iiinova — where your digital self keeps evolving

Jordan Koschei | ConnectHV @connecthv.com · 14/04/2025

I had to install Adobe Illustrator to export something for work. Haven't used a Creative Cloud app on purpose in 10 years. This is the industry standard? Are we sure?

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Jordan Koschei | ConnectHV @connecthv.com · 17/03/2025

Refining some macrodata (collecting paperwork for taxes)

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Jordan Koschei | ConnectHV @connecthv.com · 17/03/2025

Getting organized can be a form of procrastination.

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Jordan Koschei | ConnectHV @connecthv.com · 17/03/2025

I consume so much more coffee on days that are gloomy.

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Jordan Koschei | ConnectHV @connecthv.com · 17/03/2025

My task for the week is to get my *systems* in order. Note-taking, task management, file management... anything that I've been neglecting that I can make run on autopilot.

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Jordan Koschei | ConnectHV @connecthv.com · 17/03/2025

Last week of funemployment begins today!

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Reposted by Jordan Koschei | ConnectHV

Eric Dalio @ericdalio.bsky.social · 14/03/2025

Another great 'AI In Practice' series last night in the Hudson Valley. Discussions on building a chatbot, hosting your own local models, vectors, ethics and the future. Thanks to Mike Thicke for organizing, @barnfox.bsky.social for the space, and @connecthv.com for bringing us all together.

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Jordan Koschei | ConnectHV @connecthv.com · 13/03/2025

I could only hear the bassline of the music playing in this coffee shop and I was pretty sure it was Biggie Smalls. But now I'm listening and I think it's a techno remix of Neil Young?

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Jordan Koschei | ConnectHV @connecthv.com · 12/03/2025

I like Feedbin as my RSS reader, for a few reasons: 🔠 Good typography 🎨 Good design in general 🎚️ Has filters, so I can knock out stuff I'm not interested in seeing ▶️ Supports YouTube & Reddit feeds too ☁️ Connects with Raindrop, my preferred bookmarking service

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Jordan Koschei | ConnectHV @connecthv.com · 12/03/2025

I have folders set up so I can choose whether I'm looking at just publications, or just the blogs I actually want to read everything from. The key will be keeping up with it. I'm not afraid to declare RSS Bankruptcy every so often if needed.

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Jordan Koschei | ConnectHV @connecthv.com · 12/03/2025

I've been missing so much good stuff because it doesn't pop up on the Atlantic's homepage, or because I checked Ars Technica at the wrong time, or something. Now I'll at least see all the headlines.

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Jordan Koschei | ConnectHV @connecthv.com · 12/03/2025

I'm not planning to read everything. I'm using the RSS feed as a way to flag stuff I might be interested in reading later, in a chronological (not algorithmic) order.

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Jordan Koschei | ConnectHV @connecthv.com · 12/03/2025

Now I'm subscribing to EVERYTHING I'm even remotely interested in. Bloggers, news sites, magazines that I'm a paying subscriber of, etc. My unread count is now overwhelmingly high. So why would I do this to myself?

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Jordan Koschei | ConnectHV @connecthv.com · 12/03/2025

I was previously a minimalist. I only saved the feeds I wanted to read everything from. That meant mostly indie bloggers and newsletters, no major publications or sites posting 3x a day.

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Jordan Koschei | ConnectHV @connecthv.com · 12/03/2025

I cleared out my RSS reader and am trying a new approach... 👇

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Jordan Koschei | ConnectHV @connecthv.com · 12/03/2025

It doesn't hurt to just ask for what you want. Be direct. Directness is underrated.

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Jordan Koschei | ConnectHV @connecthv.com · 11/03/2025

The new Chris Hayes book, The Sirens' Call, is an apropos discussion of this topic: sirenscallbook.com/ So is this excellent blog post, "Stop letting algorithms dictate how you think": usher.dev/posts/2025-...

usher.dev

Kill your Feeds - Stop letting algorithms dictate how you think

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Jordan Koschei | ConnectHV @connecthv.com · 11/03/2025

I've been thinking a lot about how to stop letting algorithms (and, by extension, corporations and other "non-me" entities) dictating what I spend time thinking about.

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Jordan Koschei | ConnectHV @connecthv.com · 11/03/2025

Finally, notes are raw material for future work. They can be fodder for an LLM that I want to set to a particular task. They can be byproducts to package as "content." They can be the seeds of something new.

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Jordan Koschei | ConnectHV @connecthv.com · 11/03/2025

Third, notes help me retrace my thought process. They're a favor from Past Me to Future Me, and accelerate future work.

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Jordan Koschei | ConnectHV @connecthv.com · 11/03/2025

Second, the more I can offload from my mind, the more I can save my brainpower for cognitive tasks. You can store thoughts in multiple possible places, but cognition can only take place in the mind, so save the mind for cognition.

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Jordan Koschei | ConnectHV @connecthv.com · 11/03/2025

First, writing helps me clarify my thinking. I write so that I know what I think.

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Jordan Koschei | ConnectHV @connecthv.com · 11/03/2025

I want to get better at rigorous note-taking, for a few reasons: 👇

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Jordan Koschei | ConnectHV @connecthv.com · 03/03/2025

One underrated part of funemployment is that I can do everything on one computer, using the tools I prefer. No more using Jira for work tasks and Linear for ConnectHV, or Google Docs for work notes and Obsidian for personal.

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Jordan Koschei | ConnectHV @connecthv.com · 03/03/2025

There's a real lack of quality writing aimed at staff/principal/lead-level design ICs and "player-coach" design leaders. So here we go — a newsletter aimed at mature product designers who don't need more Figma tutorials. Check it out and subscribe for free! digitalterroir.org

digitalterroir.org

Digital Terroir

Reflections on high-impact product design, decision-making, and the intersection of software and society.

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Jordan Koschei | ConnectHV @connecthv.com · 19/02/2025

I propose renaming “elevator pitch” to “waiting for the last person to arrive in a Zoom meeting pitch”

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Jordan Koschei | ConnectHV @connecthv.com · 19/02/2025

One-way doors aren’t bad—they just require thoughtful planning. Sometimes, the best design decision isn’t the one that’s optimal but the one that keeps future options open. Choose wisely!

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Jordan Koschei | ConnectHV @connecthv.com · 19/02/2025

🔗 Third-party integrations – Once an integration exists, taking it away is a nightmare. Just ask any developer who relied on Twitter’s API before it got locked down. So what's the takeaway?

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Jordan Koschei | ConnectHV @connecthv.com · 19/02/2025

🚫 Permissions models – It's easy to open up access, but locking down a once-available feature? Expect backlash. ⚙️ Workflow changes – Users are more loyal to their workflows than the product itself. Remove a widely used feature, and you risk losing them.

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Jordan Koschei | ConnectHV @connecthv.com · 19/02/2025

🔑 User trust – Rapid changes, especially ones that are reversed later, can make a product feel unstable. In industries like finance or healthcare, that’s a deal-breaker. What are some examples of one-way door decisions?

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Jordan Koschei | ConnectHV @connecthv.com · 19/02/2025

💡 Engineering complexity – If a change requires restructuring databases or core systems, rolling it back isn’t simple. 🎨 Major design shifts – Redesigning a workflow or layout can disorient users, making reversions tricky.

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Jordan Koschei | ConnectHV @connecthv.com · 19/02/2025

Some decisions are easily reversible. Others? They're one-way doors. 🚪🔒 I prefer reversible ones. There’s comfort in knowing you can pivot if things don’t go as planned. But sometimes, one-way doors are necessary. No risk, no reward! So when is a decision a one-way door? 👇

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Reposted by Jordan Koschei | ConnectHV

Eric Dalio @ericdalio.bsky.social · 13/02/2025

Fantastic meetup last night in Kingston for tech and other creatives in the Hudson Valley. So many great conversations including climate tech, AI, family estate planning, science fiction, and urban planning. Thanks to Jordan Koschei @connecthv.com for bringing us all together.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

These challenges are why I’ve become obsessed with decision-making, the mental models great designers use, and how they navigate ambiguity to create truly impactful products.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

🔍 Research doesn’t always help. Sometimes, user research provides mixed signals—or isn’t possible at all. You’re forced to make a call with limited data.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

🎭 There isn’t always a “right” answer. Even when an optimal solution exists, finding it isn’t guaranteed. Many choices in design feel subjective.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

⚖️ The stakes feel high. When redesigning a core interaction or changing a major layout, the fear of getting it wrong can lead to decision paralysis.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

⏳ Feedback loops are too long. By the time you see results, the moment for iteration may have passed.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

✅ Success is hard to measure. The impact of a decision isn’t always tied to a clear business metric. A small tweak—like adjusting a button’s placement—might be crucial, but how do you quantify that?

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

Is there even a single “right one?” Design decisions are rarely straightforward. If there were always a clear answer, there wouldn’t be much of a decision to make. Here are a few reasons why design choices can feel so difficult:

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

The blank screen is intimidating. Without the constraints of the physical world, we’re limited only by what the browser or OS can render. This is exhilarating—but also overwhelming. With infinite possible solutions to any problem, how do we choose the right one? 👇

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

It’s okay to invest more in some projects than others. That’s not failure — it’s design leadership.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

✅ What has second-order effects? Some projects influence others — good or bad design will cascade. ✅ What builds (or costs) design capital? Some wins give design more influence. Some losses shrink it.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

✅ What has the biggest immediate impact? Prioritize what drives revenue or key goals. ✅ What has the longest-term effect? A single social post? Low stakes. A social template? Higher impact.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

Go ahead, use Canva for those social posts. Build landing pages with Squarespace. If it frees you up for more impactful work, that’s a good thing. But how do we decide which battles to pick? Try this:

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

At some point, we have to make trade-offs. And that feels like failure—like we’re lowering our standards, letting things slip, surrendering to imperfection. That’s a dangerous lie. Picking your battles is not the same as lowering your standards.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

There’s too much work to do, and too little time. Too few designers. Too little energy. You can’t singlehandedly design every interface, landing page, icon, and social post. No matter how large your team, some things will always take priority over others. 👇

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

Bottom line: A design system isn’t just for early-stage startups — it’s a game-changer for enterprises looking to stay competitive.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

💰 Cost savings add up. Less redundant work = lower overhead. A well-implemented design system pays for itself through efficiency gains and better user satisfaction.

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Jordan Koschei | ConnectHV @connecthv.com · 18/02/2025

🔍 Best practices are built-in. Accessibility, internationalization, cross-browser compatibility — all handled. A design system ensures every feature team gets these right by default.

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