Success Makes You Dangerous: Why Comfortable Leaders Stop Growing

In this episode, Kevin tackles a paradox that most leaders don't see coming: the moment you get comfortable in your role is often the moment you stop improving. Drawing on his decade as a CTO, he explains why success and experience can become dangerous if you're not deliberately reflecting on how you work, why you make the choices you make, and where your blind spots might be hiding.

Kevin breaks down why reflection isn't optional for senior leaders. At the C-level, you don't get much feedback or development; you're expected to figure it out yourself. Your peer group shrinks. The job gets easier because you've seen these problems before. And that comfort is exactly when autopilot kicks in, when you stop asking "why," and when you risk becoming less effective for the people who depend on you.

The episode covers Kevin's personal reflection system: a twice-yearly strategic offsite, quarterly goal-setting, monthly calendar reviews, and weekly time-tracking. But he emphasizes you don't need to copy his process; you need to find what works for you and evolve it over time. He shares practical advice on starting small, making time when you feel too busy, and why the practice matters more than perfection. Reflection isn't about having it all figured out; it's about staying deliberate, adaptive, and intentional as a leader.

Whether you're a new manager learning to step back from the work, a senior leader feeling too comfortable, or anywhere in between, this episode makes the case that you can't lead others to grow if you've stopped growing yourself.

• The Personal Strategy Offsite episode: https://itdependspod.com/episodes/the-personal-strategy-off-site/
• Own Your Calendar episode: https://itdependspod.com/episodes/own-your-calendar-work-deliberately/
• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net)
• Your host: Kevin Goldsmith (https://kevingoldsmith.com)
• ConFoo 2026 (https://confoo.ca/en/2026)