A Letter to My 18-year Old Self

Eight years ago, I was a poor 18-year-old in Orlando.

I had a part-time job bagging groceries, smoked cigarettes, and worked tirelessly to make my dream of going to an Ivy League school a reality. I had never seen snow, traveled abroad, or used a pair of chopsticks.

Since then, my life has changed in profound ways.

I’ve graduated from Princeton University, worked a six-figure job on Wall Street, traveled to over 30 countries, built a multi-million dollar business unit, used chopsticks at the world’s best restaurants, become an executive at a global tech company, and founded a thought leadership business dedicating to empowering people to live a more conscious and fulfilling life.

It’s hard to believe how much has changed in less than a decade.

On my journey, I’ve learned many valuable lessons that have improved the quality of my life. Had I known these lessons earlier, I could have had a less painful and more joy-filled journey.

Below, I’ve written a letter to my 18-year old self to pass along valuable advice and insights that I’ve uncovered over the past few years.

A Letter to My 18-Year Old Self

Hey Cal,

I’m you, writing from the future. That may seem weird but roll with it. I want to tell you a few things, and I don’t have much time. Adult life is more time-constrained than you might expect.

Anyways dude, I know that life is uncertain and tumultuous right now. I understand that you don’t have money and are angry with the world. I understand that you feel like you’re leaving your family and friends behind to pursue your Ivy League dream. I understand that you don’t know if you have the intellectual chops to survive Princeton.

It’s not easy right now. You’ve been fighting for years, and you know that there’s a lot more to do. But you also know that you can do it. You have mom’s belief, grandpa’s wisdom, and an insatiable drive that will allow you to endure the challenging journey ahead.

Anyways, let me start with the good news: it all worked out.

Shit went wrong along the way, but you made it. Within just a few years, you got further than you can imagine. And instead of the pain, resentment, and anger that you feel now, life is filled with gratitude, joy, and purpose. You’ll probably think I’m a soft hippie for saying “gratitude, joy, and purpose,” but trust me dude, this is a good thing.

I don’t want to paint too rosy a picture. Life isn’t perfect man, and there’s still a difficult journey ahead. You’re going to face inconceivable obstacles. Mom is struggling more than you know. All I can say is that you should keep being understanding, patient, and helpful. Whatever happens, you have an inner strength that will carry you through.

I wanted to pass along a few lessons that you’ll soon learn. I’m hoping these lessons will help you make fewer mistakes and better enjoy the exciting journey ahead. I realize that we often don’t learn until we make mistakes reflect on why those mistakes happened, but I still think it’s worth telling you these things. Hopefully, some of the advice sticks.

Money is important, but it’s not everything

Money is your biggest problem right now. The financial insecurity that’s characterized your life is frustrating and difficult. Keep working hard to earn a stable income. You need to get to the point where you can afford the little things in life.

But once you can buy a Starbucks coffee without thinking too much about it, money isn’t going to drive your happiness. Happiness isn’t the goal, but my point is that money can only take you so far on your journey. You can’t discount its value, but keep its limitations in mind as you move forward.

Be curious, be humble

At Princeton, you’re going to be surrounded by people who are much smarter and well-rounded than you. Don’t be intimidated. They had more resources and opportunities growing up, but you can catch up if you stay curious, humble, and tenacious.

Curiosity about the world will take you a long way. Instead of judging people, you’ll seek to understand them. And in doing so, you’ll learn a lot about the world and yourself while building more meaningful connections.

As you learn and progress quickly, you might start losing your humility. Going to an Ivy League school is a big deal, especially given where you came from. But don’t let this accomplishment get to your head. Humility is a better approach that will serve you well in the long-run.

It’s never about you

If someone is rude to you, doesn’t like you, or fails to understand what you’re about, remember that it’s not about you. They have a different context and set of beliefs driving their attitudes and actions. More often than not, they are going through something that you’ll never fully understand. Maybe they just lost a parent or had their heart broken.

You can’t discount how events happening in the lives of others influence the way in which people interact with you. But regardless of how people treat you, remember that it’s not about you. Almost no one is out to get you or actively working against you. Everyone is too consumed with their shit to care about what you’re doing.

Life is a competition against yourself

Princeton is full of ambitious people who have and will continue to accomplish impressive things. Don’t get distracted by the tempting path of comparing yourself with your peers.

You don’t need to get the best grades, be the coolest person, or have the best job to live a productive and fulfilling life. Living in line with your values and finding a meaningful way to spend your time matters much more than how you stack up to everyone else. Life is a competition against yourself, not others.

And while you find that meaningful path, realize that you are your biggest critic. Your problem will never be your drive or ambition; it will be your ability to temper that drive and ambition with compassion. Take a rest day now and then and try not to be too hard on yourself. Self-compassion will allow you to better enjoy the journey.

Don’t work for people who don’t respect you

When you enter the working world, remember that you don’t have to work for people who don’t value or respect you. Good managers are hard to come by. Often, they’re more consumed with their problems and ambitions than your well-being. That’s okay, and it’s a choice they make.

But don’t stay in an environment where the people above you don’t inspire you or value your contributions. Life’s too short to stay in toxic work environments that stunt your growth. There are companies, people, and opportunities with good leaders who will value you. It’s up to you to do the work to find those opportunities.

You don’t need to figure out what you want to do in life

Almost nobody knows what they want to do in life. Society and your peers will pressure you to have a good answer to the “big” question of what you want to do. You might feel inadequate for not having a clear answer, but don’t get trapped in this line of thinking.

If you give in to the pressure, you might start following one of the commonly accepted narratives about how to live. Get a good job. Buy a house. Marry. Have kids. Travel when you retire. There isn’t anything wrong with this path, but remember that it might not be the best path for you.

As you think about how to spend your brief time here, get accustomed to reflecting on life, listening to your energy, and questioning the commonly accepted prescribed paths for living a good life. In doing so, you’ll avoid finding yourself paralyzed in a path that sounds good on paper and checks all of the boxes, but that feels deeply unfulfilling.

If you find yourself in an unfulfilling situation, find the courage to try something different, even if you don’t know exactly what to do. You can’t connect the dots forward. Life only makes sense looking back, and taking a leap into the unknown will often teach you things that bring you closer to the right path for you.

Don’t be afraid to be vulnerable

You haven’t lived the easiest life, and you’ve had to protect yourself to get where you are. But the world isn’t as cruel as you think. I’ve traveled all around the world, and the biggest lesson I’ve learned is that most people are kind. We’re all just trying to figure out life.

If you learn to share yourself openly with people, you’ll start to connect on a much deeper level. Share your story. Share your values. Share what you’re working on. Don’t be afraid to let it out. If people don’t like what you have to say, it doesn’t matter.

Vulnerability is a sign of strength, not weakness. When you share yourself and learn to be vulnerable, you’ll eventually find people who have similar attitudes, values, and beliefs.

Surround yourself with people who care about you

You don’t need to be friends with everyone. It’s better to have a few friends who you enjoy spending time with, who value you for who you are, and who want you to succeed. These friendships will be a big part of living a good life, enduring the hard times, and finding the right opportunities.

If you try to get everyone to like you or derive values from the opinions of others, you’re guaranteed to be disappointed. At the same time, don’t close yourself off to a narrow group of like-minded people. Surround yourself with people who think differently and challenge you. And when you find inspiring people who care about you, invest in those relationships. When shit goes wrong, you’ll be glad you did.

Cal, I have a lot more to tell you man, but my time is running short and you’ll be better served to learn the rest on your own.

Keep going dude. You’re on the right path.