Dealing with Disappointment: Turning Failure into Fuel

Failure is part of the journey—but how we respond is everything. In this episode of Rollin’ With the Dolans, we open up about dealing with disappointment in real life: from parenting and entrepreneurship to marathon goals and missed opportunities. We share personal stories, a few famous setbacks (hello, Oprah!), and how faith and mindset help us move forward instead of getting stuck.

Whether you're building a business, raising kids, or just tired of setbacks, this is a real conversation on turning failure into fuel.

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Transcript

Welcome to Rollin' With the Dolans.

Our podcast focuses on the joys and challenges of blending families, our interracial marriage, parenting children of multiple ages, and the journey of entrepreneurship.

We share our daily life experiences with a positive but real perspective. And today's topic is dealing with failure. So, there's a couple of different ways you can deal with it — and we’ll hit those at a high level — that is, basically: be paralyzed by it or be motivated by it.

Okay.
 All right. You wanna start?

I did have an idea of talking about some famous failures.

Okay. All right, go ahead.

One thing that I learned was Walt Disney was fired from a newspaper for lack of creativity.

What do you mean? Fired from a newspaper?

So, he was probably like a cartoonist or something like that.

Oh, okay.

And fired for lack of creativity.

Oh, okay.

And then he was bankrupt with his early ventures.

Okay. What year was that? Did it say? How many years later did he actually become what he is now?

I don't remember.

Okay. This was a little while ago I wrote down the specifics. Oh, and then Oprah Winfrey was fired basically because she was "unfit for TV" in an early anchor position.

Yeah. I think most people know about that story.

That’s true. So basically, a lot of high-profile people who you look at as unbelievably successful have had their failures.

Yeah, that's true. All right, so you wanna talk about like one failure that you can remember?

I think you should start first.

Me?

Yeah.

Oh, one failure that I can think of is... oh, I can't think of anything. I have several, but I can't think of anything off the top. Can you?

Me, for you?

For me.

No, you're always a success, whatever.

But I will say that I was listening to this podcast actually yesterday, and it was from Side Hustle Pro — my favorite podcast. Anyway, she always interviews women entrepreneurs. Most of the time, they are minorities, which I love. But anyway, so she had Rachel Rodgers on, and she’s an author of, like, We Should All Be Millionaires — I think that’s what it’s called.

But she was saying that a lot of times as entrepreneurs, you have to change your mindset. You don’t look at those failures as failures — you look at them as research. She said when you ask a white man about failures, they don’t see them as failures — they see them as, “Oh, it was just a strategy research project we did.”

And I was like, you know what? That is actually a good way to look at it. Because a lot of times people are like, “Oh my gosh, I failed,” and then they don’t get up and recreate things because they’re so paralyzed by the failure, when really it’s not a failure. It was just God showing you — I’m gonna bring God into it — showing you that, okay, that was a little bit wrong as far as your approach, but you should learn from that and move forward.

A hundred percent. And I think entrepreneurship is a good example. There’s a lot of things... like, you can’t go through — I guess it’s analysis paralysis — where you just keep analyzing. You have to put things out there and try things before you can move forward. Sometimes, if you wait to create the perfect product or the perfect service, you're gonna take forever, and you're not gonna get any feedback. And then it might not even be the right audience.

So you do have to put things out there, and sometimes it's not well received — which I feel like a lot of entrepreneurs struggle with, because they want this perfect package to present. And I'm guilty of that too. And then all of a sudden, one day I heard a saying: "Done is better than perfect."

So sometimes you just have to put it out there, and hopefully it's not a— I don’t even want to say failure — hopefully it's not a research project. And then you just have to reset and redo things.

Who struggles with that the most? What type of entrepreneurs?

Who? New ones.

Oh, okay.

So a lot of times when you're new to creating products and services, you put too much into it the first time around. And then you learn over time: “Okay, I'm not gonna kill myself over this,” ’cause I know how the last time... the last thing happened, I had to change X, Y, and Z afterwards.

That makes sense. Yeah. Okay, so you wrote down some positive terms for failure.

Yeah. I was gonna give you, quickly, one of my recent failures.

Oh, okay. All right, go ahead. That's even better.

So, I've run hundreds and hundreds of races. And last October I ran a marathon — and I could give you about five excuses as to why — but nonetheless, I did not finish the marathon.

It’s the first-ever race that I recall not finishing out of hundreds and hundreds.

Yeah.

But would you consider that a failure?

Yes.

Oh, I didn't— if you don’t finish — your goal is to finish. You can have multiple goals, but the main one is to finish. If you don’t finish, you failed.

And yeah, I can look at the accomplishments and stuff out of it and turn it and spin it in a positive way. The biggest thing is — you know — like, I just shook it off and it was like, within a day, I planned the next marathon. And I did the next marathon in the shortest turnaround time ever — it was like a month, less than a month.

Yeah, like 27, 28 days or something like that.

Yeah.

Four weeks. That’s when we went to Vegas.

Yeah. And then also, I reserved a hotel for the same place where I failed. I booked that for the next time — 2025 — because I’m planning on doing it again.

So the main thing is, for me, it motivates me. I’m not gonna let that stop me. I’m gonna come back and beat it.

Yeah. Okay. I didn’t think that you saw it as a failure.

I did.

But maybe it’s ’cause — there’s no way I’ll be trying to run a marathon. Definitely not a full marathon.

But, okay — so I was looking at these positive terms that you wrote out that I think are great because instead of saying failure, here are some terms that you can say:

• Life lessons
• Growth opportunities
• Learning experiences
• Stepping stones
• Growth moments
• Opportunities for improvement
• Turning points
• Building blocks
• Course correction

So which one stands out to you?

I'm gonna choose building blocks, simply because the way you presented that scenario earlier.

Okay.

You know — it's not a failed product. It’s basically a building block to get to the next one.

Okay. I would say course correction, because you learn from your quote-unquote “failure.”

Yeah.

And they all are learning experiences.

Yeah.

And I did want to — if we have a minute — address one other thing.

Uh-huh.

This is — and a lot of it is — dealing with our teenage kids, and trying to get them to understand the disappointment in things. In a lot of cases, in sports, we’ve seen them put a lot of hard work and effort into things, just to get disappointed — whether or not they didn’t win the game or they didn’t get to be in the game because the coach decided they’re not the best one.

For some reason, it’s the disappointment. And a lot of these things — they might feel like they failed and things like that — but what are your thoughts on that?

I think that at a young age, it’s good for them to understand and see that things are not always gonna go the way they want them to. But I think that you have to follow that with a conversation so they don’t see themselves as a failure.

Because if you don’t have a conversation about it, they’re gonna think about it. They’re gonna stew on it. They’re gonna start hearing negative thoughts of, “Oh, you were a failure. You weren’t good enough to play the whole quarter. You weren’t good enough to play a fourth of a quarter — a quarter of the game.”

Yeah.

You know what I mean? But yeah, so their interpretation... I think we are good about talking to them about the game and figuring out how they felt about it.

Yeah.

And just — it is a life lesson.

Yeah.

To get them to understand that these things are often out of your control. There are so many different variables — whether you're an entrepreneur, or if you work for a company — regardless, there’s a lot of things involved that you can’t control.

Yeah, that’s true. That’s true. But just really teaching them they can learn from that.

And as a parent, it’s sad to see. It’s sad to see when they get so disappointed. And in some cases, they’ll just get— what’s the word?

Say demoralized.

Demoralized, in some cases.

Yeah. And you’ve heard that from your clients — in their kids as well — like, how do you deal with that so they can bounce back?

So all related.

Okay. I have one more que— I have a question for you. And this is one of the questions that you actually wrote — or I got from research. It says: How has your faith influenced your perspective on life lessons, growth opportunities, and learning experiences?

That is huge. I think that I don’t turn to it enough — which I’ve shared before — like, you’re much better as far as relying on that. But when I do, in the grand scheme of things, almost everything just seems irrelevant.

Yeah.

I think that when you look at how blessed we are, how much we have, all the different opportunities we have — you look at that and it’s like, okay, it’s not such a big disappointment anymore.

I agree. Yeah.

Okay. Any more questions?

I think that’s it.

Or comments?

No, I think — just to sum it up — is: focus on the positives as much as you can. It’s not always easy, but brush yourself off and get up the next day, and something’s gonna happen.

Yeah.

I think my huge takeaway from this is — don’t look at it as a failure. Look at it as a learning opportunity or learning experience. What do you think?

Absolutely.

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So until the next time — have a… let me see, let me get a good adjective…
Marvelous day.
Have a superb week.
Superb? Okay, wait, let me beat that — have… ooh! A faith-driven day.
Yes.
Wonderful.
All right. Bye!