North Stars

When I worked at Scale and ReadMe, I sometimes looked at the team rankings for messages sent per month. To me, this was a funny chart in Slack's analytics. I found very little correlation between that list and my mental model of perceived competence or contribution.

I'm biased because I was often in the bottom 5. But people respected me, and at least for the few months between my onboarding and leaving each company, my productivity was relatively high. It just happened that I crafted messages carefully before sending them, rather than blasting
one line
at a time
in fragments. And I didn't participate in the memes or chatter so much.

While talking the other day with a friend, she mentioned how certain leaders in her workplace are extremely intentional about their spoken contributions to team discussions. She was telling me how she wanted to emulate and practice this, in part by developing a more patient relationship with silence. She framed it as "trying to more appropriately weigh what I will say versus what other people might say to fill that same airtime."

She observed, for example, that one teammate's brief comments always seemed to shift the conversation to a completely new strategic angle. Another person always waited to speak last, but even if he was only 10% confident, he'd usually share exceptional insights. My friend felt it might be better to more often listen to his 10% instead of scratching her itch to jump in and say something that she felt 90% certain of.

Impact per word is an interesting metric to optimize on. Another friend recently remarked how catering for a large group is something he does as an investment, rather than from enjoyment of cooking. He reasons 90 minutes making a feast for a dozen guests translates to 12-24 hours of enjoyment for the collective, assuming we each spend an hour or two over the meal together. He's looking at his impact in terms of multiplicative group pleasure time per unit spent on meal prep.

My new personal metric is self-actualization impact per dollar. I've started giving out money to unlock and accelerate other people's paths to success and living their best lives. Ever since I started investing in the S&P500, this idea has appealed to me over letting those same dollars sit accumulating in my bank account.

In college, I gave a couple students from poorer backgrounds $20,000 to encourage them to build on their prototype and apply to YC. They got in shortly thereafter, and returned the cash to me when I needed it a while later. At time of donation, I definitely had less than $100k and maybe even had less than $50k total.

This was a messy transaction and I'm not exactly proud of how it was handled overall, but my underlying intent was clear at the outset—to gift them cash to accelerate their journey, knowing they were people of good character. I would survive and be just fine, even if the money never came back.

In Ecuador, I gave a lot of resources to Maya, my adopted mom. This included a $10k car, a $3k pottery kiln, hundreds of dollars of dental work, and much more over the course of a few years. Seeing her pursue her dreams, make art, and build community was a great reward. But ultimately, our restaurant and other projects didn't sustain in the positive-sum ways I had hoped. At a certain point, I had to cut off the funding to conserve my resources.

I also gave a friend in Puerto Lopez $7,000 shortly after spending our first few hours 1:1. We bonded over parental death, and they had a crushing debt burden which made it difficult to run their restaurant profitably. I was already spending so much on my land at the time, that I didn't feel like throwing this amount at another person following their dreams would be something I regretted doing.

I've written checks from $1k to $10k for at least half a dozen friends' companies. None of these "investments" aimed at profit. Rather, each one was a way for me to stay closer to my friends, following along and learning with them on their creative journeys. I enjoy monthly update emails and helping out when I can.

As soon as you go looking for ways to donate money, you can surely find them. Having run nonprofit organizations, I personally don't like donating that much and have been extremely selective with very few hyper-aligned things.

It's rare and special that an opportunity arises for me to make a unique impact on another person's life, in such a way that I see them evolving forward and rapidly touching many more lives in the future. I live for these moments. Having practiced many times at this point, I have a decent sense of how and when I can provide the best differential uplift with my words or my wallet.

Often this comes from the other person not having nearly the same level of access that I have to resources as fuel for their goals. Especially when this distinction feels arbitrary—and I judge the difference to be a few lucky months of exposure, as opposed to a more foundational gap in abilities—I'm pulled to intervene.

I especially love betting on folks who exhibit high levels of gratitude and autonomy. They do not like accepting gifts or imposing on others. I trust such people to go out of their way to be kind, in all future circumstances. I'm confident they'll do the right thing and pay my generosity forward manyfold, someday.

This sense of kindred spirit is present in most of my friends. I'm lucky to be close with dozens of incredible, successful, thoughtful, inspiring humans. I'd trust all of them with my bank account password, no fine print required. But I'm only wiring money to a few who truly need it and will maximally steward the cash for upside in the universe's future, somehow.

I almost can't help myself, especially if it's convenient and feels highly impactful. Fluids move from high to low pressure. At a certain pressure gradient, from my bank account and life trajectory intersecting theirs, I'm compelled to provide liquidity when I can. My new project entails strategically fine-tuning the criteria by which it gets sucked out of me.

Even across decades and new life chapters, there are certain constants resistant to change. With these special few people, it's like we're all looking at the sky and silently picking out the same constellations.

~~~
Thanks Aly for inspiring this blog post and reviewing an initial draft.