Personal Development

7 Steps to Take the Big Leap

Taking risks is essential if you want to live a life without regret.

Some risks are easier to take when you’re younger, like taking a gap year to travel around the world or trying different careers.

However, people often mention age as an excuse to stop taking risks. 

And that’s simply not true.

Any meaningful pursuit comes with risks.

And age isn’t the limiting factor.

Everyone can take more calculated risks – no matter your stage of life or personal factors, like wanting to start a family.

Here’s what we’ll cover:

So let’s dive in!

What does it mean to take a risk in life?

Taking risks means stepping outside your comfort zone to pursue an interest or desire. The risk itself comes from feelings of uncertainty, discomfort, and fear. 

What you consider a risk may seem easy for others, and vice versa. 

Here are some examples of what taking risks could mean:

  • Traveling to another country.
  • Living abroad for a few months.
  • Getting a promotion.
  • Changing careers.
  • Starting a business.
  • Asking someone on a date.
  • Leaving a toxic relationship.

Taking risks is something personal. And to find out what risks are most beneficial to you, you’ll have to be honest with yourself:

What’s the change you seek to make?

And what holds you back from making that change?

Why should you take risks?

Living within your comfort zone requires no effort.

It’s sometimes a nice place to be. 

Other times, you want to try new stuff, strive for ambitious goals, and live up to your full potential. It’s these moments that require you to step outside your comfort zone.

I rarely did as a teenager.

I wanted to approach more girls and achieve more financial success. But when I took action and experienced discomfort, I backed down.

It led to a lot of frustration…

Instead of pursuing what I wanted, I allowed fear to keep me from taking action. This behavior of avoiding risks hurt my confidence, shrunk my comfort zone, and caused me to feel lost.

Self-doubt was the result.

Fortunately, self-improvement gave me the self-confidence to take more risks in my twenties. I traveled, met amazing people, and learned much about life.

Taking that risk paid off. 

And many others have too. Sure, I’ve experienced discomfort, awkward situations, and many missteps and failures. But the big difference is that I’ve learned to be okay with that.

If you want to create a life you care about, you must learn how to take risks. The benefits are many.

Benefits of taking risks

Taking a risk means venturing into the unknown without knowing the outcome. And here are the benefits of that:

  • Taking risks reveals your true potential.
  • It accelerates personal and professional growth.
  • It unlocks novel experiences which make life more fun.
  • Big risks come with major payoffs and opportunities.
  • You’ll feel accomplished and proud of yourself.
  • You become bolder and more courageous.
  • You increase self-awareness.
  • And gain confidence.
  • Finally, you’ll experience fewer regrets.

Taking risks is essential to squeeze the juice out of life, experience all its flavors, and unlock the best rewards. 

The goodness lies beyond your fear, within the discomfort.

How to take more chances in life?

Imagine yourself at 80 years old, sitting in a comfortable rocking chair, looking back at your life without regrets. 

What are all the experiences you’ve had?

And what would a typical day look like?

Take a moment to visualize your ideal life. What would you consider a meaningful achievement? What about a meaningful life in general? 

In other words, what’s your definition of success?

This exercise also reveals your risk gaps.

Those are the gaps between your current and ideal life. You know, the significant actions that cause a lot of resistance and self-doubt. 

The uncomfortable truths we would rather ignore.

Identifying them is the first step. The second step is to rewrite your mental program to start taking risks and expanding your comfort zone.

Here’s how:

Ingredient 1: Fear

Every worthwhile pursuit surrounds itself with layers of fear and discomfort. So what’s the fastest way to get there?

It’s a simple answer.

The fastest way to increase self-confidence, take bigger risks, and create a life you care about is through fear.

Susan Jeffers says it best: Feel Fear and Do It Anyway

I know that’s also an uncomfortable answer. 

And it’s not surprising that most people look for shortcuts and ways to avoid taking the actions that matter.

When you persist despite fear, you will experience failure. 

You will experience rejections and discomfort.

And you’ll feel awkward and experience self-doubts.

However, if you can sit with those feelings and embrace them as part of the process, you will develop confidence. And that allows you to take bigger risks and create the life you desire.

Start by exposing yourself to small fears.

Taking tiny steps builds self-confidence in your ability to face your fears – and that you can deal with whatever comes next.

Ingredient 2: Frequency

If you want to take risks in life, you’ll need to become comfortable with fear. 

And facing your fears is similar to working out.

You might feel good for a brief moment if you do a challenging workout once or twice a year. But it will make little difference.

Approaching one stranger at a bar feels good.

But approaching a million strangers is what develops the confidence to do it at any time, at any place, whether you feel like it or not.

The same counts for getting new clients, public speaking, blogging, vlogging, or putting yourself out there in any other way.

Frequency matters if you want to increase your comfort zone, improve your relationship with fear, and ultimately, take bigger risks.

Ingredient 3: Challenge

When you do something often enough, what you once feared no longer feels scary. Exposure increases your base level of comfort.

Once again, it’s like working out.

Expanding your comfort zone is like building muscle and strength. And the workout principle “progressive overload” works here too.

The principle states that to progress, you must increase the challenge of your workouts over time. For example, by adding weight to the bar.

Failing to do so leads to stagnation. 

And that’s good if you want to maintain your gains. However, most people want to keep improving. And you can only do so by increasing the stimulus.

The same is true for your comfort zone.

If you want to become more comfortable with taking bigger risks, you want to expose yourself to, guess what, bigger risks.

That path is clear for public speaking: talk to bigger crowds of people.

But there are unlimited ways to increase the challenge with a little bit of creativity.

For example, when meeting new people, you can be more curious and encourage others to talk more.

And if you keep challenging yourself, you will prepare yourself to take the big risks in life – the ones that come with massive rewards.

7 Steps to take a bold risk in life?

What do you do when faced with a significant career, relationship, or other major life-changing decision?

Exposing yourself to fear and building your confidence is helpful because it prepares you for those inevitable moments. 

But what if there’s no time to build your confidence…?

Fear triggers a fight or flight modus. 

And it shuts off the rational brain from doing its best work. 

That’s why the following 7 steps are useful in thinking the risk through with the rational mind rather than the emotional counterpart:

  1. Identify the risk you want to take and be specific about it. What do you want to accomplish exactly?
  2. Assess the potential upside. The brain seeks to avoid pain and focuses and magnifies the downsides – no matter how improbable the outcome. So, why is it worth taking the risk?
  3. Assess the potential downsides. What could go wrong, and what are the chances of that happening? Create a plan for the downsides that have a high likelihood of occurring. 
  4. Identify the price of inaction. What happens if you avoid taking the risk? How would that make you feel? And how would that affect you in the long run?
  5. Weigh the difference. Are the potential upsides greater than the potential downsides + the price of inaction? The answer is almost always yes. Build your case by finding evidence for it.
  6. Seek advice and support from those who’ve taken similar risks if you’re not convinced yet. Other people’s experiences can push you over the edge. 
  7. Take the leap. Doing so requires courage, but if you’ve found enough leverage, you know it’s the best option. If you calculate the risk, it rarely turns out to be the wrong decision.

Be careful to avoid getting stuck in preparation mode. At some point, it’s time to take a risk – whether it fails or not, it’s often worth a shot.

At least you avoid living a life of regrets.


Taking a risk means stepping outside your comfort zone to pursue an interest or desire, especially when you experience lots of fear.

While that means different things to people, we can make two important distinctions:

  • Frequent risks, like asking someone on a date or public speaking.
  • Uncommon risks, like changing your career or asking someone to marry you.

When you want to take more risks in life, you want to identify what you fear most and expose yourself to it. Doing that often will increase your comfort zone and self-confidence.

For example, approach more girls if you want to meet more of them.

That increases your comfort level and makes it easier over time.

Increasing your self-confidence in one area also carries over to other areas. For example, developing social confidence might also help you take bigger risks in your career.

If you face a major decision and want to take a BIG risk but don’t have time to develop self-confidence, then use the 7-step approach to create leverage.

Take more risks to create a life you care about

Every week, I send tips and strategies for personal growth to help you create a more meaningful life you care about. And that includes pursuing and persisting through fears and developing rock-solid confidence.

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