3 Ways to Practice Courage While Pursuing Your Dream

I’m a huge fan of the stand-up comedian Jimmy O. Yang. In his performance and recent memoir, he discusses the struggles he faced while pursuing his passion. This includes a scenario where he left a stable career in finance to pursue opportunities in comedy, and his father’s reaction to his decision. His father said, “Pursuing your dreams is for losers. Doing what you love is how you become homeless.”

So let’s say you are Jimmy O Yang and people around you give this advice that “doing what you love is how you become homeless.” How are you going to respond to that? Are you going to give up your dreams?

Or you are going to follow your passion anyway but simultaneously struggling with relentless self-doubt and anxiety?

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The idea that “doing what you love is how you become homeless” can be intensely anxiety-inducing for a dreamer. It is so powerful, widely assumed, and your response to it will determine whether you would like to experiment and take risks in life.

Here are three tips on how to respond more effectively to something like this.

First, Be Aware of Slippery Slope

Slippery Slope is a logical fallacy that is extremely common in everyday life and is a serious contributor to anxiety and worry. It’s a cognitive distortion where you believe that one small mistake will lead to a chain of catastrophic events in your life.

Jimmy’s father’s comment – aka pursuing your dream is how to become homeless – is a classic example.

People who say things like this often don’t necessarily intend harm; it’s more of a habitual way of thinking. Sometimes, you may say things like this to yourself as well.

So let’s look closer at the statement.

The statement offers a prediction that paints an extremely bleak picture of a potential future.

It takes one potentially negative outcome, which is Jimmy not succeeding as a comedian, and then links it to a very negative consequence: personal bankruptcy and homelessness.

It argues that the former inevitably leads to the latter.

So slippery slope is like taking a roller coaster ride, where you start with one initial premise, take a wild jump, and then arrive at a scary end where you confront your greatest fear.

If you fear poverty, your conclusion may be destitution. If you care about relationships, you might imagine dying alone. And if you’re like Ron Weasley, it might be living with spiders.

How do you deal with it? Dealing with the slippery slope fallacy requires us to basically recognize it for what it is – a logical fallacy.

It’s a fallacy because it distorts probabilities to exaggerate the consequences of a single choice in life.

In Jimmy O Yang’s case, there’s always the chance that he might not achieve widespread fame as a comedian. The real possibility of complete financial ruin requires many other factors to come into play, such as money management and lifestyle choices.

Even if he didn’t become a superstar, he would still acquire valuable skills: storytelling that can make audiences laugh, and networking experiences in the entertainment industry – all of which are transferable to a lot of careers.

When you catch yourself thinking on a slippery slope, remember that this is not a rational or accurate way of assessing situations. Just acknowledging that can help you distance yourself from the anxiety-inducing thoughts.

Second, Learn from Aristotle to develop realistic courage

A second tip I would offer on how to stay calm and practice courage while following your dream is to learn from Aristotle’s concept of courage.

So in Nichomachean ethics, Aristotle says that courage depends on the delicate balance of not overestimating or underestimating risks.

He differentiates true courage from recklessness and cowardice.

Recklessness is a trait characterized by wishful thinking. For instance, aspiring to become a comedian without putting in the necessary effort and merely hoping for success would be wishful thinking

Cowardice is obsessed with potential downsides and encourages you to give up before even trying.

Both recklessness and cowardice rely on a lot of mental distortions, such as slippery slopes or overgeneralization to make their case. Both entice you to sit back and do little or nothing about your situation and potential.

True courage, according to Aristotle, lies in the ability to reasonably assess a situation, acknowledging that life is uncertain while still having the gut to do it anyway.

Develop Your Personal Philosophy for life

Third, gradually develop your personal life philosophy

If you wish to foster resilience and courage over the long term, I would highly recommend you craft your own value framework that works for you.

By “working for you,” I really mean two things.

First, your personal philosophy should be capable of addressing the most prominent thought patterns you want to alter in your life, such as chronic feelings of inadequacy, catastrophic thinking, or constant need for validation.

Your own philosophy functions like antidotes. They can counteract the toxic and irrational thoughts that hold you back.

Second, your value framework should be able to provide constant inspiration that is generally consistent with your core beliefs.

What I mean by that is, throughout the history of philosophy, there have been many thinkers who have offered insights on what constitutes a good life.

But they do so from a variety of intellectual and religious backgrounds, and they have very different primary concerns.

If you are a devout Christian, perhaps Nietzsche is less applicable to your situation than Kierkegaard or St. Augustine.

If you are primarily struggling with internalized gender stereotypes and misogyny, perhaps you want to look at feminist philosophers such as Simone de Beauvoir, John Stuart Mill, or Kate Manne rather than, say, Schopenhauer.

A qualified philosophical counselor usually has extensive training in the history of thought and could help you with your personal growth in that aspect.

Let me give you an example: How would someone influenced by secular existential writers like Martin Heidegger and Jean-Paul Sartre respond in Jimmy O. Yang’s situation?

In that situation, we have two choices: either we are going to choose the more traditional and supposedly safe path, or we are going to do something kind of crazy but that we love. But there is no right answer to this question. However, there is a right attitude to make a choice.

Heidegger would say that fear is an inauthentic attunement grounded in angst, the authentic mode of attunement.

What does that mean? When you are concerned about your financial security, you are caring about yourself, your life, the food on the table and a roof over your head.

I would say that caring for your life based solely on safety is not caring enough. Being consumed by these fears distracts you from engaging with the potential within you.

When you care more about yourself, you distance yourself from the fear and ask the more ultimate questions: Who am I? Why am I here? Do I want to live a life in supposed safety and not pursue what I am truly passionate about?

What if the supposed safe job isn’t safe? What if I suck at doing what I hate? If I fail to pursue the safe job, will I be able to say to my father, hey dad you made me choose this job and I hate my life. You are responsible for it. No, because no one is responsible for your life other than yourself.

When you no longer flee from your fear, you confront your existence, your death, and your freedom face to face. You gain an existential courage and the calmness associated with it.

You’re able to say: No matter what I choose, I stay true to myself. If I succeed, that would be even better. Either way, I am not denying the fact that I am free.

Here are my 3 tips on how to stay calm and practice courage when you are pursuing your dream. I also included the reading list down below. I’m Dr. Sijin Yan, a philosophical counselor. If you like this article, please subscribe and share. Thank you so much for reading!

Reading List

Aristotle: Nicomachean Ethics

Martin Heidegger: Being and Time  

Jean Paul Sartre: Being and Nothingness

Elliot Cohen: What Would Aristotle Do?