What Do You Want?

My friend is thinking about quitting his job, and here’s the rub.

He’s paid well, has a kind boss and smart peers, and takes enough vacation. But he’s felt unfulfilled for some time. Something is off, and he asked me what to do.

I told him what he already knows: “The job sounds great on paper, but it’s not working out. It seems sensible to quit. What’s stopping you?”

The money is good. He’s not sure if he can get another job like this one. His colleagues may think he gave up. He feels he should be grateful for having a job when people are struggling.

“Those are fine considerations,” I said. “But what do you want?”

After a long pause, he said, “Hmm, I don’t know. I haven’t really thought about that.”

And that’s when it hit me. My friend wants to make an important life decision. He’s paralyzed by doubt and hoping that someone else can give him the answer. But even the wisest friend can’t bring him any closer to an answer because he’s asking the wrong questions.

He’s focused on how he should feel about his job, how his career move might be perceived by others, and how he may never be able to have this level of money or prestige again.

But he’s not confronting the only question that matters: What do you want?

The Central Task of Adulthood

Figuring out what you want is the central task of adulthood, and it’s not an easy one.

Once you leave formal schooling, you’re catapulted into a world with infinite possibilities. You no longer have to show up at school to avoid detention or ace tests to make your parents proud. You’re finally unshackled from the training wheels of life, and now you get to decide what the hell to do.

You expect this freedom to be liberating. You get to decide where to live, how you’ll make money, and hell, you can even decide how much ice cream you’ll eat this weekend. No more nagging parents or irritating classmates to hold you back. Free at last.

But as you begin to direct your life, you quickly learn that adulthood is harder than you expected. You realize that you can (as many people do) screw up your life by making bad decisions. It becomes clear that it’s not so easy to balance your many needs. 

The burden of having real responsibility can weigh on you. And little by little, your naive excitement turns into a dark cloud of fear and doubt. When this happens, your focus shifts away from figuring out what you want and toward a different set of questions: 

What if I mess it up? What if I don’t live up to my potential? What if I marry the wrong person?

These are valid concerns. But if you give them too much attention, you may end up like my friend, unaware of what you want and unable to make important life decisions. And that’s not a good place to be if you want to enjoy your time on this spinning rock.

So what should you do? How do you know what you really want?

While I don’t have all of the answers, I can offer some tricks of the trade and help you avoid common traps that prevent you from knowing what you want and how to get it. These ideas should give you a good foundation for learning how to steer the ship of your life in the right direction. At the end of our exploration, I will return to the question of what my friend should do.

Caution: Safety is an Illusion

When you realize that you can mess up your life, you may look for a safe path that prevents you from ending up on your deathbed with regrets. This desire for safety leads you into the comforting current of cultural gravity, the invisible set of forces that move you along socially-approved paths.

Like a riptide that sweeps you out to sea, cultural gravity’s current will bring you along the default path. In a capitalist, career-obsessed society like the United States, the default path nudges you to pursue careers that allow you to preserve optionality, stockpile cash, and garner adulation via achievement.

The default path offers an alluring proposition: If you follow the rules and work hard, you will live a good, respectable life that ends with a blissful period of unlimited pisco sours on the beach. The embedded promise of this path is that you will not squander your life.

But it turns out that the default path is not a risk-free antidote to the difficult problem of figuring out what to do with your life. For every person who is satisfied with the default path, there are droves of people who wake up one day to the unbearable hangover of a midlife crisis, regret, and existential frustration. 

Taking the default path is not safe. It’s more like opting into a game of Russian roulette, where the cost of losing is wasting your one chance to enjoy your life.

Despite the many faults of the default path, the lesson is not that you should avoid it. It may work for you; it may not. The lesson is that there are no paths that can guarantee that you will move through life without any risk of messing it up. Creating a life worth living is like embarking on an ocean crossing. There is no route or amount of preparation that can ensure you won’t get caught in a violent storm.

So the first step in figuring out what you want is to know that safety is an illusion. This knowledge does give you an answer, but it does help you resist the temptation to simply do what other people are doing and assume that it will work out. Knowing this will help you remain more curious about the diversity of paths available and skeptical of anyone who claims to have an answer for how you should live.

Try More Stuff

To begin to understand what you want, you need to know what you don’t want. And the only way to figure out what you don’t want is to try more stuff.

As soon as you can, expose yourself to as many new things as possible. Travel. Change jobs. Date around. Read voraciously. Interview old people. Try new hobbies. Follow the whims of your heart.

People may call you non-commital and directionless during your exploratory period. Ignore them. What they don’t understand and what you won’t understand until later is that meandering for enough time is the only reliable way to create a higher-resolution map of your desires.

When you explore in an unfettered way, a beautiful order begins to arise from the chaos. Little by little, as you expose yourself to the many paths the world has to offer, you begin to understand the nuances of what you want and don’t want.

You’ll know you’re making progress when you discover that you’re no longer interested in mindlessly pursuing wealth, status, happiness, security, and other generic desires. 

As you move beyond surface-level desires, you start to see the quirky details of what you want more clearly. You know that you want to live in Oaxaca, teach yoga, and marry an artist named Paul. Your clarity is real and actionable because it’s not built on a mirage of safety or the shaky promise of the default path. It’s built on the strong inner foundation that formed during your time exploring.

And one day you’ll think back to your post-college self. That person had a 10-year plan for riches, success, and happiness. You were going to be a hedge fund tycoon in New York City who married her college sweetheart and spent summers on the coast of Italy. You were so sure that was the right path.

Now look at you. You’re teaching yoga in Mexico with Paul by your side. A few years ago, you didn’t even know you could live like this. As you reflect on how your life unfolded, you’ll be humbled by how wrong you were when you were young and grateful that you had the courage to deviate from the original plan.

Many people don’t find that courage. They make a plan and stick to it, even when it’s not working. They allow inertia, fear, or stubbornness to keep them on a mediocre path. And since they never had an exploratory period that clarified their desires, they freeze up when thinking about making a change. And their lives remain smaller than they could otherwise be.

So if you’re serious about figuring out what you want, don’t try to think your way to an answer. Stay curious and try more stuff. Trust that your meandering will help you learn about yourself and eventually guide you to a more enjoyable path.

Beware of Tradeoffs

I’ve been a solopreneur for two years. I make enough money and don’t have a boss, zoom meetings, or pesky colleagues. I surf four times a week and travel whenever I want.

Sounds pretty good, right?

Well, it depends on what you value. It’s great for me because I’m optimizing for time freedom so that I can pass the days of my fading youth as I wish. But in choosing this path, I’ve given up some important things.

My income is unstable and lumpy. I don’t have colleagues to learn from or laugh with. I rarely get validation and have no clear next steps to follow.

The downsides of my path would make many people miserable. I know this because I tried to live this same way in my mid-twenties and ended up anxious and unhappy. I learned the hard way that my need for financial stability at that time was more important than my desire to have an empty calendar. I took the loss and returned to full-time work six months later.

The truth is that no path has it all, and everything worth having comes with a cost. Time freedom requires uncertainty. Entrepreneurship requires risk. Marriage requires tough conversations.

When making big life decisions like where to live, what to do for work, and who to spend your life with, you need to understand the trade that you’re making with each path.

You need to know what you’re getting, what you’re giving up, and how the various tradeoffs will impact your satisfaction. You won’t always have the full picture, but thinking in these terms can help you avoid some mistakes.

Like me, you will still mess up along the way. That’s okay. What you learn from those mistakes may help you later on. That became apparent two years ago when I was thinking about leaving my stable job at a venture studio to try being a solopreneur for the second time.

Thanks to what I learned from making a similar decision in my mid-twenties, I understood the trade. I knew that I would gain freedom and lose security, money, and prestige. I felt good about that trade because I wanted time freedom more than what I had to give up to have it. And so far, it’s working out.

Be Wary of Advice

Imagine you’re a marketing executive in your mid-thirties. You’ve enjoyed your career and can optimize landing pages better than anyone. But for 10 years, you’ve fantasized about quitting your job to head to a cabin in the woods to write poetry.

As a kid, you found comfort in the words of Dickinson, Wordsworth, and Rilke. Now you’re ready to join these bold souls in giving a voice to the human experience. Before making the leap, you want to ensure that your pivot to poetry is not a naive fantasy that will lead you into a hellscape of financial ruin and depression. So like my friend who is thinking about leaving his job, you decide to talk to a few friends.

While asking other people what to do may seem harmless, it can lead you astray in three ways.

1. Most people give you advice, and what you need is counsel. 

When you ask people for help, most people give you advice. Advice is when someone tells you what they would do. And since you’re not that person, it’s rarely useful to hear what they would do. You want to know what you should do.

Counsel, on the other hand, is when someone helps you figure out what you think. Counsel is invaluable because it helps you clarify your thoughts and tap into your inner wisdom about what you should do.

If you have friends who know how to give you counsel, hold onto them dearly. These people are angels who offer a non-judgmental, listening ear that will help you find the best path forward.

2. You may not have the right people in your life. 

Friends and family are indispensable parts of living a great life, but depending on who you surround yourself with, your loved ones may lead you in the wrong direction.

One common problem is not having any people in your life who have experience with the decision you’re making. If your friends are all marketers who enjoy the default path, don’t ask them about quitting your job to write poetry. They won’t understand, and what they offer may lead to confusion and a loss of confidence in your intuition.

Or you may encounter another problem. Friends and family like you for who you are today. They do not want you to move to the woods, change, or be anything other than what they know and love. And when you ask them what to do, they may unconsciously encourage you to stay put.

This is not an intentional or malicious attempt to keep you from being happy. It’s just how people are, and this dynamic can make it more likely that you stay trapped in the inertia of your current situation.

3. Everybody comes with biases. 

If you ask a philosopher what to do, he will tell you to imagine you’re on your deathbed and to consider what your older self will have wished you did. A rationalist will tell you to use time-tested frameworks or weigh your options in a spreadsheet. And a spiritual person will encourage you to find the answer in ayahuasca, journaling, meditation, and knowledge of moon cycles. 

Everyone you talk to comes with a specific lens on the world, and so does their advice. And while their ideas can be useful fodder, they can also muddy your thinking or take you down unhelpful rabbit holes.

There is nothing wrong with talking with other people about your decisions. It can be very helpful, especially if you’re receiving counsel. Just don’t expect other people to give you clarity. There is no substitute for doing your own thinking. 

And when making a big change like giving up your corporate gig to write poetry in the woods, you’re the only one who knows if that’s a decision you can live with. Learn to trust yourself.

Life Never Comes Together

Even if you try more stuff, understand tradeoffs, and find good counsel, you will likely never figure out exactly what you want or how to get it. There are at least two reasons for that.

The first reason is that you are an unreliable madman. You are not the rational, grounded character that you want to be. You are wild and dynamic, and so are your desires.

One month, you’ll want to embrace your hedonistic impulses; the next month you’ll want to dedicate your life to helping others. A few years later, you’ll want to build a large company. And after securing a round of funding and hiring ten people, you’ll realize you actually want a relaxed life in the suburbs.

You and your desires will change in unpredictable ways.

The second reason is that dragons await you. Right when you think that everything in your life has finally come together, a ten-headed, fire-breathing dragon will block your path and send you running in another direction. 

That dragon may be the unresolved traumas of your childhood, the devastation of unrequited love, or direct confrontation with the fragility of life. These moments will shift your inner world in profound ways.

What you learn from these experiences is that life will never come together in the way you want. It will always be a half-finished puzzle. Knowing this can help you avoid the illusion that some achievement, some amount of money, or some person will finally make your life complete. The puzzle is never complete.

What Should My Friend Do?

Now that we have a better understanding of what figuring out what you want entails, I want to offer some words of advice to my friend who is unfulfilled and thinking about leaving his job. But first, I’ll like to share a story about the first big career change I made.

In 2016, I quit my job as an investment banking analyst after one year to become a marketer at a fully remote startup. Friends and colleagues told me I was making a stupid decision. When I told the head of my team I was leaving, he said, “You’re young and naive. You’re going to regret this decision.”

The rational part of me agreed with the skeptics, but my intuition told me to leave anyway. And I listened to the intuition. I had no idea if I would enjoy or be good at my new job. All I knew is that my year in investment banking taught me that no amount of money is worth spending your life in a cubicle working 100 hours a week. And that was enough to exit the game of finance and look for something else.

That decision ended up being one of the most impactful ones of my life. It sent me on a meandering path as a digital nomad and helped me develop the skills that later inspired me to start writing online. Most importantly, leaving that first job gave me confidence in later years to listen to my intuition when it told me it was time to make a change in my career, romantic life, or how I was living.

Following my intuition has not always led me to good places. I’ve made many mistakes and taken too many wrong turns.

But in learning to take action when the voice inside me says that it’s time to try something new, I’ve avoided the biggest mistake of all: allowing inertia, fear, or social pressure to keep me in a situation that I know is not right.

And over the long run, my refusal to bow down to fear and settle has gotten me closer to designing a life that I’m excited to live.

So…what should my dear friend take from this story?

Should he hear that I listened to my intuition and found a better path and conclude that he should find the courage to quit his job?

Absolutely not. That’s what worked for me, but my friend is a different person.

If there’s anything that he or you should take away from this exploration of figuring out what you want, it’s that you should not listen to me or anyone else about what to do with your life. 

Only you can answer that question. And I hope some of what we’ve discussed so far will help you with that challenge.

Before we wrap up, I do want to invite my friend to consider one more thing. When we spoke about his conundrum, two dynamics struck me. The first is that he didn’t know what he wanted. I’ve already addressed my thoughts on how to approach this problem.

The second dynamic is that he seemed to be treating his potential job change as a life-or-death decision. And at least part of his decision paralysis stemmed from this feeling that he was making an irreversible decision that may ruin his life.

My invitation to him is to think about the job change in less grave terms. Job changes are consequential, but they are not life-or-death decisions. Treating them as such impedes clear thinking. If you believe making a change may ruin your life, you will likely stay on the current path to avoid that calamity.

The reality is that every job change comes with some set of tradeoffs. You may make less money, lose prestige, or give up perks you enjoy. But in doing so, you may create space for new paths with more of what you want and value. You won’t know for sure until you get clear on what you want or try something different and see how it goes. Even then, you can never quite predict how the future will unfold.

In the end, the decision is up to my friend. And whatever he decides, my hope is that he doesn’t forget to have some fun along the way. This ride won’t last forever. And for you, dear reader, I wish the same.