10 Effective Strategies to Be Bolder in Life

Becoming bolder in life will benefit you.

And here’s why:

Society no longer requires us to be bold. Survival no longer takes risks and courage. And even avoiding simple social interactions is optional today with the internet.

Of course, all is needed for a fulfilling life.

But it’s no longer an essential need for survival.

And most people prefer comfort and avoid taking bold actions. As a result, we get stuck within our comfort zone.

The real problem?

Exposing yourself is how you expand your comfort zone. But the opposite is true too. Avoiding exposure decreases your comfort zone. 

For example, avoiding simple social interactions will increase social anxiety.

So, while modern technology increases ease and comfort, that’s also the reason why we need to be bolder. 

You should be bolder and expand your comfort zone if you want the courage to:

• Ask someone on a date;
• Connect with strangers;
• Flourish in your career;
• Start your own business;
• Live a free life, not one suppressed by fear.

Learn the 10 different strategies to becoming bolder and tap into your courage.

Let’s dive in!

#1: Know the qualities of a bold person

Mimicking a person who’s already great at what you want to improve is an effective strategy.

In other words, a starting point to becoming courageous is understanding the qualities of a bold person.

Here they are:

• Resilient: While most people fear failure, bold people understand that failure is necessary. What they learn instead is how to bounce back fast when failures or setbacks occur.
• Coping mechanisms: Bold people have methods and strategies to deal with negative feelings and emotions.
• Positive mental attitude: Nurturing a positive mental attitude means fostering the belief that the upside is better than the downside, which increases your willingness to take calculated risks.
• Confident: Strong self-belief is tied to your willingness to act courageously.
• Courage: While bold people also experience fear, they act in spite of it.
• Determination: Determination leads to an unwillingness to give up easily when setbacks and obstacles occur.
• Independence: Boldness often requires you to go against the grain and express a different opinion. Develop independent thinking if you want to challenge the status quo.
• Open-mindedness: Courageous people consider and explore new ideas and insights, even if they contradict their beliefs and viewpoints.

When you mimic the above characteristics, you will be bolder in life. The following strategies will put these qualities into practice.

#2: Seek failure

Failure is unavoidable if you want to create a life you care about.

In fact, failure is necessary.

Creating a meaningful life requires risk-taking and courage.

That includes anything from getting promoted at work to starting your own business. And from asking someone on a date to having difficult conversations that deepen your relationships.

Sure, failure is uncomfortable.

We try to avoid it at all costs.

But the only absolute failure is avoiding them at all costs. Knowing you should’ve taken action but didn’t because of fear is the failure you want to avoid. 

If you did that in the past, you might experience regret.

Avoid getting older and regretting your inactions. Instead, it’s less painful to push through fear now, knowing that you’ve maximized your life’s potential at the end of the road.

So, embrace failing more often.

Talk to the girl on the street.

Ask someone out for a date.

Present your findings at work. 

Be the person that speaks up in meetings.

Yes, you’ll experience setbacks and awkward moments – but such failures are essential to success.

So when you experience that next time, put a big smile on your face and be glad you took action despite fear.

#3: Have empathy

Most people avoid failure because they fear the judgment of others.

I was once in that position and feared opinions a lot. But I’ve realized over the years that those who make fun of others are merely masking their own insecurities.

No confident person wastes time pulling others down.

It’s like the metaphor of crabs in a bucket. If one crab tries to escape, the others will pull it back in. They’re more focused on preventing others from leaving than trying to get out themselves.

People who make fun of your failures have often given up on their dreams and aspirations. They want to see you fail because if you succeed, it means there are fewer people like them.

But it’s worth empathizing with those people.

Why?

Because no one starts as a bully. It’s someone’s experiences in life that ruins their beliefs and confidence. And it’s worth emphasizing that.

Not to justify their behavior.

But because empathy will set you free. It prevents you from falling down to their level.

So when you feel judged next time, try empathy.

#4: Expose yourself

Your comfort zone shrinks when you avoid doing challenging things.

But when you persist through fear, your comfort zone grows.

Public speaking is the skill that taught me this lesson. I feared public speaking for a long time and avoided it like the plague.

As a consequence, I never spoke in public.

And speaking to a crowd would scare the living crap out of me. Even if the group consisted of one person or my friends.

But that changed.

When I got into continuous self-improvement, public speaking was one of the fears I knew I had to conquer.

I got the opportunity to get a door-to-door sales job. That exposed me frequently to speaking to others. I also spoke at a few small public events. 

But I accelerated my speaking skills when I started my job as a marketing consultant. When I started managing clients, I often had to present findings that were sometimes negative.

My fear of speaking never went away.

But I did become more comfortable with it over time. In fact, I started enjoying speaking a lot more, despite experiencing fear.

And the reason is simple: I spoke often. 

I learned to act despite fear and that making mistakes is okay. And I learned that I could overcome these setbacks.

My confidence grew. 

Feeling fear and taking action anyway is the habit you want to develop to become bolder and more courageous. 

Overcome your fears

What’s the thing you fear most?

And how can you start exposing yourself in small ways?

• Public speaking fears? Start giving small presentations in front of the mirror to build self-trust. And a little later for someone you trust.
• Social anxiety? Ask the barista how their day is going when getting your coffee. And ask people at conferences or events how they ended up there.
• Unsure about changing careers? Learn the essential high-income skill first. Join an open day to get insights. And ask someone with that job title on LinkedIn about their experience.
• Do you want to start a business? Why not start with a side hustle and build it out? Gain some experience. And go all-in when you get traction and enough confidence.
• Low confidence overall? Take 30-second ice-cold showers after your hot one. It’s an excellent starting point to become comfortable with discomfort, besides other health benefits.

Identify your fear and start exposing yourself to it in small ways if you want to be bolder.

#5: The 5-second rule

The 5-second rule is a powerful technique from the book: Feel the Fear and Do It Anyway.

And it’s quite simple.

When you want to take action but experience fear, do it within 5 seconds. 

For some people, it helps to say something encouraging to themselves, like “fuck it, let’s go”.

Why is such a simple rule effective?

The more you think about the action, the less likely you will take it. This is because your brain wants to avoid “risky” behavior to keep you safe.

And thus, it will try to talk you out of whatever you should do to develop courage and confidence.

Give the 5-second rule a try when you’ve got the chance.

#6: The IF/THEN system

When I learned to program, I learned about simple systems to execute code, like if/then statements:

If X is true, then execute Y.

But how does this apply to your life? 

The human brain is a powerful device, but every decision takes effort. Fortunately, we can reduce the number of decisions we must make with various strategies.

The most known method is habits.

Another effective method is reprogramming your brain using if/then statements.

For example, you can set the following statement: 

• IF you walk into a new room, THEN you will smile. 
• IF you see a beautiful girl, THEN you will smile at her.
• IF you interact with someone, THEN you will make a small conversation. Think about the cashier, barista, or colleague at the coffee machine.

It seems silly and requires deliberate effort at first.

But once you develop such habits, you’ll find it much easier to act courageously because you no longer have to decide.

Creating and practicing such a simple system can help you take bold actions when it matters most.

But once again: start small.

Pick something you can put into practice consistently. For example, everyone goes to the toilet or walks through doors all the time, so those are great anchors to attach an action.

Try a simple IF/THEN system for yourself. Put deliberate effort into developing it for a month. And then decide if it works.

#7: Best/worst scenario

Examining the potential outcomes is another way to conquer your fears and become bolder. More specifically, the best and the worst possible ones.

• If you succeed, what’s the best possible outcome?
• And if you fail, what’s the worst thing that could happen?

For example, if you’re thinking about starting your own business, here are two possible scenarios:

• If you succeed, you become your own boss, experience more freedom and flexibility, and do something you enjoy.
• If you fail, you may lose some money in the process and have to look for a job again.

Is that worth the risk? 

The answer is yes if you want to be your own boss and have more flexibility.

But what if the worst outcome scares you?

First, think about the likelihood of it happening. We have many irrational fears about outcomes that have a smaller chance of occurring than winning the lottery.

Then, you can follow it up with a plan.

Even if the worst possible scenario comes to fruition, what could you do next? Would it really be as bad as you imagine?

It’s seldom as bad as you imagine.

The positive outcomes often outweigh the negatives. Besides, the negative of not taking action is regret – which is worth avoiding at all costs.

#8: Create your own plan and live by it

One of the reasons I struggled a lot with courage was that I was trying to be like other people rather than being authentic to myself.

My friends were typical extroverts and quite good with girls. On the other hand, I was an introvert and barely spoke to any of them.

So, I tried to be like my extroverted friends.

The problem?

It didn’t suit my personality. 

And it not only made me awkward, but it also burned me out.

Instead, I had to embrace my quirkiness. I didn’t have to be as smooth with girls as they were. I just had to be myself.

And I learned that this counts for anything in life, whether relationships, a career, starting a business, or more.

Who are you?

And what do you care about?

Taking bold actions becomes easier when you explore the answers to those questions.

#9: Find a reason

When you struggle to muster up the courage, find a reason.

In the book Man’s Search for Meaning, Viktor Frankl explains how he survived the Holocaust as a captured Jew during World War II despite the odds. And some even argue that he experienced more freedom than his captors.

Let that sink in for a moment.

How do you experience more freedom than your captors while you’re the captive, experiencing the most dehumanizing situation possible?

In his book, Frankl explains how.

But the short answer is that he found a reason to fight and live.

And if he found a reason to survive the Holocaust, imagine what finding a reason could mean in your own life.

Even if there are many reasons to give up, what’s one reason that makes taking action despite fear worthwhile? 

Finding your purpose can help you to be bolder in life.

#10: Embrace uncertainty

People become funny around uncertainty.

Sometimes, that’s justified.

But most times, uncertainty is a good thing. Or at least if you seek personal growth and want to live a fulfilling life.

Uncertainty hides the good stuff:

• Learning a new skill includes uncertainty.
• Approaching strangers or someone you like requires a tremendous amount of uncertainty.
• Asking your partner to marry you requires uncertainty.
• And changing careers or starting a new job too.

Anything new is uncertain.

When the brain doesn’t know something, it prefers you to stay away from it. After all, survival is its only concern.

But that’s the program you should override.

Most of the time, uncertainty signals a new and exciting adventure.

Do you want to become more comfortable with uncertainty? Then check out this article on how to shift from a scarcity to an abundant mindset.

Conclusion

Everyone can become bolder in life. 

But it does require consistent and deliberate action. 

Fortunately, there are many ways to prime yourself for success. And we discussed ten strategies that all come down to the following:

• Mental priming: Using different strategies to make you realize that failure isn’t as scary as you think. And that it’s actually essential to fail if you want to achieve success.
• Taking action: Using various strategies to start taking action. The most important one is to start small, be consistent, do it frequently, and slowly expand your comfort zone.

Let me end with this:

If you’ve got the right intentions, maintain integrity, and avoid doing things purely for selfish reasons at the cost of others, then you’ve nothing to worry about.

What bold action will you take today to develop courage?

Want even more courage?

Then sign up below to receive the weekly newsletter. I share tips and strategies to help you be bolder and create a life you care about.