10 Life Lessons That Have Brought Me Incredible Success In My Twenties


1. You Don’t Get Huge Success Without Looking Really Stupid Beforehand

One of the greatest superpowers I’ve gained in my twenties is I’m not afraid to look stupid anymore.

I play basketball. I used to be so scared of missing a shot and looking stupid that I never shot the ball. Unless it was a guarantee from, like, really close.

I finally gave that up. I started shooting the ball. I start missing a lot — but every other part of my game has upgraded.

In order to get significantly good at anything, you need to fail at it. A lot. The more you fail, the more you learn, the closer you get to success.

Most people around you are insecure and afraid of failure, afraid of looking stupid in front of others around them.

This gives you a huge opportunity — if you can be the sole person who steps forward and does the work, ignoring the embarrassment and just learning how to succeed ,  you’ll be successful.

My content has gotten millions of views in the past couple years. I’ve gained tens of thousands of followers, and made tens of thousands of dollars from my work. I have a signed book deal. I own my own business now.

But getting here was rough. I wrote lots of terrible articles. I made huge mistakes that a ton of people laughed at me for. I was publicly made fun of, criticized, and insulted for my failed attempts. I lost count of how many trolls left mean comments.

But I kept going. And now, I know more about the process than 95% of my peers — all because I kept going even though I looked stupid doing it.

Don’t be a safe member of the mediocre majority.

Be an outstanding member of the 5%.

2. To Have Great Relationships, Always Make The First Move

When my wife and I were in premarital counseling, our counselor gave us a piece of advice that would end up changing our lives:

Always make the first move.

The meaning is simple: if you can help the relationship, then do it. Don’t wait for the other person to act.

Most people have strained and superficial relationships with family and even with friends. This is because most people always wait for the other person to “make the first move”—to say hello, organize a hangout, or apologize.

This is a pride thing. It’s one of the main killers of marriages, friendships, and even families.

If you want to have deep, meaningful relationships with your friends, family, and even just the people in your day-to-day life, make the first move — even if it should be them. Be the first to:

  • Initiate the conversation
  • Send the first text
  • Say you miss them
  • Say you love them
  • Apologize and ask for forgiveness
  • Organize a hangout
  • Compliment them
  • Thank them
  • Tell them you appreciate what they did

For a long time, I felt awkward and uncomfortable telling my brothers and sister “I love you.” Three of the people whom I loved most in the entire world, and I couldn’t say it!

Now, I tell them I love them all the time. I say it over text, over casual phone calls, at crises, celebrations, and over the holidays. I tell my friends, too. Every single important person in my life — mentors, family, friends, even coworkers—know how special they are to me.

It feels silly to be afraid to say this to a loved one. Yet so many people can’t say a few simple words that would galvanize the entire relationship and deeply touch their soul.

Once you can do this, you can begin enjoying a gem most people never will: close, loving, life-giving relationships with many people.

3. Stop Competing With Anyone. Make Everyone Compete With You.

Competing with people is for chumps.

I love competition. I once took the popular Strengthsfinder personality test and got Competition for my #1 strength.

But in the words of Ernest Hemingway:

“There is nothing noble in being superior to your fellow men. True nobility lies in being superior to your former self.”

It’s no fun trying to “beat the other guy” all the time. Eventually, you just turn cold and stressed. Your energy is directed towards “them” when it should be directed towards “you.”

For a long time, I struggled with jealousy and beating other writers — for views, influence, and money. If they were doing better than me (which was true most of the time), that meant I sucked. The rare times it looked like I was doing better than them, I was just worried about what would happen when they eventually came back.

I still struggle with this behavior. I still look at other writers and authors resentfully and think, “Wow, they published this garbage? My writing is way better!” (I don’t like when I think those things.)

But for the most part, I’ve redirected my thoughts and energy into just being better than I was yesterday.

And when I do that, I’m relaxed. I’m calm. I feel free to do what I want to do, without worrying about anyone else.

Don’t compete with anyone. Make everyone compete with you.

4. Every Skill You Gain Doubles The Odds Of Your Success

A Super Bowl-winning quarterback needs to know more than just how to throw a ball.

They need to master contract negotiations, nutrition and diet, public speaking, brand management, team leadership, and a ton of other skills.

My dream for a long time was very simple: be a writer. I thought that blogging was all I needed to know.

But now that I’ve started seeing huge success, I quickly learned I needed to gain a lot more skills.

In the past couple years, I’ve had to master:

  • Email software
  • Webinars
  • Sales pitches/scripts
  • Website coding
  • Website design
  • Payment gateways
  • Self-publishing
  • Book launching
  • Public speaking (podcast interviews)
  • Brand management
  • Coaching

…and a ton of other things!

Every skill you gain doubles the odds of your success. When in doubt, learn something new.

5. Action Brings Clarity And Motivation

If you don’t know what to do, then just do something.

Most people remain stuck in their mediocre circumstances while doing more complaining and worrying than actual action. When you take massive action, you get massive results; you’ll discover you like it, dislike it, or feel neutral towards it. Another action step, another lesson learned.

Those lessons will bring clarity.

The problem most people have is that they don’t have clarity; they don’t know where they’re going or what they’re supposed to do. I feel this often myself. It’s a terrible feeling, not knowing what to do.

The solution is simple: action.

In my twenties, I’ve had a lot of indecision in every area of my life:

What kind of person do I want to date?

What job do I want?

Where do I want to live?

What movie should I go see?

The one response that has always helped me : just take action.

The worst thing you can do in the face of constant uncertainty is to do nothing, staying in your rut. Action breaks the cycle; action brings clarity and tell you what your next step is.

I’ve been writing for over six years. The first 4.5 years, I was constantly confused and unsure of what to write about. It felt like I always had writer’s block, and I couldn’t scrape more than one or two ideas without my mind going blank. I had very little clarity.

What finally ended it? Consistent, disciplined action. In May of 2017, I wrote an article on Medium almost every single day of the month.

Be warned — those articles are mostly terrible. Bad structure, confusing headlines, self-indulgent diary entries. I didn’t know what I was doing.

That’s okay — the quality wasn’t the point. Action was.

And action brought clarity.

Publishing something was better than nothing. I saw some of the articles start to stick and get traction. I followed those ideas and copied that structure for the next month. I went from 1,000 views in May to 25,000 views in June.

By September, I hit 150,000 views.

By November, I broke 300,000 views.

A small bit of action can bring enormous results very quickly.

Action brings clarity. If you’re feeling stuck or uncertain, the solution is to take action, consistently. It gets you moving and points you in the right direction — even if it’s just a few steps at the beginning.

6. Focus On Learning And Creating, Not Entertainment And Distraction

Most people are distracted right now.

They’re distracted while they’re at work. They’re distracted when they’re with family and friends.

They’re distracted at the gym, on their commute, and even in the shower.

The mediocre majority will continue going through life this way, never experiencing the fullness of a life filled with deep focus and purpose.

Most people don’t prioritize learning and creating. They don’t care enough about any efforts to invest in their personal development and growth.

Entertainment is more important. Most people have replaced achieving their life dreams and goals with TV, partying, and social media.

Their life is characterized by entertainment and distraction, not learning and creating.

As a result, they don’t have close relationships. They’re stuck in jobs they hate. Their life is on the fast-track to disappointment, and they don’t know what to do.

If you don’t want to end up living a life of mediocrity, focus on learning and education. It’s the fastest way to become extraordinary, wealthy, and successful.

In the past, I spent most of my time on entertainment and distraction — internet, TV, video games, social media. I always had this nagging dread that I was wasting my life away.

I’ve changed my mindset to have a huge focus on learning.

I read 52 books last year.

I attended my first big writing conference and a public speaking event.

I bought hundreds of dollars worth of online courses.

I bought coaching packages.

As a result, I’ve seen enormous growth in my business, income, and career. I connect with people more because they like what I’m teaching. I feel better (and now when I relax and watch TV, I don’t feel guilty because I’ve already done the work).

Focus on learning and creating, not entertainment and distraction.

7. Success Is Something You Attract By The Person You Become

When I was 22, I wanted to be a famous writer. I wanted to have millions of followers and be recognized at book signings for my #1 New York Times bestseller.

But when I got, like, 100 followers, I panicked and had no idea what to do with them. I’d send them weird emails with rambling thoughts on life, full of passion and energy because I didn’t know what else to do.

The same thing happened with money. I wanted millions of dollars. My wife and I had a budget, but if we didn’t stick with it, we could’ve made $5,000 dollars that month and by the end we’d look at each other and ask, “Um, where’d all the money go?”

In his book The Richest Man in Babylon, George Clason wrote:

“This is the process by which wealth is accumulated; first in small sums, then in larger ones as a man learns and becomes more capable.”

This profound statement was one of the biggest lessons I learned in my twenties. You have to work your way up towards success.

Because frankly, being handed $10 million dollars right now would probably destroy you.

The fame, attention, and scrutiny of being a CEO for a Fortune 500 company would destroy most people.

You have to build the discipline. If you want a lot — of money, of fame, of followers, of influence — you need to train yourself how to handle that first. Honestly, not getting your big goal right now might be the biggest blessing you have.

Success comes when you become ready for it. Stop chasing success and start working on becoming someone who could handle that success responsibly.

8. Getting Fired, Rejected, And Dumped Pays Great Dividends Later

I got fired several times in my twenties.

Once was for a startup I worked for. They told me I wasn’t good enough to work there. It was a Friday at 4:49 p.m. and I had 11 minutes to clean up my desk. They didn’t give me a box.

Once I got fired for “not being a good fit.” After six months of desperate unemployment, I was offered a writing job. (One of my old English classmates was there!) But on day two, my remote boss didn’t like my first article, so he emailed my other boss and told me to leave and not come back. (I didn’t say goodbye to my old classmate because I was too embarrassed.)

Another time, I was offered a speaking role for high schoolers at a week-long YMCA camp. My first night, I wanted to be “authentic” and “deep,” so I gave a 5-minute talk about my struggles with porn, how I overcame them, and how much better my life had become. They fired me the next day for even talking about porn. I didn’t get paid.

I don’t like writing about these things. I feel awkward and I cringe at those old memories.

But they taught me a ton, more than years at a great job with great bosses ever could. I learned resiliency, to forgive, and how to take a hard look at myself and ask, How can I be better?

You probably have a lot of similar stories. And I’m telling you ,  they’re going to serve you…even if you can’t see it yet.

9. Stop Focusing On The Outcome And Instead Focus On The Process

Look — that thing you want? The promotion, the car, the million dollars in the bank?

You can’t control getting that outcome. There are a million factors out of your control that affect that outcome.

But you can control the process — the small things you do every day to succeed.

You can control how much work you put in.

You can control your attitude and positivity.

You can control your thoughts and beliefs.

James Clear once said that focusing on the “goal” is the wrong way to succeed . After all,  goals are inherently temporary, involve a lot of painful hard work, and hey, both winners and losers set the same goal.

Ordinary people focus on the outcome. But extraordinary people focus on the process.

This is high-level thinking. Small progress, every day.

When I focus on the outcome, I get stressed out, anxious, and frustrated. Why haven’t I made more progress? What’s wrong with me? Why can’t I get this right??

But when I focus on the process, I feel calm and free, and I even enjoy the process. If I do the small things I need to do today, great — I’ve had a successful day. Then I just repeat that process every day.

10. Take It One Day At A Time

My brother-in-law recently got me this cooking game, Overcooked. Basically, you’re a chef hastily gathering ingredients and serving orders.

I suck at this game.

I always do too much .  I immediately throw in three separate orders of rice, pull out like 3 steaks, and start chopping them ,  but then the rice burns, the order runs late, I can’t get to the stove in time, and next thing you know, the whole kitchen is on fire! (Just like life! Whoa. Deep.)

Once I stopped trying to cook every order at the same time and focused on one order at a time… well, I got a lot better.

And I’ve found there’s no better comparison to dealing with life.

Take it one order at a time. One day at a time. In my 12-step program and therapy, “one day at a time” has become one of my life’s mantras. Today has enough trouble of its own.

Focus on today, not tomorrow.

My brother is 5 years younger than me. He has a lot of his twenties left to go.

He’s told me how hard things are — finding (and keeping) a good girlfriend, getting a job, paying rent, attempting to be an adult when you’re used to four months of school vacation each year.

And honestly? I don’t really have any good answers for him. I just tell him that for a while, things usually just suck. Your twenties are hard.

But these 10 lessons have helped me get through the rough patches — getting dumped, fired, rejected, ignored, laughed at — and helped me become very successful in the process.