Letter to My Past Self

Hi,

I recently wrote this letter to my past self as a reflection exercise and have been advised to share more broadly. I tried to be as honest with 2009 Sal as possible to equip him optimally for his road ahead. Others have told me that it helped them see their own path a bit differently. Hope it does this same for you.

-2019 Sal


Dear 2009 Sal,

I am writing to you from the future because I know you are at an interesting crossroads. You’re pretty stressed and excited that Umaima is due with our first child in about a month. This has made you think about strange things, like life insurance. Don’t worry, the insurance company makes good money off the first 10 years of your policy. My only advice is to buy twice as many bottles, onesies, and burp cloths as you think you need. Also, have confidence in your paternal instincts even though you feel pretty clueless right now — mainly because you are pretty clueless right now. This is going to be the beginning of a rollercoaster, but a really great one that I, 2019 Sal, am still going through. Only now am I starting to truly appreciate it and realize how fast it goes by. Spoiler alert: your son is going to be the first of three unbelievably unique and hilarious kids who’ll make you grow as much as anything in your life.

On the professional front, I know that things are even more stressful for you. Your previous boss shut down the firm, and you’ve just put yourself back into the job market as an equities analyst.

But you have this Khan Academy hobby. In a big way, it is the thing that keeps you sane. Every evening, you work on it for several hours, and it recenters you. It allows you to focus your mind on the beauty of mathematics and science. It gives you a sense of purpose. You have a secret hunch that it could be a game changer for learners around the planet. After all, never before in human history has there been the possibility of scalably meeting the individual needs of every learner. Now there is. And if learning could be accelerated for a large chunk of humanity, it would have hugely positive consequences in almost every other domain, from economic and gender inequality to health and justice. You are already starting to think about how many Albert Einsteins or Marie Curies could be fostered if they just had access to the right tools and content.

You even went so far as to incorporate Khan Academy this past year as a nonprofit with the audacious mission of creating a “free, world-class education for anyone, anywhere” thinking that, one day, it just might become a real institution that could serve billions of learners for generations to come. But you keep that to yourself since you don’t want people — even your close family — to think you’re delusional.

I don’t want to ruin the surprise of the adventure that you are about to go on in the next few years, but let me just say that you are not delusional about Khan Academy. It will become much more than a hobby. Sure, no one you know has worked on anything like this. And, yes, people are incredibly cynical about the potential to make a dent in education; after all, folks as least as smart as you, with far more influence and resources, have tried. But don’t discount the traction you have and the time and space in history in which you have found yourself. Also don’t discount your approach to learning that has already served many folks around the world so well. When we are afraid and insecure, we often look for validation by looking for other folks who have done what we would like to do. That is a mistake. Have courage to do something new. Almost every great effort started by carving out a unique lane that everyone else is ignoring. If you put your head down and keep feeding this fledgling organization with your energies, amazing people — even some heroes of yours — will join you. When faced with any major decision, don’t shy away from thinking about it in terms of an organization that one day will become an important institution for the world.

And don’t think that it is going to be an easy ride. There will be moments of incredible satisfaction but also moments of incredible stress. I hate to say this, but 2009 and 2010 will get more stressful, not less. Your savings will take a hit. You will question yourself and your ability to support your family. You’ll find yourself walking through the woods alone, reminding yourself that at least that squirrel won’t judge your many failures. But you are more stubborn and resilient than you realize and it will be worth it — not just for you finding your purpose in life, but for hundreds of millions of learners who need a bit of help in unlocking their potential. And remember that, no matter how dark and stressful certain moments seem at the time, as long as you and your family have their health, there will be another day to realize that things actually always get better.

It is also crucial that you be honest with yourself about both your strengths and weaknesses. That is the only way you can be aware of your blind spots and bring people to the cause that complement them. You can become obsessive at times. This can be great to drive big things to fruition, but it can sacrifice your ability to be in the present moment. You don’t have to make this tradeoff. I have only just started to meditate regularly and wish that I had started even before I was you. By practicing mindfulness, you will actually be more effective in this mission, all while better enjoying the beautiful, sometimes small personal moments in life.

You also naturally thrive when working alone or in small teams. 1999 Sal — remember that guy? — didn’t enjoy being part of a large organization at your first job, despite having an incredible manager and mentor. That Sal got impatient and antsy with the need to slow down or water down decisions. Because of that, both of us have been attracted to two-or three-person, entrepreneurial organizations ever since. This has helped you do a lot with few resources and try things fast, but, if you really want to change the world, you need to bring a lot of other people and partners along. Khan Academy will need to become much, much larger than what you alone can do.

As hard as it is to recognize one’s own weaknesses, it is also sometimes hard to fully utilize your strengths. For example, you are naturally an introvert, but you can communicate well. You love to tell stories. You love to discover and draw connections in the universe. When you really believe in something, it can be infectious. It can feel narcissistic to think “I’m good at this or that”, but it isn’t about your ego. It is about serving the cause. Shying away from something where you are well suited to make a positive impact — especially because it is risky or can draw criticism or unwanted attention — is just as damaging as not realizing areas where your actions are counterproductive.

Coming from the analytical worlds of technology and investing, you are cynical and think that a lot of organizations that craft good narratives don’t actually have measurable impact that scales. Because of this, you will be hard nosed about proving Khan Academy’s efficacy and scale. And this appeal to the intellect will bring many very smart people to support the mission. But the heart is just as important. I know that the individual, human stories of empowerment through Khan Academy already motivate you more than you realize.

You need to work to help others appreciate that it really is possible to empower billions around the world. And that empowerment doesn’t just result in better academic or economic outcomes. It results in millions of people learning to believe in themselves and developing their own sense of purpose, just as you are on the precipice of discovering your own. This will result in stories from learners around the globe that will seem like science fiction to even you. This effort will improve the lives of everyone, from prisoners trying to get their GEDs, to orphans in Mongolia, to young girls in Afghanistan who aspire to be scientists despite the best efforts of the Taliban to suppress their potential. And if you and your team can surface the human side of the work successfully, the world will support the effort and help you deliver on the vision.

Let me be clear. I still don’t have most things figured out. Yes, the reality of what your hobby becomes in 2019 will surpass your wildest daydreams — the impact of this work with grow 1000 fold in the next decade — but there is still a long way to go. I still suffer from the impatience that you do in 2009 and the complexity of our task only increases. Our introversion still makes it awkward for me to ask folks to support the cause; which is especially important given that fundraising continues to be a bottleneck for what Khan Academy can do for the world. And the stakes are only getting higher as we aim to empower many hundreds of millions over the next decade. This definitely increases the pressure to deliver on the opportunity and promise of Khan Academy.

For better or worse, 2029 Sal hasn’t written me yet, so I don’t know how things turn out. Given the time-space continuum and our general tendency to procrastinate, I expect his note in about 10 years. I do hope he’s around — I am avoiding carbs and working out a lot to maximize the chances that the life insurance policy over the next 10 years is as profitable to the insurer as it was the previous 10. Yes, part of that is my attachment to what I consider to be an incredibly lucky life. But a lot of it is that I really want to see how incredible the world can become when everyone, everywhere really has access to a free, world-class education.

Onwards!

2019 Sal