Legacy isn’t an artist who was ignored all their life until they died. That’s just recognition and fame. Their work was already excellent then.

you never look at [stuff in nature] and say that doesn't line up or those colors don't work or there's simply too much stuff or I don't know where to look.

It’s a good point. Who holds a design critique of a sunset?

Nature's out of line. Just right. You too.

The point isn’t to know, it’s to do:

We spent six weeks on the work, we did our best, and something worked out really, really well...

You could make the argument that we should have tried each thing separately, measured each impact, and then decided where to go next (or known when to stop). You could make the argument that changing so many things at once makes it impossible to know which variables actually mattered. You could have argued we should have been more rigorous in our evaluation so we could learn something fundamental we could apply to a future project.

You could argue all those things. While you were debating those points, spending months teasing out answers, or testing each change in high-traffic succession for statistical significance, we were already basking in the results and moving our product teams to the next project. In six weeks all the work was done, we did our best, and it worked.

The point wasn't to know, it was to do.

You probably don’t really know why [something] didn’t work anyway. It feels good to imagine you do, but there isn’t a long history of people doing the same thing again, swapping this one wrong thing for another presumed right thing, and turning it all around.

You just gotta keep doing:

Next time isn’t [the time you failed] again, it’s a time that never happened before.

If you're just going by the data, then you're confirming, not deciding.

Building software, we have this fascination with making “objective, data-driven” decisions. But it’s an illusion. Data may filter out some subjectivity, but what’s left is always subjective. It’s best we admit this to ourselves and move on.

I’d rather a human with good taste than a computer with a good algorithm.

The more you see how other people do what they do, the harder it becomes to do things differently.

So pay attention a little, but not too much — leave more room for your own ideas than for theirs.

Many companies are weighed down by all sorts of prior obligations to placate. Promises salespeople made to land a deal. Promises the project manager made to the client. Promises the owner made to the employees. Promises one department made to another.

Saying “Yes, later” is the easy way out of anything. You can only extend so many promises before you’ve spent all your future energy. Promises are easy and cheap to make; actual work is hard and expensive. If it wasn’t, you’d just have done it now rather than promised it later.

Trust me, “Yes, later” doesn’t work with little kids either.

Lots of project management software will “take the true texture of a project” and flatten it “into a false linear representation of progress”.

a number can't represent the position of a project, or a piece of work. There's easier work, there's harder work, there's known work, there's unknown work.

What does 62% done mean when the "remaining" 38% of the work is twice as hard as the initial 62%?

If you do the easy stuff first, and leave the hard, or unknown stuff to the end, 62% done isn't just misleading, it's malpractice.

We all love a good number we can use in our presentations, our reports, our promises to others — doesn’t matter how wrong it represents reality.

That's not to say that we never run these numbers, but it is to say that these numbers never run us.

It reminds me of that line from…I think it was _Fight Club_…something like, “Do you own your stuff, or does your stuff own you?”

all these metrics are downstream from simply making something people want to buy. And keeping your costs below the price you can sell it for. That's the hard part, even if it's a simple calculation.

Overkill is using five different products to run a single project. Overkill is an seven-stage interview process that exhausts everyone involved. Overkill is acting like a company 100x your size.

Overkill is building and maintaining a website whose composition and complexity is meant for a scale of billions and all you have is hundreds.

Amass what you need, but ignore even more.

At most companies, people put together a deck, reserve a room (physical or virtual), and call a meeting to pitch a new idea. If they're lucky, no one interrupts them while they're presenting. When it's over, people react. This is precisely the problem.

The person making the pitch has presumably put a lot of time, thought, and energy into gathering their thoughts and presenting them clearly to an audience. But the rest of the people in the room are asked to react. Not absorb, not think it over, not consider — just react. Knee-jerk it. That's no way to treat fragile, new ideas.

Well, when you put it that way, that does sound pretty crazy.

Me personally, I’m all for distilling your thinking through writing and allowing people the time and space for consideration — though all this “AI writes for me” seems sometimes the antithesis of that.

When it comes to choosing what to do, it's always binary for me.

Yes or no.

Now or not now.

Do or don’t.

What about maybe? Maybe is no (for now).

What about some grey area between now or later? Anything other than now rounds down to later.

Being binary about what you choose to do brings clarity to what needs to be done.

“Maybe means no (for now)” is very relevant to me.

“The tyranny of easy metrics”:

Someone asked how this "strategy" of simply letting customers cancel without questions or hassle could be substantiated by data. Like, what measurements, what tests drove us to this place? It's a perfectly fair question in a world saturated with Growth Hacking, Chief Revenue Officers, and endless aspirations for exponential growth. But it's ultimately the wrong way to look at it.

It's easy to quantify the value of these hassling and haggling measures when they somehow manage to save a few customers, even if that is just 0.1% of those subjected. See! We earned an extra $32,856 last year putting everyone who wanted to cancel through the wringer. Yes, but at what cost?

This is the tyranny of easy metrics. It's easy to measure how much money is saved by preventing cancelations, it's much harder to measure how much long-term business is lost by poisoning your reputation with the 99.9% of customers who had to jump hoops and dodge sleazeballs to get out of the subscription...

Culture is what culture does. Culture isn't what you intend it to be. It's not what you hope or aspire for it to be. It's what you do…

And the good news is that culture is really a 50-day moving average. It's not a steady state. It's what you've done recently, what you're doing now, and what happens next. It's both along for the ride, and the ride itself. It's the byproduct of behavior.

Ideas like the shower. Ideas like our pillows. Ideas like commutes. Ideas like walks. Ideas like the morning, or late nights. Ideas like daydreams. Ideas like you doing something else so they can surprise you. ... They aren't something you control — they bubble up, they arise. You don't get to have them when you want. They come to you.

That’s an interesting interview question: how do you generate ideas?

They ask me to rate my "experience". Thing is, I didn't have an experience. The delivery person just left the package by the mailbox and I grabbed it when I got home.

Maybe we’ve missed the mark.

They're trying to track everything, and asking people to attribute "experience" to things that are mere, routine happenings. Most things just don't need to be rated.

I had this experience the other day when I ran to Walmart to quickly pickup some Planters nuts and upon finishing at self-checkout aisle was asked to rate my “experience”.

I'm seeing this everywhere and I can't help but think it's generating data that's incompatible with the actual situation. Being asked to rate minutia with a 10-point scale, and ascribe depth of an experience to something that's effectively flat and one dimensional, is overshooting the goal.

You don't even think about it and it works out. You try, it doesn't. You try harder, it really doesn't.

In many ways, this feels like the story of my life. If I try, I fail. If I go in not caring, I find success.

Trying too hard narrows the desirable outcomes.

Expectations are the enemy here — they limit the number of great landing spots, and make the idealized one impossibly hard. Relax your expectations, and hundreds of positive possibilities open up.

Ever find yourself about to ship something that isn't good enough?

…"We can always come back and fix it up later".

You can, but you won't.

New priorities pull harder than old ones.

Yeah. This is too true.

A lack of quality rarely qualifies as a bug, and it's hard to justify the time, effort, and tradeoffs required to come back with a polishing cloth down the road.

It’s interesting because the quality that comes out of companies who are renowned for it—like say Stripe—never seems like a follow up. Even on their initial launches. They always seem to have their best foot forward. I guess that can be attributed to their discipline for quality? They seem to know what deserves the highest quality and they make the right trade-offs to deliver on it up front, giving the impression to folks like me that everything they do is exceptional.

you can often see what a company values by what they leave unfinished or or unloved.

when you make it up as you go, you get to do what you think, not what you thought. All plans are rooted in the past — they're never what you think right now, they're what you thought back then. And at best, they're merely guesses about the future. I know a whole lot more about today, today, than I did three months ago. Why not take advantage of that reality?

I really like this—but that might be a biased take because it’s how I live my personal life. No life roadmap. Just some “big picture directional ideas”. To be honest, I’ll probably use Jason’s rationale here for how justifying how I live my life.

I’m just really enjoying Jason’s blogging now that he’s got Hey World:

I don't think about competing. Competition is for sports, it's not for business.

HEY is simply an alternative...

And all we have to do is get enough customers to make our business work. That's it. That's how we stay alive. Not by taking marketshare away from anyone, not by siphoning off users, not by spending gobs of cash to convince people to switch. We simply have our own economics to worry about, and if we get that right, we're golden.

When you think of yourself as an alternative, rather than a competitor, you sidestep the grief, the comparison, the need to constantly measure up. Your costs are yours. Your business operates within its own set of requirements. Your reality is yours alone.

Email is the internet's oldest self-publishing platform. Billions of emails are "published" every day. Everyone knows how to do it, and everyone already can. The only limitation is that you have to define a private audience with everything you send. You've gotta write an email to: someone.

Email client as publishing platform: audience ranging from one to the entire internet. Fascinating take from Basecamp folks on publishing a blog. I think this will be great for lots of people who aren’t tech savvy and simply want to write stuff and publish it online. Not sure how they’ll handle basic blogging features in the future, like tagging and/or categorizing posts. Nonetheless, exciting to see them enter the blog space in an interesting way.