Healthy ambition, hope, success & failure
Thu Jan 08 2026
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, internally referenced, and aligned with your values
* The “vibe check” principle: how the things that go well often feel lighter, more natural, less forced
* Why clarity soothes (and how ambiguous expectations can be an act of unkindness to your nervous system)
* A winter-friendly approach: dream now, hope gently, act later (spring is for beginnings)
If you’re feeling behind, lost, or like you “should” know what you’re doing with your life by now - I hope this episode meets you softly. There’s no rush. You’re a living process. And surviving gracefully counts as success in my book.
Share your reflections: chris@chriskenworthy.co.uk
Find me on Instagram + LinkedIn: Chris Kenworthy
Subscribe to Letters to Perfectionism: perfectletters.substack.com
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriskenworthy.substack.com
More
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, internally referenced, and aligned with your values * The “vibe check” principle: how the things that go well often feel lighter, more natural, less forced * Why clarity soothes (and how ambiguous expectations can be an act of unkindness to your nervous system) * A winter-friendly approach: dream now, hope gently, act later (spring is for beginnings) If you’re feeling behind, lost, or like you “should” know what you’re doing with your life by now - I hope this episode meets you softly. There’s no rush. You’re a living process. And surviving gracefully counts as success in my book. Share your reflections: chris@chriskenworthy.co.uk Find me on Instagram + LinkedIn: Chris Kenworthy Subscribe to Letters to Perfectionism: perfectletters.substack.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriskenworthy.substack.com