WE in the News
Tony Bradley , Contributor
Success is very subjective. How we define “success” can vary greatly from one individual to the next. No matter where you start from, how you’re raised, or what experiences you have in life, though, the journey to success generally teaches some important lessons as well. I reached out to a number of people who have achieved some measure of professional success to find out about those lessons.
The idea behind this actually came to me as I pondered how to effectively guide my children. I have 7 kids with varying interests, and different degrees of motivation and focus. They each have different goals and different ideas of what “success” would mean for them—and that means that their paths to get there will also be unique. So, I thought, if I could go back to where they are now—back to high school or college—and give myself advice, what do I know now that I wish I knew then? What wisdom would I want my younger self to have?
That led me to wonder how other people might answer those questions—specifically people I perceive as being “successful”. I was surprised at how little overlap or redundancy there was in the answers. Rather than trying to weave the various responses and conversations together into a single narrative, I have shared the lessons and wisdom from each individual separately:
To the outside world, Chris Capossela has only had two jobs in his life. He went from working in his family’s Italian restaurant to working for Microsoft straight out of college. That was 26 years ago, though, and the reality is that Chris has take a number of twists and turns in his career within Microsoft.
The main lesson that Chris wished he could convey to his younger self is to have a sense of adventure and don’t be afraid to take risks with your job selections. He explained to me that most of the time he has done something that seemed risky at face value, it has turned out to not be as big a risk as it seemed. When you move to a position that’s very different than what you’ve been doing it can seem somewhat “dangerous.” You may not know the job or your new team very well and it can seem like starting over. Chris told me, however, “If you always just take a job that’s similar to the one you already have, you don’t grow and expand.”
Chris should know, too. When an opportunity came along to work closely with Bill Gates, many people tried to persuade him it was a bad idea. It was a lateral move that took him off the prescribed path for his career. I doubt anyone would deny now that the opportunity to work with and be in the sphere of influence of Bill Gates was a much greater value than whatever small promotion or financial compensation Chris may have gained had he turned it down.
Chris stressed that kids like his 15-year-old self—young people still in school or just starting their professional lives—should understand that there is no natural career progression that is just going to be handed to you. You won’t just show up and do your job and be periodically promoted up the ladder by attrition. You have to forge your own plan.
Along with that wisdom, though, Chris also pointed out that you don’t need to have a 5-year plan, or a 3-year plan, or a 10-year plan, or whatever. He said that he believes it’s fine to have one, but that it’s important to be willing to re-write the plan or throw it out and start over. Chris said, “You should be prepared to take advantage of exciting new opportunities.”
Mike relayed a story to me about his time as a junior captain in the Air Force working in communications. He told his boss about an opportunity to meet with Marc Andreessen about this “new browser thing.” The response from his boss was that Mike should stay focused on the things that apply directly to his job, and that this “small computer thing” is not going to pan out into something you can build a career on.
I don’t know where that former boss is now, but that anecdote illustrates the primary advice that Mike would tell his 15-year-old self if he had the chance: Try a lot of things.
Mike told me that he believes people need to be open to trying a variety of different things. Don’t listen to naysayers—if it sounds interesting to you, do it anyway. Once you’ve tried things out, you can zero in and continue to focus on the things you love most among the things you’ve tried.
When I spoke with Tiffany, she told me she viewed the question through the lens of a conversation she recently had with one of her own children, and what wisdom she hopes to impart to them. The first thing that came to mind for her was curiosity.
Tiffany would tell her younger self (or her boys as the case may be) that the world is so much bigger than you think. It is invaluable to realize that you don’t know how much you don’t know. It’s important to remain curious and always be on a quest to learn more.
She also told me that without curiosity you lose empathy. She stressed that curiosity is a critical element of considering different points of view and understanding where others are coming from.
Tiffany also wished her younger self knew the importance of confidence. She said that confidence may seem to be in conflict with curiosity—if you’re confident you know something, there’s no need to be curious about alternatives. She clarified, though, that when she says confidence she is referring specifically to the belief that you can succeed.
She shared that she lacked confidence early in her career, and that the lack of confidence made the first 5 years or so of her career more challenging than they should have been. She was grateful that she had strong female leaders around her to foster her confidence.
Rohit shared three things he would say to his 15-year-old self. The primary lesson is the idea that learning to learn is more important than learning itself. In other words, what you know is not as important as being adept at finding new knowledge.
Rohit told me that he has pivoted a lot throughout his professional career and thos epivots have forced him to learn and adapt to the current context. “Back when I was 15 years old, I was a regular, inquisitive student focused on learning and knowledge,” explained Rohit. I was not paying as much attention to the process of learning, or what things enhance my ability to learn.”
He also said he would stress to his younger self that it is OK to question the question. The default response is to take questions at face value—one person asks a question, and the assumption is that the question requires an answer.
Rohit told me, “During the course of my career and life I’ve realized there is so much value in trying to question the question rather than just trying to answer it.” He said that he wished his 15-year-old self understood the value in stepping back to think more critically about whether that is the right question to ask before reflexively answering it.
Finally, Rohit shared that he would tell his 15-year-old self that what people feel is more important than what they think. Whether you’re trying to market a product or service to customers, or lead a team of employees, facts and data don’t influence people as much as emotion.
If Ron could go back and talk with his 15-year-old self, there are three lessons he would share. First, is patience. He would tell himself that it takes a much longer time for people to change their minds, habits and preferences than you realize—even with sound logic, planning and communication.
Second, is empathy and respect for the perspective and history of others. He would let his younger self know that no matter how humble, honest and fair you are, you will still pay for the sins of others who came before you and were not.
Finally, focus. Ron stressed, “Never forgot your goals. If you don't have a specific goal, you will never know if you have succeeded and others will define your level of success for you.”
Stuart had a list of things he would remind his 15-year-old self about. He would tell himself things like everything will be ok, and that he should always protect those who cannot protect themselves. There are two lessons that stood out, though.
First, Stuart would tell his younger self to find his true passion. He explained, “It’s the one that never feels like work.” Along with that, though, Stuart added that he would stress that it’s important to always be honest and pursue the truth, and that if you give of yourself, it will be returned exponentially.
The second is sort of an extension of that last bit of advice. Stuart told me, “Trusting someone before it is earned is a painful way to live, but the only way to truly feel free.” He also noted the importance of letting go of the past, people’s transgressions against you, and grudges. “They only create toxicity in your life and don’t impact the transgressor’s life one iota.”
Katie had a lot going on when she was 15. She was busy hanging out in the same online forums as hackers from L0pht and Cult of the Dead Cow. They would meet up and hang out in real life—exchange hacking ideas and pick locks for fun. That was the start of a wild ride that has led her to be one of the most respected professionals in information security.
Along the way, Katie has learned a few lessons that she wishes she had known when she was 15. The biggest and hardest is to actively listen with empathy, especially when it comes to those you don’t agree with. Katie explained, “This was a complex skill, requiring multiple similarly hard prerequisite skills to build. It was the hardest to build, and I’m still building it, yet the return in kind and the positive results in the form of bidirectional changes have been worthwhile. Stare long enough into an abyss, and your eyes might adjust to see more than darkness in there.”
She also said that she would tell her younger self to place her belief in herself first—and choose friends and partners who behave as such. She wishes she had known to more quickly root out and dismiss people from her life who demonstrate through their actions (or inaction) that they aren’t really on her side.
Finally, she would tell her younger self to write a book and also to start a company. “Not in a few years. Now. The cost of failure is lower when you’re young. You can afford to try several experiments in business and in life, and you should do so as soon as you can."
Ayman echoed the belief shared by a few others I spoke with that the value of education is less about the specific knowledge you gain, and more about the skills you pick up—learning to learn. The big lesson that Ayman would tell his 15-year-old self if he had the chance, though, is embrace change.
He told me that in order to survive, businesses today need to be built for change, not built to last. Companies—and individuals—need to be able to adapt and change to adjust to a dynamic and shifting landscape. He stressed that the ability to recognize trends and adjust accordingly is more important than developing a 5-year plan.
Ayman also told me that it’s important to be challenged. “As I reflect on my career, and ask where and when did I grow the most – it was when I felt challenged?” He cautions that when you feel comfortable and you know how to do all of the things relative to your job, it’s time to move on. If you know it all, you’re not growing and learning.
Joel started off with fairly standard bits of wisdom you pick up after you emerge from your teen years and face the shocking revelation that you don’t actually know everything. He said he would tell his younger self that it gets better, and that it’s important to learn new things and expand your horizons. Then we got to the real lesson.
Joel explained that he pursued a computer science degree in college, and that he took an anthropology course during his senior year to fulfill a required credit. “It was the most boring class I ever took,” said Joel. “It was an exercise in struggling through boredom.”
20 years later, however, Joel realized the value of that class as it dawned on him that all of the good decisions he has made or continues to make are based on anthropology. He said the second-most valuable class he took, in retrospect, was psychology.
The simplest definition of anthropology is “the study of humankind”. That course in anthropology (with some added help from the psychology course) gave Joel a foundation for understanding humans and human behavior—knowledge that comes in handy for managing and motivating people. It has led Joel to build companies that are based on and driven by helping people—and that has helped Joel achieve success.
This exercise was challenging for Jennifer. She told me it’s not that she knew everything when she was 15 and couldn’t think of any wisdom she would share, but that the core lessons—take more risks, trust your gut, live life to the fullest, etc.—have simply been a core part of who she is all of her life. Actually, following through on those lessons is often easier said than done, but she already knew those things at 15.
The one thing Jennifer would tell her 15-year-old self if she could is, “Always be yourself and never change who you are just to conform to what you think others want you to be. It’s your life, and you got this girl!”
Lisa relayed a couple lessons that others have shared as well—things like it’s good to have a medium to long term plan, but it’s more important to be flexible enough to change it if it’s not working or if a new opportunity comes along. She also stressed the idea that the ability to learn is a crucial skill.
The primary lesson she would convey to her 15-year-old self, though, is to run toward problems and embrace challenges. “When you’re 15, 20, 25—you realize that people are extremely creative when they’re solving difficult problems."
Lisa said that taking on challenges paved the way to build her confidence. “I've had a chance in my career to work on a lot of interesting projects and I learned the most on the problems that were the most challenging.”
As I said in the intro, success is subjective. So are the lessons and wisdom that help you get there. All of these tips and insights are valid and could be useful to someone in high school, or college, or just starting out in their careers. They may not all apply to every person or scenario, so take what works for you and ignore the rest. At least now I have some collective wisdom to share with my kids and hopefully help them move forward toward whatever it is success means to each of them.