21 Pieces of Timeless Wisdom for Entrepreneurs (That Everyone Ignores)

A while back, I asked people on Twitter and LinkedIn what they wanted to see around the intersection of Entrepreneurship and Mental Health. This will likely become a series, but today’s topic is thanks to my friend Amanda Natividad.

The issue with timeless wisdom is it eventually becomes so common that it turns into a cliché and we dismiss its value.

But after we collectively dismiss and forget it, we rediscover its power and start applying it to our lives again until it eventually becomes so common we dismiss it again, in a never-ending cycle of rediscovery.

I scoured the internet and my own mind for the best bits of wisdom that we’ve all heard countless times but may have forgotten, so you can rediscover them and start applying them to your life.

Here are 21 pieces of timeless wisdom for entrepreneurs that everyone ignores (to their detriment), but with some fresh psychological interpretations…

•••

Give Yourself Grace

Would you talk to another human being the way you talk to yourself on a daily basis?

• You should’ve known better!
• Why would you do something like that?
• You should be more successful by now!
• People are going to think you’re an idiot for doing that!
• You just don’t want it bad enough, that’s why you’re still struggling!

But for some reason, you think it’s ok to talk to yourself like this—to bully yourself every day.

How’s that working out for you so far? Has it lead to unlimited happiness, success, and fulfillment?

Then why the fuck keep doing it?

Hey, this is tough love, not me blaming you. I do this shit sometimes, too. I have high standards for people who I know have huge potential, which includes myself. But this also makes me prone to being overly self-critical when I don’t live up to my own expectations of myself—because I have a low tolerance for when I fall short of my potential.

But when my friends fall short of their potential? I give them grace, I try to understand where they’re coming from and offer support.

Because look man..life’s hard, then you die.

I don’t know anyone who hasn’t had a hard life to some degree.

We all have insecurities. We all have things we wish we would’ve done differently, handled better, or cherished more when we had the chance. We all struggle to live up to our potential. We all feel inadequate because reality never lives up to our expectations.

We’re all just doing the best we can with the tools we have.

So did your parents, so is your mortal enemy, so is your favorite celebrity.

The sooner you realize this, the sooner you’ll be able to savor the little moments of joy, take advantage of opportunities to grow, and give yourself some grace for being imperfect.

You can’t self-flagellate your way to success.

Give yourself some grace if you’re not where you want to be yet.

•••

Perfect is the Enemy of Progress

I used to think I couldn’t take action until I had a “perfect” plan. The result? Years of theorycrafting with nothing to show for it except for a hard drive full of ideas that never saw the light of day.

Here’s the thing: Nothing in life is perfect. Perfection is unattainable. So waiting for something to be perfect before you take action is expecting yourself to attain the unattainable.

Progress, however, is always possible, because progress is relative. Are you better today relative to yesterday? Did you create something new today relative to what you did yesterday? Are you more mature, more wise, more compassionate, more ambitious, more disciplined, more skilled, etc. relative than you used to be?

Imperfect action beats a perfect idea every single time.

So if you haven’t made the progress you hoped you would by now, ask yourself:

Am I pursuing progress or waiting for perfection?

•••

Treat Others Like You Want to Be Treated

I’ve talked before about what I learned from a NYC street hustler named Cornbread and some of the sleazy sales tactics a lot of hungry (read: desperate and scruple-less) entrepreneurs use to drive sales. But ask yourself:

• Do you like being shamed for your choices? Then don’t make fear-mongering, dramatic content that makes people feel guilty for how they live (common in health/fitness niches)
• Do you like feeling like you’re being sold to? Then don’t hard sell or send tons of cold DMs with fake-friendliness (common on Twitter)
• Do you like being conned out of your hard-earned money? Then don’t needlessly upsell customers on things they don’t need, or that are low-quality, just so you can increase your CLTV (common in direct-response marketing)

So many entrepreneurs struggle with what’s called cognitive dissonance, which is where your actions and your beliefs don’t match. Cognitive dissonance can cause extreme stress because we’re living unaligned with our values. We claim to be about one thing, but our actions tell a different story.

This is especially common when we don’t treat others how we would want to be treated.

The most common way this plays out is when you chase quick cash that requires you to sacrifice your integrity.

• Promoting things you wouldn’t use.
• Creating products you wouldn’t buy.
• Building a business you don’t want to own or run.

Doing this eats at you. You know you’re better than this. You know it could hurt your reputation. You know it’s a short-term gain but a long-term loss.

Yet you do it anyway.

And you suffer for it.

But if you build a business around what you wish existed in the world, that you have conviction deserves to be built, that people truly need, then you won’t suffer from cognitive dissonance that comes from sacrificing your integrity for income.

I regularly leave money on the table because of my integrity and the reputation I’ve worked my ass off to build.

But if you build things you truly believe in, for people who truly need it, you’ll be fine.

•••

You Can’t Pour From an Empty Cup

This is especially difficult for people who are “givers.” Being selfless is a virtue, right? Which means being selfish is wrong.

For many people, practicing self-care feels selfish, so they deny themselves the opportunity to replenish their cup.

But if you truly care about other people, you have to take care of yourself. Otherwise, you won’t be able to give as much as you could.

Or maybe you’re not a giver. Maybe you think the only way to go through life is to MAXIMIZE ALL THINGS ALL THE TIME BECAUSE PEAK PERFORMANCE IS LIFE BRO. WOOOOOOOOOO.

Calm the fuck down, Chad.

I’m not a big peak performance person—I think it’s overrated and misunderstood. But let’s say you actually do want to maximize your performance, cool.

Do you know what bodybuilders and athletes prioritize?

• Not lifting.
• Not eating.
• Not practicing.

Sleeping.

Yes, lifting and nutrition are major components to performance. But everything starts, and ends, with sleep.

You can go a good bit without eating. You can go even longer without exercising.

But even a single night of poor sleep can have immediate and long-lasting effects that are hard to make up.

Sleep, rest, is the foundation of performance—peak or otherwise.

So whether you want to give as much as you can to the people you love, achieve peak performance, or just recover from burnout, prioritize rest.

Side Note: Check out Growth Equation if you want to learn more about peak performance, they have a ton of awesome, science-backed resources. Plus, Brad and Steve literally wrote the book on Peak Performance (aff).

•••

Happy Wife, Happy Life

Your home should be your sanctuary. But “home” doesn’t just mean your house. The person you choose to spend your life with becomes a kind of sanctuary too.

When you’re anxious, their presence is calming. When you’re happy, they share in your celebration. When you’re distraught, they’re there to console you.

As long as you’re around them, you feel like you’re home, regardless of where you are—because their presence acts as a kind of sanctuary from the stresses of the world (and you can do this without becoming codependent).

But a partner (wife, husband, whatever) who isn’t “happy” means your sanctuary won’t feel like a sanctuary.

It also means that if the thought of going home or spending time with your significant other ties your stomach in knots, it’s a good indication to reevaluate if the person you’re currently with is worth continuing to be with.

But if you find someone who feels like home, who accepts you as you are yet supports you to become a better version of yourself, and someone who you can spend 16 hours in a car with and never get tired of their companionship—you’ve got everything you need for a happy life.

•••

No Man is an Island

Here’s the thing, the fantasy of the “self-made” or “lone wolf” entrepreneur sounds great. But they’re just that—a fantasy.

In reality, no one succeeds alone. But pride can cause you to isolate from the people who would support you.

• When was the last time you asked for help?
• When was the last time you reached out to a friend to catch up?
• When was the last time you offered to collaborate with a fellow entrepreneur?

Humans are social creatures. This is why social ostracism has been a punishment throughout human history—feeling isolated can literally hurt us psychologically and physically.

You know what actually happens to lone wolves in the wild? They don’t survive long.

Do yourself a favor—reach out to a friend this week, catch up, ask for help, offer support, whatever—just enjoy some human connection.

•••

Practice Makes Perfect

Whatever you consistently do, you get better at—for better or worse.

Some people are Olympic-level worriers because they’ve spend decades of their life practicing how to worry.

But when they spend 5 minutes trying a relaxation technique, they say, “This is too hard, I can’t do it,” and give up.

They’re comparing 5 minutes of practicing relaxation with 30 years of worrying—of course they suck at relaxation (at first).

The same goes for copywriting, storytelling, selling, offer creation, audience building, team building, hiring, lifting, communication—everything comes down to practice.

When you learn to see something you suck at as a skills deficit that can be improved with practice, rather than an unfixable character flaw, you’ll develop an empowered mindset to move forward.

So ask yourself:

What skill do you want to get better at?

Then start practicing it.

•••

Honesty is the Best Policy

Yes, you shouldn’t lie to other people—customers, friends, colleagues, whoever.

But most entrepreneurs lie to themselves all the time.

Be honest with yourself:

• What do you actually want?
• What’s the real reason you haven’t achieved it yet?
• Are you building things you truly believe in, or are you chasing things you think you’re supposed to want because other people have told you you should want them?
• Do you want the successful version of the thing you’re currently building? Aka, are you prepared for the hidden cost of success?

Most entrepreneurs I work with either don’t truly know what they want out of life (so we do Core Value work to help them clarify what matters) or they know what they want but make excuses for why they can’t have it yet (so we work on identifying and processing their limiting beliefs, like the Four Horsemen of Fear, holding them back).

It all comes down to being brutally honest with yourself.

So the sooner you’re honest with yourself about what you want, what’s holding you back, and what you need to do to achieve it, the sooner you’ll feel like what you’re doing on a day-to-day basis matters.

Side Note: If you’re interested in the exact system I walk my 1:1 clients through to help them build a values-aligned life and business by clarifying what matters, overcoming limiting beliefs, and pursuing their purpose, check out my on-demand coaching program now:

•••

Rome Wasn’t Built in a Day

Empires aren’t built overnight, but they can be destroyed overnight.

The trick is understanding what empire you’re trying to build, and focusing your time, energy, and attention on building it.

• Your reputation is an empire.
• Your platform is an empire.
• Your business is an empire.

Anything you do to scale your impact or income is an empire.

Your empire can take a lifetime to build and an instant to destroy. So make sure you build on a foundation of integrity, otherwise it could crumble.

This piece of wisdom also acts as another reminder: Don’t compare yourself six months in to someone seven years in. Like we talked about in The Fledgling Mindset, it’s ok if you don’t already have everything figured out yet.

It’s easy to look at people ahead of you and get frustrated with your relatively lackluster results. But every empire is different—instead of looking at other people’s empires with jealousy or shame you haven’t achieved the same yet, use them as inspiration of what’s possible if you keep building brick by brick.

•••

Don’t Make a Mountain Out of a Molehill

Life is about perspective. This is one of the key pieces of advice I got from a mentor and friend, Dr. Keelon Hinton.

When we lose perspective, we suffer.

For example, anxiety causes us to be myopic, aka short-sighted. When we’re stressed, it’s often because we’re too close to the thing stressing us out. So this stressor takes up all of our visual field, preventing us from seeing anything else.

Meaning if you’re face to face with a molehill (a small thing), it will take up all of your visual field and look like a mountain (a big thing).

When this happens, we need to zoom out to get perspective on what matters and what doesn’t.

In 5 Questions To Clarify What Matters In Your Life, one of the questions I dive into is:

“Will this matter in a day/week/month/year/decade?”

This is a great question to help you put life back into perspective.

Because if it won’t matter tomorrow, it isn’t worth stressing about today. Save your stress for the few things worth stressing about (and by “stress about,” I mean devoting attention to solving).

So when the world starts to close in on you, focus on finding ways to put life back into perspective.

Your stress levels will thank you.

•••

Face Your Fears

This doesn’t mean go skydiving or sleep in a room full of snakes and spiders.

It means stop avoiding your own insecurities and limiting beliefs.

See, most people think lack of money, intelligence, or resources are what hold them back from success. So they blame these for why they haven’t achieved what they want yet.

But these things aren’t what hold most people back—limiting beliefs are.

When we fear things like failure, negative judgement, or being corrupted by success, we do things that help us avoid facing these fears like procrastinate, struggle with perfectionism, and jump from one Shiny Object to the next. (I cover this more in my video on What’s Hiding Behind Your Self-Sabotaging Behaviors?)

But when we avoid our fears, we’re often avoiding a path to fulfillment.

“Everything you want is on the other side of fear” is a cliché and oversimplification, but there’s a lot of truth in it. Facing your fear is the price you have to pay to succeed.

Here’s a simple question to ask:

What could you achieve if fear wasn’t holding you back?

•••

You Are Your Own Worst Enemy

It’s easy to blame outside circumstances for our situation, but most of the time it’s just us getting in our own way.

• Our own assumptions that cause blind spots.
• Our own work ethic that leads to burnout.
• Our own habits that trap us in mediocrity.

But this is also a good thing, because it means we’re in control of our success or failure.

If we are our own worst enemy—the main thing standing in our way—then we’re in full control to get out of our own way and move forward.

So next time you feel stuck, ask yourself:

How am I getting in my own way right now?

•••

The Grass is Always Greener

Humans are comparative by nature—we’re constantly looking at what other people have relative to what we have. So of course it always seems like everyone else is crushing it while you’re barely getting by.

But let’s pretend you could actually switch places with someone—do you really want their life?

Not a piece of their life, but their entire life. It’s all or nothing.

For example:

Maybe they have tons of money, but they’re also trapped in the never-ending cycle of chasing “more,” instead of defining “enough.” They’re never satisfied because maybe they chose the Path of Lucrative Misery.

Maybe they’re famous, but they struggle to form genuine human connections because they never know if someone actually wants to be their friend or is just using them for their fame. Talk to your famous friends, if you have any, and see how much different their average day is than yours for simple things like going to the store, taking a walk, or relaxing at a local coffee shop.

Maybe they have a hot spouse, but their spouse has deep-seated insecurities and dysmorphia that affects every aspect of the relationship. Do you really want to spend the rest of your life obsessing over every calorie, botoxing every wrinkle, pumping yourself with all the supplements, and existing in a constant state of denial about normal aging processes?

You typically don’t want someone else’s life. You just aren’t aware of why because you’re comparing your private struggles with their public wins.

Consider the Hidden Cost of Success before you wish for someone else’s life.

•••

Where There’s a Will, There’s a Way

The human mind is the greatest force in history.

• It’s harnessed nature itself.
• It’s built (and destroyed) empires.
• It’s defied its own limitations through technological innovations.

This proves one thing: The human mind is capable of just about anything (with the right incentives and resources).

You just have to learn how to harness it.

If you point your mind toward finding problems and excuses, it’ll find problems and excuses. Because you’ve “willed” it to find them.

But if you point your mind toward finding solutions, it’ll find them, too.

Side Note: Check out How to Stop Making Excuses and Start Making Changes if you want some solid strategies to do this.

•••

No Pain, No Gain

Growth of any kind requires struggle. There’s no way around it.

• Want to gain muscle? You have to go through the pain of lifting.
• Want to gain success in business? You have to go through the pain of uncertainty in early entrepreneurship.
• Want to gain a better understanding of yourself for personal growth? You have to go through the pain of introspection and change.

But we reflexively move away from pain—this is why so many fake gurus make tons of money selling bullshit snake oil that promises miraculous results without any effort or struggle. This is also why we’re seeing a decline in expertise, because people aren’t willing to invest in their crafts.

But here’s the thing—when you look back on your life, you’ll remember the struggles more than the victories because the struggles are what give life meaning and make the victories worth celebrating.

We don’t appreciate things that are freely given to us. But the things we feel like we earned, that we sacrificed and struggled for? Those mean everything.

Most people think that the gain makes the pain worth suffering through.

But the reality is, the pain gives the gain meaning.

•••

Actions Speak Louder Than Words

How many times have you told yourself that this thing is important to you, but your actions continue to indicate this thing isn’t actually that important?

The reality is, most of our actions don’t align with what we claim are our priorities.

• We say we want to get healthier, but we don’t go to the gym or eat better.
• We say we want to write a book, but we don’t set a daily word count.
• We say we want to succeed, but we don’t cultivate the skills that make success inevitable.

In Don’t Confuse Your Watchadoon, I discuss a simple exercise to help you align your actions and intentions:

Pretend a small creature from a curious species interested in anthropology is studying you today. This creature doesn’t understand anything about humans and can’t communicate with you. So all it can do is observe your actions and try to draw conclusions about what you do and what’s important to you based on your actions.

Now based on what actions you took today, what would this creature think you do? What would it think is important to you?

It’s easy to say something’s important to you, but do your actions back up this statement?

Here’s a helpful question to ask:

How can your actions speak for you today?

•••

Live. Laugh. Love. (gag)

No, I don’t have a primitives aesthetic sign of this in my kitchen, and the laissez faire women’s vagabonding movement isn’t my thing. But there are millennia’s worth of wisdom packed into these three words.

Live your life on your terms, be true to yourself, what you want, and what impact you want to have on the world instead of chasing what society tells you or trying to get validation from others.

Laugh because you have to find joy in the little moments. And life, after all, is just a series of little moments.

Love because a life well-lived is rarely lived alone, do what you love, and spend your life with people you love.

So next time you’re feeling low, ask yourself how you can live more, laugh more, or love more. You’d be surprised how much they can help.

•••

If Life Gives You Lemons, Make Lemonade

I’m a huge fan of Stoic philosophy because of how practical and applicable it is.

A central piece of Stoicism is learning to distinguish what’s within your control from what’s outside your control.

You can’t control what happens to you (aka, life giving you lemons). But you do control how you respond to what happens to you (making lemonade, crying about it, taking a flamethrower to everything, etc).

99% of what happens in life is outside your control—the weather, other people, the world around you. You can spend your life obsessing over all this and feeling helpless, or you can focus on the 1% that’s within your control.

Why give up the little bit of control you have in life?

Think of all the people who inspire you—did any of them have an easy life?

No.

The reason they inspire you is because they conquered seemingly insurmountable odds. They knew they couldn’t control what happened to them and didn’t waste their precious time bemoaning the fact they didn’t have an easier life.

They got to work making fucking lemonade.

While everyone else is bitching about the lemons they were given, you can choose to use those lemons to make a truly remarkable life.

•••

Focus on the Journey, Not the Destination

One of my favorite quotes of all time is from Jerry Seinfeld:

“Your blessing in life is when you find the torture you’re comfortable with.”

This pairs well with two other quotes I think about all the time:

“The struggle is guaranteed. Success is not.” — Tom Bilyeu

“What’s your favorite flavor of shit sandwich?” — Mark Manson

Because here’s the thing, plenty of people succeed on paper but end up miserable in reality. And plenty of other people spend their entire lives chasing something they never catch.

There’s only one destination we all arrive at…

The grave.

No matter how wealthy, famous, or accomplished you become, life is just a journey to death—so why get so caught up running toward the end that you miss out on living?

I’m a huge fan of the Stoic concept of memento mori—remember death. It’s meant to be a motivator to live fully. To cherish what you have while you have it and to make the most of the time you have left.

So instead of obsessing over the destination, how can you obsess over the journey itself?

For example, the world makes sense when I’m writing.

Running a business is cool. Doing BJJ is great. Making videos, courses, and other educational content is fun.

But, to quote Gloria Steinem, “Writing is the only thing that when I do it, I don’t feel I should be doing something else.”

Of course I want to become a mega-bestselling author so I can build generational wealth and impact millions around the world with my ideas.

But the act of writing itself is intrinsically rewarding. I’m not chasing extrinsic things. I hope to achieve them, yes. But I don’t write for accolades. I write to write.

The happiest, most fulfilled people you know are on a journey they love—a torture they’re comfortable with.

I regularly tell people that for me, writing feels like bellycrawling through broken glass. It’s excruciating to wrestle my abstract thoughts onto the page (or screen). But I can’t not write—I’m compelled to write no matter how torturous it is because it’s my torture and I love it.

So find your torture, your craft, your calling—whatever name you want to give it—and give yourself over to it. That’s what fulfillment looks like.

Ask yourself:

What journey is worth the units of my life it’ll take to pursue?

•••

Iron Sharpens Iron

Proximity is a key to unlocking your potential in any arena.

• Spend enough time around fit people and you’ll become more fit.
• Spend enough time around writers and you’ll become a better writer.
• Spend enough time around entrepreneurs and you’ll become a better entrepreneur.

Just being in the presence of other people can improve your own performance—it’s called social facilitation.

This is why I loved joining a Fraternity in college, why I joined various professional groups throughout my career, and why I’ve joined a handful of online communities since becoming an entrepreneur.

Surrounding yourself with people who support you, inspire you to be better, and who open your mind to what’s possible is one of the best things you can do for your personal and professional growth. Period.

This is also why I founded the YFC Community so that fellow coaches (life, executive, etc.) can come together to teach and learn from each other. The philosophy of the community simple: If I share what I know, and you share what you know, we both walk away knowing twice as much. Multiple this by 50, 100, 1000 coaches and imagine the possibilities of how much you can scale your impact and income.

So ask yourself,

Who do you need to surround yourself with to become the person you want to become?

•••

You’re Stronger Than You Give Yourself Credit For

You’ve survived 100% of the things you’ve been through thus far.

• No matter how hard they were.
• No matter how long they lasted.
• No matter how much you questioned your ability to make it through.

You survived.

Because you’re a survivor—you’re resilient as fuck, even if it doesn’t always feel like it.

Remember that.

•••

Wrap Up

Hopefully these nuggets of timeless wisdom are a good reminder of things you can do to succeed in life and business, and enjoy the process along the way.

What did I miss? If there’s a piece of timeless wisdom that’s improved your life that I left out, shoot me an email or DM and let me know! I’d love to hear which ones have influenced your life.

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