I just walked away from a Director title job that paid me $116,500 a year as a 26-year-old.

Friends and family thought I had lost my mind.

Heck, even I wondered what the hell I was doing.

People my age would kill for a job with that amount of pay, security, and work-life balance.

I could have comfortably stayed in that role for years earning a steady paycheck, consistent pay raises, and basking in the prestige of being a young Director.

But how much would someone have to pay you to give up on your dreams and settle for a life you know is beneath you?

$250,000? Maybe $1,000,000?

Well, I was sure as hell not going to sell my dreams for $116,500 before taxes.

And you shouldn’t either.

The traditional path in life is the riskiest and the most regrettable.

The vital career question of what is risky and what is safe has changed permanently.

The old choice was to work at a job or take a big risk of going out on your own. The new reality is that working at a job may be a far riskier choice.

Instead, take the safe road and go out on your own.

— Chris Guillebeau, The $100 Startup.

Relying on one job or employer for your income, trading your time for money, and having no financial assets or passive income streams is a fool’s bargain.

F*ck that.

If COVID-19 taught me anything is that when push comes to shove, employers will drop you like it is hot to save their own bacon.

I told myself I would rather go broke on my own terms rather than let someone else dictate my future.

Now, you can call me irresponsible or arrogant.

But not taking any risks in your 20s is a huge risk. And one many people will regret later in life.

In Daniel Pink’s book The Power of Regret, most people had regrets about actions they didn’t take rather than the ones they did. Not saving more money. Not starting that business. Not pursuing that relationship.

“Inaction regrets outnumber action regrets by nearly two to one. When we don’t act we can only speculate how events would have unfolded,” writes Daniel Pink.

Inaction regrets are more painful because they remain open, incomplete and we are constantly reminded of what we didn’t do and what could have been if we decided differently.

Remember that not deciding is still a decision and not taking a risk is a risk in itself.

“If you don’t take risks you’ll be doing the same boring sh*t for your whole life and feel empty. It’s better to take risks and make mistakes so you learn powerful lessons,” writes Tim Denning

But not all risks are created equally, so choose carefully.

Here’s how.

This big risk started as a small risk.

Big risks are sexy. They make great headlines.

We applaud entrepreneurs who put everything on the line. Bet the house and triumph over the odds.

Think of Elon Musk pouring his life savings into both SpaceX and Tesla when they were on the brink of going under.

While it makes for good viewing, that’s not my story at all.

I started to take a series of small risks over the past 2 years to learn whether I actually had the skills and mindset to make money online.

The internet has moderated risks. You don’t need to put everything on the line in order to be successful. You can actually do the exact opposite and still achieve enormous results.

Everything I did started small. One blog post on Medium, one podcast episode on Spotify, one freelance consulting client.

All these ‘risks’ had limited downside (my time) but unlimited upside. I couldn’t get anything less than 0 views or listens on my blog or podcast.

My blog post could flop and all I would lose is time. But it could go viral and change everything. On the internet, there is no promise of any audience traction, but there is also no real limit to how widely your content can go.

I had an overall vision for where I wanted to go, but I never bet the house on any particular risk.

Publishing content — music, video, audio, writing, illustrations — is the best small bet you can make. Why?

Content gives you data. It’s signal that’s separate from the noise of the internet. It provides direction to your after hours side hustle.

Most importantly, content tells you what problems YOU can solve.

Once you know, you can make tiny bets in the form of potential solutions. This gives you access to possible future customers. Customers are how you monetize a side hustle.

— Tim Denning

You can move towards any big goal you have by taking small, calculated risks that move you in that direction.

Wifi money and the power of the internet.

When I made my first $1 from writing online, it was like taking crack.

Not that I have ever tried crack or plan to, but I was instantly addicted. I had a taste and I wanted more and more.

It sounds odd, but making my first $1 was more meaningful to me than making my first $100. The first $1 proved I could make another $1 and another $1.

If you’ve got access to the internet, you are wealthier than any other generation that didn’t.

You have more opportunities at your fingertips to create the life you want for yourself than your grandparents or even your parents.

The methods of creating wealth through the internet are abundant, it is the desire that is scarce.

My plan is to live a portfolio lifestyle that prioritizes learning and freedom through microbusinesses.

I won’t start the next Facebook or Instagram or be a rockstar CEO like Elon Musk but I’ll be able to live a life on my own terms, according to my own values.

I never want to report to an emotionally inept boss again. I don’t really want to be a boss either. I want to be able to build a business while traveling.

I never want to be stuck to a desk. It is a crap way to see the world.

Honestly, I will probably work more than 38 hours a week. But every hour I work is investing in myself or my business.

I am building my own equity, leverage and accountability.

Ownership isn’t everything, it is the only thing.

Closing thoughts

This life is not for everybody. I am trading security for uncertainty. And stability for adventure.

But if you’ve had the feeling of wanting to back yourself, now is the time to do it. You don’t have to tell your boss tomorrow to shove it but you can start taking steps in that direction.

I made a plan for a over year to save a sizable nest egg to meet all my financial obligations comfortably. I also made sure I had income coming in but still allow enough time to pursue ideas I’ve always wanted to start.

The life you want is waiting for you. Are you ready to take it?

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