Healthy ambition, hope, success & failure

Healthy ambition, hope, success & failure

From Beyond the basement by Chris Kenworthy

January 8, 2026 · 38 min

About this episode

In this episode, Chris Kenworthy explores the concept of ambition and its relationship with success and failure, arguing against traditional goal-setting in January.

It’s the first episode of 2026 - and no, this isn’t a pep talk about New Year’s resolutions, grit, or “becoming your best self” by February. If anything, I’m here to make the case that January is the worst time to set goals. It’s still winter. Nature is resting. So maybe you should be too. Instead, I want to explore something adjacent: ambition. A friend told me recently, “I’m not ambitious.” And it got us into a deeper inquiry: what if ambition has become tangled up with conventional success - status, money, prestige, the “nice car and impressive job” storyline - and that’s why so many people feel allergic to the word? In this episode I share my own career arc (from “prestigious job and gravy train” → jumping off in my late 20s → an anti-corporate, frugal, rebellious 30s → a 40s return to purpose, impact, and more options). And I unpack why “success” and “failure” are often unhelpful binaries… because some of the most meaningful wins are actually how we navigate what didn’t work. We’ll also talk about: * The difference between goals (often cold, rigid, and perfectionism-triggering) and hopes (clear enough, but held lightly) * How ambition can be healthy when it’s yours…

People in this episode

Host: Chris Kenworthy

Topics covered

  • ambition
  • success
  • failure
  • goals
  • hope
  • self-improvement

Keywords

  • ambition
  • success
  • failure
  • goals
  • hope
  • self-improvement
  • winter
  • clarity

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