“When you see someone putting on his Big Boots, you can be pretty sure that an Adventure is going to happen.” – Winnie the Pooh
When my daughter, Miss O, was two or three-years-old, she took scissors to a squishy ball just minutes before we were supposed to leave to meet my dear friend, Katie. I was shocked – the mess, the destruction of a toy, our inability to be on time.
So when I apologized to Katie for being late and told her why, she laughed said one thing that changed my parenting experience forever (and for good). She said, “Everything is a science experiment.”
All of a sudden, the light bulbs went off in my head. Children weren’t supposed to sit in a corner and play according to the manufacturer’s directions – they were supposed to test things out, see what happens, and think outside the box. No wonder Katie’s children (already grown at that time) are such delightful people.
Two things stand out about this a-ha moment. First, the generosity of friends. Parenting doesn’t come with a manual so I have often relied on my friends to show me the way – and they have been so generous to do so. Second, the science experiment comment didn’t just change my expectations of how my kids should behave – it opened the door for me believing that I didn’t have to know everything about what we would try as a family.
I was fortunate to be able to explore that family adventure theme on this week’s The Life of Try episode with my friend, Natasha Dillinger. Natasha is an enthusiastic, yes-to-adventure, generous parenting friend who regularly shares her secrets on Instagram. In our conversation, three takeaways stood out to me:
- How saying yes to adventure can become a family habit
- Simple strategies for planning group trips
- Why flexibility and humor matter when plans fall apart
In our conversation, Natasha shares practical ideas for organizing group trips, helping children feel ready for unfamiliar experiences, making adventure affordable, and redefining success when things go wrong. Because sometimes the rain, the missed train, or the unexpected detour becomes the story everyone treasures most.
- Click this link to watch in a browser: The Power of Saying Yes: Raising Adventurous Kids with Natasha Dillinger
- Subscribe to The Life of Try on Spotify, Amazon Music, or Apple Podcasts
- Subscribe to the YouTube channel: https://www.youtube.com/@thelifeoftry
Links for this episode:
The Power of Saying Yes: Raising Adventurous Kids With Natasha Dillinger transcript
Natasha’s suitcasesinseattle on Instagram – If you are planning on visiting Seattle, the Pacific Northwest or just want adventure inspiration, I’d HIGHLY recommend subscribing!
Other Episodes You Might Enjoy
When Your Plans Fall Apart | How to Stay Resilient, Adapt & Keep Moving Forward
How to Create Opportunities in Life | Motive + Means = Success Mindset
The Courage to Try Something New | Lindsey Goldstein on Growth, Failure & Reinvention
Success isn’t always about finishing first. Sometimes the greatest victories belong to those who stay prepared, keep growing, and never stop trying.
(featured photo from Pexels)
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