Ask the Second Question: Scott Wiederhold on Men’s Mental Health (Episode 78) Artwork

Giving Grief Grace, a Grief Podcast for the Sandwich Generation

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Giving Grief Grace, a Grief Podcast for the Sandwich Generation

Ask the Second Question: Scott Wiederhold on Men’s Mental Health (Episode 78)

November 01, 2026 • Season 2 • Episode 78

0:00 | 57:09

Scott Wiederhold spent 30 years teaching men to close deals, and he came to see that the skills behind great sales (listening, empathy, honest communication) are rarely taught to men at home. In this conversation, the author of Small Town Has Been: F@ck Silence, I Choose Happiness shares what it was like to walk through IVF beside his wife, Teresa, as the support person no one thought to check on; how one honest conversation with his father in Idaho lifted decades of weight; and Scott and Teresa chose, together, to build a full life without children. Shared for Movember, it’s an invitation to notice the men in our lives who may be quietly carrying more than they say.

Three takeaways

Ask the second question. In the back seat of the car, Scott realized everyone was asking how his wife was doing with IVF and no one was asking how he was. Fine isn’t a feeling, so ask the caregiver, and ask the second and third question too.
Say the true thing out loud. When Teresa offered to try a third round for his sake, Scott asked, “What if our family just doesn’t look like a normal family?” and both of them could finally breathe. Unspoken feelings, he says, can turn into resentment and shame.
Take the next smallest step. One honest, curious conversation with his father lifted decades of questions. If you’re not sure where to start, try one honest sentence, one question, or writing down the hard thing for the day and the worst thing you fear will happen.

Closing quote

“I don’t care if you’re angry with me, if you’re sad, I’m here. You can say whatever you want. You’re not going to scare me away.” — Scott Wiederhold

Connect and take your next step

Pre-order Small Town Has Been and learn more about Scott: https://www.scottwiederhold.com
Follow Scott on Instagram: @smalltownhasbeen (https://www.instagram.com/smalltownhasbeen/)
Know a man who says “I’m fine”? Share this episode with him this week, and ask him the second question.
Tell Lisa about a time someone asked you the second question, or the one you wish they had. Email hello@lisahartung.com.
Follow Giving Grief Grace on Instagram: @GivingGriefGrace

However you’re carrying grief today, may someone ask you the second question, and may you give yourself grace along the way. Grief was never meant to be carried alone.

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Special thanks to:

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