Dec 22, 2021 • 10M

21 Lessons Learned in 2021

Abstraction & synthesis of the most transformative year of my life

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Today at a Glance:

  • At the end of every year, I sit down and reflect on what I learned. There is no specific aim or purpose to the exercise—the goal is to put on wings, fly up to 10,000 feet, and assess myself and the year that has passed.

  • 2021 was a uniquely transformative year for my life. So for the first time, I attempted to synthesize that jumble.

  • Today’s piece is the result of that attempt: 21 lessons learned in 2021.


21 Lessons Learned in 2021

At the end of every year, I sit down and reflect on what I learned.

I’ve been conducting this self-reflection exercise for the last 10 years, with varying degrees of structure and rigor.

There is no specific aim or purpose to the exercise—the goal is to put on wings, fly up to 10,000 feet, and assess myself and the year that has passed.

Generally speaking, the reflection has been free flowing and resulted in a jumble of words and thoughts in a notebook. But this year felt different. It was a uniquely transformative year for my life.

So for the first time, I attempted to synthesize that jumble—to abstract the chaos into something simple and coherent.

Today’s piece is the result of that attempt: my 21 lessons learned in 2021…


Engineered Serendipity

I believe that some of what we call "luck" is actually the macro result of 1,000s of micro actions.

Your daily habits can put you in a position where "luck" is more likely to strike.

Increase your serendipity surface area. Engineer your own serendipity.


Pessimists Sound Smart, Optimists Get Rich

Pessimists look at the future and see the doors that are closed.

Optimists look at the future and see the doors that are open—and probably kick down the closed doors, too.

Surround yourself with optimists—those who believe the future is bright will make it so.


The Exponential Growth Challenge

Human brains cannot fathom the insane power of exponential growth. We consistently underestimate its impact.

When you're on an exponential growth curve—stop trying to set specific goals.

Strap in, keep your head back, and enjoy the ride.


Work Like a Lion

Most people are not wired to work 9-5.

Modern work culture is a remnant of the Industrial Age—long periods of steady, monotonous work.

If your goal is to do inspired, creative work, you have to work like a lion.

Sprint when inspired. Rest. Repeat.


Overestimate a Day, Underestimate a Year

We overestimate what we can accomplish in a day, and underestimate what we can accomplish in a year.

To fight this, focus on small daily actions that compound over the long-term.

Small things become big things. When in doubt, zoom out.


Ruthlessly Eliminate Negativity

Everyone has a few negative people in their circle. They tell you to be realistic. They laugh at your ambition.

Eliminate this negativity from your life. It's a boat anchor holding you back from your true potential—cut the damn line.


Tolerance for Uncertainty

Having a high tolerance for uncertainty is a unique competitive advantage. It prevents you from settling.

When we fear uncertainty, we settle to escape its grasp.

Tolerate uncertainty for a bit longer—never settle for less than you deserve.


Step into the Arena

It's easy to stand on the sidelines.

It's hard to step into the arena. It's scary to put yourself out there, to expose yourself, to become vulnerable.

But it makes all the difference. Get off the sidelines. Be the Man—or Woman!—in the Arena.


Go For More Walks

Want to get unstuck? Go for a walk.

No phone. No music. No podcasts. Just you, your thoughts, and the fresh air.

When you let your mind wander—in its true natural state—good things happen. It works—I guarantee it.


Put Family First

In May, I woke up one morning and told my wife that I wanted to move back to the East Coast to be closer to family.

That month, we sold our house in California and moved to New York. It has been one of the best decisions I’ve ever made. The simple moments with family and friends are, quite literally, priceless.

Life is short & fragile—you'll never regret spending more time with your loved ones.


The Dots Really Do Connect

In his 2005 Stanford Commencement Speech, Steve Jobs talked about having faith that the dots will somehow connect in your life.

In 2021, I finally started to see my dots connecting. Not perfectly, but the connections are slowly coming into view. It’s a beautiful and encouraging thing.

If you haven't seen it yet, stay the course. Trust in something.


It's Darkest Before the Dawn

In May, I got rejected for a job after months of interviews.

It was a gut punch. I felt lost in the darkness. I went to sleep that night with no motivation or vision for what I would focus on the next morning. Put simply, it sucked.

But within a week, an amazing path magically came into view.

"It's always darkest before the dawn" is a cliché, but I now believe it's true.


Learn to Say No

I've always had a really tough time saying no. I would take on too much and then be forced to grind my way through it.

The ability to say no is a superpower of highly successful people.

Be deliberate about what you spend your time on—and who you spend it with.


Pay It Forward

No matter how far you go, always remember that you didn’t make it on your own.

Pay it forward. Be a mentor. Be a champion for others. Their growth should become a source of tremendous joy and pride.


Operate in Your Zone of Genius

Your Zone of Genius is where your interests, passions and skills align.

Find yours, then slowly shift your life to spend more time in it. Start playing games you are uniquely well-suited to win.

You'll find more happiness, fulfillment, and success.


The Big Change Dilemma

Small changes can happen naturally. Big changes only happen with a massive, deliberate push.

You cannot expect big changes to happen on their own. You have to force the issue. It's scary as shit.

If you believe in something, close your eyes and jump.


Delegate Uncomfortably Early

If you have to ask if it's time to delegate, it's already too late.

Trust me, I learned this the hard way...

When you're building and growing, delegate and outsource so early it feels uncomfortable. Leverage is a beautiful thing.


Say Thank You More

Show more gratitude to the people who have mentored, supported, or helped you. Not just on special occasions—every single day.

"I appreciate you" is my most frequently sent tweet and text. Why? Because it's true.

Gratitude makes the world a better place.


Talk Less, Listen More

"We have two ears and one mouth so that we can listen twice as much as we speak." — Epictetus

I love to talk. Always have, always will. But as I continue to find myself in rooms where I'm out of my depth, I've learned to talk less and listen more.

Lesson: Get in those rooms.


Build New Circles

The internet has made it possible to connect with people all around the world instantaneously. Use it to your advantage.

Build new circles—positive sum, decentralized friend groups are force multipliers for your growth.

When one person wins, we all win.


Do Things You Never Regret

A few things I never regret:

  • Calling my parents

  • Dinner with my wife

  • Going for a walk when I’m stressed

  • Drinking a bunch of water first thing in the morning

  • Exercising for at least 30 minutes a day

  • Sleeping 8 hours a night

Make your list. Spend more time on things you never regret—and less time on things you do.


There you have it—my 21 lessons learned in 2021.

This was my—hopefully successful—attempt at abstracting the chaos of my 2021 into something of value for others. It was a crazy year and I feel very lucky to have built this community of readers along the way. You have all enriched my life in so many ways and I am appreciative of each and every one of you.

THANK YOU! Happy Holidays.


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