From Steve Jobs to Oprah: 28 Leaders’ Commencement Speeches That Will Make You Re-Think Success

The best advice from Steve Jobs, Oprah, Barack Obama, J.K.Rowling, and many more on how to rethink success.

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BY Madeleine Dore - 05 Mar 2018

From Steve Jobs to Oprah: 28 Leaders' Commencement Speeches That Will Make You Re-Think Success

PHOTO CREDIT: Getty Images

It's both inspiring and comforting to hear how those we admire succeed in the face of failures, setbacks, and barriers, and there's perhaps no better format than the commencement address to uncover such gems.

For the month of February, I commenced each day with a commencement speech delivered by living definitions of success such as Barack Obama, J.K. Rowling, and Oprah, alongside the late greats, Steve Jobs and David Foster Wallace.

Along with my morning coffee, I'd dedicate 20-ish minutes to digesting timeless advice on life, elemental truths, and, often, blunt realities given to graduates who are about to enter the real world.

Many sentiments from these addresses are already frequently being repeated. Does "You can't connect the dots looking forward; you can only connect them looking backwards" sound familiar? But diving into a month's worth of these lectures equally revealed countless words of advice and insight that surprised and inspired how I approach the preceding hours in my day.

Here are the lessons I collected day-by-day that broadened my definition of success and what it means for a life to be well lived.

1. Be micro-ambitious.

"I never really had one of these big dreams. And so I advocate passionate dedication to the pursuit of short-term goals. Be micro-ambitious. Put your head down and work with pride on whatever is in front of you... you never know where you might end up. Just be aware that the next worthy pursuit will probably appear in your periphery. Which is why you should be careful of long-term dreams. If you focus too far in front of you, you won't see the shiny thing out the corner of your eye," said comedian, composer, and director Tim Minchin.

2. Enjoy the ride.

"When I agreed to give this address, I started trying to think what the best advice I'd been given over the years was. And it came from Stephen King twenty years ago... and his advice was this: "This is really great. You should enjoy it.

"And I didn't. Best advice I got that I ignored. Instead I worried about it. I worried about the next deadline, the next idea, the next story. There wasn't a moment for the next fourteen or fifteen years that I wasn't writing something in my head, or wondering about it. And I didn't stop and look around and go, this is really fun. I wish I'd enjoyed it more. It's been an amazing ride. But there were parts of the ride I missed, because I was too worried about things going wrong, about what came next, to enjoy the bit I was on. That was the hardest lesson for me, I think: to let go and enjoy the ride, because the ride takes you to some remarkable and unexpected places," said writer Neil Gaiman.

3. Better is good.

"Gear yourself for the long haul. Whatever path you choose -- business, nonprofits, government, education, health care, the arts -- whatever it is, you're going to have some setbacks. You will deal occasionally with foolish people. You will be frustrated. You'll have a boss that's not great. You won't always get everything you want -- at least not as fast as you want it. So you have to stick with it. You have to be persistent. And success, however small, however incomplete, success is still success. I always tell my daughters, you know, better is good. It may not be perfect, it may not be great, but it's good. That's how progress happens -- in societies and in our own lives," said Barack Obama.

4. Count on yourself.

"We might ask ourselves, what tools do we have? What can we count on? You can count on yourself. Believe me, your self is your best ally. You know who you are, even when sometimes it becomes a little blurry and you make mistakes or seem to be veering off, just go deeper. You know who you are. You know the right thing to do. And if you make a mistake, it's alright -- just as the song goes, pick yourself up, brush yourself off, and start all over again," said musician Patti Smith.

5. Live with integrity.

"And as you grow, you'll realize the definition of success changes. For many of you, today, success is being able to hold down 20 shots of tequila. For me, the most important thing in your life is to live your life with integrity and not to give into peer pressure to try to be something that you're not, to live your life as an honest and compassionate person, to contribute in some way. So to conclude my conclusion, follow your passion, stay true to yourself. Never follow anyone else's path, unless you're in the woods and you're lost and you see a path and by all means you should follow that. Don't give advice, it will come back and bite you in the ass. Don't take anyone's advice. So my advice to you is to be true to yourself and everything will be fine," said Ellen Degeneres.

6. How do you measure a life?

"As we move through our lives, I want you to ask yourselves: How do we measure a life? How do we measure a life -- by what means and by what measure? Do you measure it inch by inch, step by step, crawl by crawl? How will you measure you lives is the most important thing -- not only for you, students, but for all of us. I am asking myself this question constantly: How do you measure a life? Do you measure it day by day or year by year? Do you measure it by yesterday or by today? Do you measure it by the miles walked or the mountains climbed or the valleys explored? How do you measure your life?," said artist Carrie Mae Weems.

7. Stay hungry, stay foolish.

"Your time is limited, so don't waste it living someone else's life. Don't be trapped by dogma -- which is living with the results of other people's thinking. Don't let the noise of others' opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary," said Steve Jobs.

8. The different kinds of freedom.

"The really important kind of freedom involves attention and awareness and discipline, and being able truly to care about other people and to sacrifice for them over and over in myriad petty, un-sexy ways every day. That is real freedom. That is being educated, and understanding how to think. The alternative is unconsciousness, the default setting, the rat race, the constant gnawing sense of having had, and lost, some infinite thing," said writer David Foster Wallace.

9. Goals change.

"I went to college with many people who prided themselves on knowing exactly who they were and exactly where they were going. At Harvard, five different guys in my class told me that they would one day be President of the United States. Four of them were later killed in motel shoot-outs. The other one briefly hosted Blues Clues, before dying senselessly in yet another motel shoot-out. Your path at 22 will not necessarily be your path at 32 or 42. One's dream is constantly evolving, rising and falling, changing course," said Conan O'Brien.

10. Take the path less traveled.

"Let's just say, hypothetically, that two roads diverged in the woods and you took the path less traveled. Part of you is just going, "Look at that path! Over there, it's much better. Everyone is traveling on it. It's paved, and there's like a Starbucks every 40 yards. This is wrong. In this one, there's nettles and Robert Frost's body--somebody should have moved that--it just feels weird. And not only does your mind tell you this, it is on that other path, it is behaving as though it is on that path. It is doing the opposite of what you are doing. And for your entire life, you will be doing, on some level, the opposite--not only of what you were doing--but of what you think you are. That is just going to go on. What you do with all your heart, you will do the opposite of. And what you need to do is to honor that, to understand it, to unearth it, to listen to this other voice," said screenwriter Joss Whedon.

11. Failure strips away the inessential.

"So why do I talk about the benefits of failure? Simply because failure meant a stripping away of the inessential. I stopped pretending to myself that I was anything other than what I was, and began to direct all my energy into finishing the only work that mattered to me. Had I really succeeded at anything else, I might never have found the determination to succeed in the one arena I believed I truly belonged. I was set free, because my greatest fear had been realized, and I was still alive, and I still had a daughter whom I adored, and I had an old typewriter and a big idea. And so rock bottom became the solid foundation on which I rebuilt my life," said J. K. Rowling.

12. Nobody knows why they are successful.

"If you have been touched by the success fairy, people think you know why. People think success breeds enlightenment and you are duty bound to spread it around like manure, fertilize those young minds, let them in on the secret, what is it that you know that no one else knows, the self examination begins, one looks inward, one opens an interior door. Cobwebs, black, the lights bulbs burned out, the airless dank refrigerator of an insanely over-scheduled, unexamined life that usually just gets take-out," said Meryl Streep.

13. Be your own story.

"You are your own stories and therefore free to imagine and experience what it means to be human without wealth. What it feels like to be human without domination over others, without reckless arrogance, without fear of others unlike you, without rotating, rehearsing and reinventing the hatreds you learned in the sandbox. And although you don't have complete control over the narrative (no author does, I can tell you), you could nevertheless create it," said novelist Toni Morrison.

14. You are not special.

"Like accolades ought to be, the fulfilled life is a consequence, a gratifying byproduct. It's what happens when you're thinking about more important things. Climb the mountain not to plant your flag, but to embrace the challenge, enjoy the air and behold the view. Climb it so you can see the world, not so the world can see you. Go to Paris to be in Paris, not to cross it off your list and congratulate yourself for being worldly. Exercise free will and creative, independent thought not for the satisfactions they will bring you, but for the good they will do others, the rest of the 6.8 billion--and those who will follow them. And then you too will discover the great and curious truth of the human experience is that selflessness is the best thing you can do for yourself. The sweetest joys of life, then, come only with the recognition that you're not special. Because everyone is," said high school teacher and author David McCullough.

15. Remember your mortality.

"I quote Saint Benedict who said, 'Daily, keep your death before your eyes.' That may sound like a morbid practice, but as I think you know, it isn't. If you hold a healthy awareness of your own mortality, your eyes will be opened to the grandeur and glory of life, and that will evoke all of the virtues I've named, as well as those I haven't, such as hope, generosity, and gratitude. If the unexamined life is not worth living, it's equally true that the unlived life is not worth examining," said author, educator and activist Parker Palmer.

16. People will try to box you in.

"It's a tough world out there. You're going to prepare yourself for politics, bad bosses, hating employees ,and usually when you're the absolute best, you get hated on the most.Even for me, as a successful musician, in order to make the transition it was really all but impossible. People always try to box you in to what they know you best for," said Kanye West.

17. Success is giving beyond yourself.

"Now one may look at me as having great success, which I have in the strictest sense of the word, and don't get me wrong, I love what I do and I feel so fortunate to get to entertain people. But to me, my definition of success is my 16-and-a-half-year marriage to my beautiful and talented wife, Vivica. Success are my three amazing sons...Success to me is my involvement in the charity Cancer for College, which gives college scholarships to cancer survivors... No matter how clich it may sound you will never truly be successful until you learn to give beyond yourself. Empathy and kindness are the true signs of emotional intelligence," said actor Will Ferrell.

18. Everyone you need is already in the room.

"Raise the rest of your life to meet you. Don't search for defining moments because they will never come. Well, the birth of your children, OK, of course, forget about it, that's just six months. My life is forever changed, that's most defining moment ever. But I'm talking about in the rest of your life and most importantly in your work. The moments that define you have already happened. And they will already happen again. And it passes so quickly.

"So please bring each other along with you. Everyone you need is in this room. These are the shiny more important people," said actor Peter Dinklage.

19. Fame and success won't complete you.

"I've often said that I wished people could realize all their dreams of wealth and fame so they could see that it's not where you'll find your sense of completion. Like many of you, I was concerned about going out in the world and doing something bigger than myself, until someone smarter than myself made me realize that there is nothing bigger than myself!," said actor Jim Carrey.

20. Rejection is not personal.

"Rejection might sting, but my feeling is that it often has very little to do with you. When you're auditioning or pitching the director or producer or investor might just have something or someone different in mind, that's just how it is," said actor Robert de Niro.

21. There is no such thing as failure.

It doesn't matter how far you might rise. At some point you are bound to stumble because if you're constantly doing what we do, raising the bar. If you're constantly pushing yourself higher, higher the law of averages not to mention the Myth of Icarus predicts that you will at some point fall. And when you do I want you to know this, remember this: there is no such thing as failure. Failure is just life trying to move us in another direction," said Oprah Winfrey.

22. Love and work are two different things.

"Freud said there are only two things important in life--love and work. He did not say that love and work were the same thing. I'm passionate about my work. It continues to give me great satisfaction and a sense of who I am. But passion and love are different at least for me they are," said entrepreneur Larry Ellison.

23. Be guided by intuition.

"And I want to be clear that your intuition is different from your conscience. They work in tandem, but here's the distinction: Your conscience shouts, 'here's what you shoulddo,' while your intuition whispers, 'here's what you could do.' Listen to that voice that tells you what you could do. Nothing will define your character more than that," said director Steven Spielberg.

24. Utilize your inexperience.

"Sometimes your insecurities and your inexperience may lead you, too, to embrace other people's expectations, standards, or values. But you can harness that inexperience to carve out your own path, one that is free of the burden of knowing how things are supposed to be, a path that is defined by its own particular set of reasons," said actor Natalie Portman.

25. Start now.

"If you imagine less, less will be what you undoubtedly deserve. Do what you love, and don't stop until you get what you love. Work as hard as you can, imagine immensities, don't compromise, and don't waste time. Start now. Not 20 years from now, not two weeks from now. Now," said designer, writer and artist Debbie Millman.

26. Our idea of success should be our own.

"We live in a meritocratic society, where accomplishments are constantly being measured externally, where forms are always read from the outside, where comfort and lifestyle are often mistaken for success, or even happiness. Don't be fooled. Our ideas regarding success should be our own, and I urge you to pursue it simultaneously from both the inside and the outside...," said artist Teresita Fernndez.

27. Planning is overrated.

"The smartest, most interesting, most dynamic, most impactful people ... lived to figure it out. At some point in their lives, they realized that carefully crafted plans ... often don't hold up... Sometimes, the only way to discover who you are or what life you should lead is to do less planning and more living--to burst the double bubble of comfort and convention and just do stuff, even if you don't know precisely where it's going to lead, because you don't know precisely where it's going to lead.

"This might sound risky--and you know what? It is. It's really risky. But the greater risk is to choose false certainty over genuine ambiguity. The greater risk is to fear failure more than mediocrity. The greater risk is to pursue a path only because it's the first path you decided to pursue," said author Daniel Pink.

28. We are our choices.

"What choices will you make? Will inertia be your guide or will you follow your passions? Will you follow dogma or will you be original? Will you choose a life of ease or a life of service and adventure? Will you wilt under criticism or will you follow your convictions? Will you bluff it out when you're wrong or will you apologize? Will you guard your heart against rejection or will you act when you fall in love? Will you play it safe or will you be a little swashbuckling? When it's tough, will you give up or will you be relentless? Will you be a cynic or will you be a builder? Will you be clever at the expense of others or will you be kind? I will hazard a prediction. When you are 80 years old and, in a quiet moment of reflection, narrating for only yourself the most personal version of your life's story, the telling that will be most compact and meaningful will be the series of choices you have made. In the end, we are our choices. Build yourself a great story," said CEO of Amazon Jeff Bezos.