"Two roads diverged in a wood, and I—I took the one less traveled by, And that has made all the difference." — Robert Frost, The Road Not Taken (1916)

This is a newsletter about the road less traveled. The uncommon path. The passage to non-conformity. The silent revolt. The rejection of default.

Walking this road does not come without its costs. Those who choose to do so must be willing to pay the price. In discomfort. In struggle. In misunderstanding.

In a world that values sameness, standing out is never free. But those who endure unlock the door to the most extraordinary lives.

What follows is a brutally honest list of the traits I've observed in people who truly stand out.

These are the traits I aspire to live by. The road less traveled that will make all the difference...

Be anti-insecure

One of the most surprising truths I've witnessed in spending time with "successful" people is that most are deeply insecure.

The signs of that insecurity are fairly obvious:

• They constantly "flex" on things
• They chase public affirmations
• They exhibit obvious jealousy when others win
• They name-drop incessantly
• They talk 2x as much as they listen

Insecurity is the norm.

In many cases, it's clear that the insecurity is what drives the person to achieve "success" in their narrow domain, but that same insecurity will rob them of living a comprehensively successful life.

Be different: Don't flex. Don't posture. Don't perform. Let your actions and outputs speak for themselves. Real confidence is quiet. It stands out in a world where everyone is so eager to tell you all their accomplishments within two minutes of meeting you.

The person who walks quietly, listens, and asks great questions will stand out much more than the person who shouts all of their wins to anyone who will listen. The former sparks intrigue, while the latter draws jealousy or skepticism.

If you want to stand out: Be anti-insecure.

Cheer loudly (and without qualification)

In a world addicted to competition and quiet comparison, genuine support is a rarity.

Here's an observation: A lot of seemingly genuine cheers are subtly qualified by minimizing or undermining comments.

The person wants to create the appearance of genuine support, but cannot stop the underlying negativity from bubbling up in the form of the qualification:

• "It's incredible how fast she's grown her platform! Those growth hacky posts clearly work."
• "I'm so happy for him for how many books he sold. It's probably easier given it's so mass market, but still."
• "Her company just raised its Series C. I'm so happy for her! Just imagine if they didn't get that lucky break with the competitor going under."

The opposite of a cheer isn't always a boo. Sometimes it's a subtle qualification.

Those who are genuinely supportive never feel the need to qualify their support. They are confident enough in themselves that they can give genuine flowers to others. They know that a rising tide lifts all the boats. That there is always something to learn from the success of others. That curiosity is much more valuable than envy or jealousy.

If you want to stand out: Cheer loudly (and without qualification).

Practice the art of studied nonchalance

In the 15th century, an Italian courtier named Baldesar Castiglione wrote of the traits of the perfect courtier:

"I have found quite a universal rule...to practice in all things a certain sprezzatura [nonchalance], so as to conceal all art and make whatever is done or said appear to be without effort and almost without any thought about it."

This term—sprezzatura—has come to be defined as a "studied carelessness" in the modern English language.

I think of it as earned effortlessness. Effortless, elegant performances are often just the result of a large volume of effortful, gritty practice.

From the outside, it looks easy, almost unconscious, but in reality, it's the product of consistent compounding of tiny daily actions over long periods of time.

Work so hard at your craft in the dark that your performances appear effortless, even careless.

If you want to stand out: Practice the art of studied nonchalance.

Surround yourself with Truth Tellers

I recently came across a quote that stopped me in my tracks:

"The degree to which a person can grow is directly proportional to the amount of truth he can accept about himself without running away." - Leland Val Van De Wall

An observation from history is that the inability to accept the truth is the cause of the downfall of many great men and women.

As you become more successful, your own success will conspire against you:

• You will start to believe you are just that good. You will be skeptical of criticism or constructive feedback and prone to ignoring it.
• The people around you will become afraid to tell you the truth. They'll pat you on the back and tell you what they think you want to hear because it's much safer than telling the truth.

This is a perfect storm for disaster.

Find and cultivate a few Truth Tellers in your life—the rare few who are willing to give you honest perspectives from a place of love. Create an environment where they know they're safe to do so.

Consider it an investment in your continued growth, plus an active insurance policy against your downfall.

If you want to stand out: Surround yourself with Truth Tellers.

Embrace your beginner's mind

Most people maintain a fixed array of beliefs, assumptions, and understandings about the world around them. This static foundation forms the basis of how they experience, process, and make sense of the world.

The fixed nature of this map of reality insulates them from the discomfort of confronting new information or ideas that would challenge the existing base.

But this leads to negative downstream consequences: When we're too entrenched in our map, we fail to adapt. New information that "doesn't fit" is rejected and cast aside.

The antidote is the Zen Buddhist concept of Shoshin, which means the beginner's mind.

To embrace Shoshin means you are willing to:

• Say "I don't know" or "I don't have enough information to hold an opinion" when necessary
• Change your mind on a topic in light of new information
• Endure the embarrassment of being a beginner
• Ask the seemingly basic (read: dumb) questions to further your understanding

Every expert started out as a beginner. Those who embrace the embarrassment will eventually win. They thrive on that feeling of newness. They love diving into something with a child-like curiosity. The beginner’s embarrassment is actually a positive signal.

If you want to stand out: Embrace your beginner's mind.

Show up when no one is watching

Most people only show up when they're going to get credit for it.

They show up when it's going to get them recognition. When it's convenient. When it's easy. When everyone is watching.

But the real rewards in life are earned through the willingness to show up when it's none of those things.

And make no mistake, showing up consistently is the key to life.

Show up when it’s hard. Show up when it’s messy. Show up when you don't feel like it. Show up when the rewards are uncertain. Just show up. You can never bet against the person who just keeps showing up.

If you want to stand out: Show up when no one is watching.

Tolerate uncertainty a little bit longer

Fear of uncertainty is often what keeps people from building the life they deserve.

When we fear uncertainty, we settle to escape it. This means that success is ultimately about tolerating uncertainty.

It's very easy to show up with energy when something is working. When it's clicking. When the result feels predictable.

But those periods of clarity are few and far between.

The most dangerous person in the world is the one who shows up every single day even when the rewards are uncertain. Those who can tolerate the most uncertainty are the ones who will eventually win.

Sometimes the moment of peak uncertainty is the moment right before the breakthrough.

If you want to stand out: Tolerate uncertainty a little bit longer.

Do the old fashioned things well

In a world obsessed with scalability, automation, technology, and AI, the simple human things go a long way.

Some examples:

• Look people in the eye
• Do what you say you'll do
• Be on time (or early!)
• Practice good posture
• Have a confident handshake
• Hold the door
• Be kind (never gossip!)

These may sound painfully simple, but surprisingly few people do them consistently. They're free, entirely within your control, and will never go out of style.

In fact, they may become even more important in a future dominated by technology...

If you want to stand out: Do the old fashioned things well.

Go all in on the things you want

Here’s the harsh truth nobody wants to tell you: If you’re half in, you’re actually all out.

80% is a waste of time. Even 90% in gets you nowhere. There’s something magical in that last little bit, simply because so few people are willing to do it.

The tiny bit of additional energy, of extra focus, of presence, that is where you unlock new levels to the game.

This is a reflection on my own experience: Every single time I thought I could “hack” the game and still get the full reward, it got me nowhere. More often, it got me a painful (and costly) lesson.

The best things of life come from committing fully to a pursuit. The universe rewards those who are willing to step into the arena and shut the door behind them.

And it doesn't take talent or intelligence to do that, just courage.

If you want to stand out: Go all in on the things you want.

The Road Less Traveled

The world wants you to be normal.

Most people spend their entire lives trying to do just that. To fit in. To blend. To conform. To accept.

But the people you remember chose a different path. They chose to reject the defaults. They chose to live by design.

These 9 traits may not make you popular, but they will make you powerful. They will make you real. They will make you uniquely you.

So if you want to build your own version of an extraordinary life, stop following the crowd.

Take the road less traveled. It will make all the difference.