# Are you an insecure overachiever? Oliver Burkeman on why success never feels like enough Page: https://stenobird.com/podcast/how-i-work-960132/are-you-an-insecure-overachiever-oliver-burkeman-on-why-success-never-feels-like-enough Text version: https://stenobird.com/podcast/how-i-work-960132/are-you-an-insecure-overachiever-oliver-burkeman-on-why-success-never-feels-like-enough.md Podcast: [How I Work](https://stenobird.com/podcast/how-i-work-960132) Published: 2026-08-05T20:00:00+00:00 Episode link: https://omny.fm/shows/how-i-work/hiw-oliver-burkeman-2026-v2 Audio file: https://mgln.ai/e/187/traffic.omny.fm/d/clips/fa326977-3de5-4283-9b8b-af3500c58607/190bd54e-82e6-43fb-8f6a-af46001792de/57af11fc-da82-4b68-abdf-b49c0003aff1/audio.mp3?utm_source=Podcast&in_playlist=71f0c47d-eac4-4e42-b713-af46001792ec Processing state: not_requested JSON: https://stenobird.com/v1/public/podcasts/how-i-work-960132/episodes/are-you-an-insecure-overachiever-oliver-burkeman-on-why-success-never-feels-like-enough Duration seconds: 2184 ## Resource There's a particular kind of tightness that creeps in when the world feels unpredictable. We tidy the to-do list, tighten the routine, optimise one more thing, all in an attempt to feel a bit more in control.  Oliver Burkeman has a word for this: clenching. And he reckons it's squeezing the life out of us, even when it looks a lot like productivity.  In this episode, I sit down with Oliver Burkeman, New York Times bestselling author of Four Thousand Weeks and Meditations for Mortals, and former writer of The Guardian's This Column Will Change Your Life, to talk about his forthcoming book Aliveness and what he calls unclenching, learning to loosen your grip on certainty rather than white-knuckle your way through it.  We get into flexible goals, why urgency is so often someone else's agenda in disguise, and how to stop tying your self-worth to your latest achievement.  If you have ever hit a goal and felt the satisfaction evaporate within minutes, this conversation will change how you think about ambition altogether.  Oliver and I discuss:  What "clenching" is, and why our instinct to grip tighter in uncertain times actually backfires  The insecure overachiever trap, and why hitting a goal rarely feels like enough for long  How Oliver's open list, closed list approach stops you drowning in fifty half-started things  Setting a "no later than" time instead of a strict start time, and why looser goals often get more done  Why urgency is so often someone else's agenda in disguise, and how to tell when it is genuinely yours  What Oliver actually does with the emails he has not gotten to yet  Key quotes   "If you have this feeling of aliveness,… ## Actions - request_transcript: `POST https://stenobird.com/v1/public/podcasts/how-i-work-960132/episodes/are-you-an-insecure-overachiever-oliver-burkeman-on-why-success-never-feels-like-enough/transcription-requests` — Idempotently request low-priority transcript generation for this episode. - read_markdown: `GET https://stenobird.com/podcast/how-i-work-960132/are-you-an-insecure-overachiever-oliver-burkeman-on-why-success-never-feels-like-enough.md` — Read the agent-friendly Markdown representation of this episode resource. A page view does not enqueue transcription. Agents should invoke `request_transcript` explicitly when they need this episode processed. ## Transcript Full transcripts are not published on public pages unless there is a clear rights basis.