By Anna + Selena · Season 16, Episode 167
Be honest. When was the last time you asked someone you love a question that wasn’t about logistics? “Did you pick up the dog food?” does not count. Most of us are great at talking and a little rusty at real conversation, the kind that tells you something new about a person you thought you knew inside and out.
This episode, there’s no guest in the hot seat. It’s just us. Vanessa Van Edwards invited podcasters to take on her Conversation Challenge to celebrate her new book, Conversation: How to Connect with Anyone and Make Every Interaction Count. The idea is simple: pick five questions from her list, answer them with someone you love, and invite your listeners to do the same. So we did. (We picked five and answered seven. Nobody who knows us is surprised.)
After eight years of working together, we still learned new things about each other. You’ll walk away with a few laughs, maybe a few tears, and a ready-made list of questions to try with your own people this week.
🎧 Listen on Spotify · ▶️ Watch on YouTube · 🍎 Apple Podcasts
In This Episode, We Talk About:
- What Selena would do if she weren’t afraid, and the three-hour Dallas drive that proves she’s already doing it
- The seventh-grade teacher who told Anna “you can’t hack the math,” and what we want every 12-year-old girl to hear instead
- The books we’d write: a children’s book honoring Selena’s tutu and Anna’s fictional nonfiction mystery about your sphere of influence
- Anna’s passion project documenting a midlife pivot, and why she’s choosing to find the joy in it
- The last time we cried, and why a hard cry can mean you were loved that much
- Jo March, Jessica Day, big star energy, and why kindness is not a weakness
Doing It Scared Still Counts
Our first question was a big one: what would you do if you weren’t afraid? Selena didn’t hesitate. Highway driving. Fast speeds, big interchanges, the whole thing. If that fear disappeared, she’d be road-tripping to Oklahoma, to California, anywhere. “I know it prevents me from doing stuff,” she said, and that’s the part that stings.
Then Anna jumped in with a plot twist. When we met in 2018, Selena barely drove the back roads to Anna’s house. This past year? She drove the two of us all the way to Dallas. “While you’re afraid to do these things, you’re still doing them,” Anna said. “Look at the improvement.”
The same theme came back when we talked about which TV character Selena is most like. She picked Jessica Day from New Girl: socially awkward, surprisingly witty, and full of big star energy that people don’t always notice. Anna nailed it: Selena pushes everyone else out front and helps them shine. Then Selena admitted the secret: “I do it because I’m too scared to be big star energy in front of people.”
If you’re a small business owner who runs everything from behind the curtain, this one is for you. Fear doesn’t mean you aren’t brave. Showing up anyway is the brave part. As Anna put it: “No more imposter syndrome of being too scared to be your big star energy, because you’re already that thing.”
Kindness Is a Business Strategy (Aloha and Sh*t)
Our last question was “How do you feel most misunderstood?” Selena’s answer: people mistake her kindness for weakness. A family member once told her she was too soft, too kind. Her response? “Well, my kindness just landed me a $30,000 contract with my best friend.”
Anna broke down why that works. The way Selena approaches business and clients comes with a generosity that most businesses don’t match. Clients know she’ll go the extra mile, and “so much of securing contracts is a trust factor of, these people are going to deliver, and they’re gonna deliver it well.”
Then came the phrase that has become our unofficial motto: aloha and sh*t. It started between Selena and another kind-hearted woman at a retreat, and it means no matter how hard the situation, you meet it with aloha. Not as a doormat. With backbone. It shows up in our texts to each other to this day: “I hope your day’s an aloha and sh*t.”
Want to steal our questions? Here are the seven we answered:
- What would you do if you weren’t afraid?
- What have you always wanted to learn?
- Would you ever write a book? What about?
- What’s your personal passion project?
- When was the last time you cried?
- What book, movie, or TV character are you most like, and why?
- How do you feel most misunderstood?
For our listeners on a busy schedule:
[Add your Streamyard / YouTube watch link here]
Keep. Ditch. Try.
KEEP
Keep showing up, even when it’s scary. Selena still drove to Dallas with her heart pounding. Progress counts more than being fearless.
DITCH
Ditch the idea that kindness is weakness. Generosity builds trust, and trust wins business. As Anna said, “You can be kind and not a doormat at the same time.”
TRY
Try Vanessa’s challenge this week. Pick five questions from the list above and ask someone you love: a partner, a parent, a best friend, or your business bestie. Then really listen.
💡 Reality check: Your clients can feel the difference between a transaction and a relationship. The questions you ask are where the trust starts.
🎤 The Mic-Drop Moment
“You can be kind and not a doormat at the same time.”
— Anna Larson
Prefer to Watch Instead?
Meet Your Hosts: Anna Larson + Selena Conmackie
Anna Larson and Selena Conmackie are the duo behind the Keep Ditch Try podcast, where they serve up real-talk marketing for small business owners, straight up, no sugarcoat. As Fractional CMOs and digital wingwomen, they help entrepreneurs figure out what’s working, what’s not, and what to try next, without the jargon or the ego. Anna is the analog wordsmith with a paper planner. Selena is the Techie Bestie who is sure there’s an app for that. Together, they’ve spent eight years proving business besties are a real thing.
Connect With Us
- Anna in the Sunshine, Anna’s midlife pivot journey: @annainthesunshine on TikTok and Instagram
- Anna: www.nomadabout.com · instagram.com/iamnomadabout · linkedin.com/in/annadlarson
- Selena: www.thehauoli.com · instagram.com/thehauoli · linkedin.com/in/selena-conmackie
- Vanessa Van Edwards’ new book, Conversation: [add book link] · www.scienceofpeople.com
Loved This Episode?
- Rate us on Apple Podcasts. It helps more business owners find us.
- Share this episode with the friend you’d want to answer these questions with.
- Subscribe so you never miss a fix.
Find us both at: www.annaandselena.com
Let’s Be Inbox Besties
Get weekly business fixes, behind-the-scenes updates, and first access to new episodes delivered straight to your inbox.
✉️ Subscribe at annaandselena.com/email/
