An Unreasonable Investment

An Unreasonable Investment is another excellent leadership essay by Michael Lopp. Here’s something to take with us into our jobs every day:

You want some free leadership advice? You build yourself by building… by helping others. The selfless act of helping humans will teach you more about being a credible leader than any book.

Your career is not your job. It’s the humans you help along the way.


Molly Graham has a fantastic essay on how to figure out if a job is the right fit for you. The post focuses on senior roles, but there are some great tips for everyone here:

What I look for, truly, is the intersection in the two sides of the equation: does what we NEED match what this person WANTS to do? As I said, most companies and most interviews focus more on the question: can this person do what we need? But if you’re trying to recruit the best talent in the world, it needs to start with them. Who are they? What do they love doing? What are their ambitions? How does their past shape what they want for their future? What are they insecure about? What do they want to prove? My interview style is really about mapping that.

Work for love

I love JJ Skolnik’s essay Love + Work for Flaming Hydra (paywalled but well worth it—this newsletter is great). JJ used to work at Bandcamp and reflects on “loving your work” when it doesn’t love you back. And he has some wonderful reflections on the meaning of music too:

Underground music is vital because it is an experience that cannot be replicated in capitalist language. No matter how much one tries to distill it down to a matter of commodity exchange—there is nothing that can capture the joy of a bunch of freaks making the music they want to make and sharing that in community with one another. This is true no matter how much money is poured into it. Money isn’t what makes it grow.

Quality vs Quantity

Mike Fisher preaches the good stuff in Quality vs Quantity. He talks about the importance of shipping small, incremental releases to customers:

By prioritizing the quantity of opportunities to learn, teams encourage a culture of continuous learning and flexibility. Each iteration becomes a learning opportunity. This method aligns more closely with real-world conditions where customer preferences and market dynamics are constantly evolving. Furthermore, this approach reduces the risks associated with big launches like Windows Vista, where a significant investment is made in a single, large-scale product release. Instead, smaller, more frequent releases allow for adjustments and refinements based on actual user feedback and engagement.

5 Different Types of Debt That Can Hinder Your Product Organization

I like Jason Knight’s take on 5 Different Types of Debt That Can Hinder Your Product Organization. There’s the usual “tech debt” advice, of course, but also some good insight on other types of debt to look out for, such as…

Revenue debt builds up as companies scale up through unstructured sales-led growth, selling to anyone they can, meaning that they start to build dependencies on a disparate set of customers who have sometimes substantially different needs. This makes focusing, or even saying no, too difficult because there’s too much revenue tied up in each segment.

My Comments Are in the Google Doc Linked in the Dropbox I Sent in the Slack

This post is like watching “Portlandia” as a Portlander (or HBO’s “Silicon Valley” as a tech worker). It’s obviously satire but too close to reality to be funny… My Comments Are in the Google Doc Linked in the Dropbox I Sent in the Slack:

You still don’t see the link? It’s right there on the bottom of the Slack thread from yesterday about which shared drive folders link to Dropbox folders that contain all the shared PDFs. Oh, my mistake; it’s actually at the bottom of a thread about what everyone had for lunch yesterday. Here I’ll send it to you again. I just replied to an email to Jeff with the link and asked him to forward it to you. The subject line is ‘Email.’

Say the quiet part out loud: simplifying communication in high context environments

The Culture Map by Erin Meyer is a great book about how to improve communication between different cultures when you work at a company with a global workforce. Recently I’ve been thinking about how these concepts apply not just at a (geographical) global level, but within the systems of a single organization. What are the norms of how people communicate with each other in meetings, in email, over Slack? What type of confusion/misalignment might happen because of those norms, and how can it be improved?

There’s one dimension the book covers that I think applies particularly well to modern organizations, and that is the difference between high context and low context communication.

High context settings are those where communication relies heavily on implicit understanding. The assumption is that everyone has the same frame of reference, which means a lot is left unsaid, with the belief that everyone “just gets it.”

Low context environments, on the other hand, are those where things are spelled out more clearly. There’s less assumption that everyone has the same background information or knowledge, leading to more explicit communication.

For instance, if you often don’t know what people are talking about in meetings and it makes you feel like you missed something obvious, you might be in a high context environment. Perhaps things move so fast that there’s an assumption that everyone already has all the context of the previous 10 meetings that happened about a topic. It’s natural for this to happen—but it reduces the effectiveness of our work and the health of our relationships.

I’ve been trying to be more deliberate about addressing this issue—at least for myself and the people I work with most closely—by actively going more “low context” in my communication. When something is implied through context, but not explicitly stated, I aim to go out of my way to make it explicit.

The goal is to ensure that no one has to feel like they can’t contribute (or be scared of making the “wrong” contribution) because they weren’t part of every conversation. By making the implicit explicit, we level the playing field. It’s not just about adding clarity to our communications, it’s about fostering an environment where everyone, regardless of their starting point or level in the organization, has the same opportunity to understand and contribute.

By breaking down our messages into clearer, more accessible information, we’re not dumbing down—we’re opening up. We’re building a foundation where everyone can work confidently, equipped with the knowledge they need to contribute meaningfully.

Keep an eye out for opportunities to say the quiet part out loud. To clarify a statement, or state the thing that appears to be said between the lines. It takes work and concentration, but it’s a shift that can make a big difference in how we work and relate to each other.

How Group Chats Rule the World

This essay on How Group Chats Rule the World (NYT Gift Link) is really great, and I agree with all of it.

The group chat can sustain indefinitely this thin wire of connectedness. Some might argue that this feeling is a deception, another screen-based way to stave off loneliness; I would say instead that it glows with potential. Because there is no practical end to the group chat, it can be a means of keeping the lights on, constellating a set of people who would otherwise be entirely separate.


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