A Learning a Day

There’s a trail on the South Rim of the Grand Canyon called Shoshone Point. Most of the South Rim works the same way: you drive, or take one of the free shuttles, pull up to a viewpoint, and step right out into a view of the canyon. It’s spectacular, but you’re never alone.

Wherever the view is easy to reach, so is everyone else.

Shoshone Point is different. You park, then walk about a mile along a quiet dirt trail. That small bit of resistance changes everything. At the end, the trail opens onto a wide, unobstructed view of the canyon, and almost nobody else bothers to make the walk.

It’s a good analogy for life. Plenty of beauty is available to anyone willing to show up to the right place.

But the places that ask for a little extra effort, the ones most people skip, are usually the ones that end up feeling the most extraordinary.

One way to think about the impact of social media on a person is to think of the two things it does at once.

On the one hand, it keeps feeding you people and content that align with your worldview, confirming what you already believe.

At the same time, it sprinkles in people and content that are the exact opposite, enough to spark outrage. Both extremes generate engagement, so the feed keeps serving both.

No feed is built to make you think better or sharpen your views. It’s built to maximize the hits from confirmation and outrage.

Zoom out to the scale of society, and you get exactly what you’d expect: extreme loyalty to people who already agree with you, and extreme hostility toward everyone who doesn’t.

A simple definition for AI work slop: it’s when the output outruns the thinking.

Or to use an old saying, it’s when you see a ton of lipstick on a pig.

A good friend has a term he uses when he coaches people on how to be a better direct report. He calls it “show the ramp.”

The idea is simple. Don’t go from “everything is okay” one day to blindsiding your manager the next. Showing the ramp means your manager can see you move from okay, to here are some reasons to be upset, to actually being upset. It gives them a chance to react while there’s still time to do something about it.

People value predictability. A problem that goes from calm to five-alarm fire with no warning is jarring, even if the problem itself was always there.

It’s advice for managing up, but it applies to any healthy relationship. Showing the ramp is just what being a good counterpart looks like.

I’ve played a lot of pickup soccer over the years, with plenty of players who were genuinely good. Not Messi good. Pickup good.

Within that group there’s a tier of players who have the full trifecta: ball control, game intelligence, and communication. The ball seems to stick to their feet, and they always seem to have more time on it than everyone else.

But even within that tier, only a few rise to being great.

The difference is what they do with their skills. Great players lift the team up. They give feedback, they push the bar higher, but they do it as a light, not as a judge.

The skilled ones, who often have the exact same technical attributes, tend to make life harder for everyone around them, not because their instruction is wrong, but because of how they deliver it.

I see the same pattern at work. People who seem unhurried, who always find the right pass, whose communication shows up as much in how they act as in what they say.

It’s a beautiful thing to watch and to aspire to.

I took some time recently to reflect on the three things I find most annoying about myself at the moment. It’s a useful exercise to revisit periodically. My current list is:

(1) Letting people finish their thought instead of letting excitement or impatience get the better of me. This is a long-term project. It’s the dark side of a strength: a bias for action. The balance is tricky, but I’ve made some recent progress in my own self-awareness around it, and that gives me hope.

(2) Removing “like” and other filler words has been an on-and-off project for years, and it’s been consistently on my mind this past year. My awareness here isn’t consistent yet, and that’s usually the first step.

(3) Changing my relationship with my phone entirely. I wrote about this recently and my effort to simplify how I use the internet. I’m testing a few things and I’m excited about testing leaving the phone in one room of the house after work, so I get used to not having it on me. I’m hopeful it continues.

As with most things like this, noticing isn’t enough. I’ve made some commitments and added this to my weekly review. I’m hoping to be annoyed by different problems twelve months from now.

More to follow.

I was using Ramp’s app for a work expense recently and realized I’d forgotten to upload the receipt, which normally kicks off an exceptions process.

Except the receipt was already there.

I asked how, and learned Ramp has a direct integration with Toast, the restaurant payment system. Pay with a Ramp card at a merchant on Toast, and the itemized receipt gets attached to your transaction automatically. No photo, no upload, nothing from you.

This is what good integrations do. They take manual load off the user without asking for anything in return.

It’s also one of the hardest things to prioritize when you’re building a product, because integrations like this rarely show up on a roadmap next to the flashier features competing for the same slot.

But the experiences that become invisible, because you made them that easy, are the ones users end up remembering most.

I heard someone recently describe a formative moment from his childhood. Every time something difficult happens to him now, he thinks back to what his mom said every time he told her something bad happened: “Oh honey, things could always be worse.”

He imitated her voice as he said it, and the whole group chuckled.

He said it’s the reason he’s an optimist today, because things could always be worse.

It isn’t a new idea. But hearing the story brought it to life in a beautiful way.

One ideal I’ve found hard to live up to: being consistently loyal to people who aren’t in the room. So much of what we talk about is our reaction to other people, because so much of our life is shaped by them.

Here’s an alternate ideal I’ve found helpful to aim for. With the people you work with regularly, or care about, be someone they know will tell them directly when there’s a problem. So, you never let things fester.

That way, when you do end up talking about them behind their back (and you likely will), the conversation stays focused on getting to the root of the problem.

Often what’s missing isn’t data. It’s insight.

Just as often, what’s missing isn’t good ideas. It’s clarity.