Photo by Keith Caden taken at Shake Party Chicago

Year of Yes, But…?

You may notice some new paint and a little new wallpaper around here. 2025 was a season of growth for me or what I like to call my Year of Yes. New opportunities kept presenting themselves, and I said yes often enough to learn in real time what hit the mark and what was a colossal fail. That experiment was useful in separating signal from noise and led to 2026 being the “Year of Yes, But…”

Just this morning someone asked me the dreaded “So…what do you do?” question to which a certain 1 Million Cups emcee who shall not be named playfully answered “I hope you’ve got a few hours…” and that truly reinforced the point — when someone asks that question, I can’t reliably answer it the same way from one day to the next.

This isn’t a design flaw. It’s an asset. It’s the reality of being a multi-hyphenate, of living within the constraints of context— and more importantly, of being an architect of adaptability.

Repeated Patterns

I speak with 20-30 people a week and have rich, insightful conversations about progress, but rarely about people or process.

Founders, operators, executives, and community builders tend to focus on isolating a single issue rather than addressing a broader systems failure. Everything is going swimmingly, then pow! Things suddenly fall apart at decision time (and yes, I experience this too.)

Decisions stall because of gaps in relational infrastructure.

A founder assumes buy-in. An operator has different priorities. The customer is misaligned. Any one of these can become a point of failure that can derail a project or an entire company. Aligning the right people on a shared goal and achieving it through shared decision-making that actually lasts is more difficult than it looks on the surface.

This gap is costly. It rears its ugly head as: burnout, distrust, scope drift, missed deadlines and opportunities, lost revenue, and reputational erosion. Effort usually isn’t the problem.

Translation often is.

So What’s the In Good Company Co.?

In Good Company Co. was born from this reality.

Rather than trying to collapse the breadth of my work, I reinforced the through-line across every context. I used to think what I did was primarily operations and process improvement. But it runs deeper than that.

I build relational infrastructure.

I translate ideas, energy, strategy, and systems into shared understanding. I help people develop the trust and accountability required to articulate value and move from conversation to commitment.

That’s the work.

Relational operations isn’t “vibes.” It’s not culture either (though it’s a huge part of it). It shows up in very real ways across marketing, operations, GTM strategy, and communications.

So this branding shift isn’t cosmetic. It’s about articulating this often-intangible “glue” work more clearly and reinforcing the role relational operations play as the oil that keeps systems running smoothly.

My job is to work with people to identify and name these points of failure and to design systems that reduce and eradicate them without sacrificing clarity, trust, or sanity.

What’s Next

I’m excited to be rolling out new formats this year, including workshops, intensives, and new partnerships designed to support this work in more focused and accessible ways.

You’ll also see TechWalk continue to evolve as a living experiment in relational infrastructure that brings people together to connect, literally produce momentum, and bridge the Chicago tech ecosystem, one step at a time.

More soon.

Events

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The Page Unturned Book Club

I’m currently finishing up Enshittification by Cory Doctorow.

I started reading this because I was drawn to the funny name, but what stuck with me isn’t just how systems degrade over time, but it’s the nasty idea that many adverse outcomes aren’t unexpected at all. Sometimes they’re tolerated. Often times they’re incentivized. Sometimes they’re simply the path of least resistance.

It’s making me think differently about where organizations label points of failure as “unintended consequences” when they’re actually unexamined design choices.

If this resonates, hit reply — I’ll be sharing more as these experiments take shape.

See You Outside,
Chrystal

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