15 Life Rules Worth Breaking

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Today at a Glance:

“The young man knows the rules, but the old man knows the exceptions.” - Oliver Wendall Holmes, Sr.

As children, we are taught to live by an ever-expanding set of rules. The rules keep us safe. They limit our downside during a fragile period of our lives. They also limit our upside, as they create artificial constraints on our movement and collisions as we travel through the universe.

Rules are good—but just like the old man in the quote above, you have to know when to bend and break them.

15 Life Rules Worth Breaking

I’d like to open with one of my favorite quotes of all time:

“The young man knows the rules, but the old man knows the exceptions.” - Oliver Wendall Holmes, Sr.

Read that again.

So much wisdom contained in such a short, concise statement.

As children, we are taught to live by an ever-expanding set of rules. This is (mostly) good—it gives us a concrete, stable way to view the increasingly complex, dynamic world that we have entered.

The rules keep us safe. They limit our downside during a fragile period of our lives.

The problem? They also limit our upside, as they create artificial constraints on our movement and collisions as we travel through the universe. They force us to walk down a narrow path with bumpers on both sides—they eliminate the flashes of serendipity, the asymmetries that define the lives of the greatest among us.

Rules may limit your risk, but they also limit your reward.

Rules are good—but if you’re looking to play asymmetric games—those with low downside and uncapped upside—you have to know when to bend and break them.

Here are 15 life rules worth breaking:

Wait for the Perfect Moment

This rule has paralyzed would-be action-takers for generations.

The reality: there is no such thing as the perfect moment.

Sometimes you just have to open the door, jump out of the plane, and hope you packed the parachute tight.

You Have to Work Hard to Succeed

Hard work is important—but it's relative, not absolute.

In the Digital Age—when creative and inspired work stands out and is rewarded—what you work on is more important than how hard you work.

Play your game, not theirs. You’ll play it better.

Become an Expert, Not a Generalist

Society celebrates experts in any given field.

But as David Epstein finds in Range, many experts succeed because of the range of pursuits that preceded their main endeavor.

Become a polymath. Generalize first, specialize later.

Let Things Play Out

This isn't a movie that you're watching on your TV.

You are not a passive observer of your own life. There are times to sit back, and there are times to push.

Learn to identify the difference and never be afraid to provide a little push.

Don't Ask Too Many Questions

Children are born with an insatiable curiosity, but somewhere along the line, we are told to stop asking questions.

The most successful people in the world never listened—they broke this rule.

Ask questions. Be curious. Be interested.

If It Ain't Broke, Don't Fix It

Complacency will always lead you down a bad path.

Just because something isn't broken, doesn't mean it can't be improved.

Continuous improvement is the way. Focus on small, incremental improvements—day in, day out.

Get a Stable Job

This might have been a good rule in the Industrial Age, but its foundation is crumbling in the Digital Age.

The way we work is fundamentally changing—opportunities for creative, unstructured career paths are endless.

Find your Zone of Genius and operate in it.

Stay in Your Lane

A rule of the fixed, stagnant, and hierarchical—often used to keep employees in line.

It's great to double down on your strengths, but never let external pressures prevent you from expanding your domains.

Growth mindsets rule the world.

Think Through Every Big Decision

We are told to methodically consider the pros and cons of every big decision in our lives.

As a result, many of us have decision paralysis.

With big decisions, you're actually better off making them fast—let your gut and instincts guide you.

Don't Talk to Strangers

A classic we are told as children—the residue of which carries into adulthood for far too many.

When we open up to those around us, we stimulate, learn, and grow.

"There are no strangers here; Only friends you haven't yet met." — William Butler Yeats

Get a Four-Year Degree

For decades we told children they had to attend a traditional four-year college, or else they were a failure.

That is a lie—and we loaded a generation with student debt because of it.

Four-year degrees make sense for many, but not for all.

Follow YOUR path.

Save Now to Enjoy Later

All mainstream financial advice tells you one thing: save now to enjoy later.

I agree, with a caveat...

You have to enjoy the prime of your life! Now and then, it's ok to save a bit less to go to that concert with your friends.

Find your balance.

Have a Plan & Stick to It

It's important to have a plan.

But as Mike Tyson famously said, "Everyone has a plan until they get punched in the mouth."

Plans have to be dynamic—and punch-proof! You'll only go as far as your ability to absorb and pivot on the fly.

Don't Be Self-Promotional

It's easy to condemn self-promotion when you're at the top.

But when you're first starting out, you may be the only one in a position to promote.

When you put in the work, energy and love, share it with the world! Genuine pride is infectious.

Be Realistic

It's not up to anyone else to decide what is possible for you or your life.

Are there constraints outside of your control? Sure. Is that a reason to settle? Hell no.

As Will Smith says in Pursuit of Happyness: "If you want something, go get it. Period."

There you have it: 15 life rules worth breaking.

I’d love to hear from you. What common rules am I missing? Comment below!

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Until next time, as always, stay curious, friends!