So, you’re wondering how to be successful?
Well…that depends on what you mean by successful.
The word gets thrown around a lot, but it’s rarely defined. Ask 10 people what success looks like and you’ll probably get 10 different answers.
But before we dig into the how, you need to figure out…
What the heck does “success” mean to you?
Ten years ago, my answer would have been:
- Make a lot of money
- Get millions of people to read my work
- Quit my full-time job
I eventually did all three, but I don’t define success that way anymore.
Today, success has much less to do with outcomes and much more to do with how I spend my days.
- Did I create something?
- Did I spend time with people I care about?
- Did I love others as I love myself?
- Did I talk to God?
- Did I help someone—a client, a friend, a stranger?
- Did I move my body?
- Did I eat well?
If I ticked off those boxes for the day, I was successful.
Sure, I like making money. I take satisfaction in my career and business. I’m a builder, and I’d be bored sitting around doing nothing.
But making money, status, and ambition the center of my life didn’t work the way I thought it would.
It probably won’t work for you either.
There’s a striving-for-better drive that you’re equipped with—and you should strive to improve your life—but make sure you come at it from the right place.
How do you define success?
Take the time to really think about it, and define success in a way that makes sense for you.
Are you successful if you make a billion dollars but you didn’t get to watch your kids grow up?
Are you successful if you’re rich and famous but nobody around you seems to love you for the real you?
Are you successful because people cheer for you? Are you a failure if they boo?
I’m not saying career and business success can’t be a part of your definition, but I’d advise against making them the entire definition. You want to build a successful life.
Here are some patterns I’ve noticed about humans. When it comes to work, we want to:
- Follow our curiosity
- Get better at something
- Make an impact
- Have the freedom to pursue what matters
- Earn respect for what we’re good at
Outside of work, it’s not that different. Most of us want meaningful relationships, experiences we’ll remember, freedom from constantly worrying about what other people think, and enough presence to enjoy the life we’re building (instead of always chasing the next thing).
Maybe your list looks different. That’s ok. Because success starts becoming much easier to define once you stop borrowing someone else’s definition.
Ideas to help you shift your mindset
Beliefs about success are often programmed into us by our culture, families, and other external factors. Here are a few ways to reframe your thinking.
When you’re considering what success means to you, try applying the regret minimization framework, which can give you a clearer perspective on the short-term drawbacks of a particular path vs. the long-term gains.
People almost always regret things they wish they had done, but didn’t do—much more than the things they tried and failed.
I love the inversion heuristic Charlie Munger provides. Instead of trying to find success, avoid failure. Here, we can use something like the inversion of Bronnie Ware’s 5 regrets of the dying:
- I wish I’d had the courage to live a life true to myself, not the life others expected of me.
- I wish I hadn’t worked so hard.
- I wish I’d had the courage to express my feelings.
- I wish I had stayed in touch with my friends.
- I wish that I had let myself be happier.
Let’s invert them:
- Live a life that’s true to who you are instead of what others expect of you
- Work on what matters without being a workaholic
- Express yourself freely and unapologetically
- Keep tabs on the people you love and keep them in your life
- Allow yourself to be happy right now; you don’t need a reason
Keeping the above in mind, I have a definition of success I’ve heard from people I admire and respect, like John Wooden and Earl Nightingale.
John Wooden led the UCLA men’s basketball team to 88 straight wins and 3 consecutive national championships. He cared a lot about success, but winning didn’t matter to him at all. It was an afterthought.
His definition:
Success is peace of mind, which is a direct result of self-satisfaction in knowing you did your best to become the best that you are capable of becoming.
He developed something called the pyramid of success for his student-athletes, 15 traits to adopt to be successful. Let’s look at a handful:
- Cooperation
- Loyalty
- Initiative
- Intentness
- Skill
They’re all inputs. They’re also a combination of traits related to performance and moral character.
Then there’s Earl Nightingale’s definition of success:
Success is the progressive realization of a worthy ideal.
Now, consider the full portrait of success in this new context:
Success is living a life true to yourself, working on what matters, doing it with intent, loving others, showing compassion, focusing on what you can control, and developing skills and competence. It’s maintaining connection with the people you care about most, expressing yourself freely, being in the present moment, and not letting outcomes define you. It’s that progressive realization: If you make a move today, you’re successful.
Freedom looks good on you.
Learn how to lead yourself, build real-world autonomy, and create the kind of freedom most people wait years to earn.
As you’re thinking about how to be successful through this new lens, let’s get into 6 truths to remember when going after your goals.
1. “Overnight success” takes a decade
I teach writers to improve their skills, make money online, and build careers as full-time writers.
Here’s what I tell them to do:
Go to the archives of your favorite writer or content creator and see how long they’ve been working on their craft.
It helps them lose the get-successful-quick mentality.
Tony Robbins has a quote:
Most people overestimate what they can accomplish in a year, but underestimate what they can achieve in two or three decades.
When you’re externally-oriented and focused on the reward instead of the input, you’ll quit if you don’t get results fast enough.
Skills compound. You won’t see the results of the work you’ll do until years from now.
I made almost no money in the first three years of my writing career. Then, in the fourth year, I made more money than the previous three years of my work history combined.
I stayed the course because I was internally oriented. I liked writing. It fed me and fueled me so I was happy to do the work.
Take the pressure off for now, just move an inch today. Then do it again tomorrow.
2. Answer this question to become successful
Are you willing to pay the price?
Outcomes come with a price tag—you have to give up something in exchange for what you want.
If you want to get in amazing shape, the price is eating healthy and exercising.
If you want to build a business, the main price is going through the psychological pain and turmoil it takes to build something.
Now, you don’t have to do anything. Not everyone will build a business or become the next great author.
At the same time, though, consider the paths you’d take if you dared to be who you are instead of who others expect you to be.
I think of this David Deida quote:
If you were absolutely fearless—would you be earning a living in exactly the same way you are now?
That’s the real price, isn’t it? Facing your fears.
The fear of judgment. The fear of failing. The fear of coming up short.
Most people would rather die than pay that price. Such is human nature. Think about what will matter at the end of your life to help you decide what to do now.
Related:
3. You don’t just get to “do what you love”
I love to write.
I don’t love doing tech stuff on my website, keeping track of my finances, sending out individualized emails to pitch my work, dealing with rude customers, or answering a bunch of emails.
But they’re part of the gig, and I’m willing to do them because they help me do what I love.
I’m all about finding your purpose and living a life of passion, but too many people confuse that with only doing what you love. All the time. Their obsession with pleasure prevents them from achieving the true happiness that comes with living a life of meaning and purpose.
Remember the UCLA basketball team mentioned earlier? Yes, all of the players, I’m sure, loved to play basketball. But did they love everything else that came with it?
Like how their coach sat them down at the first practice of every season and taught them how to pull on their socks without wrinkles and lace their shoes tight so they wouldn’t get blisters?
Probably not, but in service of the greater goal, they did it. And dare I say, they began to love the fruits of all the work by the time they hit the court.
The grunt work in service of your main thing makes the main thing possible.
Related:
4. The deck might be stacked against you
You can tell yourself all sorts of stories about why your circumstances are preventing you from building the life you want.
And some of those stories are true.
You didn’t choose your parents or your upbringing. You might be judged on immutable characteristics.
You can’t choose your IQ, your looks, or how tall you are. Maybe you’re not as naturally gifted as other people in certain ways, like being charismatic, good with numbers, or being disciplined.
But one idea from psychologist Alfred Adler completely changed how I think about this:
The important thing is not what one is born with, but what one makes of that equipment.
Adler believed we often have the relationship between our past and our behavior backward.
Most people think: My past created who I am today.
Adler asked a different question: What purpose is my current behavior serving?
Here’s a simple example.
Imagine someone says they have social anxiety because they were bullied as a kid.
That might be true.
But Adler would argue that avoiding people protects them from being rejected again.
In other words, the behavior isn’t just caused by the past—it’s also serving a present goal (i.e., to avoid rejection).
If your current behavior is helping you avoid rejection, embarrassment, or failure, then it’s working exactly as designed. The problem is that those goals often come at the expense of the life you say you want. Once you see that, you can choose a different goal.
It’s 2026. You have YouTube, AI, online courses, books, mentors, and more free information than any generation in history.
Have you exhausted every option?
Or, are you trying to stay small because being big takes courage?
Instead of finding all the reasons why it won’t work, start focusing on all the reasons it will.
Reset your goals.
Make them about the process instead of the outcome.
Your goal is to write, not to be praised.
Your goal is to express how you feel, not to be understood by everyone
Your goal is to be true to yourself, not to be liked.
Which reminds me of this next truth that truly defines what it takes to be successful.
Related:
5. You have to climb Cringe Mountain
Adler has another mantra that’s talked about in the book “The Courage To Be Disliked” that espouses the psychologist’s philosophy:
All problems are interpersonal relationship problems.
Meaning that your problems all stem from your relationships with other people and how you see yourself in relation to other people.
The courage to be disliked is the lynchpin to being successful when success is defined by the progressive realization of a worthy ideal, rooted in making a living in a fearless way, while expressing yourself freely the entire time.
To condense the psychobabble, what’s holding you back is: You don’t want to be cringe.
One of my clients was this really smart guy. He worked as a managing director at one of the biggest real estate companies on the planet. Billions in assets under management—just him. Not the company. He’s angel-invested in startups, coached CEOs and executives.
Wharton undergrad and Harvard MBA.
But he refused to post on LinkedIn to grow his client base. He didn’t wanna look cringe in front of all of his academic friends, posting on LinkedIn like a content creator.
He stood at the bottom of Cringe Mountain and the climb looked too high.
Cringe Mountain means you have to go through the phases of being cringe in public until you have so much authority that people respect what you’re doing.
Climbing Cringe Mountain means that you have to share a POV, experiment, and break norms. Why isn’t it cringe to share on LinkedIn that you’re going to college or that you got a new job? Because everybody does it.
Expressing yourself freely can feel cringe at first, because it’s rare. Feeling cringe is a symptom of the repression developed over years of setting that present goal to feel small.
But everything you want in life comes on the other side of being cringe. Not so much because of the outcome, but what you’re free from as a result of putting yourself out there—freedom from managing others’ perceptions and judgments.
Most of us live inside an invisible set of rules about how we’re “supposed” to act. We stay inside those lines because stepping outside them risks embarrassment, criticism, or rejection. The people who seem the most alive are the ones who stopped asking for permission. The antidote to a life of regret? A little irreverence.
The free soul is rare, but you know it when you see it—basically because you feel good, very good, when you are near or with them.
—Charles Bukowski
6. You’re never going to arrive
Stop waiting for a moment that’s never going to come—when you reach the pinnacle of success, completely content, free of problems, and full of bliss.
Here’s what will actually happen:
You’ll achieve a new milestone and it will feel amazing for a small and fleeting amount of time.
You will quickly get used to your new level of success, status, wealth, or whatever “thing” you thought would make you feel whole.
When you solve one set of problems you will simply be handed a new set of problems. They’ll be more expensive and better problems, but problems nonetheless.
You’ll chase the next milestone thinking that will fill the void. Let’s say you make $10,000 per month and you say to yourself, “When I hit $20,000 per month, I will be happy.” Then you will hit $20,000 and say to yourself, “When I hit $50,000 per month, I will be happy.”
You’ll go through multiple cycles of this “hedonic treadmill” effect until you realize the point of the game.
The point of the game is to play the game.
You will never arrive and that’s okay.
Remember to enjoy the progression. There’s no where to actually go. There’s nothing up there for you, so climb for the sake of climbing.
Wash, rinse, and repeat for a life well-lived.
