Plot Twist! Reinventing Your Life Halfway Through It with Henry Oliver

Send us a text

You ever get that nagging voice saying, This isn’t it? That “oh crap” moment where you realize you’ve been climbing the wrong mountain? That’s exactly what happened to my guest today, Henry Oliver—former policy wonk turned style blogger and unapologetic vibe curator.

Yep, Henry ditched the government life to dive headfirst into what actually lit him up: writing, personal style, and, let’s be real, loafers. This episode is a total permission slip to pivot hard, even if you’ve invested years (or decades!) going in one direction.

We get into why midlife reinvention doesn’t have to be a crisis—it can be a party. And Henry breaks down the subtle but powerful difference between asking, “What do I want to do? ” vs. “Who do I want to be? ”

If you’ve ever felt stuck or like your life is technically fine but secretly soul-sucking—this one's for you. You’ll laugh. You’ll think. You’ll probably Google “good tweed jackets.” Henry’s got that effect.

What’s Inside:

• How Henry made a major midlife career pivot (and what helped him finally take the leap)
• The identity crisis that can come with “success”
• Why style isn’t shallow—it’s a portal to authenticity
• A powerful reframe for asking, “What do I really want? ”

So, real talk—

Are you living a life that actually feels like you? Or are you just playing a role you fell into 10 years ago and forgot to question? If you’ve been craving a fresh start—or even just a fresh vibe—this episode might be the sign you needed. I want to hear your thoughts: if you could change one thing about your life right now, what would it be? DM me on Instagram and let’s talk plot twists.

Mentioned In This Episode:
Henry Oliver’s blog (The Common Reader)
The Second Act
Registration is now open for the Membership Experience
Oonagh Duncan (@oonaghduncan) on Instagram
Fit Feels Good
Goals, Grit and some Woo Woo Shit with Oonagh Duncan