And every time, I think: this is hard. Why is this still hard?

The engineer's dilemma

I used to be an engineer, and engineers have a beautiful reflex: if something important hurts twice, you RCA it, build a system, and never feel that pain again.

For many years, part of me kept waiting for the meta-fix for this job. Better processes, more experience, some book, now AI. Surely at some point the job stops being hard.

It hasn't. And for a long time I read that as failure. Either mine (I haven't figured it out) or the industry's (we as a whole still haven't figured this out).

But it's supposed to be hard

The role exists because a few things are permanently hard: getting humans to work together, shipping into the real world, keeping everyone up to date, absorbing surprises.

A firefighter doesn't conclude the fire department is broken because there keep being fires. Same here.

AI won't fix it

Every tool that removes friction raises ambition: when shipping gets easier, we ship more, coordinate more, promise bigger. The hard doesn't disappear, it migrates to the latest frontier.

Tips for the next hard week

1. Rename the feeling. When you catch "why is this so hard," swap it for "this is the part I'm for."
2. Budget for fires. Expecting the unexpected makes it expected. Leave slack.
3. Pick hard problems on purpose. If a roadmap item scares no one, it probably matters to no one.
4. Talk to other PMs. Everyone is having some version of the same week.
5. Zoom out. Any given Tuesday is chaos. Any given year, things shipped and people grew.

You get stronger, the game gets harder

I love roguelite games. There's one I like a lot called Brotato. You're a potato holding six weapons, surviving waves of aliens. Between waves you shop, level up, come back stronger. But the next wave comes back stronger too. You scale, it scales. The reward for winning is a harder game.

Same for Product Managers. The waves get bigger because you're getting stronger. So don't worry. It's supposed to be hard.

It was in the room when they discussed his promotion. He wasn’t.

He changes. It changes slower.

He has never seen it, but everyone else has.

They call it his brand.

“As long as I am alive,” says the man, “neither can you.”

“Yes, ma'am,” the driver replied, adjusting the mirror. “Wherever you need to go.”

“And... what will you do when I’m not in the car?” she asked, puzzled.

“I’ll wait for you,” the driver said simply.

She blinked. “Wait for me? Like, just sit here and do nothing?”

“Yes, ma'am. That’s my job.”

“Okay, that’s too much,” she said, shifting uncomfortably. “I can't take it. Go somewhere, do something.”

He laughed, “Probation review? I thought that was just a formality.”

His manager raised an eyebrow. “It’s to see if you’re a good fit.”

“Bro, I’m not leaving,” he said, half-joking.

The manager smiled. “We’ll see.”

“Yeah, seriously, you’re making the rest of us look bad,” another added.

He blinked, confused. “But I’m just doing my job.”

“Exactly,” they groaned in unison. “You’re doing too much of it.”

He stared, “But... it's an expected discretionary bonus.”

"Can you unexpect it?"

"No chance in hell."

“So, what if we launch our next product… into space?” someone suggested, barely keeping a straight face.

“Wow, I love it.”

Confidence growing, they continued, “Ooh, and we crash it back onto Earth as a meteor, then ‘discover’ it in a dig site, claiming it’s alien technology we’ve reverse-engineered.”

"APPROVED!"

His phone buzzed again, flashing with bright images, colorful notifications, and catchy sounds. “Look at me! I’ve got everything—memes, videos, likes!"

The book sighed, its pages limp. “Ugh, whatever. I can’t compete with that. Just go.”

“Isn’t it great?” the new joiner beamed, loading up their plate.

The old-timer sighed deeply, as if the world had ended. “My day is ruined.”

“Over a free lunch?” the new joiner asked, surprised.

The old-timer looked up, eyes filled with disappointment. “You wouldn’t understand.”

"What offsite?" one of them blinked, confused.

"You know, the company retreat," he continued, trying to sound nonchalant.

They exchanged glances. "We didn’t get any invitation."

He slowly backed away, hands up. "I didn’t say anything."

But there is no hoodie.

I asked HR, thinking maybe they’d forgotten. They just said, "Oh, we don’t do company swag here."

I mean, what's the point of a dream job if you can’t wear a hoodie to brag about it?

"Actually, we use a hot desk system."

"But I always sit here."

"I booked it for today."

"THAT IS MY DESK! BE GONE, YOU DESK USURPER!"

"I don't know. It just doesn't have a vibe."

"What's a vibe?"

"I don't know. It's a single word of copy."

"It says 'Send.' What’s there to vibe?"

"I'll know it when I see it."

His colleague, the one he always looked up to, suggested, "But what if we did it this way instead?"

"You’re right," he said reverently. "Of course, you’re right." He was all in, as if his previous certainty had never existed.