“A ship is safest at harbor, but that’s not what ships are built for.” - John A. Shedd

"It's better to be safe than sorry."

"It's better to be safe than sorry."

"It's better to be safe than sorry."

This phrase was drilled into me as a kid.

I heard it on the way home from school.
I heard it at the grocery store.
I heard it at the dinner table.

And I heard it from the person that loves me the most; my mom.

Every time, without fail, when faced with an option, she’d say: “it's better to be safe than sorry.”

And for 20+ years, I accepted that phrase as an irrefutable, self-evident, fact.

When given those two options, who in their right mind would choose being sorry over being safe?

No one.

We all want to be safe. No one wants to be sorry, right?

To be clear: my mom’s an amazing woman, wife and mother. I love her dearly and owe a lot to her. The world would be a better place if everyone had a mom like her. I’m incredibly grateful for her. And yes, she absolutely had the best intentions of trying to protect me, by drilling that phrase into me.

But…that framing ultimately didn’t serve me.

How can that be?

No well-intentioned mother would promote being sorry over being safe, right?

Well, it’s not that simple… that’s actually a false dichotomy, and the core focus of my argument.

When we accept the framing of “safe vs. sorry” we've pre-loaded the decision with a cognitive bias. We’ve defined the alternative to safety as regret, before we’ve even looked at what all the alternatives actually are. That framing doesn't help us make better decisions. It just makes the “safe” option feel like the only reasonable one, and that often leads us to make sub-optimal decisions.

And the opportunity cost for making sub-optimal decisions has never been greater.

Real World Example: Block Lays Off 40% Of Workforce

This week, Jack Dorsey, the founder of Block, the company that makes Square and Cash App — announced it was laying off more than 4,000 employees. Nearly half its global workforce, gone. The reason Dorsey gave wasn't financial trouble. Block had a strong year. Gross profit was up 24%. The reason was AI.

In his letter to shareholders, Dorsey was unambiguous:

"Intelligence tools have changed what it means to build and run a company. A significantly smaller team, using the tools we're building, can do more and do it better."

Then he added the line that should make every employee in every industry pay attention:

"I believe the majority of companies will reach the same conclusion and make similar structural changes within the next year."

This isn't a tech story. This is an economy story. And it is the loudest possible signal that the “safe” playbook most of us were handed: go to college, be a good employee, keep your head down, don't take risks, trade your time for a stable paycheck, is becoming obsolete.

In the era of AI, the “safe” path is no longer safe.

Rich Dad Was Right

One of my favorite books is Rich Dad Poor Dad.

It absolutely changed my life.

The core theme of the book is that the real path to financial security doesn’t come from trading your time for a paycheck — it comes from owning assets.

It helped me see how the world actually works, not how I was told it did.

It took intellectual courage to accept that many of the beliefs that I’d held weren’t actually true.

It’s one of the main reasons why I left my job at Apple after having two previous entrepreneurial failures. Yes, being an employee has its benefits, but it has diminishing returns after a certain point. I’d reached that point and the math no longer made sense to stay. When I ran the numbers, it was overwhelmingly clear that the opportunity cost of playing it safe would be incredibly expensive over a 5+ year period; both financially and in terms of life fulfillment.

One of my favorite quotes from Robert is:

“…my poor dad told me that I shouldn’t start a business because 9 out of 10 businesses fail. My rich dad told me, that if 9 out of 10 businesses fail, I should start 10 businesses.”

When I first read that sentence, it blew my mind.

It immediately pointed out the fallacy associated with the “it’s better to be safe than sorry” logic. It revealed the false dichotomy that if you start a business and it fails you’re screwed. It helped me see that the real skill successful entrepreneurs have isn’t avoiding failure; it’s learning from and rebounding from it. While conventional wisdom and the formal school system teaches us to avoid failure, the real world rewards those that add value, regardless of how many times they fail.

It helped me understand the value of courage and the cost of cowardice.

What Really Matters: Living Fully

The purpose of an investment isn't to be safe: it's to multiply your capital. You're not putting money to work so it can sit still. You're deploying it to generate the highest risk-adjusted return you can find. And here's the thing about risk-adjusted returns: the best ones are almost never the safest options.

Take a look at the best performing stocks over the past 30 years and you’ll notice one thing in common: all of them generated extraordinary returns precisely because they weren't safe bets.

The safety-first investor missed every single one of them.

The upside comes in stock-investing, careers, in business, in life, etc. is not evenly distributed. It is highly concentrated in the outcomes that most people were too risk-averse to reach for.

Optimizing for safety will never produce the best possible return.

The best returns require a fundamentally different question — not how do I avoid being wrong? but how do I maximize what happens when I'm right?

Those two questions lead to entirely different lives, which reminds me of this quote from Hunter S. Thompson:

“Life should not be a journey to the grave with the intention of arriving safely in a pretty and well preserved body, but rather to skid in broadside in a cloud of smoke, thoroughly used up, totally worn out, and loudly proclaiming “Wow! What a Ride!”

This is exactly why I’m so passionate about building DailyCourage. It’s my life’s work.

Anais Nin said “Life shrinks or expands in proportion to one’s courage” and I couldn’t agree more.

My mission is to positively impact as many lives as possible, by helping people systematically become more courageous.

I know from first-hand experience that most people are living smaller than they're capable of; not because they lack talent, not because the opportunities aren't there, but because somewhere along the way they picked up a version of it's better to be safe than sorry and never put it down. They built a life around it. And now they're in the harbor, safe, wondering why it doesn't feel like enough. It doesn't feel like enough because we were built for open water.

The people who will thrive in what's coming aren't the ones who found the safest harbor.

They're the ones who learned to sail.

Here's your reflection for the week:

Think about the opportunity cost of your safest big decision. Pick the biggest "safe" decision you've made in the last five years — the job you took, the one you didn't, the risk you passed on. Now honestly calculate the other side of the ledger: what was the potential upside you walked away from? Not to generate regret, but to get honest about the fact that safe choices have a price too.

Here's your challenge for the week:

Identify ONE area where you've been in the harbor too long — and take one step toward open water. Don’t worry about making a big splash. The ship doesn't leave the harbor all at once. You don’t have to jump over board. Start with ONE small step aboard the ship that’s heading to the destination of your dreams. That’s it.

With courage,

Jonathan