Can you imagine yourself running a company? You might think it’s a stretch now (it takes a lot of hard work, not to mention patience and perseverance to get there), but it’s also important to remember that everyone has to start somewhere.

To get insight into how CEOs—accomplished people by default—succeeded, here are five lessons they’ve shared with The New York Times’ “Corner Office” column.

1. Dream Bigger

Sometimes when I’m mentoring people, I’ll say, ‘What’s your biggest dream?’ and it will be something small and I’ll say: ‘Dream bigger. Just give yourself the ability to say, “I want something bigger,” because who cares if you fail? Truly, who cares? So dream bigger because no one else is going to do it for you.’

Alexa von Tobel of LearnVest

Have you ever felt that you had no right to want something? The feeling seems real enough, but it’s all inside your head. You don’t need anyone’s permission to want more in your life or to have bigger goals and higher expectations—just look at Alexa von Tobel, CEO of LearnVest, who started her own successful company before she was 25. Sure there are obstacles in life, but we’re talking about dreams. You can and should dream whatever you want.

2. Be Patient

When it comes to managing a career, patience is extremely important because people set goals for themselves that often are unrealistic. It’s great to do that because you want to be ambitious, but you don’t have control of a lot of circumstances. And when you set these goals and they’re not met, the reasons are beyond your control, it creates impatience and you then make career decisions out of impatience. That’s a big mistake. One of my bosses once said that just when you think nothing’s going to change, everything changes.

Bob Iger of Disney

Having lofty dreams is great, but achieving those dreams does not happen overnight. Take it from the CEO of Disney, a place that basically makes magic—you have to be patient. There’s no way to wish it away. Anyway, putting in the blood, sweat, and tears makes the experience of attaining those goals even better. So, buckle up and enjoy the ride. Just when you’ve about had it, something will surprise you.

3. Just Ask

If you don’t ask, the answer is always no. That’s my favorite thing to tell them. What’s the harm in asking? What’s the worst that’s going to happen? Just ask—that’s been the story of my life.

Angus Davis of Swipely

Patience is, of course, extremely important, but don’t forget to set yourself up for success, too. People can’t help you unless they know what you need. Angus Davis didn’t become the CEO of Swipely on his own. So, tell people about your dreams and aspirations. Ask them for help. Accept advice and assistance. You’re not going to get anywhere alone.

4. Fail Gracefully

If you’re going to live a bold life, and if you’re going to take risks and try to step out of your comfort zone, you are going to occasionally fail, make some missteps and disappoint yourself…Grace is meeting those moments on the journey, then picking yourself back up, being humble enough to learn and not being too hard on yourself.

Michelle Peluso of Gilt

With all this talk about success, it’s important to acknowledge that if you’re pushing yourself, at some point, you’re going to fail. You might even fail a lot. That’s okay. Battle scars are great for stories as long as you make sure the story is about how you overcame, as Michelle Peluso of Gilt Groupe puts it, not how you lost it and got banned from some public space for life.

5. Talk to Yourself

The most important is to make sure that you talk to yourself, that you think hard about what’s important to you and gives you meaning…It’s so healthy and important to be thinking, “Oh, I could have done that better.” Or, “What about this idea?” But nowadays, we’re on our iPhones all the time, and you don’t have time to talk with yourself, to analyze. It’s very important for people to know what gives them meaning. But it’s hard for people to figure out if you’re not connecting with yourself and taking the time to just be introspective and daydream.

Daniel Lubetzky of KIND

Even the most accomplished people in the world need to wander aimlessly sometimes. Daniel Lubetzky, CEO of KIND, can attest to this. We can make all the five-year plans we want, but without some time to just let our minds go where they will, we can only get so far until we lose sight of why we’re working so hard to begin with.



All of this is to say, even CEOs aren’t all about the hustle. Sometimes the best thing you can do for your career is to take a stroll and let your mind meander.


Photo of woman in field courtesy of Shutterstock.