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. The future is bright.
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.

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.

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.

But within a week, an amazing path 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.
Find 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.

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
• Drinking a bunch of water
• Exercising for 30 minutes

Spend more time on things you never regret (and less time on things you do).
Well there you have it—21 lessons learned in 2021.

I’ve been reflecting and working on that one for a while, so I hope you enjoyed it.

Follow me @SahilBloom for more—big plans for 2022!

I also go deeper in my newsletter. Join 55K+ others and subscribe. sahilbloom.substack.com
And be sure to check out my new podcast with @gregisenberg—Where It Happens—for casual conversations with amazing guests on the most interesting topics in business and tech. whereithappens.trwih.com
Oh, and to anyone that responded rudely or negatively to this reflection, please see Lesson 6 below:

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More from @SahilBloom

19 Dec
Where It Happens episode with @Scaramucci is live!

- Web3/crypto inevitability
- Reimagining the World’s Fair
- Getting fired/rehired by Goldman Sachs
- Embracing risk & failure

This episode is jam packed with insights and laughs…

Check it out at the links below!
Here are the episode links👇

Apple: podcasts.apple.com/us/podcast/how…

Spotify: open.spotify.com/episode/1oFozc…

YouTube:

Please listen, subscribe, share, & enjoy!
Special Giveaway: We will be giving $250 to 4 lucky winners before Christmas.

All you have to do is join the Discord and leave us a review on Apple Podcasts. DM me a screenshot of the review on Discord to enter! discord.gg/6s6t8wHE
Read 5 tweets
17 Dec
“Take risks, hit the pavement, and be a super ball.” — @Scaramucci

We hosted Anthony Scaramucci on Where It Happens to discuss turning bad situations into opportunities, the future of live events, and why he's bullish on Web3.

I’m biased, but this is an absolute gem…
Special Giveaway: We will be giving $250 to 4 lucky winners before Christmas.

All you have to do is join the Discord and leave us a review on Apple Podcasts. DM me a screenshot of the review on Discord to enter!

discord.gg/wyVQFQhG
Listen to the episode now!

Apple: podcasts.apple.com/us/podcast/how…

Spotify: open.spotify.com/episode/1oFozc…

YouTube:
Read 4 tweets
12 Dec
10 common errors in reasoning that undermine arguments:
Ad Hominem

Latin phrase for "to the person”—an attack of the individual rather than the argument.

Instead of addressing the argument and its merits, the offender attempts to refute the opposition on the basis of personal characteristics.

All-too-common in political debates.
The Sharpshooter

A man fires a gun at a barn wall and then paints a target around the tightest cluster of bullet holes to create the appearance of accuracy.

The offender selects and highlights evidence that supports the conclusion—while ignoring evidence that may refute it.
Read 14 tweets
11 Dec
10 common mental errors that derail decision-making:
Survivorship Bias

History is written by the victors.

But in studying and learning from "survivors”—and systematically ignoring "casualties”—we create material distortions in our conclusions.

We overestimate the odds of success because we only read about the successes!
Naïve Realism

Humans generally think very highly of themselves.

We tend to believe that we see the world with perfect objectivity.

We also assume that people who disagree with us must be ignorant, uninformed, or biased.

This error sits at the core of many societal problems.
Read 14 tweets
10 Dec
Hey @espn, I’d like to buy and reimagine the X Games.

Here’s my plan (RT if you’re interested):
The X Games are an annual extreme sports event organized, produced, and distributed by ESPN.

The first X Games took place in 1995 in Rhode Island.

For many years—including most of my childhood—the X Games were an incredible spectacle.

But now is the time for a refresh…
The X Games is being held back from achieving its full potential as Disney and ESPN prioritize other areas of the business.

The athletes—and the passionate community of fans—have not been able to participate in the immense value that the X Games can create.

So how do we fix it?
Read 20 tweets
9 Dec
I’m fascinated by how founders generate business ideas.

I think I’ll start hosting a regular conversation where I dive deep with 1-2 successful founders on the idea generation process that led to their startup.

Who’s interested?
What would be the best format for the discussions?
Idea would be to keep it short (<30 minutes) and extremely tactical.

How did you come up with the idea?

What daily actions lead to business ideas?

How did you diligence your idea?

Etc.
Read 4 tweets

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