Pessimists sound smart, optimists get rich.When choosing who to spend time with, prioritize spending time with optimists. Pessimists see the doors that are closed. Optimists see the doors that are open—and probably kick down the closed doors.Pessimists are “black holes” in your life that need to be removed in order for you to get lucky.

Hang Out With Optimists

"Don't talk to strangers" is a classic we are told as children—the residue of which carries into adulthood for far too many people.New relationships spark new ideas, insights, and opportunities—these compound just as well as any financial investment.Broad Network = Broad Luck.

Talk to Strangers

The idea that free time is bad is one of the greatest lies you’ve been told.In investing, it’s often said that cash is a call option on future interesting investments. Well, in life, I believe that free time is a call option on future interesting opportunities. When you have free time, you have the headspace to pursue new ideas and go down rabbit holes.Plan for more of it.

Schedule Free Time

Everyone has a few negative people in their circle. They tell you to be realistic. They laugh at your ambition. They argue.Eliminate this negativity from your life. It's a boat anchor—a major black hole—cut the damn line and run away from it as fast as you can.Negative people are quite literally the anti-luck.

Ruthlessly Eliminate Negativity

We really need to normalize boredom. Some of your most creative moments come during periods of boredom.On a walk, in the shower, at a dinner by yourself. You’re bored, your mind wanders, your thoughts mingle. Bam! Insight strikes.Boredom creates luck. Go for more walks (sans technology), go for more drives, sit quietly and think. You’ll never regret it.

Creative Boredom

Twitter is an insanely valuable resource if you use it well.You can literally reach almost anyone in the world from your couch. You can connect with many amazing people through sending them a cold DM—even if you don't have any followers.Use my simple guide to hack the process. Shoot your shot.

Send More Cold DMs

You should spend your 20s saying yes to almost everything.Saying yes puts you into uncomfortable situations that lead to new relationships, opportunities, and growth.These unexpected moments are luck-rich. Embracing them is how you capitalize.

Embrace the Unexpected

If you are exceptional at one specific thing, luck tends to find you.Your expertise becomes a magnet for new and interesting opportunities you never knew existed.Public awareness of your expertise is a plus. Share your work to widen the reach of your magnet.

Become an Expert

Cold emails are responsible for some of the biggest breaks in my life—new mentors, relationships, and career opportunities.Cold emails are a force multiplier for your efforts.Follow the principles in my Cold Email Guide to enhance your odds of success.Always remember: Shooters shoot.

Send More Cold Emails

Shallow men believe in luck. Strong men believe in cause and effect.

Humans are born with astonishing curiosity. But somewhere along the way, we're told to stop asking questions.Push back.Learn to follow your curiosity—trust it. Curiosity drives you to knock down doors and enter new rooms.Fortune favours the curious.

Follow Your Curiosity

If you have a choice between entering two rooms, choose the room where you are more likely to be the dumbest one in the room.Once you’re in the room, talk less and listen more. It’s bad for your ego, but it’s great for luck.Good things tend to happen in these rooms.

Be the Dumbest in the Room

There’s luck through persistence, hard work, hustle, and motion. This is when you’re running around creating opportunities. You’re generating a lot of energy, you’re doing a lot to stir things up. It’s almost like mixing a petri dish or mixing a bunch of reagents and seeing what combines. You’re just generating enough force, hustle, and energy for luck to find you.

It’s hard to get lucky watching Netflix at home on the couch.It’s (relatively) easy to get lucky when you’re engaging with people, interacting, and learning—in physical or digital worlds.Spend more time engaging and you'll find yourself in more positions to get lucky.

Get Out & Engage

The world has changed—you no longer need to live in a big city or have a fancy degree to connect and build valuable relationships.The rise of digital communities is real. Consider the fact that one of the co-founders of the largest play-to-earn game in the world started out as a member of the community in the very early days (now he’s worth tens of millions!). The opportunity playing field is levelling out.Join a Discord, engage in good faith. Create value, receive value.

Spend Time in Digital Communities

Diligence is the mother of good luck.

There's no luck on the sidelines—the arena is where it strikes.It's lonely and vulnerable, but it's the only path that bears real fruit. When faced with two paths, choose the path that puts you in the arena—where collisions happen, where luck can strike.Furthermore, surround yourself with people who are also in the arena. Sideline rock slingers never get lucky.

Get in the Arena

Much of what we come to call "luck" is actually the macro result of 1,000s of micro-actions. Your daily habits put you in a position where “luck” is more likely to strike.
In order to get lucky, you have to remove the “black holes” (anti-luck) from your existence. You have to take action to expand your personal luck surface area.

Luck Is Programmable

When you write and publish your ideas and insights, you are casting a web of magnets out into the world.Those ideas and insights will attract some people to you—and perhaps repel others.As your web grows, the connections—and luck—compound accordingly.

Write in Public

When you have a bias for motion, good things happen. You create more random collisions in your ecosystems—it’s like chaos theory.A bit of hustle goes a long way.

Hustle Hard

It pays to bet some hard cash on new ideas that you have heard from smart people around you. The skin in the game forces you to dive deeper. Sometimes you learn more and fold; more often you learn more and double down. These are small bets with outsized returns.

Put Skin in the Game

The best things in life come to those who create value with no expectation of a return.When you put out good energy, it tends to come back to you—often multiplied.Be genuine. Create value. Good things will happen.

Create Value Without Expectations

When you meet new people, find ways to stand out. Asking great questions is a clear way.A few to get you started:What are you most excited about that you're working on right now?What is your favourite book that you’ve read recently?I know almost nothing about your field of expertise. Can you tell me more about that?It gets the other person talking—plus they’ll remember you for future opportunities.

Ask Great Cold Questions

Observe the weekend projects of the smartest people in your circles. These passion projects are disproportionately likely to be a looking glass into the future.Make asymmetric bets on these areas.

Ask Great Cold Questions

Similar ideas to Ask Great Cold Questions

7. Ask Questions

Ask specific questions

Questions to ask a mentor