Advice to my younger self

I had the privilege of speaking to some Berkeley students last week. Below is the talk reprinted in full:

If you could call yourself 10 years ago and speak for a minute, what would you say?

That's the thought that was going through my mind when I got asked to speak here. What would I say to my past self? What would have been useful knowledge when I was your age? This is a particularly pertinent time for me to be thinking about this given I'm just about to turn 30.

First of all, it's an honor to be here. I never thought I'd be speaking at Berkeley.

I'm Alex, I'm founder and CEO of a company called Clearbit. We're about ~100ish in terms of headcount, five years in, and last valued at $250m. Unlike you, I never had a college experience, I dropped out of high-school at the age of 17.

So, to get back to the question, what would you say on a one-minute phone call to your younger self?

Ten years is a huge amount of time. To put it in perspective, think about the difference between you as an 11yr old, and you as a 21yr old. It's a massive difference and you have little way of predicting what will happen.

The elaboration

Over the last decade, I've experienced a huge amount of personal growth. Most of the advice I have is related to that. You might ask yourself why I'm talking about personal growth to a group of people interested in entrepreneurship:

Three reasons:

I suspect others haven't talked to you about this
Personal growth is important for being a good human. It is certainly important for achieving any kind of success.
It's critical to be emotionally mature if you're going to employ people

Now, to be really honest with you, I'm not sure how useful this talk will be. I think about giving my younger self this speech and I'm not sure it would have sunk in... it might have to have been lived to be learned. Regardless, here goes:

Average of your five friends

One of the biggest truisms is that you're the average of your five closest friends.

When I think about my five closest friends, my heart fills with love. They are incredibly deep and kind people, with ambitions and qualities I want to emulate. And I met all of them in the last decade in San Francisco, the city that changed my life.

To give you an example, one quality I deeply admire is a zest for life, making the most of every moment. At my stage in life that requires a degree of open-mindedness and creativity; saying yes to adventures and thinking about all the possibilities life offers.

It struck me that I had a friend who really embodied that quality, Jesse. When I met him he was an intern at Stripe. Then he taught himself to code, managed to get transferred from community college to Stanford, and then in his free time taught himself to fly planes. He's consistently pushing himself and thinking of new ways to have fun.

So what do you think I did with Jesse? I moved in with him of course. I now share an apt with him and another friend I really admire, and I feel like we all compliment each other.

Focus on your strengths

A classic trap people get into is they focus on their talents and not their strengths. Now, what do I mean by that?

Well, I define a talent as an innate ability, and a strength as something that gives you energy.

Most people are familiar with what their talents are. You're good at math, or piano, or simplifying complex ideas. However, the mistake people make is they don't think about what their strengths are when planning out their life. This leads them to get stuck in a job they're good at, but saps their energy. And then you get burnout and regret.

One sign that something gives you energy is that you stay up all night doing it. For me, that was programming. I found programming when I was looking for an excuse to get out of my school's army training when I was about 14. Instead, I offered to maintain the school website and bought a satchel's full of programming books. But I had a problem, the more that I programmed, the more my grades fell. It came to a tipping point where I had to choose between school and coding. I knew coding gave me energy, so I picked that and dropped out at the age of 17.

Ask for help

I'd say the fact that I'm willing to ask for help is the single biggest reason I'm a CEO of a successful company. Initially, asking for help is how you gain knowledge and fast-track your learning in an area. Ultimately, it's how you delegate and scale yourself.

I have so much help in my job these days. I have a leadership team of incredible executives running every aspect of the business, I have an exec coach, a speech coach, a personal trainer, and a therapist.

Asking for help is a form of vulnerability. That's why people tend not to do it, they're afraid of displaying a lack of strength. But really, vulnerability is an incredible strength.

Let me give you an example. I was 20, having dropped out of school 3 years before and worked as an engineer in London. I wanted to move to San Francisco full time, the Mecca for anyone in tech. There was one problem. The US government doesn't let in anyone without a degree. I not only did not have a degree, I hadn't finished high-school!

So what did I do? I asked for help. Specifically I found a visa called the O1 visa, or to give you its full name, Alien of Extraordinary Ability. This visa doesn't require a specific degree, but it does require you to do something extraordinary. Being an average 20yr old I had done nothing out of the ordinary. So I decided to write a book on programming to try and demonstrate what an extraordinary alien I was.

I met an editor for O'Reilly Media (a tech publisher) at a party, and I asked her if O'Reilly would consider publishing my book. They said sure, we can't pay you an advance (because you're 20), but why not. I ended up writing a few books for them, and got the visa!

Lean into your fear

Most people live life on autopilot. They have two basic inputs: fear and short-term gratification. They use those inputs to direct their decisions in life. They live aimlessly and unconsciously. And then they die (often without leaving their home town).

Unless you learn to face your fear you will never achieve anything. Fear of failure, fear of rejection, fear of shame. These are the things that get in between us and our potential.

When you feel fear it's a sign that you should lean in. Learn to sit in your fear rather than recoiling. Try to trace the fear back to its origin. Often, you'll find its source is way back in your past. Some deep-seated insecurity or childhood experience. I've found therapy a great way of exploring this.

I've had many fears in my life. A fear of public speaking. A fear of not being in control. I got rejected twice from YCombinator, and once had to leave the country when my green card got denied. Each time I faced my fear and fought back.

Happiness conditional on external factors

It's true that money doesn't buy you happiness. That seems obvious. But what's less obvious is that it doesn't buy you safety. In fact, any feeling you want cannot be realized by anything external to you. Every feeling, every emotion, they're all generated internally. If you try to satisfy them externally then you will fail.

People often seek validation from others, and this kind of makes sense; if you're just validating yourself in a vacuum then who's to say you're not delusional.

The problem with validation comes twofold:

When you seek validation from people who you don't know
When you peg your self-worth to validation

Simply put, by pegging your self-worth to the validation of others, you will never feel worthy. And how can you love yourself if you never feel worthy?

And then there's safety. It's something we all crave, but it's an illusion.

Let me tell you a story about safety. I recently realized something about myself: I'm a bit of a control freak. It's one of the reasons I'm running my own company. I want to control who is, and who isn't in my life. I hire a lot of my friends because I want them to be safe and secure.

And then, a month ago, I realized it was all an illusion. One of my colleagues, Brian, was biking home and got hit by a car. I got a text saying Brian had been rushed to the emergency room. As soon as I read that text, my illusion of safety came crashing down.

I'd created this sense of safety, this sense of control, but the reality is it can be taken away from you in an instant. There is no safety in the face of our own mortality.

Brian was lucky. He escaped with a few screws in his right hand, but the lesson stuck.

Embrace your body

Let me give you an analogy I first heard from Warren Buffet.

Let's say that I offer to buy you the car of your dreams. You can pick out any car that you want, and then when you get out of class this afternoon, that car will be waiting for you at home.

There's just one catch.. It's the only car you're ever going to own in your entire life. Now, knowing that, how are you going to treat that car? You’re probably going to read the owner’s manual four times before you drive it; you’re going to keep it in the garage, protect it at all times, change the oil twice as often as necessary. If there’s the least little bit of rust, you’re going to get that fixed immediately so it doesn’t spread — because you know it has to last you as long as you live.

That's exactly the position you're in regarding your mind and body. You have one mind and one body for the rest of your life. If you aren't taking care of them when you're young, it's like leaving that car out in hailstorms and letting rust eat away at it. If you don't take care of your mind and body now, by the time you're 40 or 50, you'll be like a car that can't go anywhere.

In your early twenties you take your body for granted. You can eat whatever you want, you barely need to workout, you feel invincible. When I was in my early twenties I mostly viewed my body as a transport mechanism to get my brain to different places. And not my full brain, mostly the upper left part of it.

As you age things stop working quite as well. You can no longer sleep through the night. You knees make a weird clicking noise when you get out of bed. And you can get out of shape.

The key is to make healthy habits. Only in the last few years have I started taking care of myself. Embracing my full body and what an incredible tool it is. Eating healthily, working-out every day, improving my sleep. I would think about these sooner rather than later.

Be less tied to being right

When you're young you feel so sure about everything. You got it figured out. You know what's what. Then, if you're anything like me, as you age you find out you were so fundamentally wrong about certain things, that it makes you question everything.

There's a very interesting book called Principles by hedge fund manager Ray Dalio. By creating a truth-seeking environment that puts the focus on curiosity rather than being right, Ray turned his hedge fund Bridgewater into the most successful hedge-fund of all time.

At Clearbit we have a set of practices called Conscious Leadership that gives us a framework for curiosity. There's a book we use called the 15 Commitments of Conscious Leadership that we get every new employee to read. Living in this fashion has changed my entire life.

Be kind to yourself

Lastly, be kind to yourself. You don't have to have it all figured out on day one. Indeed, you will never figure it out. Nobody does.

Have you ever taken a long shower and had a fictional argument in your head with someone? Or fumed about some situation, letting yourself spiral into a depressed hole. On the surface of it, this quite silly. You are letting that voice in your head run wild concocting stories that have little basis in reality.

This voice in your head, the one that tells you that you're not good enough, that you embarrassed yourself, that someone is out to get you, that you are not worthy of love, that you are not worthy. That voice is just not helpful. Do not dwell on it or let it run your life.

Realize you are not that voice. How could you be? That voice is paranoid, jealous, and irrational; that's not you? The very fact that you can observe it, means it's not you.

Learning to quieten that voice, and realizing the stories it comes up with are just that, stories, is a key part of mental health. There are a number of tools you can use to quieten it like meditation.

The phone call

So to sum up, let me take a stab at at the phone call:

Hello Alex, it's future Alex. I don't have much time, so here's some hard-learned advice:

Move to San Francisco and surround yourself with clever people. You are the average of your five closest friends.
Focus on your strengths, not just your talents. Do not do things long-term that don't give you energy.
Ask for help. It's your super-power. Get an exec coach and a therapist.
Vulnerability is a strength, practice it.
Lean into your fear and learn to sit with it. Understand the different types of fear and where they come from.
Happiness conditional on external factors will always be unobtainable. The same thing goes for validation and safety. Money will not make you feel safe; nothing will. There is no safety in the face of your own mortality.
Stop living in the top-left side of your body and embrace the full thing. Create healthy habits in your life and stick to them. Will-power is a form of self-love.
Be less tied to being right. You're right less often than you think. This particularly applies to stories you have about yourself. You're going to change significantly.
Be kind to yourself. Beware your inner voice.