A Learning Day Feed

What you’re solving for

alearningaday — Fri, 09 Oct 2026 11:06:00 +0000

One of the more important lessons you learn over time: whether a choice is good or bad depends entirely on what you’re solving for.

Stopping the spiral

alearningaday — Thu, 08 Oct 2026 11:18:00 +0000

A colleague told me a lovely story recently. His toddler goes through fits of complaining, one thing after another. So they started a ritual: when it happens, they ask him to pause and name one good thing, one thing he’s grateful for.

What they’ve found is that once he starts, it’s easy for him to find a second thing, then a third. The complaining just stops.

It’s a good reminder that we’re all capable of spiraling down a negative path once we get moving on it. And sometimes all it takes to reverse that is interrupting the momentum.

You see the same pattern in professional sports. One team is dominating, then the other team gets a single good moment, and the entire momentum of the game swings.

Applies to our days, and to our lives.

Maybe life is trying to teach me something

alearningaday — Wed, 07 Oct 2026 11:03:00 +0000

A simple way to make the most of unpleasant experiences: train yourself to respond with “Maybe life is trying to teach me something.”

That idea alone opens the door to what the experience might actually be teaching you.

Almost every unpleasant experience has a lot to offer, if you’re willing to ask.

Fear that keeps you alert

alearningaday — Tue, 06 Oct 2026 11:07:00 +0000

A friend and I were talking about organizational behavior recently, and one of her observations stuck with me. Public markets are unforgiving. When performance slips, the market notices, and that pressure, assuming reasonably mature leadership, tends to force a culture of accountability.

Take that pressure away, and the opposite tends to happen. Without real consequences for weak performance, culture drifts toward the performative. More politics. More energy spent covering yourself than doing the work.

It reminded me of Richard Parker, the tiger in Life of Pi. Pi Patel’s fear of the tiger sharing his lifeboat is constant and real. But he also shared his gratitude for that same fear because it kept him alert, focused, and alive through an impossible ordeal.

Consequences drive behavior.

Container ship, leaky boat

alearningaday — Mon, 05 Oct 2026 11:04:00 +0000

I have a new favorite analogy for when people ask how work is going. It’s been six months since I moved from a large company to a very small one, and the shift feels like moving from a container ship to a leaky boat.

A large company is a container ship. You’re out on the same ocean as everyone else, but you barely feel the waves given the size of the thing. You have one specific job, the ship has a course, and it has enough telemetry and momentum that it mostly just keeps going where it’s always gone. It can turn, but slowly.

A very small company is a leaky boat. You fix the biggest leak, whether or not it’s technically your area. You hope to upgrade the boat in a year, but for now, this is the boat you have. It turns fast, moves fast for its size, and you feel every single wave. A happy customer feels like a tailwind pushing you forward. An upset one feels like it might capsize you.

And the muscle that I find myself needing the most is the one that summons equanimity.

Five a weekend

alearningaday — Sun, 04 Oct 2026 11:20:00 +0000

I’ve been overdue for a password audit. Both LastPass and Chrome have been nagging me about a growing pile of passwords that need updating, and looking at the full list is overwhelming.

But, if I do five a weekend, it’ll be solved in a few weeks.

Same thing with ironing. Three weeks of clothes in one pile feels like a lot. One week’s worth at a time is much simpler.

It’s a lesson I apparently need reminding of on a loop: when in doubt, break it down.

Small bits of progress add up quickly.

What’s important to you is important to me

alearningaday — Sat, 03 Oct 2026 11:21:00 +0000

A friend shared a story about a conversation with someone who was many steps ahead of him in his career. He’d gone to this person with a career decision where he was deciding between two very different paths.

It was late on a Friday evening but this person committed to figuring this out. As their conversation progressed, his wife called as he was supposed to be at a party. He explained he had to skip it.

Then his boss called, and he again said he was in the middle of something and he’d call back tomorrow.

Then his biggest client called, and, once again, he shared he was in the middle of something important.

This friend was stunned. He was leaving the company after all. At the end of their conversation, he asked him why he upset a bunch of important people just to help him?

His answer was: “You are important to me. And for you, this is a life-changing decision, which makes it important to you. When you are important to me, what is important to you is important to me.”

It is an idea that Stephen Covey shares in the “7 Habits.” But there’s nothing like a good story to make it memorable.

Normal is a subculture

alearningaday — Fri, 02 Oct 2026 11:02:00 +0000

What we consider normal is a function of the norms of the culture we grew up in. Behavior encouraged in one culture can be entirely unacceptable in another.

That’s why it’s easy to label something as weird: it simply doesn’t match the norms of whatever subculture shaped us – a combination of our family, our neighborhood, and our institutions.

It’s also why diverse teams are so hard to build. Different points of view mean different assumptions, and different assumptions look like weird behavior, at least at first.

But those weird behaviors are often exactly what break through groupthink. The assumptions worth questioning are usually the ones nobody in the room thought to question, because everybody in the room grew up with the same “normal.”

The limits of optimizing

alearningaday — Thu, 01 Oct 2026 11:26:00 +0000

A group of us play a pickup soccer game together every weekend, with plenty of banter along the way.

Recently, after one game, a casual conversation about the result spiraled into talk of tracking stats: who’s on which team, goals scored, win rates. That escalated further quickly, all the way to using an app for team assignments and stat tracking.

Then the following weekend, we played with all of it in place. Everyone was excited going in. But the game itself was far more competitive than usual. People played tighter, more aggressive, more conscious of every touch.

Which defeats the entire point of a Sunday pickup game: work out, have fun, don’t get hurt.

My takeaway afterward was that the game became a lot more competitive and a lot less joyful the moment people knew they were being tracked.

It is a good reminder that many things in this life are best left un-optimized.

The tighter shoe

alearningaday — Wed, 30 Sep 2026 11:24:00 +0000

If you play a sport with a lot of dynamic movement, quick starts, stops, direction changes, buy shoes that fit almost perfectly, even if they feel slightly tight in the store.

A looser shoe feels more comfortable walking around the aisle. On the court or field, however, that same looseness costs blisters, chafed skins, and worse.

I’ve learned this one painfully, more than once.

It has a decent analogy for life too. The option that feels more uncomfortable up front can often be the one that serves you best over time.

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