Sal Khan’s Letter to Himself is a Masterpiece in Leadership Coaching
I received an email last week from Sal Khan that had been sent out to the entire Khan Academy community. I’m sharing it below, because even though it was not intended as such, it’s a leadership coaching tour de force.
For those of you not familiar with Khan Academy, it is a free web-based learning platform and truly a global educational movement: Used by over 100M people, 60M registered users, 190 countries, over 10B practice problems solved. Yes. Big. My kids use it (even in college), and chances are yours do to. Enso had been their partner for their first big promotional launch with a shared mission that Sal had coined “a growth mindset intervention for the world”.
In the email was a letter the “2019 Sal” had written to the “2009 Sal” as a means to get in contact with the wisdom and learning he had gained since starting Khan Academy. His team had encouraged him to share it with the community. As a leadership coach overseeing enso’s Leadership for Impact program, I was kind of blown away at the points of advice that Sal Khan was giving to himself — every one was what we find to be key interventions to free leadership to create at a whole new scale (which shouldn’t have been a surprise to me given what Sal and team have done in 10 short years).
What follows is the “2019 Sal” letter to “2009 Sal”. I have italicized key advice that Sal provides from a leadership coaching perspective, and immediately follow those with [bracketed, bolded comments that underscore the importance to leadership]. I hope you get as much from Sal Khan’s letter to himself as I have.
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“Hi Everyone,
I wrote this letter to my past self as a reflection exercise and have been advised to share more broadly. As a part of the Khan Academy community, you’ve been on this adventure with me so I thought you would enjoy. I’d love to know what you think (seriously, I try to read as many emails I get as possible; though I can’t respond to them all).-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 our wife 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.
[Leadership: The coaching here to trust our heart, gut, and innate wisdom more than our judgements of ourselves, and to lovingly accept that no one is born an expert — we dare to venture out and experience, and through that, we learn.]
This is going to be the beginning of a rollercoaster, but a really great one that I, 2019 Sal, am still going through.
[Leadership: The powerful acknowledgement that our growth is a journey, not a destination. It’s a journey that will continually have what we perceive as ups and downs, and it’s in how we relate to those ups and downs that lies the true nature of our experience (ie “…but a really great one…”) ]
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.
[Leadership: Encouragement that choosing in, and moving toward what connects us to our center, our soul, and brings us a sense purpose, is what we’re here to do — it’s what we’re here to contribute to the world.]
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.
[Leadership: Underscoring the power of intention and holding a bold vision of success as both a north star and an enduring design function for making sure what we build will be true to our vision.]
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.
[Leadership: Such a beautiful expression to trust what we are authentically being called to do, even if it’s never been done before, as opposed to defaulting to the illusion of safety in repeating what others have. Despite the illusion of being lost, we know we’ve arrived at our true journey when the visible path ends, and we are meant to now to make our own.]
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.
[Leadership: Demonstrating that we reach our greatest power of creation when our actions align with our intention. This thought from William Hutchison Murray: “Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too. All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one’s favor all manner of unforeseen incidents and meetings and material assistance, which no man could have dreamt would have come his way.”]
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.
[Leadership: The awareness and acceptance that the feelings and thoughts of self-doubt, stress, fear, and failure, are a part of any life and any endeavor, and are always transient. They are therefore not worth attaching ourselves to, as opposed to our vision of success.]
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.
[Leadership: The power of being in loving acceptance of what we don’t know or are not fluent in yet, and the subsequent gift of exponentially greater creation we give ourselves by inviting others in to our mission to fill those gaps.]
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.
[Leadership: This is so huge. We do not have to default to choosing between outer achievement and inner peace and presence — inner peace and presence actually powers our achievement and the ability to actually enjoy it!]
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.
[Leadership: This takes on one of the biggest misperceptions held by leaders that impedes mission success — that acknowledging our own strengths and openly applying them is egotistical or self-aggrandizing . We have been given our gifts with purpose — to not acknowledge and use them, as we would with any other member of our team, is to not be in service to the our mission and purpose on the planet. This point coming from this source means a lot — having had the privilege to have worked with Sal Khan, I can say I have not met a person as quietly humble while having achieved so much.]
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.
[Leadership: “The heart is just as important”. It is easy, when in the world of business we are judged by quantitative measurements of success, to forget that the way there is not through intellect alone. We forget that all around us, and the only thing ultimately real, are people. And the only thing ultimately real to them is the feeling they get from the experience they are in. Therefore, our communication and care to them needs to be more heart-to-heart than head-to-head. If we want them emphatically engaged with us, we need to find the intersection between their own inner purpose and ours. At the intersection between their heart and our heart is exponential creative power.]
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. Fundraising also continues to be a bottleneck for what Khan Academy can do. And the stakes actually get 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
