What I Wish I Knew When I Was 20 | Secrets to Success


What I Wish I Knew When I Was 20 (Amazon), written by Tina Seelig, is an excellent book that I read earlier this year. Funny enough, I’m more than a few years past 20, but I found great value in reading it and I am going to share the key points with you all. So regardless of your age, I’m confident you will find some valuable nuggets of information from this book summary. Like my other book review on the Subtle Art, I will be summarizing the author’s points but also inserting my own commentary on things I agree or disagree with, along with relevant examples from my personal life.



The premise of this book as is as follows: major life transitions, such as starting college, or graduating college and starting a career, can be daunting. There are an infinite number of possible paths to take, and no one is able to tell us whether we are making the right choice. Success, no matter how you define it, is not part of a simple equation. While there are common traits among those we deem successful, there is no clear delineated path or recipe for success.

Success is not part of a simple equation

Tina Seelig is a faculty director of the Stanford Technology Ventures Program and received her PhD in Neuroscience from Stanford School of Medicine. She is an excellent teacher and has won several accolades in recognition of her education work. This book summarizes her model for reaching our highest potential and her life philosophy. That being said, this information is relevant regardless of age.


What is An Entrepreneur?

Tina sets the tone early on by jumping straight into what makes an entrepreneur. I love her definition, which is “an entrepreneur is someone who is always on the lookout for problems that can be turned into opportunities and finds creative ways to leverage limited resources to reach their goals.” Note that her definition does not mention anything about businesses, finances, or money. Being an entrepreneur means seeing the world as opportunity rich. Tina argues that entrepreneurship is important for just about everyone to develop. After all, it “cultivates a range of important life skills, from leadership and team building to negotiation, innovation, and decision making.”

A common mindset that most of us fall into is to frame a problem or situation too tightly. In one of her lessons, Tina challenges the students with the following: earn money in 2 hours starting with just $5. They had time to plan their approach, but once the envelope was cracked open, they only had 2 hours to generate as much money as possible. Standard responses would be to start a car wash or lemonade stand, using the $5 to purchase the starting materials. However, teams that made the most money didn’t use the five dollars at all. They realized that focusing on the money framed the problem too tightly – so they reframed the problem as “what can we do to make money if we start with absolutely nothing?” The teams found incredibly innovative solutions, some bringing in upwards of $600. Some of my favorites included offering a service to sell reservations to restaurants so customers did not have to wait around in line. As a cycling enthusiast, I also enjoyed hearing of the story where a team set up a stand to measure bike tire pressure for free. If the tires needed air, they would inflate the tires for $1. When they switched from charging a fee to becoming donation based, their income soared.


School is Not an Accurate Representation of the Real World

I am in no way saying that competition is a bad thing. However, the current educational system often hinders collaborative team efforts. In school, students are evaluated as individuals and graded on a curve. This means when one student wins, someone else loses. This adds unnecessary stress and is not an accurate representation of how the real world works. Outside of school, people work on teams with a shared goal, and when they win so does everyone else.

Another great point she makes is how students learn. I’m sure all of you can relate to being assigned a textbook chapter, carefully reading and taking notes, and being tested on the material later. After college, however, you become your own teacher and must figure out what you need to know, where to find the information, and how to absorb it. Tina calls life the “ultimate open book exam.” “The doors are thrown wide open, allowing you to draw on endless resources around you as you tackle open-ended problems related to work, family, friends, and the world at large.”

We have been taught all our lives that problems are to be avoided and are something to be complained about. By removing ourselves from these situations, we will view problems as opportunities in our everyday lives.


Learn to Fail

In contrast to school, most situations outside of school have a multitude answers to every question, many of which are correct in some way. More importantly, it is acceptable to fail. Tina actually encourages more failing, as failure is an important part of life’s learning process. “Just as evolution is a series of trial-and-error experiments, life is full of false starts and inevitable stumbling. The key to success is the ability to extract the lessons out of each of these experiences and to move on with that new knowledge.”

I have been in this situation, and I am sure many of you can relate. There are times where I have felt like I need to pick the one right answer when there is a wall of choices in front of me. It can be overwhelming. And although family and friends will be happy to give advice, it’s ultimately up to us to choose our own direction. But the important part to remember is that we don’t have to be right the first time. Life presents us with many opportunities to experiment with and recombine our skills and passions in new and surprising ways. For instance, I would have never guessed that I would combine my passions for medicine, education, and technology into Med School Insiders.

Tina requires her students to write a failure resume. That means they craft a resume of their biggest screw-ups: personal, professional, an academic. For each failure, the student describes what he or she learned from that experience. This forces students to come to terms with the mistakes they have made along the way and remind them that these are opportunities for growth above all else.

Many successful people believe that if you aren’t failing sometimes then you aren’t taking enough risks.

In some cultures, the downside for failure is so high that individuals are allergic to taking any risk at all. This is in sharp contrast to the Silicon Valley, where failure is acknowledged as a natural part of the process of innovation. On the most basic level, all learning comes from failure. Think of a baby learning to walk. He or she starts out crawling and then falling before finally mastering the skill that as an adult we take for granted. The entire venture capital industry essentially invests in failures, since the majority of the companies they fund eventually go under.

Many of you have probably heard Steve Jobs’ commencement speech at Stanford in 2005. He explained getting fired from Apple, the company he started, and how devastating that experience was. He was a very public failure, but then something began to dawn on him – he still loved what he did. He had been rejected, but he was still in love. So, he started over. He said that getting fired from Apple was the best thing that could have ever happened to him. The heaviness of being successful was replaced by the lightness of being a beginner again, being less sure about everything. He entered one of the most creative periods of his life, during which he started NeXT, Pixar, and found the woman who later became his wife. Pixar became the most successful animation studio in the world, Apple bought NeXT and used its technologies at its core, and he married Laurene and they started a family. He was pretty sure that none of that would have happened if he had not been fired from Apple. It was awful tasting medicine, but the patient needed it.

When we think of career trajectories on a graph with time on the X axis and success on the Y, we imagine a line steadily pushing up and to the right. But in reality life is riddled with failures and ups and downs. As you move further along in your career, you will have great successes but also great failures. Take Steve Jobs’ story as an example. Most individuals’ paths are riddled with small and enormous failures. The key is being able to recover from them.

“For most successful people, the bottom is lined with rubber as opposed to concrete. When they hit bottom, they sink in for a bit and then bounce back, tapping into the energy of the impact to propel them into another opportunity.” Failures can serve as incredible opportunities in disguise. They force us to reevaluate our goals and priorities, and often propel us forward much faster than continued success.  Failure is the flip side of success, and you can’t have one without the other.

Remember, if you do take a risk and happen to fail, remember that you personally are not a failure. The failure is external. This perspective will allow you to get up and try again and again.


Have the Right Attitude

“Attitude is perhaps the biggest determinant of what we can accomplish. True innovators face problems directly and turn traditional assumptions on their head.” And I don’t mean this in a lets-start-a-business sort of way or lets-make-money way either. Problems are really just opportunities yet they go unnoticed more often than not. Problems are abundant and are waiting for those willing to find inventive solutions. This requires observation, coordinated teamwork, the ability to execute a plan, willingness to learn from failure, and creative problem solving. But above all else, it requires having the right attitude; the attitude that the problem can be solved.

So why is it that most of us don’t always focus on the opportunities that surround us each day and take full advantage of them? The reason is that most of us are not naturally good at identifying and challenging assumptions. We follow the herd mentality, meaning people are influenced by their peers to adopt certain behaviors. Often times the status quo is so entrenched that those closest to the situation cannot imagine anything different. Tina calls this “problem blindness”.

A brilliant way Tina approaches this issue is to have her students identify a problem, and then pick a random object in their environment. They then need to figure out how that object will help them solve the problem.

There is considerable research showing that those willing to stretch the boundaries of their current skills and willing to risk trying something new are much more likely to be successful than those who believe they have a fixed skill set and innate abilities that lock them into specific roles. This goes back to the fixed mindset vs growth mindset that many of you have probably heard about. Those who have a fixed image about what they can do are much less likely to take risks that might shake that image. But those with a growth mindset are typically open to taking risks and tend to work harder to reach their objectives. They are willing to try new things that push their abilities, opening up entirely new arenas along the way.


Embrace the Impossible

By not limiting ourselves to the status quo, we are able to take on grand projects, make choices that seem radical, and carve out a new path that leads us to unchartered territories. And that’s where the magic really happens. Instead, we watch these people, like Elon Musk, in awe and limit ourselves from ever taking the risks or thinking in a similarly radical way. Here’s another ingredient to the secret sauce: the more experience you have tackling problems, the more confident you become that you can find a solution.

It’s difficult to figure out when rules are just suggestions, and when suggestions morph into rules. On a daily basis, we see physical signs that tell us what to do, written instructions direct us on how to behave, and social guidelines urge us to act within specific parameters. We also make a lot of rules for ourselves, which are in large part encouraged by others. These rules become woven into our individual fabric as we go through life. Once you whittle away the recommendations, you realize there are often many fewer rules than you imagined.

Larry Page, co-founder of Google and badass-extraordinaire, gave a lecture where he encouraged the audience to break free from established guidelines by having a healthy disregard for the impossible. Think as big as possible. It’s easier to have big goals than it is to have small goals. Why? Because with small goals, there are very specific ways to reach them and more ways they can go wrong. With big goals, you are usually allocated more resources and there are more ways to achieve them. All the cool stuff happens when you do things that are not expected. The well-worn path is there for everyone to trample. But the interesting things often occur when you are open to taking an unexpected turn and question the rules that others have made for you. It’s easier to stay on the prescribed path, and that’s why many stay to it, but it is more interesting and exciting to discover the world of surprises off the beaten path.

The well-worn path is there for everyone to trample. But the interesting things often occur when you are open to taking an unexpected turn and question the rules that others have made for you.

Here’s another brilliant exercise that Tina uses. First, teams come up with a problem that is relevant for the group. For example, a group of executives in the utility business may be trying to find a way to save energy. Then each small team is come up with a best idea and a worst idea for solving the stated problem, and write each on a piece of paper. She then takes the best ideas, shreds them, and redistributes the worst ideas. Each team now has an idea that another team thought was terrible. And they are instructed to turn this bad idea into a fabulous idea. After looking at this horrible idea, they realize it isn’t so bad after all. It’s all about reframing perspective and embracing the impossible. I love this exercise because it demonstrates that most ideas, even if they look silly or stupid on the surface, often have a least a seed of potential. Ideas don’t have to be feasible to be valuable. Sometimes the craziest ideas, which seem impractical when initially proposed, turn out to be the most interesting in the long run.


Money is Not the Answer

Guy Kawasaki said it best – “it’s better to make meaning than to make money.” If your goal is to make meaning by trying to solve a big problem in innovative ways, you are more likely to make money than if you start with the goal of making money, in which case you will probably not make money or meaning. Plain and simple.


Grant Yourself Permission

Tina explained that “Over time, I’ve became increasingly aware that the world is divided into people who wait for others to give them permission to do the things they want to do and people who grant themselves permission.” Nobody needs to tell you that you can or should do something – just do it.

Tina explains that she told a friend she planned to write a book. The friend responded, “what makes you think you can write a book?” She couldn’t imagine taking on such a project without the blessing of someone in a position of greater authority. Some look inside themselves for motivation and others wait to be pushed forward by outside forces. There’s a lot to be said for seizing opportunities instead of waiting for someone to hand them to you.

I started a biomedical incubator at my school, meaning an organization that helps students create start-ups in healthcare. I didn’t ask anyone for permission. In fact, three separate faculty who I approached for guidance told me it was a nice idea but impossible. They had tried the same thing in the past and failed – they were also much more experienced in this sort of thing than I was – what made me think it would work out this time? Although a couple months behind schedule, my team and I did not just successfully launch the incubator, but it is now thriving, growing, and a source of pride for the University.

Those who are successful find ways to make themselves successful. There is no recipe, no secret handshake, and no magic potion.


Know When to Quit

Tina emphasizes that more of us need to know when to quit. We give into sunken costs, the “too-much-invested-to-quit-syndrome”, which is a powerful driver of human behavior. We justify the time, effort, suffering, and years we devote to something by telling ourselves and others that there must be something worthwhile and important about it or we never would have sunk so much of our lives into it.

Tina goes on to explain that quitting is incredibly empowering. It’s a reminder that you control the situation and can leave whenever you like. You don’t have to be your own prison guard, keeping yourself locked up in a place that isn’t working. But we are taught that quitting is a sign of weakness – she argues that in many circumstances it is actually the opposite. Quitting is often brave because it requires you to face your failures and announce them publicly.

Persistence is to be admired, but when does it become foolish to continue working on something that’s never going to fly? We often stay in dead-end situations way too long. We often do this when we stay in jobs or relationships that make us miserable, hoping the situation will improve. Tina suggests doing the following: “listen to your gut and look at your alternatives.”

Listen to this advice carefully. I personally believe most people give up on pursuits too easily – Tina is not advising you to give up whenever things get tough. Have the grit to make it through the challenging times – however don’t be your own prison guard.


Choose the Right Career for You

We often hear that we should follow our passions and use that to guide our career choices. This is misleading and simplistic. Passions are just a starting point. You also need to know your talents and how the world values them. If you’re passionate about something but not particularly good at it, then it’s going to be frustrating to try to craft a career in that area. Say you love basketball but aren’t tall enough to compete, or you’re enthralled by jazz but can’t carry a tune. In both cases, you can be a terrific fan, going to games and concerts, without being a professional.

The sweet spot is where your passions overlap with your skills and the market. If you can find this spot, then your job enriches your life instead of just providing the financial resources that allow you to enjoy your life after the workday is over. The goal should be a career in which you can’t believe people actually pay you to do your job.

Taoist philosopher Lao-Tu sums this up brilliantly: “The master of the art of living makes little distinction between his work and his play, his labor and his leisure, his mind and his body, his education and his recreation, his love and his religion. He simply pursues his vision of excellence in whatever he does, leaving others to decide whether he is working or playing. To him, he is always doing both.”

Don’t be afraid to change trajectories. People who are close to you often expect you to make decisions about your career and stick with it. They want you to be a “fire and forget” missile that zeroes in on a target and pursues it relentlessly. But that’s not how life works – it’s ok to change course many times before finding the best match for you.

I love how Tina compares career trajectories to traveling:

“Planning a career should be like traveling in a foreign country. Even if you prepare carefully, have an itinerary and a place to stay at night, the most interesting experiences usually aren’t planned. You might end up meeting a fascinating person who shows you places that aren’t in the guidebook, or you might miss your train and end up spending the day exploring a small town you hadn’t planned to visit. I guarantee that the things you’re likely to remember from the journey are those that weren’t on your original schedule.” Don’t be in a rush to get to your final destination—the side trips and unexpected detours quite often lead to the most interesting people, places, and opportunities.

Like Steve Jobs said, it’s easier to connect the dots looking back. You can’t connect the dots looking forward. The road ahead is always fuzzy and full of boundless uncertainty.

It’s critical to surround yourself with incredible people. By surrounding yourself with quality people, you increase the quality of the opportunities that flow your way. Great people support each other, build valuable networks, and create a steady stream of new opportunities.

It is important to reassess your life and career relatively frequently. This self-assessment process forces you to come to terms with the fact that sometimes it’s time to move on to a new environment in order to excel. Most people don’t assess their roles frequently enough and so stay in positions for years longer than they should, settling for suboptimal situations.


Become Lucky

What do you mean become lucky? You can’t change that. Actually, “lucky people” share traits that tend to make them luckier than others. First, lucky people take advantage of chance occurrences that come their way. They don’t go through life on cruise control – they pay attention to what is going around them and are able to extract greater value from each situation. Lucky people are also open to novel opportunities and willing to try things outside of their usual experiences. They’re more inclined to pick up a book on an unfamiliar subject, to travel to less familiar destinations, and to interact with people who are different than themselves.

Lucky people also tend to be optimistic and to expect good things to happen to them. This becomes a self-fulfilling prophecy, because even when things don’t go as expected, lucky people find ways to extract positive outcomes from the worst situations. Their attitude affects those around them, and helps to turn negative situations into positive experiences.

Tom Kelley, author of The Art of Innovation, says that every day you should act like a foreign traveler by being acutely aware of your environment. In everyday life, we tend to put on blinders and cruise down well-worn paths, rarely stopping to look around. But as a traveler in a foreign country, you see the world with fresh eyes and dramatically increase the density of your experiences. By tuning in, you find fascinating things around every turn.


Other Insights

Here are a few other brilliant points I want to touch on briefly:

  • One of my favorite tips from the book that I use often in my daily life is the following: There will be difficult situations where you are not sure how to behave. One way to figure out how to handle these situations is to imagine how you will describe what happened later. Meaning if you had to tell the story to someone later of what happened, which way would you be proud to tell the story? Behave in that manner.
  • Take responsibility for your mistakes. Knowing how to apologize is important. Simply acknowledging that you messed up goes a long way. There’s no need for long speeches and explanations; just say “I didn’t handle that very well. I apologize.”
  • Another skill rarely taught in school is negotiation. A common mistake of negotiation is making inaccurate assumptions, such that the two sides have opposing goals. Parties often share interests, even when they believe they’re on opposite sides of an issue.
  • Learn the art of helping others. As Guy Kawasaki says, “You should always try to be a ‘mensch.’” He continues, “A mensch helps people who can’t necessarily help them back. Of course, it’s easy to be generous to someone whom you think will be able to help you, but being a mensch means helping others even if you’re pretty sure they can’t help you. You can call it karma if you like, but people who are generous and helpful to others are those that others want to help in return.”
  • Never forget that the world is very small and you will likely bump into the same people time and time again. Protect and enhance your reputation—it’s your most valuable asset and should be guarded well
  • Excuses are bullshit. We use excuses to cover up the fact that we didn’t put in the required effort to deliver. There’s a big difference between trying to do something and actually doing it. We often say we’re trying to do something – losing more weight, exercising more, etc. But the truth is, either we are doing it or we are not doing it.


Final Thoughts

In summary, never miss an opportunity to be excellent. Life is like investing. Imagine starting with $100 with a 5% return versus investing the same $100 with 105% return. The values compound over time. This is what happens in life. You get out of life what you put in, and the results are compounded daily. Give yourself permission to challenge assumptions, to experiment, to fail, and to test the limits of your abilities. Don’t take yourself too seriously nor judge others too harshly. Have a healthy disregard for the impossible, and seize every opportunity to be excellent.


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