Is This It? Rethinking Success, Discontent, and the Midlife Audit

Is This It? Rethinking Success, Discontent, and the Midlife Audit

Encouragementology

Kendell Boysen reframes the so-called midlife crisis as a practical midlife audit, questioning borrowed measures of success and the pressure of timelines. Through gentle coaching and reflection, she invites people to see discontent as information and update their scorecards to match what truly matters now.

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30:0025 Jun 2026

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Is This It? Turning the Midlife Crisis Myth into a Midlife Audit

Episode Overview

  • Question whose scorecard you are using by asking who defined your measures of success and whether they still fit your current values.
  • View a midlife audit as an honest evaluation, not a crisis, focusing on awareness rather than blame or dramatic life changes.
  • Assess multiple life areas using a whole-life view, rather than judging your entire life by a single weak spot like finances or career.
  • Recognise the arrival fallacy by noticing where you’ve linked happiness to a future milestone and instead look for alignment in the present.
  • Treat discontent as a possible messenger, asking what it is trying to show you and what areas of your life deserve more attention now.
Discontent is not always evidence that your life is broken.

Curious about how others manage their sobriety journey and wider life questions? This conversation with professional life and recovery coach Kendell (Kendall) Boysen takes a calm, honest look at that quiet midlife whisper: “Is this it?” Instead of dramatising the classic “midlife crisis”, the episode reframes it as a “midlife audit” – a straightforward stocktake of where you are, what matters to you now, and whose scorecard you’ve been using.

Kendell talks through those everyday moments of reflection, when you’re folding laundry or driving home, and suddenly find yourself asking, “Is this what I thought my life would look like?” You’ll hear how many people measure their worth with someone else’s ruler – job titles, bank balances, milestones by 30, 40, or 65 – and why that can make a perfectly decent life feel like a failure.

Kendell shares tools from her coaching work, including the “wheel of life”, to help people see beyond one shaky area and recognise where relationships, health, faith, or purpose might actually be thriving. She highlights ideas like the “arrival fallacy” – the belief that happiness sits on the other side of the next promotion, goal, or milestone – and contrasts achievement with fulfilment: “Achievement answers the question, what have I done?

Fulfillment answers the question, who have I become?” The tone is gentle but direct, with a clear weekly challenge woven in: conduct your own midlife audit, update your scorecard, and ask not “What’s wrong with me?” but “What is this feeling trying to show me?” For anyone in recovery, or anyone reassessing life in the “middle chapters”, this offers structured reflection, a five-day journaling companion, and plenty of reassurance that discontent might be a messenger, not a verdict.

So, is this it – or is this the moment you start measuring success on your own terms?

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