Willing to Fail

Being willing to fail is different from being reckless, and being careful doesn’t mean avoiding risk. Yet, too often, we treat risk as a binary choice: go all in or play it safe.

The truth? Smart risk-taking lies in the middle.

Balance is key … too cautious, and you miss opportunities; too reckless, and you invite disaster.

Across industries, progress comes from calculated risks:

• Entrepreneurs invest in new ventures, but only after research and planning.
• Engineers make changes that can break systems, but only after testing.
• Scientists expect failure, but use it to fuel discoveries.

So how do we take risks wisely?

• Redefine failure: it’s not the end; it’s more data to try again.
• Encourage experiments: a proof of concept prevents analysis paralysis.
• Think critically: some risks aren’t worth taking, but avoiding them entirely is its own risk.
• Build resilience: mistakes are embarrassing, but always playing it safe is worse.

Why does this matter in software?

Move too fast, and you break production. The systems we support are often mission-critical. Outages cost, time, money, and trust … not just lost productivity, but in missed opportunities to serve customers.

Careful engineering doesn’t mean standing still. Systems must evolve … updating platforms, managing tech debt, and delivering new functionality to remain valuable.

The key? Take smart, calculated risks. Experiment. Learn. Adapt. That’s how we build software — and careers — that thrive.