Men, Menopause & the Mic with Sheena

From drunken open mic disasters to emceeing festivals for 17,000 people, Sheena didn’t “find” her voice, she fought for it.
This one’s about stage fright, self-respect, perimenopause, bad dates, and raising kind humans in a messy world.

Summary

This week in The Pond, Siobhan sits down with singer, performer, and emcee Sheena Lokelani for laugh-through-the-chaos conversation about music, motherhood, dating, and growing into your power.

Sheena shares how her music journey started in a Filipino family band in her twenties, paused for motherhood, and then unexpectedly reignited through open mics (including one gloriously boozy, very nervous first attempt at Fireside). What followed? Festival stages, packed restaurants, and emceeing crowds of up to 17,000 people, while still admitting she gets stage fright every single time.

They dig into what almost made her quit music (spoiler: too many opinions not enough joy), how she reclaimed it on her own terms, and why music has to stay therapy, not pressure. From there, the conversation moves fluidly through divorce, co‑parenting with respect, online dating disasters, perimenopause realness, raising emotionally intelligent teens (including a nonbinary kid), and what it means to have standards without bitterness.

Funny, tender, political without being preachy, and deeply human, this episode is about saying yes to scary things, protecting your energy, and remembering that being kind, and staying soft in a hard world, is still radical.

Sheena Lokelani

Sheena Lokelani is a Bay Area–based singer, guitarist, and emcee whose solo acoustic sets and festival appearances have quickly made her a local favorite. She’s hosted and performed at major Filipino cultural festivals in San Francisco and Alameda, and holds recurring gigs at neighborhood bars and restaurants where she’s as likely to get the whole room singing as she is to make you cry with a ballad. A devoted mom of two, Sheena balances late-night shows with raising teenagers, co‑parenting, and using music as her primary form of therapy and storytelling.

💡 Key Takeaways

  • You can be terrified and still do the thing.
    Stage fright doesn’t have to disappear for you to step on stage; courage is often just saying yes while scared.

  • Redefining success after divorce and motherhood.
    You’re allowed to shift from “just a mom” to artist, performer, and full human with your own dreams.

  • Boundaries are self-respect in action.
    From co‑parenting to ex-friends to creepy fans, you can opt out without being cruel—and that’s powerful.

  • Dating after 30+ is…a whole saga.
    You’re not alone if you’re exhausted by apps, weird encounters, and trying to explain your layered life story.

  • Raising decent humans matters more than your highlight reel.
    Teaching kids kindness, nuance, and critical thinking may be the most important legacy you leave.

“Maybe they just think it’s my version of the song. Maybe this is the remix…where I skipped three verses.”

– Sheena

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