written by
Srinivas Rao

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

46 min read
most important decisions

The paradox of life is that people seem to deliberate more carefully over little choices than the big ones. Before buying a car, they read all the ratings, check out resale values on the internet, and so on. But when it comes to choosing a vocation, they just sort of slide rather than decide. They slide incrementally into a career because someone gave them a job. They marry the person whom they happen to be living with. - David Brooks, The Second Mountain

Every decision you make, from your choices to how you respond to the circumstances of your life shapes your destiny and how your life will turn out.

A decision you make today could affect your life tomorrow, a week from now or 10 years now.

Destiny is the ripple effect of every decision you make over a lifetime.

When I started writing this piece, I asked my community on witter and Facebook what they thought were the 5 most important decisions in your life. There were consistent themes that emerged in every answer.

These 5 decisions will have a disproportionate impact on your life and are often the most challenging ones you'll make.

They will impact everything from your emotional well being to your finances. Some of you have may have already made these decisions, while others are in the process of making them.

Professional poker player Annie Duke says "Decisions are bets on the future and they aren't 'right' or 'wrong' based on whether they turn out well on any particular iteration." That's why it's useful to understand the decision-making process before looking at each of the 5 most important decisions of your life.

3 Parts of Decision Making Process

most important decisions

In every decision you make, there are 3 parts: the decision, the desired outcome, and the probability.

The Decision with the Outcome of Becoming a Professional Tuba Player

Say that you have some musical talent and make the decision to pursue it as a career. For example, when I was in high school I made the decision to pursue a career as a professional tuba player. Since I made All-State Band multiple years, I thought the probability of my success was high.

The Probability

But the reality was very different. For the sake of this example, assume there are 5000 professional orchestras in the world. There's only one tuba player in a professional orchestra. The probability of getting that job are 1 in 5000. Since you have to wait for the other tuba player to die once he gets the job, the probability of my success as a professional tuba player was even lower.

This is what my dad more or less told me when he talked to me about pursuing a career in the arts.

Bad vs Good Decisions

Does it mean you've made a bad decision by pursuing a career in the arts that doesn't lead to the outcome you want? Not at all.

All of us will make decisions in our lives with undesirable outcomes. We'll have relationships that end, bosses we can't stand, and attempt things that lead to failure. But we make those decisions believing that the probability of a good outcome is high.

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

That doesn't of course mean that there aren't bad decisions. If you take your next month's salary and bet it all on one number at the roulette table, you're not risk tolerant. You're an idiot. That's a bad decision.

most important decisions

1. Values

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

Your values will determine every other decision you make. The decisions we regret are usually the ones out of alignment with our values. That's why choosing your values is one of the most important decisions of your life.

Where They Come from and What They Are

We assimilate our first set of values from our family because they are the first influence in our lives. As you experience more of life you collect more data points. You assimilate values from your environment, peer groups, people you work with, and life partners. Because of that, your values will also change throughout your life.

Discovering Your Values

The simplest way to figure out your values is to ask: what matters to you? What can't you live without in your life? What doesn’t matter and what can you live without?

Another way you discover your values is through the power of contrast.

Say that 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 you'll have to work weekends, holidays and deal with long hours. The second job might pay less, but give you more time to spend with your family and have time for hobbies that interest you.

The choices you make tends to reveal your values. But context also matters. Depending on whether you're a recent college graduate or have a family, you might make a different decision. Choosing between two careers is just one example of a decision that can reveal your values.

Look back at your life and the moments when you were choosing between two alternatives. Then ask yourself why you chose one option over another. Each of those little decisions can reveal the values you want to be clear on when you make the most important decisions of your life.

If you repeat this exercise with multiple personal and professional decisions and rank them from most important to least, you'll discover your personal hierarchy of values.

Status Values

These are values like pedigree, prestige, and luxury. Having status values doesn't make you a horrible person. We all have status values.

If you're reading this on iPhone or Macbook, you value the status of buying Apple products. All the shirts in my wardrobe come from Proper Cloth. I value the status of wearing custom-tailored shirts.

Where status values bite us in the ass is when we use them to make decisions about people. If you only associate with people who went to "prestigious universities", you'll miss out on incredible people both as friends and people you could work with.

Some of my best friends didn't even go to college and they're the smartest and most successful people I know.

Perceived status is something that impacts a great deal of people's judgment on the internet. They assume the number of followers someone has directly correlates to the influence someone could have on their life. But they rob themselves of so many possibilities when they do this.

My most influential mentor had 150 followers and was a nobody. He came up with the name Unmistakable Creative, taught me to run a business, and planted the seeds for everything I accomplished after we parted ways.

One of my other mentors was my reference for my raising my first round of investor money. He's practically invisible online.

If there's one thing you learn about status from a moment or two in the spotlight, it's that it fluctuates, and is always fleeting. If it's at the top of your list in terms of what's important, you're setting yourself up for a life of profound disappointment.

Character Values

Character values are the ones that matter most because they're all you're going to have left when you lose your status. Generosity, kindness, and unconditional love are character values.

My best friend's wife is exemplary of what it means to have character values. He shared this story with me about telling her he'd lost his job 6 months before their wedding.


That to me is character.

Faith Values

Faith means different things to different people. But at the core, it appears to be the belief in a higher power with forces we can't necessarily understand or explain with logic.

Even though I'm not religious, I've had plenty of podcast guests who are and they've taught me invaluable lessons for life.

But the moment I realized I had faith even if it isn't in the form of religion was the day of my sister's wedding. One hour before the ceremony the wind was howling and the guy who had built the platform my sister and brother-in-law would be under said, "There's a one percent chance this thing could fall. We didn't anticipate this. Can you get some people to hold the beams?"

I scrambled to find relatives. My dad prayed. The moment the priest started the ceremony the wind died. In that moment, I realized that there are things in the universe we'll never be able to explain or understand.

How do Values Change With Age and Experience

"One of the most serious problems with never encountering other opinions is you'll never have cause to question your own beliefs. " - Sarah Rose Cavanaugh

Each life experience reveals what we couldn't previously see, giving us the opportunity to reconsider our values and question whether they were ours to begin with.

  • New friends who stretch your perception of what's possible and what you really want
  • A job you hate or love causes to you to reconsider what's important in your career
  • Meeting a mentor reveals what you aspire to become

As you expose yourself to different models of possibility and influences, you might realize that your values are no longer aligned with the ones that you inherited when you were younger or from an earlier chapter in your life.

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

My parents' values played a substantial role in where I went to college and in the first few jobs I chose. As a culture, Indians value prestige and pedigree. And I chased success on those terms instead of my own until I had a resume of failures that resembled a rap sheet, was 30 years old, broke, and living at home.

Sometimes it takes hitting rock bottom to discover how high you're capable of climbing.

Guests on The Unmistakable Creative each showed me a different model of possibility and helped me see that I was no longer aligned with values I inherited when I was younger.

2. Friendship/Social Circles

most important decisions

There's a famous quote about the idea that you become the average of the 5 people that you spend the most time with. The problem with viewing friendship through this lens is that it might cause us to choose our friends according to resume values instead of eulogy values.

But that doesn't negate the fact that your social circle will have a significant impact on your well-being. So who you choose as your friends is without question one of the most important decisions you'll ever make in your 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 will face adversity, loss, and heartbreak in different ways. Our friends prevent 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're in pain, and someone to share life's most treasured experiences with.

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

The right friends can make the most boring place on earth amazing and being in a place with no friends can make one of the 7 wonders of the world boring. When you discover that the backdrop matters less than the people you're with, you learn why friendship matters so much.

Friends for Life

Much like our values, we form our early social relationships by default instead of design. They are the kids we go to school with and the ones we meet through our parents. Sometimes those friendship sticks. And other times they don't.

As somebody once said to me, every person comes into our life for a reason, a season or a lifetime. Three factors determine that.


"The thirties.... are sometimes described as the decade where friendship goes to die, killed off by marriage, children, jobs, relocating. Mismatched friendships - one has kids, the other doesn't - can be especially hard to sustain." - Lydia Denworth, Friendship

Of all things that change a friendship, life circumstance is at the top of the list. People have kids, start families and we find ourselves in different chapters of our lives than some of our closest friends.

My oldest friend from college got married and started a family when she was in her 20's. I'm 42 and single so the circumstances of our lives are quite different.

When she stopped inviting me to her daughters' birthday parties my mom said, "She doesn't invite you anymore?" And I told my mom, "What the hell am I going to do at a 5-year-old's birthday? There are no single women there or booze."

Even though I've maintained this friendship since my freshman year in college, it's not better or worse, just different. She's still my oldest friend and I adore her.


Pamela Slim and Desiree Adaway have the kind of friendship you could make a movie about. When I asked Desiree about their relationship, this is what each of them told me.

I accept her. Exactly. And Holy as she is. And there's nothing that anybody on this earth can do that can make me not love Pamela Slim, including Pamela Slim. She's been one of the most amazing gifts of my life and I'm very fortunate to have her as my BFF. And she's hysterical because y'all don't know like Pam is banana pants. But I make it my business to talk to Pam every day. Can I go three and four days without talking to her? Sure. I could. But it's what our friendship takes, it's just a daily check-in. So I can make sure that she's okay. She doesn't need anything. Then I'm done. That is intentionality.

Their friendship is exemplary of the reciprocity you need to have a best friend for life. When I asked Lydia Denworth about the people we might have been close to in the past, but don't reciprocate, she said the following:

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 out and then those who are even further out 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 kind of shuffled the furniture of your friendship to an outer room. That person is a little bit less central in your life. And what really matters for your health and well being is that you have a core group in the center. For most of us, it's an average of just four people, right? So it's not a lot.


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

In my early 20s, I was lucky enough 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 speak that often. When we do talk or see each other every few years, we reminisce about the drunken antics of our youth, have some good laughs and it's like old times. But we're nowhere near as close to each other as we used to be.

Contrast that with my friend Gareth and I who were in high school band together. He was 2 years younger and were always friendly but never close friends. When I was living with my parents, I discovered that he was still living in Riverside. We met up for dinner and started to develop a deep friendship. I was Gareth's best man, and he'll likely be mine (of course I need to meet someone first).

He moved to Colorado, and when I found that I was here quite often, 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, because of proximity and reciprocity, circumstance has not prevented a deeper friendship between all of us and these are the guys I see in my wedding party when I imagine that day.

3. Environment

most important decisions

According to Jim Bunch, there are 9 environments that make up your life. Whether we like it or not, all of us are products of our environment, which include are geographic location, physical space, and people who surround us. For the purpose of this article, let's assume the environment is your geographic location.

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

  • You might live in a small town in the middle of a country where people place a high value on faith. That might impact how you raise kids and who you marry.
  • A bad neighborhood, poverty, or circle of friends who had frequent trouble with the law could cause to develop resilience and a tolerance for adversity. Or you might end up in jail.
  • If you're living in a big city like New York, LA, or San Francisco you're going to have access to career opportunities that might not be available in a small town.
  • Living in a different city, state or country might open you up to things you never considered doing before.

But let's look at how where you live can drastically alter the trajectory of how every other aspect of your life turns out.

The environment in the Rao Family

As immigrants to the United States who grew up in India, their life outcomes were binary. It was security or poverty, nothing in between. As a result, 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 met later in life. And I've always been envious of the people who have friends they've known since they were kids.

And there's a good chance there's someone I know in most places I go in the world.

Living in the Bay Area during the first dot com boom led to my interest in technology. 6 months of living in Brazil was the beginning of my love affair with surfing and the immense value I place on freedom, thereby causing me to look for jobs that would not get in the way of my ability to surf.

A Different City Might Lead to a Better Life

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

insert interview

My best friend Gareth was living in San Diego, working part-time, and additionally working on what would eventually be his third failed business. Within a month of moving to Colorado, he landed a high-paying job at a startup. And after getting laid off from that job, he started a business that consistently makes five figures a month.

Insert interview

Every single place we live leaves an imprint. I'd never want to live in Bryan, Texas. But I also have fond memories of my time there. There's no such thing as "the best place to live", only the best place for you. There are pros and cons to all the places you could live... Traffic sucks in big cities, and there's not as many options for food, entertainment, recreation, and culture in small ones.

Finding a better job isn't the only good thing that could happen when you change your environment. You might 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 is 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 we have to do everything in a linear timeline, with a life plan that we often craft before we even knew anything about ourselves. If you live according to such a plan, you'll find it impossible to follow your calling when you arrive at the crossroads of should and must.

The truth about a life plan, whether you're 21 or 41, is that it doesn't account for the uncontrollable (pandemics, recessions, etc). Talk to someone who is 41 and you'll see that their life looks nothing like the one they imagined when they were 21. They couldn't have anticipated a good amount of what's unfolded in their lives.

So unless you have a time machine, life plans are more of a compass than a map. And many are complete bullshit. What's interesting about a life where you know exactly how everything will turn out?

Many people begin to consider potential career options when they enter college. They approach college majors, career paths, and life plans as if they're picking items off a fast-food menu.

Making a decision about a career path before collecting a single data point is like marrying someone before you've ever been on a date with them.

That approach is unlikely to lead to discovering the kind of career you will be passionate about.

Curiosity vs Career Paths

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

Writing was something that drew me in from the time I read The Great Gatsby in high school. I fell in love with books after that and had plans to be an English major. But I walked into a career fair my first week at Berkeley. When a recruiter at Accenture told me they didn't hire English majors, I never took a class again that I didn't think would help me get a job.

To this day, I've never applied for a job at Accenture.

There's one main difference between my story and Ori's. He followed his curiosity. I attempted to follow a career path and missed out on so many amazing opportunities and experiences because of it.

That's the profound power of curiosity.

Prestige vs Responsibility

The natural temptation for many young people at the start of their careers is to choose the jobs at the most prestigious company with the largest starting salary and most impressive job title. This is even more true in elite schools. As a Berkeley undergrad, my peers were some of the smartest, most ambitious overachievers I've met in my entire life.

All of them went on to attend top law schools, medical schools, and business schools. Because of their pedigree, they have more access to those opportunities than other people do. I saw how true that was when I came to Pepperdine for my MBA where few of those opportunities were available to us.

The definition of success in environments like this is getting a job at Google, McKinsey or Goldman Sachs, going to law school at Harvard or medical school at Stanford. And my classmates have all accomplished similar professional goals. Given that I could never do that, this is meant as no disrespect to them.

But in over 1000 interviews with people ranging from billionaires to startup founders who have taken companies public, almost none of their stories follows a similar arch to the average student at an elite university.

None of my Berkeley classmates would have pegged Dan Martell as someone most likely to be a millionaire given his back story of trouble with the law. I would have probably thought he was headed nowhere given the cognitive biases my environment caused.

According to Eric Barker, high school valedictorians are rarely the ones who become CEOs.

Most elite schools don't appear to be breeding grounds for future billionaires.

What is happening here?

The social programming of people who end up at elite schools is what puts them there in the first place. People like me and my classmates are taught early on to choose from the options in front of us and are 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 to work the system.

But in the pursuit of prestige, we overlook 2 important lessons that I had to learn the hard way.

Your First Boss

According to Liz Wiseman, what's far more important than your first job or the company you work at is the first boss you choose. That can have a profound impact on the trajectory of a persons' career. Biz Stone, co-founder of Twitter, echoed a similar sentiment in his book, Things a Little Bird Told Me.

The role that a great mentor can play in the arch of you career is undeniable. And one way to find that person is to choose a great boss.


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

Ryan Ferrier is a smart guy. But for his very first job, he didn't pursue anything that might appear impressive on a resume. He was the CEO's assistant at a startup. From that experience, he started his own company and sold it.

When I started interviewing for summer internships while at Pepperdine, my dream job was to work at Harrah's. But the company didn't recruit at Pepperdine. I contacted every person who had been a summer intern the year before and asked for an informational interview with all of them.

One of them told me, "Don't go to any of what you think might be great locations like Vegas. Go to a small market because you'll be given more responsibility."

What Tina Seelig Teaches Stanford Students about Career Paths and Passion

Tina Seelig is the kind of teacher we should all be fortunate enough to encounter in our lives. Because she's at Stanford, her students are among the most ambitious and intelligent in the country. In her interview on The Unmistakable Creative, she described two types of students who come to her office.

  1. Students who have their whole life already planned out
  2. Students who feel like they no idea what they want to do with their lives

She encourages both types to follow their curiosity. The power of curiosity is one of the most potent forces for helping you discover what you find engaging and something you're passionate about.

  • Tina cites curiosity as an essential ingredient in a successful and rewarding career.
  • Brian Grazer built a career-making movies and televisions shows that capture our hearts from his curiosity.

As Tina once said to me, passion follows engagement. And curiosity precedes them both.

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

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

The first night you go to Stanford you have an advisor. This could be somebody on the faculty or anybody associated with Stanford, who's like a grownup.

My advisor told me something that I thought was really amazing. She said, "Ramit, there's going to be a lot of your classmates who are going to take 20 units."

She's like, "You should take 12. Don't take more than 12 units per quarter." 12 is the minimum you can take. And that was really different advice. I'm like, "Why?" She's like, "You can always take more units later."

"You need to go and participate. Go find the clubs you want to join. Go talk to professors, go make friends, don't worry about all the class load right now." And that was some of the best advice I got, which was to focus. I ended up focusing, number one, on friends; number two, on my own personal interests in clubs and research and number three, on academics.

Now I do think you need to be good at academics. I don't believe in this adage of 'just get by' and you shouldn't go to school because everybody's an entrepreneur. I don't believe that. I think you should. You should excel at what you're doing. That's the thing that I learned from my parents.

I knew that I wanted to scrape all the meat off the bone that I could at Stanford.

And I remember that I was speaking to this researcher out there, because I had told one of my professors, "Hey, I'm interested in this," and he said, "You should go talk to this person." So I go over there and I was walking past the door and it said: 'The Persuasive Technology Lab'. Well, I was like, "What? That's amazing. I'm interested in persuasion. I'm interested in technology. What is this thing?"

So I knock on the door. Nobody's there. I go home and look it up and find out BJ Fogg is a director of this lab. So I would go by every week - it's pretty far out there. It's by the med school and no one was ever there.

So finally, I sent an email to BJ and I was like, I'm interested, etc. And I don't know if he replied, maybe I had to follow up. Long story short, he's like, "We don't take freshmen as researchers." Basically, no lab does. But I was persistent. And I finally found a way to meet up with him. And I remember we went out for coffee and we started talking.

And basically he could tell that I was taking the initiative and I said, "I'll do whatever it takes. I just want to be around this lab and learn what's going on." And so I started working with him and I ended up working with him for several years.

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.

The day I graduated from school, the world handed me a pair of dice and pointed me towards a familiar board game. Except for this time instead of a Rolls Royce, I was sporting a busted-ass MetroCard. The parameters of this game were simple. Just follow the board, round and round, and the longer I stayed on the board, the more times I could pass Go, the more stupid little greenhouses I’d get to buy, the more railroads I’d procure - the more wealth I’d accumulate. All of which would culminate into me turning into a happy rich guy with a white mustache and a top hat.

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.

2 alternatives to "Follow your Passion"

Passion as a career strategy sounds good in graduation speeches and self-help books. But it doesn't work very well for most people in the real world.

  1. If you're not good at something you're passionate about, nobody will pay out to do it.
  2. If there's no market for what you're passionate about, nobody will pay you to do it.
  3. You might 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.

There are two better frameworks.

The first is to become so good they can't ignore you. It means to master a craft and develop rare and valuable skills that the market rewards financially.

The second framework is from Chris Guillebeau's book Born for This. It involves finding the intersection of joy, money, and flow.

  • If your works give you joy, you'll have a sense of purpose and a reason to get up in the morning.
  • When it pays, you're not going to be sweating 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 of the people who do work they love only call it passion in retrospect. But for many of them, it doesn't start that way.

Critical Elements of Rewarding Careers

There are certain elements in their careers of people who not only love their work but experience success at the highest level in every field. Talk to them and their works is more than a paycheck. It's a calling.

These ingredients have nothing to do with job titles, salaries, or any of the external motivators that often drive people's career choices. Yet, it's the people who prioritize finding these ingredients that end up also succeeding by external factors.


If you talk to people with creative careers, extreme sports athletes and top executives, every one of them lives 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 on what you can accomplish in your career. It's the creative superpower that sends all aspects of performance through the roof while making the work you do its own reward.

Flow fuels a virtuous 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.


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


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

Watch a master of his or her craft like Jiro, a world-class musician or computer programmer. You're not seeing someone do work. You're seeing someone who is so present that nothing about what they're doing feels like work.

The natural temptation for most people when they read something like this article or most self-help books is to reverse engineer what they've read and attempt to replicate it. But they fail to take context into consideration and overlook the obvious variable that throws off every formula for success: themselves.

When we look at anything we learn from personal development or books about success, we need to take context into consideration and treat the knowledge we gain as frameworks instead of formulas. We're not widgets, we're humans. Approaching self-improvement through the lens of formulas causes us to overlook the strengths we already have and the gifts we already posses.


The more ambitious a person's career goals are, the more obstacles they will face. As someone once told me, if you're going to push edges, you're going to invite a greater set of challenges into your life. As your capacity to take on these challenges increases, so will your ability to take on great ones.

But unless there are a purpose and meaning behind your ambitions, it will be difficult to sustain. You'll be more likely to quit in the face of adversity. When there are purpose, meaning, and mission behind your goals, it's easier to muster up the resilience and grit you need to accomplish them.

A critical ingredient of Simon Sinek's framework for Finding Your Why is having multiple data points. That's impossible unless you expose yourself to a wide variety of life experiences, people, and potential career paths.

People often find their work unrewarding because they choose their professions for the wrong reasons. When extrinsic motivators such as prestige, status, money, and validation determine their career choices, they risk ending up in careers that aren't meaningful.

When work isn't meaningful, a job is just a paycheck or means to an end, people will do just enough not to get fired. It's unlikely they'll succeed in any significant way because of many of critical ingredients that lead to lasting success are missing. Money is important. But when it is the primary factor that determines their chosen profession, people will place an unintentional limit on what they can accomplish.

The paradox of ambition is that when you let go of your attachment to success, but retain your commitment, you increase the odds of accomplishing a goal.

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

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

I learned that lesson again when I wanted to get a book deal with a publisher.

First, I received a gift from Betsy Rappaport who kindly told me 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 habits, discipline, and motivation to write every day.

Even though I've finished two books and don't have a contract for a third, writing a 1000 words a day is still something I do today and will continue to do for the rest of my life. Nobody pays me to do this 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 I've had in my career.

When I asked about the 5 most important decisions you'll ever make in your life, career choice came up over and over. If you make a career choice, or for that matter, any other decision based on the ego-driven pursuit of a life that looks good on paper, you will be severely disappointed when your results don't meet your expectations.

The spotlight always fades. Rankings fluctuate. In any hierarchy (corporations, governments, and creative industries), there's always going to be someone ahead of you and someone behind. As I told a podcast host who interviewed me, a few weeks from now the last thing on anyone's mind will be Indian Matchmaking.

The only thing you really have is the work.

Most of my working life takes place in quiet room, with nothing but a microphone, laptop, a notebook, some pen and paper. There are no fancy job titles, an audience that's clapping, or any of the other things that cause to confuse attention with accomplishment. If you're not in love with the part of it where you're going to spend the majority of your time, your ambition won't ever be enough.

Choose accordingly.

Why Outliers are Lousy Role Models for the Rest of Us

The people who stand before kings may look like they did all by themselves. But in fact 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 others can not. - Malcom Gladwell

When you see an outlier, it's tempting to reverse engineer their success. But when you do that, you fail to take context into consideration. And context matters when you're making the most important decisions of your life.

We're more vulnerable to the outlier problem in career choices than almost any other decision we make.

If someone reverse engineers their path to success and offers it 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 primary one being that you are not that person. You didn't grow up with their parents, have their life experiences, or any of that.

That doesn't mean you can't learn from that person. And you don't have to let those things keep you from achieving what YOU are capable of.

But when you don't take context into consideration you ignore numerous cognitive biases.

There's what Douglas Vigliotti calls the private interest problem. If someone tells you everyone should start a podcast and they sell a course on how to do that, its a private interest problem. If I put a piece of content here from my blog and tell you it's worth reading, that's in my interest.

Or if you hire a life coach, discover your calling is to become a life coach and start a business as a life coach, it's possible you've fallen victim to similar bias. (No offense life coaches, many of you have been our podcasts guest and have been fantastic).

We try to boil down the process of success in any field to reversible formulas, ignoring probability, cognitive biases, and choosing delusional optimism over rational optimism. This can lead to bad choices when it comes to the most important decisions of our lives.

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

Of all the 5 decisions, this is 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.

My personal experience with marriage and relationships can be summarized through the South Asian cultural arms race for impressive biodata. People who will never live with the consequences of your choices seem to very invested in how your life turns out.

Despite the fact that it's arguably the most important decision you'll make in your life, Indian people seem to believe 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 those unfulfilled dreams really 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.

If there's one thing I've learned in my attempt to meet a life partner, it's that 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."

When I surveyed two of the questions that Nick brings up in his blog post, came up in all of their answers.

Do I want kids?

If there's anything I learned from talking to Janelle Hanchett about her fight against meaningful parenting advice 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.

No matter what you do you're going to fu@#2 your kids up. - Philip McKernan

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, there's interdependency with the most important decisions of our lives.

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, even with the most important decisions we'll ever make in our lives. Maybe it's the job you choose, significant other or friendships.

Some of my closest friends have gone through the pain of losing life partners, divorces, getting fired and so much more.

When it comes to the decisions we regret, most of us tend to 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 stupid decisions are the ones that lead to the greatest level of wisdom.

I've said things I've regretted that cost me friendships both in personal and professional settings, had relationships that nearly destroyed me and never once been told that I was destined for something great at a corporate job.

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.

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.

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