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A Humbling Experience, Lessons Learned, and Adventures in Self-Hosting

A recent failed intro call shows how even seasoned advisors stumble when unprepared, and why recognizing imperfections and planning ahead is essential for technical leaders.

The piece opens with a stark moment: the author, a trusted advisor to CEOs and engineers, blunders on an intro call by launching into technical detail when the listener was looking for business impact. The embarrassment of being caught doing exactly what he advises others to avoid crystallizes the core insight - humility and self-awareness are as critical as expertise.

He recounts how the interruption forced him to confront a deeper problem: a lack of preparation. By winging the conversation, he missed the chance to align his message with the audience's expectations, a mistake that spiraled into a night of rumination. The analysis pinpoints the root cause - assuming the call would be easy and not investing time to script answers to common CEO questions.

From that failure, he outlines concrete actions: be selective about which intro calls to accept, and always spend time preparing a concise narrative that translates technical outcomes into business metrics. This shift from reactive advice-giving to proactive self-coaching illustrates how technical leaders can turn personal missteps into systematic improvements.

The article then pivots to a broader theme of self-hosting, arguing that controlling one's own infrastructure mirrors the need for personal control in leadership. By reducing vendor lock-in and building resilience against geopolitical and commercial pressures, self-hosting becomes a practical exercise in applying the same disciplined preparation and ownership championed in the earlier anecdote. The author's enthusiasm for tinkering underscores that disciplined self-improvement can be both strategic and personally rewarding.

Source: makemeacto.substack.com
#self-hosting#technical leadership#engineering management#devops#software development#leadership

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