August 18

5 of the Most Important Decisions You Will Make in Your Life

Every decision you make, from your choices to how you respond to the circumstances of your life, shapes your destiny. A decision you make today could affect your life tomorrow, a week from now, or 10 years from now. Destiny is the ripple effect of the small and big decisions you make throughout a lifetime.

When I started writing this article, I asked my community on Twitter and Facebook what they thought were the 5 most important decisions in your life. There were consistent themes that came up in every response.

These are 5 of the biggest decisions you will make in your life. They will impact everything from your emotional well-being to your finances. You may have already made some these decisions or you might be in the process of making them.

What Is a Decision?

Professional poker player Annie Duke says, “Decisions are bets on the future, and they’re not ‘right’ or ‘wrong’ based on whether they turn out well at a particular iteration.” Understanding the steps in the decision-making process gives you a strategy for decision making.

How Do You Decide Which Decisions are Important?

There are two main kinds of decisions. One way to figure out which kinds of decisions are important is to divide them into what Annie Duke calls dating decisions and marriage decisions.

Dating Decisions

These are low-risk daily decisions and the outcome won’t make a difference in the grand scheme of your life. They include things like ordering a meal at a restaurant, going on a date with someone you’re not compatible with, or buying an item on Amazon.

You can always order a different meal, pass on a second date, or stop reading that book you don’t like. Although their long-term impact is minimal, we attach unnecessary importance to dating decisions.

Marriage Decisions

These are decisions where the stakes are high and the outcome will make a big difference in your life. They include things like who you marry, a big financial decision like buying a house, etc. Marriage decisions are the most important decisions you will ever make.

According to Annie Duke, very few decisions are irreversible. But the opportunity cost of a bad choice is much higher for the biggest decisions in your life.

3 Steps of the Decision Making Process

most important decisions

There are three main steps in the decision-making process: The decision, the probability, and the outcome. Choosing a career path is one of the biggest decisions you will ever make. So let’s look at an example.

1. Decision

Music was a big part of my life in high school. So, I decided to pursue a career as a professional tuba player

2. Probability

Because I made the All-State band in high school, I thought the probability of my success was high even though it wasn’t. There is only one tuba player in each orchestra. Assuming there are 5000 professional orchestras in the world, the probability of getting the job is 1 in 5000. Since you have to wait until the other tuba player dies to get the job, the probability is even lower.

3. Outcome

Even though I got accepted to the USC School of Music, my dad talked me into not going. And I’m glad he did, because tubas aren’t versatile, and I didn’t want to be a high school band director or music teacher.

Following the steps of the decision-making process gives you a reliable strategy for decision-making.

Good Decisions vs Poor Decisions

If you pursue a career in the arts and it doesn’t work out, you didn’t necessarily make a poor decision.

What makes a decision great is that not it has a great outcome. A great decision is the result of a good process, and that process must include an attempt to accurately represent our own state of knowledge.

Annie Duke, Thinking in BEts

We will all make choices in our lives that have undesirable results. We will have relationships that end, bosses we can’t stand, and try things that lead to failure. But if you learn to separate the quality of your decisions from the results, you will live without regret.

The 5 Biggest Life Decisions

The biggest decisions you will make in your life are what Annie Duke calls “marriage decisions.” These include your personal values, who your friends are, where you live, what you do for a living, and of course, who you marry.

1. Values

most important decisions

It’s a mistake to simply accept the received ideas of the world around you. You have to come up with your own values, your own worldview. – David Brooks, The Second Mountain

1. Personal values

It is a mistake to simply accept the received ideas of the world around you. You have to come up with your own values, your own worldview.

– David Brooks, The Second Mountain

Your personal values will determine every other decision you make. The ones we regret are usually not in line with our personal values. Therefore, choosing your values is one of the most important decisions in your life.

What are Personal Values and Where Do They Come From?

We pick up our first values from our family because they are the first influence in our lives. As you gain more data points in life, you pick up values from your environment, peers, people you work with, and life partners. Because of this, your values will also change throughout your life.

Discover your core values

The easiest way to find out your values is to ask:

  • What is important to you?
  • What can you not live without?
  • What is not important?
  • What can you live without?

Discover Your Core Values Through the Power of Contrast

Let’s say you have two job offers.

The first job comes with a six-figure salary, a corner office, and an impressive job title. But it also means long hours, holidays, and weekends. The second job may pay less, but it gives you more time to spend with your family and time to pursue hobbies that interest you.

But context matters, too. A recent graduate may make a different decision than someone who has a family

Look back on your life and the moments when you had to choose between two alternatives. Then ask yourself why you chose one option over the other. Your choice reveals your values when you make the most important decisions in your life.

Repeat this exercise with several personal and professional choices. Rank them from most important to least important. And you will discover your hierarchy of personal values.

Status values

Status values include lineage, prestige, and luxury. Having status values doesn’t make you a terrible person. We all have status values.

If you’re reading this with an iPhone or Macbook, you value the status of buying Apple products. All the shirts in my wardrobe are from Proper Cloth. I value the status of wearing custom shirts.

Where status values bite us in the ass is when we use them to make decisions about people. Perceived status is a cognitive bias that causes people to confuse vanity metrics with the impact someone might have on their lives. Social media platforms reinforce this bias.

  • If you only surround yourself with people who graduated from “prestigious universities,” you’re missing out on incredible people, both as friends and as people you could work with. Some of my best friends didn’t even go to college and are the smartest and most successful people I know.
  • My most influential mentor had 150 followers and was a nobody. He came up with the name Unmistakable Creative, taught me how to run a business, and laid the foundation for everything I accomplished after we parted ways.
  • One of my other mentors was my reference in raising my first round of investor money. He’s virtually invisible online.

Status fluctuates and is always fleeting. If status is one of your most important personal values, prepare for a lifetime of disappointment.

Character Values

Character values are most important because they are all you have left if you lose your status. Generosity, kindness, and unconditional love are character values.

My best friend’s wife is an example of what it means to have character values. He told me this story about how he told her he lost his job 6 months before they got married.

Faith Values

Faith means different things to different people. But at its core, it seems to be a belief in a higher power with powers we can’t understand or explain with logic. I’m not a religious person. But I’ve had many podcast guests who are, and they’ve taught me invaluable life lessons.

I realized I had faith the day of my sister’s wedding. An hour before the ceremony, the wind was howling. The man who had built the platform under which my sister and brother-in-law would stand said, “There is a one percent chance this thing will fall. We didn’t count on that. Can you get some people to hold the beams?”

I searched frantically for relatives. My father was praying. The moment the priest began the ceremony, the wind died down.

How Personal Values Change with age and experience

“One of the biggest problems with never being exposed to other opinions is that you never have reason to question your own beliefs. ” – Sarah Rose Cavanaugh

Our life experiences reveal to us what we couldn’t before. They give us the opportunity to rethink our values and question whether they were ours in the first place.

  • New friends who expand your perception of what is possible.
  • A job you hate or love makes you rethink what’s important in your career
  • Meeting a mentor reveals what you want to become

Exposure to different models of possibility and influence may make you realize that your values are no longer aligned with those you inherited.

My roommate Tim Wolff grew up in an extremely religious household. As he got older, he felt like it was all bullshit. But that doesn’t make him a bad person or someone without a moral compass.

Because Indians value prestige and pedigree, my parents’ values played a major role in where I went to college and the first half of my career. And I sought success on those terms, not my own, until I had a resume full of failures that resembled a rap sheet, was 30 years old, broke, and living at home.

The guests at The Unmistakable Creative each showed me a different model of possibilities. They helped me realize that my personal values had changed.

2. Friendship/Social Circles

most important decisions

2. Friendship/Social Circles

There is a famous quote that says you become the average of the 5 people you spend the most time with. The problem with looking at friendship through this lens is that it can lead us to choose our friends based on resume values instead of eulogy values.

Instead of choosing friends who will be there when we need them, we choose friends who we think will do something for us. But that doesn’t negate the fact that your social circle has a significant impact on your well-being. Who you choose as your friends is one of the biggest decisions in life.

Why Friendship Matters so much

According to the work of many happiness researchers, social scientists, and psychologists, social connection is one of the biggest determinants of our emotional well-being.

“There is a bottom line – a biological need for connection that must be met to achieve basic health and well-being. That is why social connection is rapidly becoming an issue of public health,” says author Lydia Denworth.

Throughout our lives, we face adversity, loss, and heartbreak in a variety of ways. Our friends keep us from turning a temporary circumstance into a permanent reality. They give us an ear to listen when we need to vent, a shoulder to cry on when we are hurting, and people with whom we can share life’s most precious experiences.

The setting is less important than the people you are with

When I went to India in 2018 to shop for my sister’s wedding, I saw Taj Mahal for the first time. A friend was supposed to come with me but couldn’t due to a family emergency. Although it was so breathtaking, it was the least memorable part of my entire trip because I was alone.

The right friends can make the most boring place in the world amazing and being in a place without friends can make one of the 7 wonders of the world boring. When you discover that the setting is less important than the people you’re with, you learn why friendship is so important.

1. Friends for life

Much like our values, we form our early social relationships by default, not by design. It’s the kids we go to school with and the ones we meet through our parents. Three factors determine whether our friendships last a reason, a season, or a lifetime.

2. Circumstance

The thirties … Are sometimes described as the decade when friendship dies, killed off by marriage, children, jobs, moves. Incongruous friendships – one has children, the other doesn’t – can be especially hard to maintain.

Lydia Denworth, riendship

Of all the things that change a friendship, life circumstances are at the top of the list. People have children, start families, and we are in different stages of life than some of our closest friends.

My oldest friend from college got married and started a family when she was in her 20s. I’m 42 and single, so the circumstances of our lives are very different. When she stopped inviting me to her daughters’ birthday parties, my mom said, “She’s not inviting you anymore?”

And I said to my mother, “What am I going to do at a five-year-old’s birthday party? There’s no single women or alcohol there.” But we’ve remained friends since my freshman year of college. Our friendship isn’t better or worse, just different. She’s still my oldest friend, and I adore her.

3. Reciprocity

Pamela Slim and Desiree Adaway have the kind of friendship you could make a movie about. They both told me this when I asked them about their friendship.

I accept her. Absolutely. And sacred as it is. And there is nothing anyone on this earth can do that would make me not love Pamela Slim, including Pamela Slim. She is one of the most amazing gifts in my life and I am very lucky to have her as my best friend. And she’s hysterical because you all don’t know what Pam Banana Pants is like. But I make it a point to talk to Pam every day. Can I go three or four days without talking to her? Sure. I can. But that’s part of our friendship, a daily check-in. That way I can make sure she’s okay. She doesn’t need anything. Then I’m done. That’s intentionality.

This is an example of the reciprocity that makes a best friend for life.

When I asked Lydia Denworth about the people we may have been close to in the past but who were not reciprocated, this is what she said:

The analogy I like to use is that if you think of your friends as groups of concentric circles, first you have the people closest to you. Then you have friends who are a little further away and then those who are even further away and so on. Having a friend in one of the more distant circles doesn’t mean you stop being friends with them, but you’ve moved the furniture of your friendship to an outer space, so to speak. This person is a little less central to your life. And what’s really important for your health and well-being is that you have a core group in the middle. For most of us, that’s only four people on average, right? So it’s not a lot.

4. Proximity

When I was in high school, my parents lived on 2 continents, in 3 different countries, and I attended 9 different schools. For some reason, the school district played area roulette during our 7 years in Texas. So I have almost no close friends from high school.

In my early 20’s I was fortunate to be blessed with an amazing group of friends. When we were young, I even thought one or two of them would be the best man at my wedding. But as we got older and they moved away, things changed.

We don’t talk as much anymore. When we do talk or see each other every few years, we reminisce about the drunken escapades of our youth, laugh a lot, and it’s just like old times. But we’re not as close as we used to be.

In contrast, my friend Gareth and I were in high school band together. He was 2 years younger and we were always friendly, but never close friends. While I was still living with my parents, I discovered that he still lived in Riverside. We met for dinner and began to develop a deep friendship. I was Gareth’s best man, and he will probably be mine (of course, I have to meet someone first).

He moved to Colorado, and when I realized I was here quite a bit, I wasn’t far behind. My roommates Matt and Tim and my friend Joseph are all here in Boulder.

Despite the fact that Joseph and Gareth have kids, the proximity and reciprocity haven’t prevented a deeper friendship between us all, and those are the guys I see at my wedding party when I imagine that day.

3. Environment

most important decisions

Whether we like it or not, we are all products of our environment, which includes geographic location, physical space, and the people who surround us. For the purposes of this article, let’s assume that environment is your geographic location.

Where you live affects everything from your values to who becomes your life partner.

  • Perhaps you live in a small town in the middle of a country where people place a high value on faith. This could affect how you raise your children and who you marry.
  • A bad neighborhood, poverty, or a circle of friends who were frequently in trouble with the law could cause you to develop resilience and a tolerance for adversity. Or you could end up in jail.
  • If you live in a big city like New York, LA or San Francisco, you will have access to career opportunities that may not be available in a small town.
  • If you live in another city, state, or country, things may open up to you that you never considered before.

Where you live can drastically change the trajectory of every other aspect of your life.

The environment in the Rao family

As immigrants to the United States who grew up in India, their life choices were binary. There was only security or poverty, nothing in between. Consequently, they optimized for security and predictability and passed that on to us. It took me a long time to understand and accept that.

Because my parents dragged me around the world for most of my childhood and exposed me to so many environments, my closest friends are people I didn’t meet until later in life. And I’ve always been jealous of people who have friends they’ve known since childhood.

And there’s a good chance I know someone in most of the places I’ve been in the world.

Living in the Bay Area during the first dot-com boom led to my interest in technology. A six-month stint in Brazil was the beginning of my love affair with surfing and the immense value I place on freedom, which led me to look for jobs that wouldn’t get in the way of my ability to surf.

Another city can lead to a better life

My former business partner Brian was at a low point in his life a few years ago. The MLM group he had joined had turned into a religious cult. And he was working until 2 or 3 in the morning in the cold trying to build a better life for himself and his wife. A mentor suggested he move to California. In the years after the move, he received promotion after promotion and his income continued to double.

My best friend Gareth was living in San Diego, working part-time in addition to working on what would eventually be his third failed business. Within a month of moving to Colorado, he got a well-paying job at a startup company. And after being laid off from that job, he started a business that consistently brought in five figures a month.

Every single place we live leaves a mark. I would never want to live in Bryan, Texas. But I also have fond memories of my time there. There is no such thing as “the best place to live”, just the best place for you. There are pros and cons to all the places you could live… Traffic sucks in big cities, and small towns don’t have as many options for food, entertainment, recreation, and culture.

Finding a better job isn’t the only good thing that could happen if you change your environment. You could meet your future life partner.

4. Careers

most important decisions

Because work is so important in terms of the amount of time it takes and the intensity of effect it produces in consciousness, it is essential to face up to its ambiguities if one wishes to improve the quality of life. –

Finding flow Flow, Milhaly Csikzentmihalyi

Society’s life plan teaches us that life is linear. We design a life plan before we know anything about ourselves. The truth about a life plan, whether you are 21 or 41, is that it does not include the uncontrollable (pandemics, recessions, etc.).

Talk to someone who is 41 and you’ll see that their life doesn’t look like what they envisioned when they were 21. They could not have predicted much of what has occurred in their life.

Unless you have a time machine, life plans are more like a compass than a map. And many are complete bullshit. What’s interesting about a life where you know exactly how everything is going to turn out?

Collect Data Points

Many people start thinking about possible career options when they enter college. They approach majors, career paths, and life plans as if they were picking something off a fast-food menu. But making an informed choice about a career path before you’ve collected a single data point is like marrying someone before you’ve even been on a date with them.

Follow Your Curiosity Instead of a Career Path

The author Ori Braffman and I were students at UC Berkeley at the same time. In his books, he talks about the professors who became his mentors and the research he did in their labs. His Berkeley experience sounded so different from mine that it felt like he was describing a different university.

Writing was something I was drawn to ever since I read “The Great Gatsby” in high school. After that, I fell in love with books and really wanted to major in English. But my first week at Berkeley, I went to a career fair. When a recruiter at Accenture told me they weren’t hiring English majors, I never took another class I didn’t think would help me get a job.

To this day, I have never applied to Accenture. There is one main difference between my story and Ori’s. He followed his curiosity. I tried to pursue a career path and missed out on so many great opportunities and experiences as a result.


The natural temptation for many young people at the beginning of their careers is to go for the jobs at the most prestigious company with the highest starting salary and the most impressive job title. At elite schools, this is even more true.

But with people ranging from billionaires to startup founders who have taken companies public, almost none of their stories follow a similar arc to that of the average student at an Ivy League university.

According to Eric Barker, high school valedictorians are rarely the ones who become CEOs. Most elite schools don’t seem to be breeding grounds for future billionaires.


The highest paycheck will increase your current earnings. The highest level of responsibility will increase your earning potential over time. The more responsibility you are given, the more skills you will develop. And each of those skills will increase your earning potential.

What’s going on here?

The social programming of people who end up at elite schools is what gets them there in the first place. People like me and my classmates were taught early on to choose from the options in front of us, but they were blind to the possibilities that surround us. These environments often encourage and reward conformity, but chew up and spit out those of us who can’t figure out how the system works. But in the pursuit of prestige, we overlook two important lessons that I had to learn the hard way.

Choosing your first boss is one of the most important decisions you will make in your career

According to Liz Wiseman, your first boss is more important than your job title or company. Your first boss can have a profound impact on the course of a person’s career. Biz Stone , the co-founder of Twitter, expressed a similar opinion in his book, Things a Little Bird Told Me.

The role that a great mentor can play in the arc of your career is undeniable. One way to find that person is to choose a great boss. You hire him just as he hires you.

Ryan Ferrier is a smart guy. But for his very first job, he didn’t pick anything that would look impressive on a resume. He was the assistant to the CEO at a startup. From that experience, he started his own company and sold it.

What Tina Seelig Teaches Stanford Students about Career Paths and Passion

Tina Seelig is the kind of teacher we should all experience in our lives. Because she is at Stanford, her students are among the most ambitious and intelligent in the country. On the site Unmistakable Creative she describes two types of students who come to her office.

  • Students who already have their whole lives mapped out.
  • Students who have no clue what they want to do with their lives.

She encourages both types to follow their curiosity. The power of curiosity is one of the strongest forces that helps you discover what you find exciting and what you are passionate about.

Tina cites curiosity as an essential ingredient for a successful and rewarding career.Brian Grazer’s curiosity has created films and television shows that capture our hearts. As Tina once said to me, “Passion follows engagement. And curiosity precedes both

The Stanford Student Who Became a New York Times Best-Selling Author

Ramit Sethi’s story has many of the same ingredients. When I interviewed him on Unmistakable Creative, he shared this about his Stanford Experience.

What Tina, Ramit, and Ori all had in common is a willingness to follow their curiosity, collect data points, and make decisions based on their data. As a result, they’ve had successful and rewarding careers.

The Investment Banker Who Became a Remarkable Misfit

When your career choices are out of alignment with your values, you get caught up in the ego-driven pursuit of a life that looks good on paper instead of designing a life that is.

This is exactly what happened to Unmistakable Creative guest AJ Leon, who was one promotion away from being second in command at an investment bank. In the Life and Times of a Remarkable Misfit, he describes it as follows.

Of course, soon enough I realized that I was essentially spending the vast majority of my existence rolling the same stupid dice over and over again, following the same board to a completely prescribed life plan, taking no risks, tucking away every dream I ever had, living for the weekend and peering off the board from time to time, dreaming of the glory of a life that could have been.

Soon after this realization he left his job, started a creative agency, and started to live a life of intention, meaning, and purpose.

Do not follow your passion

Passion as a career strategy sounds good in graduation speeches and self-help books. But there are many hidden dangers in following your passion.

  • If you’re not good at something you’re passionate about, no one will pay you to do it.
  • If there is no market for what you are passionate about, no one will pay you to do it.
  • You could end up turning a passion you love into a job you hate.

It’s easy for someone to say this in a graduation speech when they have a billion dollars in the bank.

Two alternatives to following your passion

The first alternative is to become so good that you can’t be ignored, master a craft, and develop rare and valuable skills that the market will reward financially.

The second alternative comes from Chris Guillebeau’s book Born for This. It’s about finding the intersection of joy, money and flow.

If your work brings you joy, you will have a sense of purpose and a reason to get up in the morning. When it pays, you won’t sweat about how to keep food on the table. Flow causes your work to become its own reward and puts you on the path to world-class performance.

Most people who do work they love don’t call it passion until after the fact. But for many of them, it doesn’t even start that way.

Critical elements of a rewarding career

For successful people who love what they do, work is more than just a paycheck. It’s a calling. The ingredients that make their careers rewarding have nothing to do with job titles, salaries, or other external motivators that often drive people’s career choices. But they are also driven to success by external factors.


In his podcast, How to get Rich, Naval Ravikant, says that the purpose of wealth is the freedom to be your own sovereign individual. Real wealth is not about McMansions and Ferraris. It’s about autonomy.


The more ambitious you are, the more obstacles you will face. As someone once told me, when you push your limits, you will invite a greater number of challenges into your life. As your ability to accept these challenges increases, you will be able to accept greater challenges.

But if there is no purpose or meaning behind your ambitions, it will be difficult to sustain them. You are more likely to give up in the face of adversity. When there is a purpose, meaning, and mission behind your goals, it is easier to muster the resilience and courage you need to achieve them.

If the work is not meaningful, a job is just a paycheck or means to an end, people will do just enough to avoid getting fired. They are unlikely to succeed in any way because many of the critical ingredients that lead to lasting success are missing. The paradox of ambition is that if you let go of your attachment to success but maintain your commitment, you increase the chances of achieving a goal.

Intrinsic motivation

When intrinsic motivation and Daniel Pink’s trifecta of autonomy, purpose, and mastery drive a career choice, people increase the likelihood of reaching their full potential.

This is a lesson I learned not only in my corporate career but also in my writing life. In my corporate life, it was clear that I didn’t care about the work I was doing, I only cared about the potential for money, promotions, and job titles. And we all know how that story ended…

I learned that lesson again when I was trying to get a book deal with a publisher. First, I received a gift from Betsy Rappaport, who kindly informed me that I wasn’t ready. Between the conversation I had with her in 2012 and the time I landed my first book deal, I developed the habit, discipline, and motivation to write every day.

Even though I’ve finished two books and don’t have a contract for a third, it’s still something I do today and will do for the rest of my life. No one is paying me for it right now and I have no idea where it will lead. But the intrinsic motivation to put pen to paper day after day has given me every opportunity in my career.

The Ego Driven Pursuit of a life that looks good on paper

If you make a career choice or any other decision based on the ego-driven pursuit of a life that looks good on paper, you will be sorely disappointed when your results don’t meet your expectations.

The spotlight always fades. Rankings fluctuate. In any hierarchy (corporate, government, creative) there will always be someone ahead of you and someone behind you. As I told a podcast host who interviewed me, in a few weeks the last thing on anyone’s mind will be Indian Matchmaking.

Most of my work life takes place in a quiet room with nothing but a microphone, a laptop, a notebook, some pen, and paper. There are no fancy job titles, audience clapping, or any of the other things that cause people to confuse attention with performance. If you’re not in love with the part of the job where you spend the majority of your time, your ambition will never be enough.


Most jobs train people for competence instead of mastery. When a person makes the commitment to value mastery over metrics, meaning over money, and purpose over profit, it ignites a lifelong fire within them. And the external standards of what makes them successful paradoxically rise.

Watch a master of his craft like Jiro, a world-class musician or computer programmer. You don’t see someone working. You see someone who is so present that nothing they do feels like work.

The natural temptation for most people when they read something like this article or most self-help books is to replicate what they read and try to replicate it. But they fail to consider the context and overlook the  variables that play a role in someone’s success.

When we consider anything we learn from personal development or books on success, we need to consider context and treat the knowledge we gain as frameworks rather than formulas. We are not widgets, we are people. When we approach self-improvement through the lens of formulas, we overlook the strengths we already have and the gifts we already possess.


People with creative careers, extreme athletes and top executives, live what Steven Kotler calls a high-flow life. As he joked in his “Zero to Dangerous” seminar about his co-author Peter Diamandis, “Peter doesn’t keep starting companies because he needs money. It’s because he needs to experience flow.”

Without the presence of flow, there will always be limits to what you can accomplish in your career. Flow drives a positive cycle of progress, intrinsic motivation, momentum and ambition. To have never experienced flow is to live your life without access to one of the highest states of consciousness available to us as humans.

Why Outliers Are Lousy Role Models for the Rest of Us

The people who stand before kings may look like they did it all on their own. But in reality, they are invariably the beneficiaries of hidden advantages and extraordinary opportunities and cultural legacies that allow them to learn and work hard and make sense of the world in ways that others cannot. – Malcolm Gladwell

When you see an outlier, it’s tempting to try to replicate their success. But when you do that, you’re ignoring context. And context matters when you’re making the most important decisions of your life. We’re more prone to the problem of outliers in career choices than in almost any other decision we make.

If someone recreates their path to success and offers to sell it to you, it’s unlikely you’ll end up with their result. That’s because there are many variables that are left out, the most important of which is that you are not that person. As Ozan Varol says, you can’t copy and paste someone else’s path to success.

5. Marriage/Life Partners

Who you marry is the most important decision you will ever make. Marriage colors your life and everything in it. -David Brooks, The Second Mountain

Who you marry is the biggest decision in your life. It’s also the one I feel least qualified to write about.  For that reason, most of what you’ll find here comes from our podcast guests, the books I’ve read, and some happy couples who were willing to share their insights on this with me.

The South Asian Cultural Arms race for impressive biodata makes a lot of Indian people think there’s some arbitrary deadline for marriage, with little consideration for whether you’re marrying the right damn person.

Shattering the Romantic Comedy Myth

We all grow up and through music lyrics, romantic comedies, and movie moments popular culture teaches us to believe in the Disney Movie version of love. But the reality is nothing like that.

Terri Cole once said to me in a conversation about love and boundaries.

So I’ll always say to my clients, you know, how did you think it was going to be? Because a lot of times thoseunfulfilled dreamsreally negatively impact, like can weigh down where you are right now. So it’s about allowing yourself to be where you are. And embrace where you are and still have whatever hope, whatever desire it is, but, but don’t have a strict way that it has to look.

One thing I’ve learned in my attempt to meet a life partner, is that the other person doesn’t complete you. If you don’t show up whole and complete, they are just filling a void. In the end that always blows up in your face.

“If you’re looking to get into a serious relationship — you both need to answer some big questions and figure out what’s important to you,” says Nick Notas in an article on his blog about why shouldn’t just settle for anyone.

These are important questions that reveal the difference between what it means to be in love with each other and be able to build a life you love together. As Nick says, “There are some major viewpoints in life you both need to agree on. Or at least be able to compromise.”

Do I want kids?

If there’s anything I learned from it was that raising kids is not something you take lightly. When I’ve asked my podcast guests about parenting, their answers have ranged from hilarious to heartwarming.

Being a parent is kind of a giant shit show. You basically tell the kid, we’re going to do the best we can. But we’re going to screw you up and your job is to spend years in therapy as an adult fixing the damage we did. – Sarah Peck

The only thing I’ve gathered from the fact that my parents have had to deal with me for 42 years is that raising kids is a lot of work.

What are our financial goals?

When it comes to financial goals, everyone has a different idea of what it means to live a rich life. But I think Ramit Sethi summed it up best when he said that we should be asking 30,000 dollar questions instead of 3-dollar ones. What Kind of Lifestyle Do You Want?

As someone with an appetite for adventure, I’d be bored out of my mind dating a girl who wanted to sit around all weekend gossiping with relatives and watching Bollywood movies (some Indians call this socializing). A life of accumulating possessions to show off to people is of little interest to me.

Interdependency, Regret, and The Unpredictable Nature of being Human

Very few, if any of the decisions we make in our lives are made in isolation. Like any complex system, the biggest decisions in life are interdependent. The decisions we make have a ripple effect.

One small decision you make today can impact a decision you make 10 years from now. You make the decision to move to a different city, meet your significant other, and decide to marry that person.

Life rarely follows a predictable arch where everything happens on your timeline. That might be the most important thing that surfing has taught me. You’re on Mother Nature’s timeline, and some days she wants to dance, other days destroy you and on the worst surfing days ignore you (i.e the ocean is a lake).


At some point in our lives, all of us will make a decision that we regret. . Maybe it’s the job you choose, significant other or friendships. When it comes to the decisions we regret, most of us confuse the quality of the decision with the quality of the outcome.

When I told my friend Michelle Florendo, who is a decision engineer, about a break up that made a mess of my life, she said, “The important thing is not to confuse the quality of the decision you made with the outcome. It wasn’t a shitty decision, just a shitty outcome. You did the best you could with the information you had at the time.”

From high-speed car chases in Tijuana to trying to bribe police in foreign countries, drunken nights I’ll never remember with friends I’ll never forget, some of my decisions would make my parents wonder what they did wrong. Sometimes poor decisions lead to the greatest level of wisdom.

Conclusion: The Next Best Version of You

Even the decisions we regret inform how we become the next best version of ourselves.

Getting your heart broken teaches you how to love yourself, develop self-compassion, internal self-worth, and develop all of the qualities that only will make you attractive to the next person who comes along. It allows you to open your heart without feeling like it’s going to get shattered each time something doesn’t turn out how you hoped it would.

Losing a job gives you an opportunity to rediscover your values and begin a journey down a path you might never have considered possible before.

No matter what decision you make, your perfect life plan is an illusion that doesn’t account for the divorce you didn’t anticipate, a global pandemic, economic recessions, a president who is fucking up your country, and your dating life at the same time.

So there’s no sense in closing yourself off to the adventure that could unfold with a scripted, predictable, life plan that’s unlikely to happen anyway.

You Never Know How Things Will Turn Out

After 42 years, the only conclusion about every decision I’ve arrived at is that you never know how anything will turn out. This is not the life I thought I’d have. I’m not the person I thought I’d be. You probably won’t be either.

Sometimes our decisions will lead to losses. Nature abhors a vacuum. Something will eventually fill that space. It’s up to you whether you’ll make your next decisions out of fear or love, comfort or courage, inspiration, or desperation.

Want help making some of the most important decisions of your life?

Get access to a list of interviews to help guide you. Learn how a professional poker player and Stanford engineer use their expertise to make decisions, how a therapist and meditation teacher help their clients meet the love of their life and other experts put their vast knowledge of personal finance and career development to use.


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