The Best Career Advice From 100 Episodes of the 5 Questions Podcast

Since the start of my career, I've been a strategic advisor to corporations and a champion of workers. My goal is to evangelize human-centric workplaces that enable workers to achieve career success and be fulfilled, while their organization's profit. Through the combination of my regular conversations with prominent figures, and leading over 50 research projects, I've amassed a repository of both qualitative and quantitative data in order to uncover and promote the most important workplace issues while offering real-world solutions. I began my career by giving inspirational, motivational, and tangible career advice on social media, and I've continued to as I turn 37-years-old today. I am dedicating the rest of my life to pursuing, investigating, analyzing, and shaping the global conversation around work-life topics that affect us all, using my platform, energy, and heart.

Over the past 13 years, I've interviewed over 2,300 of the world's most successful and interesting people from a variety of industries, professions, and backgrounds. But, since 2018, I've produced and released one hundred episodes of my 5 Questions podcast with a selection of these incredible humans. In all of my interviews since I was 23-years-old, I've consistently ended them by asking, "what is your best piece of career advice?" While the question is simplistic in nature, it challenges my guest to think really hard about the single best piece of advice they can offer. Over the years, there have been long pauses, redos, and hesitations when I ask the question because it forces them to be thoughtful while committing to a single piece of advice for my audience.

To celebrate my birthday, I've selected my favorite pieces of career advice from my guests AND my own best piece of career advice!

The best pieces of career advice from my guests

• "Discipline equals freedom. Be disciplined as an individual, as a leader, as a follower, as a team, and as an organization. The more discipline that you have the more freedom that you're going to end up with and that's the freedom to move, to execute, and to live. Without discipline, you become a slave to timelines, to costs, to your emotions, to frustrations and regret. Be disciplined, work hard and you will end up in the right place with the maximum amount of freedom in your life." - Jocko Willink, former Navy Seal, from episode 11
• "Take yourself incredibly seriously. You have a unique dent that you're going to make in your working life and your life beyond work. The only person who really understands what your strengths are is you. The only person who really understands what meaning matters to you is you. The only person that can refine your natural strengths and meaning into contribution and skills that someone will actually pay for is you. No one can do any of that for you at all. The best careers are always scavenger huts. You're always looking and hunting. You're not hunting to fill in the empty canvas of yourself. You're not empty, you have some unique ways of engaging the world, building relationships, and being motivated but you're the only one who can identify those red threads - the activities that are made of the material that lifts you up. Find your red threads in what you do and weave your red threads into the jobs that you're in, and then over time into the career that you've built. If you take your red threads seriously, we will feel the dent you make in the world." - Marcus Buckingham, bestselling author, from episode 24
• "Always have a plan b. Do not allow that one thing that you make your living off of be the one thing that makes you feel fulfilled. You always have to have other things that you can find fulfillment in. It's good to have goals, but it's also good to find other ways to keep yourself fulfilled and keep your heart filled, and sometimes that's not what you do at all for a living." - Alyssa Milano, actress and activist, from episode 29
• "Pay attention to identity capital. If you can do something interesting than forever after in every job interview, in every dinner conversation, people will ask you “what was it like to be a yak herder in Mongolia” and you'll have a peace of identity capital." - David Brooks, New York Times Op-Ed Columnist, from episode 30
• "Be nice to everybody. Honestly, I want it to say 'he was nice to work with' on my tombstone. I have had former assistants become bosses and hired me for jobs and I have ended up hiring most of my former bosses for jobs. I can't come up with a better argument to be graceful with everyone that you meet." - Adam Savage, host of Savage Builds, from episode 32
• "Job titles are temporary but purpose is everlasting. I think it's important that we remind ourselves of that because so often we cling to certain job titles, or a certain salary or a certain career path as part of our identity, as the things that come to define us in the world. We should think about our lives, and our careers, as a series of dreams realized. You don't have to be defined by just one thing or just be one title for the rest of your life. It's important to stay rooted in your purpose and let that guide your career decisions." - Elaine Welteroth, former editor-in-chief of Teen Vogue, from episode 34
• "Trust your instincts and don't let anyone get you down. Take everybody's thoughts and listen to their considerations but take it with a grain of salt because you know yourself better than anyone else does." - Chris Kattan, former SNL star, from episode 37
• "My best piece of career advice is to surround yourself with great people. When you get in the vortex of things going on, you need people that are standing on the inside, outside, and all around you that can give you perspective. You need to have people you can really count on, that you can believe in, that have balance, experience, awareness, and the same values. Without question, surrounding yourself with great people is one of the most critical aspects of my success or anyone’s success. You’ve heard all the bad stories about people that have been swindled out of their money or have made bad career decisions, and that usually has to do with the people around them. So, surround yourself with great people." - Guy Fieri, Food Network star, from episode 38
• "Worry about being good, don't worry about being popular because if you worry about being good, you have a chance of becoming popular for the right reasons. If you just worry about being popular, you will probably fail and not be good because you won't be as good as someone who practices and why would anyone care about you if you aren't popular." - Mike Posner, singer and songwriter, from episode 40
• "Embrace failing. Failing is the greatest thing you can ever do. If you're going to work in any business you're going to fail. You need to accept the fact that most of what you try isn't going to hit, most of what you sell isn't going to work, and most of what you make isn't going to accomplish what you initially set out to do. As long as you have the steps in mind of what you hope to accomplish than I don't think there's any such thing as failure. Everything becomes a stepping stone that gets you to the next thing." - Morgan Spurlock, documentary filmmaker, from episode 52
• "Do the hardest things at all times. You will ascend a pyramid with powers of solutions that others don't have and then force others to beat a path to your door because you took harder classes than anyone else did. If you take easy classes than everyone is equally as talented as you and then there's no way to distinguish you from anyone else in the workplace." - Neil Degrasse Tyson, Director of the Hayden Planetarium, from episode 57
• "Get a good foundation for your first job. Learn things. Don't be too impatient. Watch what other people have done in terms of when they leave and when they start something else. People tend to leave too early before they've learned enough lessons and then they are confronted with situations they can't handle well and then they make a mess." - Steve Schwarzman, CEO of Blackstone, from episode 60
• "Don’t listen to your friends. That's my best career advice. Particularly for young people who want to know what their friends are doing who are graduating from the same school as they are or their friends that they're hanging out with. Your friends might be able to figure out what they want to do with their life, but they're not going to be able to figure out what you want to do with your life. And so when you ask people for career advice, they give you the advice for them, but you need the advice for you and the advice for you has to come from you ultimately so don't listen to your friends." - Ben Horowitz, venture capitalist, from episode 66
• "The want to creates the how-to. If you want something bad enough you will figure out how to do it. If you want to be an actor, go to New York, go to LA, go to where the opportunity is. If you want to be a farmer, then buy that piece of property with the house that's not that nice but that has a bit more land. When you want something you will creatively problem solve and that's how you know you really want it. There are a lot of goals out there that are easy to push to the side and procrastinate on, but when it's your passion, and the thing that you want more than anything, you will figure out how to do it." - Hilarie Burton, star of One Tree Hill, from episode 81
• "There's no one defining moment. Your success is never linear and is never going to go in a straight line up, even if it's a small degree. It's going to go down, and you have to follow it going down and as it's going down, your gut will let you know if you're on the right track. Your gut will be a big part of your decision. That failure that you see in front of you, will also tell you if you're willing to continue going forward. You have to trust your gut. It's not necessarily getting up on and jumping back on the same horse. You definitely have to keep getting up but you might have to jump on a different horse." - Steve Aoki, DJ and producer, from episode 83
• "Find someone whose career that you want for yourself and then try to support them, work for them, and emulate them. If you can find that person and you can add value to that person's organization, you're going to be in great shape. And on the flip side, if you look around and you can't find anyone whose life and career you want, then you should probably have some feelers out there to find something else. If there's no one in your organization whose career you want, then it's highly improbable to lead you there." - Andrew Yang, former U.S. Presidential candidate, from episode 85
• "For young people and who are coming out of college or graduate school for their first or second job, you should find a company that you really admire, where you really like the product and admire and like the people that you're going to be working with because I don't know about you but I spend more time at work than I do with my family and probably have over the last 40 years." - Meg Whitman, CEO of Quibi, from episode 86
• "Do not edit your ambitions. Too often we are told to scale down, to scale back, and to look for someone who has done it and if it hasn't been done, it can't be done. I don't believe that. My ambition is to serve and my responsibility is to always to find the best place to stand to do that work. If it doesn't work out the way I want, it's not an excuse to sit down. I will never edit my ambitions and no else should either." - Stacey Abrams, politician and author, from episode 89
• "Every year pick something that you're loving, something that you're learning and something that you're launching. The loving gives you satisfaction and happiness, the learning gives you excitement and curiosity, and the launching gives you a new learning curve, a new risk, and a new excitement." - Jay Shetty, author of Think Like a Monk, from episode 99
• "Always be learning. You don't have to have a great plan, but you always want to be learning on the job and if you ever don't feel you're learning, then it's time to move on." - Reed Hastings, co-founder, co-CEO, and chairman of Netflix, from episode 100

My best piece of career advice

I think that someone's best piece of career advice has to come directly from their first-hand experience so it's authentic and they are a case study to prove its effectiveness. My best career advice has always been to do as much as possible as early in your life as possible. Early in my career, I always felt like the competition to get jobs was going to be extremely fierce, so that motivated me to work extra hard to build up my resume.

I had my first internship in high school, seven more in college, and started my first company in college. Upon graduation, I worked at a Fortune 200 technology company, while working on several passion projects on nights and weekends. By having all of these experiences, working with different people, in different industries, at different size companies, performing a variety of tasks, encountering challenges and learning, it gave me the perspective to have a more focused long-term career. I learned about the type of culture I would work well in, what my talents were, what I disliked and through the process of elimination, I gained self-awareness, confidence, and focus. By doing as much as I could when I was younger, I set myself up for success for my entire career.

That's why I recommend, regardless of how old you are, to experiment. You don't know until you know, meaning that unless you actually have a job experience, you may assume what it would be like but you'd never actually know for sure. No matter what you do, have a positive attitude, learn as much as possible, meet as many people as you can, and then gravitate to what's working so you can invest enough energy in that career to excel at it.

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