The magic of asymmetric life bets: the small risks that could lead to massive upsides

Hey all, I hope your Christmas was fun and you got what you wanted.

Here’s something to think about as we enter a new year…

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Most people get risk completely backward and suffer the consequences for decades.

They pour their life savings into restaurants without testing the concept.

They buy franchise licenses that lock them into decades of debt.

They max out credit cards, starting businesses they don't understand.

They sink years and fortunes into degrees they never use.

I was guilty of this last one. I invested heavily in a master's degree in real estate and was convinced it would open doors. I enrolled on a whim, excited about developing properties from the TV.

After finishing, my degree gathered dust while I built a design business from scratch that had nothing to do with my education.

High risk, limited upside. Mistake.

Naval Ravikant, the philosopher-founder of AngelList, champions the concept of asymmetric betting. It's beautiful. His insight is simple: Look for opportunities where the downside is limited or capped, but the upside is unlimited.

This has worked for me massively in content creation over the last 15 years.

The worst case would be that I lost a few hours each week sharing insights online. But gradually, I turned this work into a thriving business with multiple income streams.

That small bet of consistent content sharing changed everything for me even when no one was reading.

Asymmetric bets are the way to go in any life decision.

Here are some more examples:

Newsletter-building

This might mean spending a few hours writing to a small audience each week.

The downside is that some time is spent writing to a few people. But even then, you develop your writing skills and discipline.

The upside? You create financial freedom in the longer term, selling your products and services via the Internet like I do now. Also, look at Morning Brew's $75 million newsletter exit.

Each subscriber you create becomes a potential customer or advocate, building an asset that works while you sleep.

Investing

Never invest more than you can afford to lose, obviously.

For example, early Bitcoin investors turned hundreds into millions by thinking independently while others scoffed. Bitcoin has reached a point where global adoption as a currency is becoming undeniable.

Those investors saw beyond criticism to understand blockchain's revolutionary potential.

The asymmetric opportunity is there for those with open minds who are long-term thinkers.

Building in public

There's never been a better time to show the world what you're working on.

Some might judge you. So what? You build a loyal audience who trust you and create unexpected opportunities.

That's a massive upside in an attention economy. Every one of your failures becomes content, and every lesson becomes value.

The magic happens when authenticity meets consistency.

Dating Intentionally

Temporary rejection vs. finding someone who multiplies your happiness makes a whole lot of sense to me.

Each 'no' gets you closer to the right 'yes.'

That goes for you saying 'no' too. Look goofy on a date that goes south? Big whoop.

One right connection could exponentially improve every aspect of your life.

Learning a second language

Sure, you may have some awkward conversations and hours spent learning.

However, the upside is access to new markets, friends, cultures, and global opportunities that most never see.

Your brain literally rewires itself, giving you an unshakeable advantage that flows into other life areas.

Starting a side project

Launching your own project involves some evenings and weekends of focused work.

Even if it doesn't take off, you learn invaluable lessons about business, how to appeal to users and product development.

But what if it resonates and takes off?

You've built something that generates wealth while you sleep and gives you complete ownership of your future. Worth it.

Writing an ebook (creating a product)

Most of us worry about spending a month writing something nobody will read.

But that's the worst case. And not even that - you can still share the book chapters as online articles. The bigger upside is that you create an asset that sells forever, building your authority and opening doors to speaking gigs, consulting, and courses.

Even a 'failed' ebook teaches you skills that transfer to so much more.

Teaching online

Creating your first course or workshop takes effort.

There's planning content, recording videos, and marketing your work. But each course can become a permanent asset that generates income for years. And most of it can be based on your own experiences, which are in your head anyway.

More importantly, you develop expertise that grows with every piece of student feedback, creating compound returns on your initial time investment.

There's little, if any, downside.

Building a personal brand

The investment here is consistency: sharing insights, engaging with others, and producing valuable content.

Critics might call it 'doing it for attention'. But where's the criticism there if you do it to help the world, even in a small way?

You learn more about yourself, and you develop mental strength by putting yourself out there day after day.

A strong personal brand can become a lifelong magnet for opportunities you couldn't access otherwise. 100% worth it.

Naval's wisdom lies in recognising that playing it safe is the riskiest bet in a world of infinite possibilities.

Each day you follow the herd, play it safe and take silly risks with little thought is a bet against yourself.

The question isn't whether to make these bets.

It's which one you'll start with today?

What are other asymmetric bets? Share them below.

If you’d like to build the unlimited upside of a personal brand, one that earns you money while you sleep, creates new connections, and helps you live with an enlivening sense of purpose, you’ll want to learn how to write better.

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