Dailey Resources

Three Questions from the Road

May 05, 20252 min read

Alyce and I were traveling with our daughters recently, and in between the fun, the logistics, and all the togetherness, we’ve found ourselves in some really meaningful conversations.

What surprised me wasn’t just the depth of the talks, it was that they weren’t planned. Nothing scripted. Just natural moments that turned into something deeper.

These are the kinds of questions I think are worth asking in any season, especially as life gets more complex and staying connected as a family takes more intention.

Here are three that really stuck with us:

1. What’s an area you’ve grown in recently that you’d like to be recognized for?

One thing we’re noticing: our girls are growing in ways we don’t always see. As they get older, more and more of their life happens outside our view.

It’s like a tree—the branches are visible, but it’s the roots underground that determine health and direction.

This question is about recognizing those roots.

  • What’s shifted in you that others might not notice—but still matters?

  • What growth deserves to be seen, even if no one else brings it up?

2. What’s an inconvenient request you have of the family?

Over dinner, I said, “We’re entering a season where connection is going to get more inconvenient. And our willingness to be inconvenienced for each other will matter more than ever.”

So we asked:

  • What’s a request you have, something that might be inconvenient, but still feels important to you?

One of our kids said, “Can we all agree to visit each other when we start having kids?”
Another added, “I want you guys at my milestone birthdays.”

These aren’t just future plans they’re relational commitments. Quiet ways of saying: I want you there, even when it’s hard.

3. Where are you showing up more like a thermostat than a thermometer?

This one’s simple but powerful.
A
thermometer reacts to the environment.
A
thermostat sets the temperature.

So we asked:

  • Where in your life have you stopped just reacting—and started setting the tone?

  • Where are you becoming a calming presence? A steady leader?

  • Where are you influencing the room instead of letting the room influence you?

These conversations weren’t planned. They happened between bites of dinner on a road trip. But they stuck.

And we think they’re worth bringing home whether it’s around your dinner table, on a walk, or on your next drive together.

Which one speaks to you most right now? Let me know I’d love to hear.

blog author image

Seth Dailey

Seth is the Co-Founder of both The Dailey Group and Keller Williams Gateway in Baltimore, Maryland. He serves as the Operating Principal for the brokerage and as the team leader for The Dailey Group, which consistently helps over 150 families a year. Seth, a Montana native, is passionate about empowering leaders and teaching people to make smart financial moves. Prior to real estate, Seth held his CPA designation and worked as a mortgage lender before joining forces with his wife of 20 years, Alyce. Seth can usually be found at the nearest coffee shop with a personal growth book in hand while scribbling down his next great idea on the back of a napkin.

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