How To Bet On Yourself

Nobody will bet on you the way you bet on yourself.

In 2008, while enjoying a thriving and lucrative acting career, Matthew McConaughey made a decision that changed the course of his career and life.

Bored, unsatisfied with his work, and not getting the desired roles, he pivoted. He stopped accepting the rom-com roles that he had found his fame performing.

In his own words, “I wanted to be in stories that at least challenged the vibrancy of the life I was livin, and play characters that at least challenged the liveliness of the man I was.”

He bet on himself.

Unfortunately, most people never take this risk in life.

Leading to unfulfilled lives, deep frustration, and unsatisfying assignments.

It’s better to place a bet on yourself than to bet that the world will figure your life out for you. 

- James Clear

Choosing to pivot and live with more intuitive guidance isn't easy, especially when you don't know the outcome.

It forces you to push beyond comfort. Despite training your whole life to seek comfort.

As Winston Churchill wrote:

“To each there comes in their lifetime a special moment when they are figuratively tapped on the shoulder and offered the chance to do a very special thing. What a tragedy if that moment finds them unprepared or unqualified for that which could have been their finest hour.”

When was the last time you bet on yourself?

Even if it meant drawing a line in the sand and walking over to the side of uncertainty. Forcing yourself to choose the more challenging path.

One with less comfort and more struggle—filled with uncertainty and potential failure.

Because if you want to pursue an epic life without deep regret 20 years from now, you have to bet on yourself from time to time.

Here's how to bet on yourself:

Step 1: Design your greatest vision

Your life won’t develop much meaning without vision.

Distractions in the world have never been louder. So, your vision has never been more critical to making sure you're on the right path.

You don't have to plan your next ten years. But don’t wait for life to magically unfold in favor of your plan. Start taking action.

Journal prompts:

  1. What does your greatest life look like?

  2. What area of life do you need to take a bet on yourself?

  3. What would your life look like if you succeeded in this bet on yourself?

  4. What areas of life do you need to raise your standards to stack things in your favor?

Step 2: Trust your instinct

Nobody knows you like you know yourself.

Don’t ignore the inner voice that’s guiding you with courage. Ignore the voice that shoots fear into your life.

  • Stop listening to the many negative voices in the world (including yours)

  • Stop looking for the perfect time

  • Stop looking for guarantees

Audit your environment ruthlessly. Pay close attention to what you read and listen to, who you spend time with, and what you waste your energy on.

Drown out the negativity, perfectionism, and uncertainties.

Focus your energy on what you want to accomplish.

Step 3: Push through your fears and uncertainty

Without courage, your growth in life has very little upside.

“There is nothing worth doing that is not scary,” wrote Ryan Holiday, “There is no one who has achieved greatness without wrestling with their own doubts, anxieties, limitations, and demons.”

Uncertainty has been around since the beginning of time.

It’s only in the last 200 years that we stopped worrying so much about where we would get our next meal.

The world as you know it was practically built by people who heard a voice in their head repeating: “Will (fill in the blank) actually work?”

Heroes aren’t fearless.

They’re just better than you at facing what’s in front of them with actions that lead to triumphs.

Say "Yes" To Your Epic Life

For two years after McConaughey chose to seek more fulfilling roles, his phone didn't ring.

But by giving his life permission to say "yes, by saying no" he returned to leading roles. This time, roles that challenged and excited him.

In 2014, McConaughey won the Oscar for Best Actor for his role as Ron Woodroof in Dallas Buyers Club.

With so much at stake and at the height of his career, McConaughey courageously bet on himself.

And that's what you should do, what we all should do.

Listen to that voice that leads with courage.