I only have a couple of data points [1] but I’ve been enjoying watching videos by accomplished people giving long talks at conferences- particularly, videos that few people seem to have watched in their entirety. I get a sense that I’m exploring something lost, forgotten, ignored- like secret books. (I’m reminded now of how– according to Paul Graham at least– at one point the Most Important Task for academics and intellectuals was simply to transcribe the lost work and wisdom of the Ancients- the Greeks and all.)

So far I’ve watched talks by Ev Williams, a chat between Paul Graham and Marc Andreessen, Harley Finkelstein, a talk by the Airbnb Growth team, and most recently a keynote by Tobias Lutke of Shopify. And a few others that don’t immediately come to mind. (Transcriptions: ev, tobi, harley, airbnb)

That last one was the most recent and I want to write about my thoughts about it.

Tobi talked about his personal growth as an individual- from being a kid in school obsessed with getting a pair of Air Jordan sneakers to impress the popular kids, to being an apprentice at Siemens with a great mentor, and then to becoming the founder and CEO of a company that sold snowboards- Shopify.

He described well how at each point in life he was in a ‘box’- a self-contained world that’s internally consistent. The Siemens box was larger and more complex than the middle school box. More hierarchy, more players, etc. The world becomes more rich.

He then talked about how he had a mentor whose box was so much bigger than his- and how just spending time with him was enough to expand his mind (which reminds me of my experience first joining ReferralCandy- which I think I sometimes take for granted). He closed his talk with a video narrated by Carl Sagan, who had a huge box- thinking in terms of millenia, at the level of the species and beyond.

I think I’m sold on the idea that this is how life should be spent, despite the inevitability of our own deaths and the death of the universe. To do otherwise is stale, boring. Only by breaking your existing boxes- by deliberately seeking out the seams and breaking them- do you keep learning.

And I guess here I have to make a realization and confession- which is that I HAVE gotten complacent. It’s a strange thing to say because I’m working harder than I’ve ever worked in my life. But I guess that’s what happens after you leave a box that you’ve been in for a very long time- perhaps all your life. When is it time to start on the next box? The answer is now, of course. It’s always now, unless you need to rest or take a break- but once you can look up and get up, you’re on to the next box. That’s the nature of the infinite game.

I got comfortable where I am. I allowed myself to be a little messy, a little inefficient. I got overwhelmed and I lost sight of my next box.

I also like how Tobi made a point to talk about the importance of working on things with other people who are also aware of their boxes, who are also working to transcend them. I think it’s very difficult (for me at least) to stay focused on some sort of personal development goal without meshing your goals with others.

And I realize that’s where I want to be. It’s scary and difficult and painful, but it’s also challenging and interesting and exciting. When did I start becoming afraid of challenges? It’s so subtle and insidious. But I have time. I’m young. I’m hungry. I’m privileged. I can and will break my boxes and help other people break theirs. We’ll keep doing it, and we’ll help to realize the visions of Da Vinci and Ben Franklin and Sagan- and if it’s not up to us, then we’ll make it possible for those who come after us. That’s it, that’s entirely it, that’s all we have.

And it starts so small. Laughably, amusingly small. It starts with sleeping habits and eating habits and how I spend my little chunks of time- as well as how how prioritize my days. Very sobering to think that how I manage my own time might have an impact on people less privileged than me, because if I grow and learn faster, I can help more people. Kind of a scary thought, because it makes me responsible for the things that I haven’t done, and that feels really odd and counter-intuitive. And it would also leave me eternally unsatisfied, and I don’t want to live like that. I suppose the only thing you can do is measure yourself against the effort you’ve put in. You have to go to bed every day feeling like you’ve made a good effort, and you review that effort, and you do better the next day, and the next week. I mean, none of this is new, none of this is rocket science. But hey, I’ve been shipping these word vomits at a nice frequency the past few days. I don’t want to get too fixated on it- the idea is to keep going, not to pat myself on the back and then slip. Because I often slip- I’ve always slipped.

But hey, I quit smoking. And I quit social media. And I can and will quit slipping, at least 99% of the time.

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[1] A funny thought- I think I have quite a lot of data points of me saying “I only have a couple of data points”. I wonder what I can infer from that. Nothing I don’t already know, I guess- I get bored and distracted too early, even from things that I say I want or things that I care about. I suppose the thing is to then pre commit to the long haul. Which I’ve done with work, with marriage, and with these word vomits. It won’t work out by itself, but it will work out- because I will make it so. I just need to make myself make it so.