“Take the high road…you’ll find out there’s not much traffic there,” shares Guy Kawasaki.

Those years have been full as he’s worked at Apple twice, started several tech companies, became an investor, keynote speaker, thirteen-time author, brand ambassador, and “chief evangelist” for Canva.

In his latest book Wise Guy, Kawasaki shares what he calls “miso soup for the soul”, a wide-range of stories that have helped him grow.

He pulled out the top eleven lessons he’s learned that have helped him achieve success in work, play, love, and family in hopes that it will inspire and encourage you, too.

1. Find people who challenge you

Kawasaki advises that we should seek out and embrace people who challenge us rather than those who hold us to lower standards, much like Steve Jobs did for him. “The bottom line is always to put yourself out there, not to take the easy path, to stretch yourself, and then those people will appear in your life naturally,” he explains.

2. Know when to quit

Quitting isn’t always bad. But how do you know when it’s time to quit versus keep pushing? Kawasaki shares, “I’m an Asian-American, and in the mid-70s, I quit law school. Back then, it was an honor and a strike of lightning to get in. I got in and I hated it. My parents had only gone to high school. My father was a State Senator in Hawaii and there’s all this pressure of 2000 years of my ancestors working for me to get to this point. And in the midst of that, I had to quit. To my utter amazement, my parents did not disown me. In fact, my father said, ‘It’s okay. Just make something of your life before you’re 25.’ So that’s the Asian-American version of cutting you slack.” Kawasaki trusted his instincts knowing that it was time to quit, against all odds.

3. Question everything

“Challenge the known and embrace the unknown,” is a famous quote from a commencement speech Kawasaki made at Menlo College. The unknown is typically something we fear, but he elaborates, “When somebody tells you something’s for sure, you should question that. And when somebody tells you that something absolutely is not true, you should question that, too. Basically, you should always be skeptical. I think that’s what leads to breakthroughs in life. Life is kind of counterintuitive. Of course, I encountered this time after time at Apple where people said, ‘No one needs a new operating system. What’s wrong with MS DOS and Apple II?’ My observation is you should basically question everything.”

4. Never stop learning

We are often socialized to believe that learning stops when school ends, but that isn’t true. Kawasaki explains believes that “ If you’re not learning, you’re dying. Learning is not an event that ends. It’s not the 100 yard dash where you cross the tape and it’s done. It’s more like a marathon. At 62, I decided to take up surfing. Let’s just say that at 62, you’re about 58 years too late to take that up.”

5. Prioritize Relationships

“I think the statement that I’m so busy I have no time to develop relationships is a total cop-out. Nobody is that busy. Maybe a single mom with four kids is that busy. In the venture capital business, companies get funded not because of the quality of the pitch. It’s because a venture capitalist knows a corporate finance attorney, for example, who knows a CEO. The corporate finance attorney says, ‘I just incorporated these two gals. They have the most exciting company I’ve seen since Google.’ This is all about personal contact. It’s not because you have the best digital PowerPoint or keynote pitch. The irony is that many digital technologies make analog relationships better, faster, and broader. Now, I could also make the case, somewhat contradictory, that what’s important is not only whom you know, but also who knows you,” encourages Kawasaki

6. Customers can’t tell you how to innovate

During his tenures at Apple, the top lesson he learned was, “Your current customers cannot tell you how to innovate. They can’t tell you about the next curve, the revolution, the next category, because a current customer is always boxed in by what you are already providing them. If I’m buying film from Kodak, all I can think is better film, deeper colors, cheaper. But you wouldn’t go to Kodak and say, ‘I really don’t want to use film. I want to use a digital sensor.’ Of course the irony of this is in 1975, Kodak did invent digital photography, but they defined themselves as a chemical company that puts chemicals on film. What they should’ve done is define themselves as being in the business of preservation of memories. If you’re in that business, you don’t care if it’s film, instant development of pictures, or if it’s a digital sensor. You just want to preserve memories.”

7. Learn how to sell, even if you’re not ‘in sales’

Not in sales? Doesn’t matter. Everyone is selling something. Here’s why: “It comes down to two fundamental skills in life: you’re either making it or selling it.  Even for someone who can make, you’re going to be selling to get approval, to get funding, to get people to buy what you’re making. And in a day-to-day context, you’re selling to get a seat upgrade on a flight or to get the ocean view at your hotel. The assumption that your awesomeness is so inherently obvious that you don’t have to sell is a very, very foolish assumption. Everybody has to sell.”

8. Say ‘yes’

“Fundamentally, I believe you should default to ‘yes’ unless people give you a reason not to do something. My experience is by defaulting to ‘yes’, you open up opportunities that never would have happened. The perceived downside of this is, ‘What happens if people take advantage of you?’ But my experience is that truly very few people try to take advantage. The upside of helping people all the time far exceeds the downside of being screwed a few times. Having said that, this doesn’t mean I say ‘yes’ to everything. I’m thinking ‘yes’ all the time, but if somebody says, ‘I’m having this conference in Croatia, would you fly over and give a one-hour talk for free?’ The answer is ‘no’ and it’s because the limiting factor on me is having four children. I’m not going to spend four days going to Croatia for free so that you can have a better conference that you’re selling to people.”

9. Don’t take things personally

A lot can shift when you don’t take offense. And, it can be a lot more challenging to enact than it sounds. Kawasaki shares his experience: “I was once in front of my house in San Francisco, and I was cutting the hedge, and an older white woman came up to me and said, ‘Do you do lawns, too?’ because I’m Japanese-American. That’s a case where you can easily be offended. That was my first reaction. A couple weeks later, my father comes to visit me and I tell him the story, fully expecting him to go off. And instead, he says to me, ‘Son, where you live, she was right to assume you were a yardman. Statistically, she was right. So get over it.’ And I learned a very valuable lesson: Don’t look for problems. Give people the benefit of the doubt. Don’t be so easily offended. If not, you’re going to be angry your whole life.”

10. Be yourself

Ever nervous to be your true self in professional environments? Kawasaki suggests, “Just be who you are because it’s so hard to maintain a façade. It’s easy to be honest because typically there is only one truth. But if you are trying to be dishonest to make something seem true that isn’t true, you’re going to have to remember your lie.”

11. Ask for help

Asking for help can be challenging, but can pay dividends both in your relationships as well as in your own advancement. “One of the ways that you can start and strengthen relationships is ironically, maybe surprisingly, to ask for help. In my optimistic view, the reason for this is that, generally, people are helpful. It’s satisfying to help people. So, asking people for help is a way of starting a relationship as opposed to the thought that, ‘They’re going to hate me because I’m asking for something right up front.’ Of course, you have to follow up asking for help with gratitude and reciprocation. It’s not a one-way street. But I think the concept that you should never ask someone for help because you’re going to ruin the relationship or never have a relationship is false,” he explains.

This article was first seen on Forbes and was written by Darrah Brustein.


Jon Flatt is the CEO of KERV Interactive, which produces award-winning interactive video technology that is revolutionizing visual storytelling for brands and advertisers. Before KERV, he was CEO and founder of Red McCombs Media, which was acquired by LIN Media.