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

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.

3 Parts of Decision Making Process

most important decisions
most important decisions

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.

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.

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.

1. Values

most important decisions
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

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?

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.

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.

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.

How do Values Change With Age and Experience

  • A job you hate or love causes you to reconsider what’s important in your career
  • Meeting a mentor reveals what you aspire to become

2. Friendship/Social Circles

most important decisions
most important decisions

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.

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.


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.


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.


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.

3. Environment

most important decisions
most important decisions
  • 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.

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.

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.

4. Careers

most important decisions
most important decisions

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.

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.

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 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.

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 feel like they no idea what they want to do with their lives
  • Brian Grazer built career-making movies and television shows that capture our hearts from his curiosity.

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.

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.

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 there’s no market for what you’re passionate about, nobody will pay you to do it.
  2. You might end up turning a passion you love into a job you hate.
  • 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.

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.


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.”


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.


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.

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.

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.

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.

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.

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.


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.

The Next Best Version of You

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

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. Click Here.

Order An Audience of One: Reclaiming Creativity for Its Own Sake:https://amzn.to/2LVjgQa Listen to the @UnmistakableCR podcast in iTunes http://apple.co/1GfkvkP

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