A former CTO shares how emotional stability, transparent doubt, output-focused goals, founder communities and tackling the toughest tasks first helped survive the roller-coaster of early-stage startup life.
Leaving a 600-engineer organization to launch a three-person startup forced the author to reframe the leadership habits built as CTO. The biggest shift was learning to separate feelings from actions: emotional stability lets you acknowledge disappointment without letting it cloud analysis, turning each crisis into a learning moment. Emotional transparency became a duty, because founders who hide doubt set a tone that can cascade through a small team and amplify risk.
Goal setting also changed dramatically. In a mature company the focus is on outcome-driven OKRs, but early-stage reality demands output-centric targets-turning a revenue goal into a number of demos or a conversion lift into shipped experiments. This forces leaders to iterate fast and accept that outcomes are unpredictable.
The author discovered unexpected community value: while CTO forums feel mechanical, founder circles provide deep, personal conversations that reduce isolation and surface practical help. Participation in YCombinator's S21 batch exemplified how shared vulnerability accelerates learning.
Finally, the habit of "doing the thing you hate most first" proved critical. Administrative work like legal and accounting can cripple a startup if delayed; tackling it immediately prevents a double-dose of pain later. This practical prioritization habit helps founders keep the ship moving while other pressures mount.
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