Originally published on August 15, 2022

Let’s start with a story.

It’s one you’ve probably lived through in some form, if you’ve spent more than ten minutes in the software industry.

The Origin Story (and Its Inevitable Sequel)

A company forms. There’s an idea, a goal, a dream. Usually it involves building the next great thing—a widget, a platform, a barely differentiated SaaS for onboarding PDFs. The founding team is small and experienced. They might be well-compensated, but more often they’re paid in the warm, fuzzy promise of equity.

There’s camaraderie. A shared mission. A mutual understanding that the clock is ticking. The first funding round is finite, and a working product needs to exist yesterday.

So corners are cut. Design is… suggestive. Testing is “coming soon.” CI/CD is an acronym someone wrote on a whiteboard once.

But hey—progress! The product starts to take shape. Something ships. A few users appear. Stakeholders smile. More funding rolls in.

Then Comes the Growth Hangover

Within the next 12 months, the company starts hiring. Culture shifts. The new hires weren’t there for the all-nighters or the existential caffeine binges, and no amount of onboarding will recreate that original sense of shared chaos.

And right around this time—almost like clockwork—something breaks. In production. Badly.

Cue the panic. Releases slow. Guardrails are bolted on in every direction. Now we have processes. Review checklists. Release committees. Sprint reports. A standing Wednesday meeting called “Release Readiness Sync.”

Confidence must be restored. So we backfill unit tests. Write volumes of documentation. And begin the long, slow process of retrofitting stability onto a system that was duct-taped together in a sprint-fueled haze.

Development velocity falls off a cliff.

The Pendulum Problem

So what just happened?

I think of it like a pendulum.

On the far left: a scrappy, nimble team. Shipping fast. Testing nothing. The Wild West of software development.

On the far right: process. Documentation. Ceremony. A meeting to discuss the agenda for tomorrow’s meeting.

And the swing between them? Predictable. I’ve watched that arc play out more times than I can count.

In most companies, it takes 3–5 years to settle somewhere in the middle. Long enough to build tooling, write tests, refactor the worst offenses, and realize that neither chaos nor bureaucracy is sustainable.

What Comes Next

That middle ground—the balance between autonomy and accountability, speed and stability—is where the real work begins.

I plan to use this blog to explore what that looks like in practice. The tools, the habits, the trade-offs. The stuff that’s not in the job description but makes or breaks a team.

In the meantime, I’d love to hear how your own pendulum has swung.

And if you’re ready for part two, where I dive into how to stop the cycle before it repeats:
→ As the Pendulum Swings