It’s still a long December

Also what companies learned while doing 4-day work week trials

Dec 20

I find it impossible not to reference A Long December incessantly as things start to wind down ever year. And I imagine if you are of a certain age, the song is stuck in your head all month too. Last year was an especially fruitful one for us Long Decemberites, because “60 Songs That Explain the ’90s” did a wonderful episode about it that you simply must listen to:

Second Counting Crows album comes out in 1996. Called Recovering the Satellites. I love this record. The displacement and disenchantment and unhappiness radiating from this record make me very happy. The second-to-last song is called “A Long December.” This one seems to make a lot of people happy, or at least, it makes a lot of unhappy people slightly less unhappy.

I don’t want to make this a “year-end reflections about me” post, but I will say this: there has been a lot of change this year. Postmark got acquired and we joined a new team in a much larger company. Being in the middle of the merging of two different cultures is never a completely smooth ride, and we certainly had our moments. But as I mentioned to the team in a post this week (that absolutely 100% definitely referenced A Long December, come on now), I am grateful that we were able to stick together. We all learned a great deal about ourselves, our product, and its potential.

I am crawling towards 2023 still believing the words “maybe this year will be better than the last,” just like I have ever since the song came out in 1996. As for this newsletter, there’s some stuff I want to get out of me at some point—about my 6 years at Wildbit and what I learned, about scaling Postmark with a small team, about the process of adapting our product strategy as part of a new org, and so much more. So if you’re willing to come along for that ride, I think we’re going to have a good time. Or at least learn some things together.

See you next year.

💛

What I’m reading

Deb Liu has some great product management and leadership advice in Communicating at the Right Altitude:

Often, the difference between a good leader and a great one is altitude. Being able to navigate at the right level for the conversation, whether you’re doing a deep dive into the details with a colleague or discussing high-level strategy with executives, is a rare skill. But it is also crucial to hone in order to be successful in the workplace.
This is a delicate balancing act. Too detailed, and you are seen as being too “in the weeds.” Too high-level, and you are seen as “lacking detail orientation.” Knowing exactly where you want to fly in a given conversation is critical to landing your point.

This point also resonated:

Often, we think that when things get stuck, it’s because someone is at fault. In reality, many times it’s a result of the process, the culture, or a lack of clear ownership.

She goes on to give some very useful tips for how to communicate at the right altitude, including some questions to ask yourself before going into any meeting.

Here’s a good summary from Bruce Daisley about what companies learned while doing 4-day work week trials. For instance, while there was no decline in total productivity, “producing the same amount in a compressed period required focus and a fair degree of ruthlessness.”

This resonates with my experience at Wildbit. The biggest challenge was figuring out what meetings we didn’t need, and which tasks could move async. It’s not just about reducing the week by 8 random hours; it’s about being intentional about removing 8 unnecessary hours.

In The micromanager’s dilemma Matthew Ström argues that maybe there is a time and a place for that approach:

In this essay, I’ll show you that micromanagement isn’t just a nagging habit; it’s an inevitability. That’s the paradox: micromanagement is both bad management practice and a key component of the best management strategies. So in addition to explaining this paradox, I’ll offer some lessons from similar paradoxical problems. In the end, I want to demonstrate that, with the right approach to micromanagement, managers and their reports can thrive.

He has some really good general management tips at the end, so this one is well worth reading!

Some stray links

📷 The 2022 Comedy Wildlife Photography Awards are out. They are, indeed, quite comedic.
🌏 I Don’t Want to Be an Internet Person is so great. Must-read. “Internet people, or people whose entire identities are wrapped up in their online presence, represent a new direction of culture. You don’t have to live in or know about the real world to be important.”
🎟 The sneaky economics of Ticketmaster. “Rosen believed venues, not concertgoers, were his company’s real customers, and flipped Ticketron’s model: Instead of charging venues to use their ticketing system, Ticketmaster offered to pay them with a cut of the service charges. In exchange, Ticketmaster became their exclusive ticketing platform.”
🤳 These ‘Luddite’ Teens Are Abstaining From Social Media (NYT 🎁 link). “Eventually, too burned out to scroll past yet one more picture-perfect Instagram selfie, she deleted the app. ‘But that wasn’t enough,’ she said. ‘So I put my phone in a box.’”
🧓 This week’s “for my fellow olds” link: Gen Z’s slang and emojis are confusing older colleagues at work.
📈 Last week’s most clicked link: My project plan template on Github.