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Why Fear Costs More Than Failure Ever Could
We think failure holds us back—but it’s fear that quietly costs us the most.
Daniel Lancaster
October 25, 2025
Good morning!
What we’re building here is extraordinary.
Most investing research platforms focus on stocks picks. That’s important, but by no means the most important. Have you ever heard of someone getting rich by following a stock-picking platform? It’s happened, I’m sure, in the same way that a lucky few have won the Powerball.
But stock picking is only a very small (and even unnecessary) part of wealth building.
What’s necessary is a harmony of actions that springs from mindsets aligned with wealth.
That’s what we’re aiming to build here. A community that is focused on action and encouragement: celebrating wins, learning from losses, and exchanging strategies along the way.
The Wealth Expedition membership is going to be unlike anything else.
If you haven’t already, take your place on the Founding Members Waitlist to secure the perks reserved for our earliest supporters. The goal is to make our wealth journey fun, exciting, and transformational from the inside out.
In that same spirit, let’s examine a type of wealth that’s often overlooked. One that forms the foundation to building lasting financial wealth.
Onward together!
-Daniel
Disclosure: This post contains affiliate links, which means I may earn a small commission if you purchase through them. I only recommend resources I personally find valuable and relevant.
📽️ I’ve also covered this topic in a short YouTube video—check it out here.
PARADIGM SHIFT
Freedom From Fear: The Hidden Wealth Multiplier
When it comes to building wealth, most people focus on the wrong levers: picking just the right stocks, timing the market, or finding the next big opportunity.
Yet the research is clear: over time, two factors determine the bulk of investment success.
The willingness to take appropriate risk
The ability to stick with the proper asset allocation
It sounds simple, but few actually do it.
Because both depend on mastering something much harder than math: the emotions that rise when things go wrong.
Knowing Your True Risk Tolerance
“Know thyself,” said the ancient Greeks.
An excellent maxim that’s easier said than done, especially when it comes to money.
Risk tolerance is about two things:
Your ability to stay the course through tough times
Your capacity to maintain other types of wealth while pursuing financial wealth
Those other forms include a positive mental attitude, physical health, strong relationships, and peace of mind, according to Napoleon Hill (author of Think and Grow Rich).
If we take on more risk than we’re emotionally ready to endure (even if we have the financial capacity to do so), we endanger those other forms of wealth.
In chasing time, flexibility, and purpose, we may ironically forfeit them: our minds consumed by fear of loss.
Emotion and the Market
It’s easy to believe we could handle a 15% market drop if that risk means higher long-term returns. But when it actually happens, the experience feels very different.
Markets never fall in silence. They drop in a cacophony of voices explaining, predicting, doomsaying. Imaginations run wild. The world changes. And suddenly we make poor decisions based on emotion and overconfidence.
The same pattern appears in entrepreneurship.
You can run the numbers, creating Plans A through F. But when faced with temporary failure, you find out what “risk tolerance” really means. The true test isn’t financial; it’s emotional. It’s your ability to stay grounded in chaos.
Gaining Perspective When Tested
Roman Emperor Marcus Aurelius (121-180 AD), who ruled over much of the known world in his time, wrestled with this same challenge. In Meditations, he wrote:
Reflect often on the speed with which all things in being are swept away… Existence is like a river in ceaseless flow… scarcely anything stands still. So it must be folly for anyone to be puffed with ambition, racked in struggle, or indignant at his lot.
Consider how he took the greater perspective.
To be puffed with ambition. What’s the use, he asks. All temporal things and creatures pass away and change into another form.
To be racked with struggle. Why should we be? What are we working so hard for?
To be dissatisfied and bitter about the way our lives have unfolded. For what?
Everything changes. Nothing stays the same for long. We’re not in an eternal continuity.
Aurelius reminds us that everything changes. Nothing, be it success or struggle, lasts forever. To cling too tightly to either is to lose perspective.
Reframing Loss
We must awaken to the fact that we cannot lose the past. The past is what it is.
Losses or failures do not take away our present either.
What we perceive in loss is that it takes away some part of our future. But that’s a false way to frame it.
In the future, if we are to live a fulfilling life, we will be doing something of value regardless of what happens to us in the present. And that something of value will be not simply for ourselves, but for the sake of others. It is within our power to control what that something is. And when true value is produced, income is not far behind.
What’s Worth Pursuing
Aurelius also wrote:
At break of day, when you are reluctant to get up, have this thought ready to mind: ‘I am getting up for a man’s work. Do I still then resent it, if I am going out to do what I was born for, the purpose for which I was brought into the world? Or was I created to wrap myself in blankets and keep warm?
It’s tempting to dream of ease: a life of early retirement, endless leisure, or passive income without effort. But as Odysseus learned on Calypso’s island, an eternal holiday quickly becomes a cage.
We are wired for purpose, not comfort alone.
And it’s critically important that we learn this as soon as possible in life. Otherwise we will spend our lives chasing an illusion.
True fulfillment comes from doing valuable work: creating, serving, and building something that outlasts us. That’s as true for investing as for life.
The Parable of Risk and Reward
Jesus revealed what he thought about fear of loss when he told the parable of the talents:
You wicked and slothful servant!…You ought to have invested my money with the bankers…So take the talent from him and give it to him who has ten.
For to everyone who has will more be given…but from the one who has not, even what he has will be taken away.
The servant’s failure wasn’t in losing money. It was in refusing to try out of fear.
Fear led to paralysis, and paralysis led to loss in the end.
Money is replaceable. The dominating fear of losing it is a sure path to poverty, either materially or spiritually. Fear of loss keeps us focused on our small lot, at the expense of the whole world. It keeps us counting pennies rather than taking a risk to make a bigger difference in the world with what we have.
Courage, not certainty, is what multiplies our potential.
Freedom From Fear
Napoleon Hill listed “freedom from fear” as one of the highest forms of riches in Think and Grow Rich.
Until we conquer fear, we cannot step fully into opportunity.
Wealth—financial, spiritual, and relational—flows toward those who act with clear minds and steady faith in the long game. Fear guards the gate. Only those who move through it find what’s beyond.
Action Step
This week, reflect on one area of your financial life or business where fear might be holding you back.
Ask yourself: If I wasn’t afraid of temporary loss, what action would I take?
Then take one small step toward that action.
Be the hero in Joseph Campbell’s monomyth (The Hero With A Thousand Faces).
Cross the threshold into the unknown.
The internal transformation developed through courage to face one’s fears will prove to be even greater than the material wealth accumulated along the way.
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