Remember You’re Dying: Annie Dike on Change, Courage, and Finding Meaning Without Tidy Answers

Описание: Welcome to What’s the Point? — the show where we explore what shapes us, what changes us, and what gives our lives meaning over time. In this episode, I’m joined by Annie Dike — a writer whose life has moved through wildly different worlds: a complex early life in Clovis, New Mexico, a career in law, years living and working at sea, and a steady commitment to writing as a way of making sense of experience.

Annie begins in Clovis — a place she once wanted to escape, but later came to appreciate for what it gave her: creativity, closeness with her brother, and a tough kind of resilience built in a childhood without many resources. She also talks about what it was like growing up between two very different environments after her parents divorced — traveling across the country to Alabama and experiencing how different landscapes, people, and family structures can expand your world.

From there, Annie takes us into what she calls her “supposed to” track — the version of success built on prestige, degrees, salary, and stability. She pursued law largely because it felt like a parachute: a way to avoid the financial struggle she knew as a kid. And while she became successful on paper, she also became deeply unhappy — especially working defense for corporations and insurance companies. The more she sensed her work didn’t align with her core, the harder it became to ignore.

Annie also shares the personal side of that same season: marriage, divorce, and the quiet shame she carried as she tried to keep her life looking “fine” from the outside. But that divorce became a turning point — proof she could change something hard. And soon after, she faced the bigger question: if I can change this… can I change everything else that isn’t working too?

A major part of Annie’s next chapter is Philip, her partner — someone who saw strengths in her that she couldn’t see in herself. She describes imposter syndrome as a constant companion, yet also shows how trust and relationship can become a bridge to courage. Their sailing life becomes a living metaphor: night watches, shared responsibility, and the kind of communication that has to be honest because the stakes are real. Annie makes a powerful point: trust is built through communication — even the awkward, pride-challenging kind.

We also talk about identity — how hard it is to answer “what do you do?” when your life doesn’t fit a neat box. Annie’s story is a reminder that purpose isn’t always discovered in one dramatic moment. Sometimes it’s built through reinvention: lawyer, cruiser, writer, speaker, and now novelist again — someone who keeps returning to the work of meaning through words.

Toward the end, Annie reflects on what she hopes readers take from Clovis: a willingness to accept change, and deeper empathy for people different from us — including her brother’s experience and the layers of struggle that can exist beneath the surface. And when I ask the question I ask every guest — “What’s the point?” — Annie answers with a line that lands like a bell: “Remember you’re dying.” Not as darkness, but as permission: take the risk, be brave, do the thing, and live awake.

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Guest Links:

CONTACT INFO:

Website http://www.anniedikeauthor.com
  / anniedike.author  
  / anniedikeauthor  
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The author’s chapter by chapter reading of Clovis
BOOK: Clovis https://www.amazon.com/Clovis-Annie-D...

Quick Episode Summary:

00:00 – Welcome + who Annie Dike is (writer, law, life at sea)
01:00 – Clovis, New Mexico: childhood, poverty, creativity, family
03:10 – Parents divorced + traveling between New Mexico and Alabama
05:00 – Annie’s dad: bull riding, cowboy life, resilience + humor
08:40 – “Get out of Clovis”: school, achievement, pressure, exhaustion
10:00 – Choosing law on the “supposed to” track (money, stability)
12:00 – Practicing defense law + the work not feeling right
13:00 – Marriage, divorce, and keeping it quiet out of fear
14:10 – Realizing divorce was possible… and work might need to change too
17:00 – Leaving the firm: fear, freedom, and starting over
21:40 – Imposter syndrome + Philip seeing strengths she can’t see
23:10 – Agreeing to sail around the world + becoming a strong “cruiser”
25:00 – Cruisers vs sailors (what that really means)
26:40 – Trust on a boat: night shifts, responsibility, judgment calls
29:30 – Redefining success + “enough” + becoming a sailing writer
33:00 – New chapter: selling the boat, travel, writing novels
34:00 – Why Annie avoids “Hollywood endings” in her books
41:20 – Brother’s story + learning to empathize beyond labels
45:40 – Advice: “remember you’re dying” + take the risk
48:00 – “What’s the point?” Annie’s answer + closing