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The Sash Company Blog

Where we share all things sash & stole!

The Sash Company Blog

Where we share all things sash & stole!

Advice About Fear & Failure from the Best Graduation Speeches of All Time

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The best graduation speeches of all time focus on the importance of overcoming fear and striving despite failure. Because that’s what our lives are all about. Fear, failure, and the human spirit’s capacity to overcome both. 

The Sash Company has a long history with graduations. We have been creating custom graduation sashes for 20 years and with that in mind, we scoured the internet to find the best graduation speeches about fear and failure, and we cherry-picked the best advice for graduates we could find. 

These are speeches by some of the most influential people in the world that you may or may not have even heard of. But all of them took their own advice about overcoming fear and pushing through failure and look where it got them!


"There are few things more liberating in this life than having your worst fear realized." — Conan O'Brien's 2011 at Dartmouth (2011)

Conan OBriens 2011 at Dartmouth 2017

Late night talk show host Conan O’Brien delivered his eye-opening graduation speech about the importance of failure. His advice for graduates was to remember that you have to fail and that through failure you will realize your true potential and develop a unique character that cannot be matched. 

Failure is what allows you to change your dreams and update your goals for the rest of your life. It may be painful, but it forces you to change in the most fundamentally important ways possible. 

If you never fail, then you will always be scared of failure and the ‘what-ifs’ of your life. You will become a slave to fear itself. But once you have failed, you will understand that your fears were ultimately misplaced and that you can face anything that life throws at you. 

“It is our failure to become our perceived ideal that ultimately defines us and makes us unique. It’s not easy, but if you accept your misfortune and handle it right, your perceived failure can become a catalyst for profound reinvention.” Conan O’Brien. 

This is also one of the funniest if not the best graduation speeches of all time, so we highly recommend you check it out for yourself. 

You can watch Conan O’Brien’s full graduation speech here


“There will be times where you shouldn’t compromise your core values or your integrity and you will have the responsibility to speak up against injustice.” Barrack Obama at Howard University (2016).

barrack obama at howard university

If there’s anyone who understands focusing on your core values, it’s the former president of the United States. And hey, the best graduation speeches are typically given by people of character, and Barrack Obama is no exception. 

His advice for graduates is to focus on being the change they want to see. In an age of social media activists, it’s easy to simply ‘click like and share’ and assume you are contributing to effective change in the world. 

So how does fear play a role in this advice for graduates? Ask anyone who’s had to stand up for their beliefs, or their core values, in the face of hate, or hardship, and you will understand just how scary that can really be. 

To change anything you must first learn to truly stand up for what you believe in. And to do that, you must first truly know what your core beliefs are. 

“If you want to make life fair, then you have to start with the world as it is. That’s how you change things.” President Barrack Obama. 

You can watch Barrack Obama’s full graduation speech here


“Had I ever succeeded at anything else I might never have found the determination to succeed in the one arena where I felt I truly belonged.” JK Rowling at Harvard (2008)

JK Rowling Harvard speech

There are few if any authors who can call themselves billionaires. JK Rowling wrote one of the most important series of all time: Harry Potter. And in that series, she hones in on the importance of empathy, of human connection, and how struggling against your own internal demons is just as important as fighting the ones you face in real life. 

Rowling echoes the same sentiment that Conan O’Brien pushed in his graduation speech. That there is real value in failure if you can just stand to push past the fear of it. 

Avoiding failure is a recipe for a mundane life at best. Rowling talks about her fear of disappointing her parents, and her fear of living under the poverty line, just as they did. 

But ultimately, she thinks it may be better to fail often, fail fast, and learn how to recover gracefully. 

Rowling also talks about the importance of the people you surround yourself with because when failures do happen, you need a support system that builds you back up. 

It seems her proclivity for human connection abounds beyond just her novels. 

“I want to make it clear that I do not blame my parents for their point of view. There is an expiry date on blaming your parents for steering you in the wrong direction. The moment you are old enough to take the wheel, responsibility lies with you.” JK Rowling. 

You can watch JK Rowling’s full graduation speech here


"You can fail at something you don’t want, so you might as well take a chance doing what you love." - Jim Carrey at Maharishi International University (2014)

Jim Carrey MUM graduation speech

It seems failure is a theme in most of the best graduation speeches of all time. And for good reason. Even one of the funniest people alive, chose to focus on overcoming fear in his best graduation speech (maybe only graduation speech come to think of it).

Fear can manifest itself as a sense of practicality. We’re convinced that it’s not that we're afraid to follow our dreams, or to make a decision that could change our lives forever… no. We tell ourselves that it’s not fear, it’s realism. We are just being practical and ultimately, we need that safe job because without it we would not be able to pay our bills. 

But giving into that fear disguised as practicality is a slow journey to unhappiness. The more you focus on what’s practical, the more you lose touch with what’s possible. And that can lead to a whole life lived without a real sense of purpose. 

So face the fear early and often. Or risk being conquered by it ever so slightly, every day, until it’s too late. 

“So many of us choose our path out of fear disguised as practicality, what we really want seems impossibly out of reach and ridiculous to expect so we never dare to ask the universe for it... I'm here saying, that I'm the proof, that you can ASK the universe for it, please.” Jim Carrey. 

You can watch Jim Carrey’s full graduation speech here


“If I’m going to fall, I don’t want to fall back on anything except my faith. I want to fall forward. I figure at least this way, I’ll see what I’m going to hit.” Denzel Washington at the University of Pennsylvania (2011)

Denzel Washington at the University of Pennsylvania 1

There is something special about getting worldly advice from a man who has seen almost everything. 

Denzel Washington focuses his graduation speech on how to fail like a true professional. How to take the licks that life deals you and keep on going anyway. 

In his career as an actor, Denzel Washington spent years getting rejections but going out to auditions anyway. Because you have to keep trying despite what seems like consistent failure. 

Washington remembers the famous story of Thomas Edison. Who tried and failed 1,000 times to create the incandescent lightbulb, and finally succeeded on the 1,001st try. 

It’s the ability to keep falling forward and to keep learning from our mistakes that leads to greatness. 

“Every graduate here today has the training and the talent to succeed. But do you have the guts to fail? If you don’t fail you’re not even trying. Because to get something you never had, you have to do something you never did.” Denzel Washington. 

You can watch Denzel Washington’s full graduation speech here


“Your time is limited, so don’t waste it living someone else’s life” - Steve Jobs at Stanford (2005)

Steve Jobs at Stanford 1

If you’re reading this post about the best graduation speeches of all time on an iPhone or a Macbook, then you have Steve Jobs to thank. He singlehandedly revolutionized the internet age and will go down in history as one of the most important people of all time. 

And his advice for graduates was simple and maybe even slightly cliched. He told the 2005 graduating class of Stanford to follow their dreams. To listen to their gut. And to remember that you have a limited time on this Earth, so don’t hold back. 

It sounds like something you hear all the time from the adults in your life and it’s easy to dismiss this life-changing advice. 

The truth is, that it takes weekly or even daily reminders to follow this simple advice. It’s fear that keeps us following someone else’s dreams. And it’s fear that prevents us from taking that first small step in the direction that our soul is beckoning. 

And, ultimately, it takes courage to overcome that fear. And it takes real courage to simply become yourself. And that may be the best advice for any graduate. 

“Have the courage to follow your own heart and intuition. They somehow already know what you truly want to become.” - Steve Jobs. 

You can watch Steve Jobs’ full graduation speech here


“The really important kind of freedom involves attention, awareness, discipline, and being able to truly care about other people and sacrifice for them, over and over” - David Foster Wallace at Kenyon (2005)

David Foster Wallace at Kenyon

To anyone born after the year 2000, the name David Foster Wallace might not mean much, so why bother listening to his advice for graduates and young people today? 

Because he is one of the most important writers of a former generation and a philosopher that had no contemporary match. He released Infinite Jest in 1996 which was instantly heralded as one of the best American Novels of its time (pick up a copy asap).

His now famous college speech has been given the title “This is Water” and in it, Wallace discusses how important perception really is. Instead of talking about the lofty goals that graduates will accomplish, or the potential they have, he focuses on a single, boring, mundane day in their future lives. 

“Learning how to think, really means learning how to exercise some control over how and what you think. It means to be conscious and aware enough to choose how to construct meaning from experience. Because if you cannot exercise this kind of control in adult life, you will be totally hosed.” - David Foster Wallace.

Fear plays a massive role in creating a default setting in your perception. All of us find comfort in these default settings, and changing our perception, or our reality brings with it a fear of the unknown. So some would rather have a frustrating, mundane life than face their fear of the unknown. Change your default setting, and change your life. 

You can watch David Foster Wallace’s full graduation speech here


Final Thoughts

So what have we learned from the best graduation speeches of all time? Fear is only as inevitable as failure and the two go hand in hand. You can use fear to avoid failure and you can let failure infect you with fear of the future but either choice will leave you stranded in life. 

You have to overcome both fear and failure if you want to do anything great in the world. You have to overcome both if you want to be something truly uniquely: you.

Remember that we all get one chance to be ourselves, and no amount of fear or failure should ever get in the way of that. So go forward and be you. That’s the best advice for graduates we gathered from the best graduation speeches of all time. 

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