberately

Be well and enjoy the moments,

Derek Henderson