Key Insights

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  Greg pivoted from architecture to tech and UX without initially knowing it was called UX.

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  Increased competition and ageism impacted Greg’s search for enterprise UX leadership roles recently.

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  Greg’s current consulting focuses on outcomes-first AI strategy for SMBs and enterprises using design thinking.

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  Letting go of professional identity was key for Greg to successfully pivot away from chief design officer roles.

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  Flexibility between startup and enterprise environments comes from understanding core design and leadership principles, not context.

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  Greg and Jorge Arango’s Unfinished practice involves service design methods but not building software themselves.

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  Successful AI adoption requires understanding an organization’s existing systems, tacit knowledge, and readiness to change.

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  Greg uses intention statements and periodic self-evaluation to guide his evolving career direction.

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  The biggest challenge in consulting with traditional companies is managing long-term vision versus their readiness for change.

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  Having trusted partners and accountability structures supports sustainable entrepreneurial pivots.

Notable Quotes