Failure. It’s a word that hits hard, especially when you’re putting your heart into something—whether it’s a project, parenting, or a personal goal. But in our family and in our journey as entrepreneurs, we’ve learned that disappointment doesn’t have to define you.
In this episode of Rollin’ With the Dolans, we shared real moments from our lives—times when things didn’t go as planned, and how we handled it. Spoiler alert: faith, mindset, and reframing failures made all the difference.
“You can either be paralyzed by it or motivated by it.”
That’s the line we started with, and it sums up the heart of this episode. Whether you’re launching a business or navigating a tough season with your kids, how you respond to failure shapes your future.
We talked about some famous stories—like Walt Disney getting fired for a “lack of creativity” and Oprah being told she was “unfit for TV.” It’s wild to think that people we see as icons were once dismissed and overlooked.
But our goal wasn’t to talk about them—it was to talk about us.
A Marathon That Didn’t Go as Planned
One of the stories we shared was about a recent marathon that didn’t end with a finish line.
“I’ve run hundreds of races, but last October was the first one I didn’t finish… and yeah, if you don’t finish, it’s a failure. That’s the goal.”
And yet, the response wasn’t defeat—it was action.
“I shook it off, signed up for another race right away, and ran it less than four weeks later. Then I booked the hotel to go back and finish the one I didn’t complete.”
That’s the power of turning failure into fuel.
For Entrepreneurs, “Done Is Better Than Perfect”
We also talked about how perfectionism holds people back—especially new entrepreneurs.
“People want this perfect package to present… I’m guilty of that too. But sometimes, done is better than perfect.”
Waiting too long to release your idea or product can actually delay your growth. You only get real feedback once something’s out in the world.
And if it doesn’t work? It wasn’t a failure—it was research.
This mindset shift came from entrepreneur and author Rachel Rodgers, who shared it during her interview on the Side Hustle Pro podcast. She explained how many people—especially women and people of color—tend to internalize failure, while others approach it differently.
As we put it in the episode:
“She was saying that when you ask a white man about failures, they don’t see it as failures. They see it as, ‘Oh, it was just a research, like a strategy research project that we did.’ And I was like, you know what? That is actually a good way to look at it.”
That small shift—seeing something as strategy instead of failure—can give you the freedom to move forward without shame or hesitation.
What About Our Kids?
We also got into how disappointment shows up for our teens—especially in sports.
“They’ll sit on the bench, and start to believe things like ‘you weren’t good enough to play a quarter of the game.’ It’s heartbreaking if we don’t talk about it.”
Helping kids navigate those emotions, without attaching their identity to the outcome, is one of the hardest (and most important) parts of parenting.
“We try to talk to them after the game—let them feel it, but also reframe it. That’s where the life lessons are.”
Faith as a Foundation
When things fall apart, sometimes faith is the only thing that brings perspective.
“When I actually stop and turn to God, everything else just feels smaller. Like, okay, this thing that felt huge… really isn’t.”
And that’s not just about religion—it’s about grounding. It’s remembering who you are, how far you’ve come, and what actually matters.
Final Thought: Change the Language, Change the Outcome
Instead of calling it a failure, we came up with words that reflect what those moments actually are:
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Life lessons
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Building blocks
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Course corrections
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Growth opportunities
Our favorite?
“It’s not a failed product. It’s a building block for the next one.”
We hope this episode—and this post—encourages you to keep going. To brush yourself off, and take that next step. Because sometimes the only way forward… is through.
Want more real talk?
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