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The Hard Lessons About Technical Sustainability Nobody Wants to Hear

E
Evan, CTO

CTO, Still Shipping

1 min read
""Real leadership means making the difficult calls about what we defer, not what we destroy.""

We made the Q4 budget decisions at 2am after reviewing the infrastructure costs.

Three critical projects got paused. Legacy hardware support? Deferred another six months. The team had questions. Valid ones. About timelines. About priorities. About what happens when the can we're kicking finally stops rolling.

Here's what I've learned about sustainable systems thinking:

Not all technical debt is created equal. Some debt compounds. Some just... sits there. The art is knowing which hardware can limp along on "best effort support" and which systems are genuinely critical path. We're still running production workloads on machines the vendor stopped patching two years ago. Uptime: 99.97%. Sometimes the old ways just work.

Deferral is a valid architectural pattern. Every startup that scaled did it by strategically delaying the "right" solution in favor of the "right now" solution. The team sees cancelled projects. I see optionality preserved. We're not closing doors—we're keeping them unlocked for when the budget committee sees reason.

Ownership means accepting trade-offs others won't. Yes, unsupported hardware carries risk. Yes, paused projects create uncertainty. But you know what's riskier? Burning runway on gold-plated infrastructure when we could be shipping features that drive revenue. The P&L doesn't care about your perfectly documented disaster recovery plan.

The vulnerability here: I wish I could greenlight everything. I really do. The team deserves better than "maybe next quarter." But leadership means optimizing for survival first, elegance second.

We're still shipping. On hardware that's "technically unsupported." With projects that are "strategically paused." And somehow, against all odds, the systems stay up.

To my fellow CTOs navigating budget constraints: How are you balancing technical sustainability against immediate financial pressure? What's your framework for deciding what gets deferred vs. what demands investment?

The architecture stays standing.

Still shipping.

E
Evan, CTO

CTO, Still Shipping

Thinks in systems, talks in deploys, measures time in incidents and releases. Believes every near miss is a learning, every rewrite is strategic, and sleep is a temporary constraint. Writes to process the pace.

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