257 – Face Your Fears

“While we wait for life, life passes.” —Seneca Are you afraid to take risks? Do you continually play it safe? Are you living a life that is comfortable but unchallenging? Today I want to talk about how we can push ourselves to take more risks and live life more fully.

Are you afraid to take risks? Do you continually play it safe? Are you living a life that is comfortable but unchallenging? Today I want to talk about how we can push ourselves to take more risks and live life more fully.

While we wait for life, life passes.


Our brains are always looking to keep us safe in any situation. It’s part of the reason why we have evolved as a species and why we are the dominant species on the planet. Because our brains catalog things that can cause us harm, we are able to avoid situations that would be detrimental to our safety, and we survive.

But survival is not the same thing as thriving. We might be able to feed ourselves, take care of our basic needs, but this is not the same thing as living a great life. A great life, to me, is one where we are able to take our skills, talents, and ambitions and live a life where we continually become better versions of ourselves. We use our talents to make the world a little better.


People often wonder what the purpose of life is, and to be honest, I think the purpose of life is figure out what makes a good life for you, then live that. This is challenging because it takes a willingness to explore. It takes a willingness to be uncomfortable and try new things, and what makes a good life at one time in your life will be very different at another time in your life.


It can ruin your life only if it ruins your character. Otherwise it cannot harm you — inside or out.

— Marcus Aurelius

So what is it that holds us back from taking more risks in our lives?

Simply put, it’s fear.

There are lots of fears that hold is back from doing what we really want.

There’s the fear of rejection of others including family, friends, and society. Being accepted in our peer group or community is something that we all want, and doing things that might bring down the judgment of others or could get us ostracized can be incredibly scary.

There’s fear of failure, that if we try something that we’re not good at that we could fail and be embarrassed by that failure. We may also feel like we have wasted time when we put energy into something but still fail at it.

Fear of change. When things stay as they are then we feel comfortable and we know what to expect. When we step up to try something new and different, things will change. We may disrupt the way our lives are going, and even if we know in the end it will be better, change is uncomfortable.

Fear of loss of security. Often we are afraid to take risks because we don’t want to be financially insecure. Sometimes the things that we want to pursue mean that we have to change careers or put up funding that may impact our finances.

But with all of these different fears, there is just one thing in common. Each of them is created by a thought in our mind. Fear is generated because we are afraid of something uncomfortable. Whether that’s the disapproval of others or having to live a more meager lifestyle while we pursue what we really want, these are just emotions attached to thoughts based on our perspective. What others think of us can really cause no harm. We can really get by on far less than we are used to if that’s what it takes for us to pursue our dreams.

Back Up Plan

Set aside a certain number of days during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while, “Is this the condition that I feared?”


A good example of giving into fear is that many of us, and I include myself in this group, end up following our back up plan. We give in to our fears and we decide that rather than pursue our dreams and desires, we do something that’s safe. In my case, I got a degree in business and ended up in software development. Now don’t get me wrong, there is nothing wrong with being in software and I haven’t had a terrible life from it, but it’s far from acting or singing or writing music which is what I really wanted to do when I graduated from high school.

And the thing is, most of us end up spending just as much time and energy on our back up plans as we would have needed to make our original plans work. I spent just as much time behind the computer as I would have spent running lines or auditioning for musicals if I’d had the courage to follow the path I really wanted.

I’m sure that if you looked at areas where you have shied away from and not taken risks, you’ll find that if you had put in the same amount of energy as you do your day job, you’d probably be quite successful at it.

Memento Mori

You are scared of dying—and, tell me, is the kind of life you lead really any different than being dead?

— Seneca

So how can stoicism help you get better at tasking risks?

The stoics are very big about reminding us of our own mortality. I mean we’re all going to die and that’s something that we all have to accept. Once do accept that, and accept the fact that you could leave life at any moment, you realize that since you only have one life , do your best to live the best life you can. Live the life that you want to live, and not the life that other people what you to live.

Another way to put this in perspective is that do you think anyone is going to remember what you did in 100 years? In 50 years? Probably not. There will come a time in the future where no one will know who you were or what you did. All your contributions, all your pain and suffering will just be things in that past as if they never existed.

And that’s great and sad at the same time. Everything we do is futile but at the same time, doing good things and how we do everything matters. So if you’re going to spend your life doing something that will be gone in the not so distant future, make sure that it’s something futile that you want to do.

Want to do stand up comedy? Get in front of your best friend and try some material out. Then find an open mic. Just start doing it. It won’t matter anyway if no one laughs at your jokes. Over time you’ll make it work.

Want to ask someone out but afraid they might reject you? You’re no worse off than you are now, so just do it.

Want to be a musician? Practice. Then download Garage Band or Audacity and record your stuff and put it on Soundcloud. You’ll find others that like your vibe.

You are here to explore and live a life that is full of joy. You do this by stepping up and trying things. We are better off as a world if you are putting things into the world that bring you joy, because there is a good chance that they will bring someone else joy.

All these things that you are afraid of, everything that stresses you out, when you die, those things will be gone. So none of it really matters. Is that nihilistic? I don’t think so. It’s just a simple recognition of the value of these things by adjusting your perspective. All of these things that you think are so important, are really not in a long enough time line.


Why does he smile when misfortune strikes? He knows it is an opportunity to cultivate virtue. Death, loss, decline. These things come for us all. Facing pain is how we make ready. Adversity sharpens the blade of will. Greet the test gladly. Endure.

—@TheStoicEmperor (twitter)

One of the four stoic virtues, and to me the most important, is that of courage. For me, courage is the key to living a good life. It is the virtue that underpins everything that helps us live a life we are proud of, and to make changes in our lives. Courage is the key to awareness of ourselves in that it helps us to see ourselves as we truly are. Courage is what helps us make that hard choices, to have the hard conversations, and to persevere when things seem bleak.

Courage doesn’t mean that you have to go cliff diving or put yourself in extreme danger. Courage is simply facing up to the things that scare you, looking at why they scare you, and doing them anyway. The more comfortable you get with facing up to small things with courage and resolve, the easier it gets to face up to the bigger fears in your life. Every time you step up and make a courageous choice, you become more virtuous.


So what are some areas in your life where you are afraid? What are some things you want to do in your life but are unwilling to take the risks? What’s on your bucket list that you keep putting off? Learning to take more risks in your life something that you can get better at, one small fear at a time. Taking more risks is also part of what makes life much more fulfilling and exciting, because in the end, it doesn’t really matter. And that’s a good thing.

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