July 9, 2025
Resilient Optimism
Ever feel like you're drowning in challenges while trying to stay positive? That tension between acknowledging reality and maintaining hope is exactly what this episode explores through the lens of resilient optimism. We dive deep into the entrepreneurial journey — not the glamorized social media version, but the raw reality of sitting in 95-degree heat for hours to make $40, losing $1,200 worth of merchandise before a major event, and somehow maintaining belief that better days are ahead. T...
Ever feel like you're drowning in challenges while trying to stay positive? That tension between acknowledging reality and maintaining hope is exactly what this episode explores through the lens of resilient optimism.
We dive deep into the entrepreneurial journey — not the glamorized social media version, but the raw reality of sitting in 95-degree heat for hours to make $40, losing $1,200 worth of merchandise before a major event, and somehow maintaining belief that better days are ahead. These aren't just business lessons but life lessons about how we face adversity.
The distinction between blind optimism (naively ignoring problems) and resilient optimism (acknowledging challenges while maintaining confidence in your ability to overcome them) frames our conversation. As Winston Churchill wisely noted, "Success is moving from failure to failure without loss of enthusiasm" — a perfect description of the entrepreneurial mindset required for long-term success.
What makes this approach so powerful isn't just feeling good — research shows resilient optimism leads to improved performance, greater satisfaction, better health outcomes, and enhanced wellbeing. It's a mental framework that allows you to navigate difficulty while maintaining forward momentum.
The beautiful thing? Resilient optimism isn't something you're born with — it's a choice and a muscle you can strengthen. Even the most pessimistic person can make a decision to approach challenges differently starting tomorrow. What we focus on expands; what we appreciate appreciates. Are you ready to transform your relationship with obstacles by viewing pressure as a privilege and problems as opportunities? Listen now to discover how.
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00:00 - Introduction to Resilient Optimism
07:30 - Fair Season Begins
16:15 - The Reality of Small Business Ownership
23:50 - Battling Negativity and Self-Doubt
31:20 - Blind vs. Resilient Optimism
37:10 - Choosing a Positive Mindset
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Resilient optimism is a mindset that combines a positive outlook with the ability to bounce back from setbacks.
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It's not about ignoring difficulties, but rather facing them with a belief in one's ability to overcome challenges and find a path forward.
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Today, on Share the Struggle Podcast, we dive headfirst into resilient optimism.
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Let me tell you something Everybody struggles.
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The difference is some people choose to go through it and some choose to grow through it.
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The choice is completely yours.
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Which one you choose will have a very profound effect on the way you live your life.
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Will have a very profound effect on the way you live your life.
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If you find strength in the struggle, then this podcast is for you.
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If you have a relationship that is comfortable with uncomfortable conversations.
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Uncomfortable conversations challenge you, humble you, and they, they build you.
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When you sprinkle a little time and distance on it, it all makes sense.
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Most disagreements, they stem from our own insecurities.
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You are right where you need to be Black on time.
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We're eating flatbreads the whole day gone.
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We're living our lives what it, do what it hot.
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Do-do-do-do get loud.
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Oh my, am I so excited to be back with you.
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Oh, it's true, girl.
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You know it's true.
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I miss you, boo.
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Hope all is well.
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I hope your week is going swell.
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Okay, welcome to another winning Wednesday, episode 261.
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And I hope you're ready to have a little fun on today's episode of Share the Struggle Podcast 261.
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Y'all already knows what that means.
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That means we've been doing this week after week after week for over five hard years baby 261 consecutive episodes.
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It all lives at wwwsharethestrugglepodcastcom and available on all major podcasting platforms.
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I appreciate y'all.
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I thank y'all.
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Happy 4th of July to y'all.
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I hope everybody had a terrific 4th of July.
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A few weeks ago we discussed all them folk out there trying to cancel our independence, out there trying to deny us a celebration.
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So I trust all you beautiful, loud, proud Americans out there, y'all celebrated your asses off for the 4th of July.
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It was a special one for me this year because this was the first 4th of July with my little baby girl.
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So we went to the fireworks, a small local fireworks show that does a great job.
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She wasn't too excited about it.
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The ear muffs, head muffs, headphone scenario uh, she was kind of fighting that, not trying to keep that on her little squash.
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So big daddy cradled her and got her out of the chaos and she watched some of it from a distance and all that good stuff.
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But uh, it was just.
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It was just fun and fulfilling to do those things with my little girl and my wife and my mom.
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So that was something off the bucket list, right there y'all.
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So I hope you guys found a way to have a bucket list.
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4th of July Things are getting super crazy over here at Loud Proud American because I am proud to announce to you it's fair season.
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Baby, oh my goodness, do I love a good fair.
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Now here's another confessional for you.
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I'll grab that Cabela's catalog, I'll place my left hand on the catalog, beat your little eyes to the sky and give a full frontal confessional from the sky.
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When I first started the brand, I took every single fair that I could take because I just love doing fairs and I just traveled around doing as many as I possibly could.
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But over the years, over the five years or so that we've been on the road doing these things, we've adapted and molded and changed our schedule quite a bit.
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It's changed a lot this year and I do feel it's going to change even more next year.
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So currently we only have three fairs on the schedule, but we're excited that the first fair of the season is this week.
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On the day that this episode drops, on a winning Wednesday, I'll actually be headed to the fair to start the setup.
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It's always a ton of moving parts when it comes to fair season, so I'm just going to give you a little screenshot of this, and this is going to really roll into a question that I get all the time hey man, what's it like owning your own apparel brand?
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So, small business owners out there, entrepreneurs, you often get those questions like what's it like to own your own business?
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What's it like to work for yourself?
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And specifically for us, it is what's it like to own your own apparel brand?
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And for us, there's a lot of hard work and sacrifice.
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There's a lot of give and give, we should say, because there's not a lot of give and take, right, there's a lot of give, give, and that trickle down effect happens not only for me but for my entire family.
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So just to give you a little synopsis as to how things are going and what we're up to around here my wifey.
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I don't know if we had the opportunity to announce this on the podcast or not, but she bought a brand new camper Well, not brand new, brand new to us, I think it's a 2018.
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And last week we were getting set up for the 4th of July at Bentley Saloon and we I had a showing with a couple and showed these folks our old camper and they ended up buying our old camper.
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Allie agreed to deliver it.
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So last week just to kind of make this connection here, let's start on Thursday On Thursday I'm up at five in the morning, bring my mom to work, I go to the saloon and I start building the tent by myself in the morning, setting everything up before it gets super hot.
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Allie wakes up, takes the baby, brings her to a friend's house where she spends time with Allie and Joe and their family, which she absolutely loves, which is fantastic and a blessing.
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So I'm working on the tent until about noontime.
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Pick up the baby, run to Home Depot, come home, show the camper to these folks.
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They agree they want to buy it.
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Allie takes a lunch break, goes to the bank, does the bill of sale, sells the camper.
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I end up going to pick my mom up from work, come home, do a couple things, try to work.
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Allie gets out of work, we hook on to the camper and we deliver it 45 minutes away.
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Come home, get back to work.
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That's a scenario for one day, okay.
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Friday morning get up, get coffee with my mom, get the baby settled in, go to the saloon, finish my setup for my display, open and sell all day.
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This year 4th of July was a Friday, right, so that was a pretty successful day for us.
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Friday get done, meet the family, go do some fireworks.
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That whole deal.
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Saturday another day at the saloon, trying to do all I can to make as much money as possible.
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Allie's running around getting things for the new camper, getting ready for fair season.
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Fast forward to Sunday morning.
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Now I'm just going to let y'all know it's been a hot ass week around here.
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We're talking 90 plus degrees on Saturday and Sunday.
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Sunday morning I get up.
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A really good friend of mine, a brother of mine, a loyal one, a great one, jay Lemery, decided to volunteer his time to help me and my mama over here.
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My mom's deck that my dad built is falling apart.
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It's no good.
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So we're trying to do a little deck demo.
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So here we are first thing in the morning on Sunday trying to get some demolition done before at 9 in the morning.
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We get as much work as we can get done on that and then we transition over to doing some work on the camper before the wife has to haul it off to the fair.
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Ali um has um to take off and go to the saloon and open up our vendor display.
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My mom has to take the baby, me and jay do a few things on the camper and then roll over to the saloon and we switch places.
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Ali takes off, comes home, her and my mom hook onto the camper, they drive up to the fairgrounds, drop the camper and get everything settled in there and I sit in the parking lot of the saloon with Jay trying to sell stuff.
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And as we start talking about what's it like man owning your own apparel brand, you think about all those sacrifices, all those things we're talking about, different families making commitments to help us right.
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So Allie's, our friend of ours named Allie, is watching the baby.
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Her and her family are taking time and one of these days Jay's taking time, allie's dad's taking time.
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My mom is my wife is.
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You understand what I'm saying?
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That's what I mean by sacrifice, and not all sacrifices come just from you.
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So you get to spending Sunday at the saloon, me and Jay hanging out, and it's 90, 95 degrees, super freaking hot, and I sat there all day.
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We opened the saloon vendor spot at 11.
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And it was about 4 o'clock when I decided I have an opportunity to close this thing and start packing.
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So just put this in its perspective, folks.
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We're talking 95 degrees.
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Okay, I just wanted to pause on that.
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So you think about it.
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I'm not built for this kind of heat.
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Okay, I'm built more for the Arctic.
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Let's be honest Five hours, 95 degrees, in a tent you know what I mean.
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Or shall I say, sold 40 bucks, $40.
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We had $40 in sales.
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And by the art of bus math here, folks, there's also a cost involved with this right.
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That's $40 gross.
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That's not profit.
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Let's just say, on a very fortunate scenario, you made 20 bucks profit.
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So, 95 degrees, sitting around.
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What did we say?
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It was five hours for 20 bucks.
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Here is your business owner, this glorious entrepreneur lifestyle, owning an apparel brand, making $4 an hour, selling t-shirts in 95 degree heat.
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But if that doesn't make you want to quit your day job and start a small business, man, I don't know what does.
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Here's the thing, folks.
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It gets worse.
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Okay, it gets worse because it's the last day of the event.
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You know what I got to do.
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I got to pack baby.
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I got to pack.
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My wife and my mama and my baby are at the fairgrounds dropping the camper.
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Here I am having to pack all right, 20 by 20.
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Tent, display loader with apparel, all the good stuff, tent screwed into the pavement, electrical run, all the stuff, right, all the things.
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I gotta tear all that down by myself, 90 plus degrees in the heat and um, that's just the cost of doing business, baby, that's just the price of living L-I-V-I-N.
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That takes me about two hours, two hours to pack the bus.
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So you do the math here, folks, right?
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What are we at?
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Like seven hours, $40 grows, maybe $20 profit Somewhere around $3 an hour, pay to own your own business.
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It's a glorious lifestyle, I must say myself.
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But the great Winston Churchill said Success is moving from failure to failure without a loss of enthusiasm.
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Because here's the thing I'm sitting in this tent sweating my ass off, not making any money, then having to pack, and I'm feeling optimistic.
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I am full of optimism Because, as I just said to y'all, fair season starts.
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It's a new place, it's new face.
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Fair season starts, it's a new place, it's new face, it's new things, new opportunities, new goals, the whole nine.
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It's a dose of optimism.
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Things are changing, things are happening.
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When I think about being a small business owner, it's probably one of the biggest qualities that you have to have is optimism.
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You have to remain optimistic, you have to have this positive outlook.
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You have to see obstacles as opportunities.
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And I got to say, over the past few weeks I caught myself doing something and we've talked about it on here week after week.
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I allowed myself to let too much negativity enter my circle.
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I allowed myself to shed a little self-confidence and listen to the doubters.
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I allowed myself to listen to the naysayers, to be affected by the gossip about the nonsense runaway negative train.
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You know what I mean.
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We've talked about that over the past few weeks.
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When people are saying things behind your back, you're hearing things, you're not feeling welcome, those things start to have a trickle-down effect on you and your positive outlook.
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And if you go into an event, if you go into a scenario not feeling positive, you're not going to have positive results.
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Now I'm going to say I went into the 4th of July stoked.
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So it's not like I went in there thinking like, hey, I'm not going to make money and woe is me.
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That's not the case.
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But over the course of time I've realized I've let too much negativity enter into my mind and change my mindset, and that's not something that we need to sign up here.
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For folks Okay, that goes for all of you it doesn't matter what it is.
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You don't need to be a business owner, you just need to live, to be affected by negativity.
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To allow that negativity, some of that doubt, some of the trash talk, to enter your mind and create self-doubt, to create self-sabotage.
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It doesn't matter what area of the life it is.
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It could be your work, it could be your family life, your close personal relationships, it could be your marriage, your relationship with your children, it doesn't matter.
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You let your mind create self-doubt and self-sabotage.
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It will derail you.
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But the thing is, folks, your mind is working against you, not because it hates you but because it wants to protect you.
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Your mind is wired for protection.
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It is wired for safety.
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It is fight or flight.
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Our mind is worried about all the negative.
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It's worried about all the nonsense that's going around so that we can identify it, acknowledge it, protect ourselves.
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But the thing is that's what our brains focus on.
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That's some of the shit that, like news channels and you know, clickbait articles and social media ridiculousness focuses on.
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It's that shock and awe headline that's going to grab your attention.
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That's going to make you read.
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It's the crazy ads and photos that you just need to look at.
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It's rubbernecking an accident on the interstate, because you have to see what's going on.
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Those things that grab our mind's attention.
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That's what happens when you let doubt in.
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That's what happens when you let naysayers in.
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I do the best I can to not let anybody else in, because I am a resilient optimistic.
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You like that, right?
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You like resilient optimism?
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I believe you do, because I know that I do, because I was sitting around in the tent sweating.
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You could say sweating and regretting, and the only thing I mean about regretting is I'm so damn busy right now.
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If I knew ahead of time I was going to make $40,.
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I would have got up at five in the morning, packed my tent before the sun got real crazy.
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I would have done all the work I needed to do at home and then I would have locked myself in the air conditioned office and worked my ass off to get ready for fair season.
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But you don't know that.
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That's the scratch ticket.
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That's the chance you got to take.
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So I got to go set up.
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I got to meet the people, I got to try to sell, I got to try to do the best I can to provide for my family.
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So I have to open.
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So, not knowing what you don't know, you got to show.
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If you don't know how it's going to go, you don't know the outcome.
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So you got to show up and you got to put up the fight and you got to make it work.
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So as I'm sitting there sweating and regretting because if I knew that I wasn't going to make any money, I would have been a lot more productive as I'm sitting there, I'm thinking about how optimistic I am.
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I'm thinking about how excited I am for a familiar event on the schedule and a brand new event to soon to be part of the schedule, all those things has me feeling pretty damn optimistic.
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And I started thinking about it.
00:17:49.243 --> 00:18:02.184
And you guys are going to think this is funny because I'm sitting there thinking about myself and my outlook and I said, man, blind optimism, that's me right now, blind optimism.
00:18:02.184 --> 00:18:05.911
I don't have eyes for anything but positivity.
00:18:05.911 --> 00:18:08.743
I'm focused on making things happen.
00:18:09.144 --> 00:18:14.871
If you guys have been listening over the past few weeks, you know some of the struggles, you know some of the the mistakes, you know what we're up against.
00:18:14.871 --> 00:18:21.863
I'm not going to beat my chest all over being in the red and missing payments, like we talked about last week.
00:18:21.863 --> 00:18:23.409
We already know that story right.
00:18:23.409 --> 00:18:30.508
But here I am saying, man, you're blind to it, you're immune to it, you're just an optimistic son of a bitch.
00:18:30.508 --> 00:18:34.663
You need an optimism SOB t-shirt, just thought about that.
00:18:34.663 --> 00:18:37.939
So I'm getting all jacked up thinking, man, this is pretty cool.
00:18:37.939 --> 00:18:42.867
I don't think anybody has ever used the words blind and optimism.
00:18:42.867 --> 00:18:45.112
This is going to be so cool.
00:18:45.112 --> 00:18:48.663
Okay, you are onto something, joe, cool.
00:18:48.663 --> 00:18:50.886
Well, I looked it up.
00:18:50.886 --> 00:18:54.113
It's not the best quality, okay.
00:18:59.339 --> 00:19:06.912
Blind optimism is an excessively positive outlook that ignores potential problems or risks, often leading to inadequate planning and negative consequences.
00:19:06.912 --> 00:19:18.631
It's characterized by a refusal to acknowledge negative realities and a tendency to overestimate one's abilities and underestimate potential obstacles.
00:19:18.631 --> 00:19:21.442
You, son of a bitch, get out of here iPhone.
00:19:21.442 --> 00:19:21.942
I don't need to.
00:19:21.942 --> 00:19:22.905
No, I don't.
00:19:22.905 --> 00:19:24.569
That's not me.
00:19:24.569 --> 00:19:25.673
I don't need to read that.
00:19:25.673 --> 00:19:32.489
But I got all jacked up thinking I was onto something, and then I started reading this because I convinced myself this is you, this is you.
00:19:32.579 --> 00:19:35.390
And then I found out well, this actually is a thing that exists.
00:19:35.390 --> 00:19:44.714
And then I peacocked my chest out and go get my feathers up and say, hey, you're preparing to read the greatest definition of you ever.
00:19:44.714 --> 00:19:51.151
And then I start reading Excessively positive outlook that ignores potential problems or risks.
00:19:51.151 --> 00:19:55.784
That could be me, but it makes me angry.
00:19:55.784 --> 00:19:58.148
If it is, that's not me.
00:19:58.148 --> 00:20:01.241
Okay, often leading to inadequate planning.
00:20:01.241 --> 00:20:02.525
Okay, my wife would say.
00:20:02.525 --> 00:20:04.669
I'm not always organized.
00:20:04.669 --> 00:20:05.490
Is this me?
00:20:05.490 --> 00:20:07.721
No, no, no, this better not be me.
00:20:07.721 --> 00:20:09.845
Why did you have to look into this?
00:20:09.845 --> 00:20:11.807
This is what happens in my little mind.
00:20:11.807 --> 00:20:13.210
So I said to myself.
00:20:13.210 --> 00:20:17.516
I said self, it's going to be a different version of optimism.
00:20:17.516 --> 00:20:18.540
That's me.
00:20:18.540 --> 00:20:25.673
So I let that stew, I let that simmer in my noggin, I pack up.
00:20:25.673 --> 00:20:36.205
I come home, lay down on the freaking floor in the living room, playing with the baby and talking to the wife and asking her how her day was and how on the camper was.
00:20:36.205 --> 00:20:46.267
And and I said to her do you know how hard it is to remain positive in the face of failure?
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I just made 40 bucks.
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