June 25, 2025
When Loyalty Becomes a Barrier to Growth
Ever notice how that familiar routine you once loved suddenly feels like a prison? That's exactly what hit me this week as I found myself sweating in my garage, recording this episode while contemplating one of life's hardest truths: I've outgrown my comfort zone. After 13 years of entertaining crowds at Bentley Saloon's bike week—hosting pinup contests, DJing events, and building my brand—I faced an uncomfortable realization. What once felt like my safety net had transformed into a source o...
Ever notice how that familiar routine you once loved suddenly feels like a prison? That's exactly what hit me this week as I found myself sweating in my garage, recording this episode while contemplating one of life's hardest truths: I've outgrown my comfort zone.
After 13 years of entertaining crowds at Bentley Saloon's bike week—hosting pinup contests, DJing events, and building my brand—I faced an uncomfortable realization. What once felt like my safety net had transformed into a source of restlessness and anxiety. Despite the amazing memories, loyal customers, and friendships formed (including meeting my daughter's godparents!), something had shifted. That nagging feeling of boredom wasn't just fatigue; it was my inner voice screaming that it's time for change.
The signs were everywhere. Declining attendance at motorcycle events mirrored my declining enthusiasm. I was stepping over dollars to pick up dimes, clinging to guaranteed income while missing bigger opportunities. My loyalty to familiar routines had become chains rather than support. This episode breaks down the telltale signs you've outgrown your comfort zone: boredom with once-loved activities, stagnation in skill development, fear of trying new things, and that strange anxiety that creeps in during familiar situations.
Making this decision wasn't easy. Leaving behind guaranteed events means stepping into uncertainty. But growth demands discomfort. As I shared the vendor confrontation that ended with my now-infamous line "You want to help me? Get the f*ck out of my tent," I realized something profound—I'm ready for new challenges, new stages, and new opportunities to serve my business and family better.
What security blankets are you clutching that might actually be holding you back? Remember, feeling restless about once-beloved activities isn't failure—it's evolution. Your potential exceeds your current circumstances, but only if you're brave enough to step into the unknown. Subscribe to the Share the Struggle podcast and join me as we navigate this journey of growth, authenticity, and self-discovery together.
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00:00 - Outgrowing Your Comfort Zone
05:44 - Recording in the Garage Heat
10:02 - Living Too Comfortably
15:47 - Bike Week Revelations
24:34 - Signs of Comfort Zone Imprisonment
30:11 - Making the Decision to Move On
38:17 - The Vendor Confrontation
43:38 - Celebrating Change and Growth
WEBVTT
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When you start to feel boredom, restlessness or a desire for more challenge in your familiar routines and activities, you have likely outgrown your comfort zone.
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This feeling indicates it is time to step outside and pursue new experiences and opportunities that will lead to growth and self-discovery.
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This week, I learned a long, hard lesson that I am too damn comfortable and it is time to take on new challenges.
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All that and some aggressively funny stories Today on Share the Struggle Podcast.
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That's it and that's all.
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Biggie Smalls.
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If you're a Loud, proud American and you find yourself just wanting more, find me on YouTube and Facebook at loud, proud American, or the face page, as my mama calls it.
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If you're a fan of the Graham cracker, you want to find me on Instagram.
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Or all the kids by tickety talking on the tick tock.
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You can find me on both of those at loud, underscore, proud, underscore American.
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A big old thank you to the boys from the Gut Truckers for the background beats and the theme song to this year's podcast.
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If you are enjoying what you're hearing, you can track down the Gut Truckers on Facebook Just search Gut Truckers.
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Give them, motherfuckers, a like too.
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Feel the pain, make it bleed, I hate to say.
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I taught you.
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So I truly thank you for supporting my American dream.
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Now, go wash your fucking hands, you filthy savage.
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Ooh, ooh, ooh, ooh.
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What it do, what it ha Do-do-do-do-do-do-do-do-do do, do, do, do, do, do, do, do, do, do, do, do, get alone, almighty.
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Am I so excited to be back with you.
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Oh, it's true, it is damn true, boo, y'all know I love you, mm, mm, mm, mm.
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Episode 259, and I'm feeling, oh, so fine and so fine and a touch sweaty.
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Wow, maybe real sweaty and short on breath.
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I mean, maybe that's just something to do with my overall thick physique.
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All kidding aside people, the old weatherman and my iphone app is telling me it is 99 degrees here in sunny Arundel, maine, but it feels like 299.
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Good God, almighty, is it hot?
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It's a hot 99, y'all, it is thick like my thighs.
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You know, when you sweat so hard, it just gets in your eyes and burns.
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Oh, man, everything about today is hot and disgusting.
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I'm just going to put it out there.
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Man, it ain't safe to be out there.
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People Don't do it.
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Who am I kidding?
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I did it anyways.
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We all did it.
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But it is what it is, man.
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We got to deal with it right.
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Here we are.
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We'll be bitching about snow and cold temps before you know it.
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But I'm setting the scene to paint the picture, to pave the road for the story to be told, to let y'all know, I'm recording in the garage today.
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Okay, I am in the garage doing a little recording here because I'm trying to stay cool.
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And if I record in the house then I got to cut the air conditioning because that humming noise would not make for proper audio for the fans here of the podcast.
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You know what I mean.
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So I'm gonna be sweating to the old these in the garage with y'all.
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I can't, uh, go upstairs, cut the power on the air conditioner and then let the house just get smoldering and we make the whole family suffer it now.
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So I shall suffer alone.
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I shall do all the suffering.
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It's all part of the commitment, the sacrifice.
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You know Just the plan that we have at hand.
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This is why we have 259 consecutive weeks of the podcast, because I do dumb shit like this Recording the podcast in a garage surrounded by laundry that needs to go upstairs.
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Anyways, here I am.
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Can't promise you how long I'm going to be here, folks.
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Rather, I'm going to pass out with the record button still on and you'll hear a lot of awkward silence and maybe some snoring or gurgling for air.
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But I'm here.
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That's my commitment to you.
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All my day ones out there, my loyal ones, my day one listeners, get your ones up.
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I appreciate you, I acknowledge you and I thank you for your nearly five years of support.
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All of my new ones welcome to Share the Struggle podcast, where we get on here and we just share our struggle.
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We speak our truth because we know that there is strength in our truth, in our stories.
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You just got to be willing enough to share it in our stories.
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You just got to be willing enough to share it.
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And I know there's a lot of new ones out there because I've seen a nice bump in listenership every single week.
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So thank you and welcome all the new ones.
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I know some of y'all are hooked because you're going back to the catalog and starting from scratch.
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So I appreciate that.
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I encourage anybody that's listening, that's enjoying the show, to go back and get caught up and follow along and listen.
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We are available on all major platforms.
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You can also find us at wwwshadestrugglepodcastcom.
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Yeah, it's funny man.
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Every week there's a new story to be told, there's a new struggle to overcome.
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There's a new obstacle to handle.
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A new struggle to overcome, there's a new obstacle to handle.
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There's a new challenge, right?
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That's kind of how things work.
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Last week, we were on here talking about being taken advantage of, and when you start to feel like you're being taken advantage of and we went through a whole list of good, powerful questions to ask yourself to identify if you are being taken advantage of, if you really value that relationship then we even identified some questions that you can ask to set some clear boundaries and put some things on the table.
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But there's another layer to the whole being taken advantage of that I feel like I'm kind of dealing with as well.
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That kind of just puts all things together, right?
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I guess when you start to analyze things and you start to peel back the onion a little bit and figure out what it is that's going on in your little world, you start asking yourself all those questions, like we talked about last week, and I identified something else, and that something else is that maybe I've allowed myself to live in my comfort zone, and I know there's a bunch of you out there right now listening that have been listening for a while, being like dude, you ain't living in a comfort zone, you've been taking chances and starting dances and wildfires.
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Man, you haven't been living in your comfort zone.
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And I will say to you you're right and thank you.
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I appreciate that.
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There's a lot of areas in my life where I'm not in my comfort zone, I'm jumping out.
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But there's also this little blankie, this little security blankie that I've been holding on to that every single year.
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I can count on that, I can depend on that, I rely on.
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It's become this safety blanket for me, this little comfy blanket.
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All I can think about right there.
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When I said that is Tommy Boy, when Chris Farley's at the diner ordering chicken wings and he has a little roll, he's my little pet and he's naughty and I pat him and I massage him.
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You're naughty, you're naughty little pet.
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Anyways, that's all I could think about was Chris Farley in a dinner roll right there for some reason.
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But the truth is there's a big portion of my schedule and of my life that I've taken the easy road on that I've just said.
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Well, here's a few things that go into this.
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Number one my loyalty to the people.
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Number two my connection to the people, my connection to the customer base, to my friends, to my family, all these things.
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I start to check off the easy button, the convenience button, and then you start to sit there and realize, man, maybe I feel a little bored, maybe this boredom actually turns into restlessness, where I'm just no longer happy doing what I'm doing, where I just I don't even know how to explain it, guys when you have something that's been a source of comfort for so long, when you have something that's been a source of security for so long, all of a sudden be a source of restlessness, that's tough when it also starts to create some anxiety and you start to think, man, maybe this just isn't right for me.
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Well, if I start to connect some of our recent episodes my wife coming on here talking about removing negativity, me coming on here talking about being taken advantage of to now connecting the dots to a comfort zone what I've learned is there's some things that I'm doing, there's some things that I've kept on my schedule for my business because they've been comfortable and they've now become a source of restlessness and it's time to pull the plug, to cut the cord and to head in a different direction.
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So, after being at Bentley Saloon for bike week, doing what I've always done and what I've always loved.
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I've sat around and asked myself a lot of questions and I started to realize that I was just feeling a little bit different about things.
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So, with that said, I'm going to highlight some stuff.
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I did a little bit of research and there's going to be some questions in here or some identifiers for you that maybe, as you're listening today, you can start to ask yourself is there something that I'm doing just because it's comfortable, because it's routine, because it's the easy button, because it's just expected of me?
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That no longer is servicing me, it's not benefiting me.
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So I'm going to have these things and we're going to talk about them, we're going to work through some things and we're going to share some details about them things and we're going to have some fun with all these things.
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That's the plan today on episode 259.
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So if you are starting to feel boredom, if you are starting to have some restlessness or a desire for more challenge in your familiar routines and activities, then you have outgrown your comfort zone.
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This feeling indicates it is time to step outside and pursue new experiences and opportunities that will lead to growth and self-discovery For me.
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One big giant red flag for me was my recent Bike Week experience, because at the tail end of Bike Week there's a couple of events that I just love to do.
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One of them is a tattoo contest that I came up with and worked with a good friend of mine, tommy Tommy from Tommy's Tattoo Conventions, and we brought this to Lisa Bentley Saloon and then I was able to handpick some judges that I wanted One of the best tattoo artists in Maine, chad Chase, and a super cool, awesome, badass traditional tattoo artist that won Ink Master Season 13, jimmy Snaz and put everybody in the same room and had this super fun contest and I loved every single thing about it.
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I had an absolute blast but even with that said, there was just a kind of a draw on my energy knowing that I had to get up and ready for all these things after a long week of struggling in a parking lot to make ends meet.
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You know what I mean let's just say poorly attended bike week.
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Know what I mean?
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A, um, let's just say poorly attended bike week.
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I do feel like a lot of these biker rallies are just not what they used to be.
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I'm not throwing shots at, you know, like bettany saloon, I'm just saying the whole motorcycle industry isn't what it is.
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I'm willing to bet there's no more than a half a dozen dealerships in the entire country that could honestly tell you they've experienced growth year over year for the past three to five years.
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It's not possible.
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People just aren't buying motorcycles like they used to.
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Motorcycles aren't getting produced like they used to.
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That market, that industry is, in my opinion, like a dying breed.
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I'm not going to say that it's ever going to just die off, but it's probably never going to be what it once was.
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The market's been oversaturated and a lot of the population that loves to ride motorcycles has unfortunately died off.
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If you go to a school today, like a high school, when you look around they're not going to find motorcycles in the parking lot, maybe one.
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When I was a kid, cool kids would ride to school on their motorcycles.
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Now it's diesel pickup trucks or lowered, ridiculous stupid Subarus with fart cans for exhaust or whatever They've moved on.
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The super cool thing isn't motorcycles.
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So until they get that population back, it's going to be tough to grow that right.
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And then you start to think about distracted drivers and self-driving vehicles and road rage and you start to think about protests and riots and streets and stuff and a lot of people just don't want to be on a motorcycle anymore so that's kind of dying off.
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So when you're not selling and producing as many motorcycles and motorcycle related events don't have as many people going to them, and I feel like I experienced that when I went to Daytona.
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The local bike week for us is Laconia Bike Week in Laconia, new Hampshire, and I'm just going to say it, it's the least fun of all the bike weeks you can think of.
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The local, I guess you would say not really the business owners, but it's a big political thing Like a city council type of scenario, law enforcement.
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They've really taken the fun out of Laconia Bike Week over the past few years so it's just not really heavily attended.
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So when we're depending on traffic from that bike week for the success of our events, it's just not going to be there.
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Over the past few years it just hasn't turned out like it used to.
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It seems like every year the results for me as far as sales goes down and down and down.
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This year I was down 20% over last year, which was down, I would say 20-25% from the year before.
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So it's just not trending in the right direction, right.
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So when you're out there suffering through some slow days, it's kind of hard to build up the excitement for an event that you're going to do.
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Now the big symbol for me, the big shining beacon of light that said go in a different direction, is I had to host the pinup contest, which I've been involved with the pinup contest for 13 years.
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I've always told everybody it is the best day at Bentley Saloon, it is the busiest day at the Saloon, it's the funnest, and I get to control the crowd, the tempo, the environment, the energy, the whole thing.
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I love everything about it.
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I went from being a judge to being an announcer, to emceeing and DJing at the same time, and I love it.
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I've made so much of it right and I'm proud of it.
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I love it.
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I've made so much of it right and I'm proud of it.
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But I'm bored of it and I realized that I'm just kind of over it.
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And Saturday I had to drum up the energy to make it happen and I did the best I could and I think it was a great time and I feel happy to go out on a great performance.
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But when I realize that I'm bored, I'm bored with a routine with an event that I used to love and get excited about.
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That feeling is telling me it's time to step outside and pursue new experiences.
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I got to find new opportunities that will lead to growth and self-discovery, and it's tough because I have so many wild, different things on my schedule every year, so many chances that I have to take that.
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This has been that security blanket for me that I just fall back into and know I can count on.
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Hey, I have these three events, I have these DJ gigs.
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I can just schedule them, set it and forget it.
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Know it's going to be there for me, but I found myself feeling bored.
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So, when you start to think that you might be outgrowing your comfort zone, I got some identifiers we're going to have to go over here.
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You ready the first one.
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We've already been touching on boredom and lack of excitement.
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When your daily routine feels monotonous and lacks any spark or novelty, it's a sign that you've likely stayed within your comfort zone for too long.
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Now, as we're going over these things, I want a lot of you guys that are driving to work today, that are on treadmills, that are just jamming out.
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I want you to think about this and think about areas in your life.
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Is it a career, you know?
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Is it like hobbies, different activities?
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Start to just ask yourself all those things For me it's part of my schedule for business, part of my routine, part of my event plan, right?
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So for me it's not really daily routine, it's just things that are on my calendar that now have become monotonous and they lack spark.
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And that's a sign to me that I've kind of outgrown those things that I've come to grow and love so much, right?
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The next thing is stagnation.
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If you feel like you're not learning anything new, developing new skills or making progress towards your goals, it's a signal to challenge yourself.
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For me, I guess you could say after 13 years, I don't really feel a challenge in what I'm doing, but I have challenged myself to do different things all along the way, like I just said, to go from a judge to announcing, to go from announcing to incorporating music, to DJing, to doing all these different things.
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So I'm always trying to learn something new, but I guess it's I'm at a point where I realized I'm not making progress towards my goals, like I'm not making a massive difference.
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So if you're out there and you're starting to feel a little stagnant, then maybe you've outgrown your comfort zone.
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Another one is fear of trying new things.
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If you find yourself consistently avoiding new situations, activities or social interactions due to fear or discomfort, you might be limiting your growth potential and that right there, folks, is a surefire sign that you've been living in your comfort zone for too long because you're using that as a safety blanket, as a safety net.
00:18:57.520 --> 00:19:02.141
Right, you are avoiding new situations because you're going back to what's comfortable.
00:19:02.141 --> 00:19:05.881
You're not trying new activities, so you stay in your comfort zone.
00:19:05.881 --> 00:19:11.057
You don't go out and meet new people because you have this safety net and group of people that are comfortable.
00:19:11.057 --> 00:19:22.490
But the moment that that safety net starts to feel restless, it starts to be a source of anxiety or boredom, then you're not living a fulfilling life, you're holding yourself back.
00:19:23.252 --> 00:19:27.786
The feeling of being uneasy or anxious in familiar settings is another one.
00:19:27.786 --> 00:19:33.978
Sometimes what was once comfortable can start to feel stifling.
00:19:33.978 --> 00:19:37.744
This can manifest as anxiety or restlessness.
00:19:37.744 --> 00:19:43.318
This is telling you it is time to explore new environments.
00:19:43.318 --> 00:19:53.718
It's crazy for me to say this, but a place that I love and hold so dearly, that is a source of great memories and experiences and friendships.
00:19:53.718 --> 00:20:11.701
I could literally go on for hours and bore you for the entire time with details and experiences that I've had at the saloon that have molded me, changed me, impacted me in so many ways.
00:20:11.701 --> 00:20:18.461
What's crazy is I didn't feel comfortable last week.
00:20:18.461 --> 00:20:26.903
There were so many times where I just didn't feel comfortable and that can come up as like a source of anxiety.
00:20:26.903 --> 00:20:31.460
For sure that was telling me it's time to go somewhere else.
00:20:31.460 --> 00:20:33.123
It's time to do something new.
00:20:33.123 --> 00:20:35.497
It's no offense to anybody there.
00:20:35.497 --> 00:20:37.213
They've been great to me, they've supported me.
00:20:37.213 --> 00:20:42.713
I'll continue to support them, to send people to them, to hopefully make apparel for them.
00:20:42.713 --> 00:20:49.472
All those great things, but there's time for me to make a change right.
00:20:50.736 --> 00:20:53.483
Another thing is missed opportunities.
00:20:53.483 --> 00:21:02.182
If you constantly turn down opportunities for personal and professional development because they seem too daunting, you may be missing out on valuable experiences.
00:21:02.182 --> 00:21:21.030
If you are holding on to your comfort zone, it's going to prevent you from professional development and it's going to keep you from new opportunities, new experiences, because you would much rather stay on the couch eating Fritos because it just feels right For me.
00:21:21.030 --> 00:21:29.280
I've missed out on different events and opportunities that could potentially build my business, grow my business.
00:21:29.280 --> 00:21:34.205
Because I was loyal to doing events for the saloon.
00:21:34.205 --> 00:21:40.054
I was loyal to being there year after year for these events and for these dates.
00:21:40.054 --> 00:21:46.570
There's no guarantee that if I took a different event would be any better.
00:21:46.570 --> 00:21:53.771
There's also no guarantee that I would make more money or I would have these great experiences or anything like that.
00:21:53.771 --> 00:21:57.720
I could fail miserably, but that's part of living in your comfort zone.
00:21:58.340 --> 00:22:02.654
I took these things for granted and I scheduled them in every single year.
00:22:02.654 --> 00:22:09.015
So what I typically do is I take my calendar, I ask the saloon what they need, what they want.
00:22:09.015 --> 00:22:13.813
I know what their key events are, I fill those into my book and then I work backwards.
00:22:13.813 --> 00:22:27.008
And that's been great and it's been tremendous for me and the customers that have become friends and family, and the connections made and all the continued growth and business and support from the saloon.
00:22:27.008 --> 00:22:28.151
I appreciate all of that.
00:22:29.313 --> 00:22:51.451
But it's crazy to all of a sudden feel uncomfortable, to feel restless, you know, or to not enjoy the things that you look forward to so much, and at that point you start to think, well, maybe I'm missing something else, maybe there is something else, maybe I need to try some new experiences and try some different things.
00:22:51.451 --> 00:22:59.614
But I've held on to the security for multiple reasons, right, for the fact that I know what's going to be there.
00:22:59.614 --> 00:23:08.332
I can bank on what's going to happen, like I can schedule it in my book, right, I can write it down and I can project roughly this is how much money I'm going to make.
00:23:08.332 --> 00:23:10.160
I can bank on this for the business.
00:23:10.160 --> 00:23:16.721
And when you live in a world of wide open unknown, it feels damn good to put in some known facts.
00:23:16.721 --> 00:23:22.837
You know, and they've been tremendous to me through all the years, so it's hard to walk away from those things.
00:23:23.730 --> 00:23:36.519
I used to do Labor Day there as well, and I had to go to them and say would it be okay with you if I took Labor Day off and started doing the Windsor Fair, because I think it's just going to be more beneficial for my business?
00:23:36.519 --> 00:23:41.419
And they were extremely supportive and they told me yeah, absolutely go, do that.
00:23:41.419 --> 00:23:42.615
We want to see you grow.
00:23:42.615 --> 00:23:47.582
So I know they're going to support me having the conversation that says I think it's time for me to move on.
00:23:47.582 --> 00:24:10.929
But it's crazy for me that I'm coming to the realization that I need to move on and and that I've been holding myself back and I've been living in this comfort zone and this business is all about taking chances and taking risks and it's scary to take one of the biggest, most guaranteed things in your schedule and just taking it off.
00:24:10.929 --> 00:24:28.019
And I say that not because it's my biggest event, but there's a multiple amount of events and there's other say that not because it's my biggest event, but there's a multiple amount of events and there's other things that go into it and you know, like once a month, djed events and things like that that I'm no longer going to do With.
00:24:28.019 --> 00:24:31.253
That said, I haven't even had the conversation with them.
00:24:31.394 --> 00:24:40.540
I'm kind of having the conversation with you, but July 4th I am going to be at the saloon as a vendor and it will be my last time vending at Bentley Saloon.
00:24:40.540 --> 00:24:50.201
It's a commitment that I've now made to myself and to my family that if I'm going to do this business and bank on this business, then I got to do different for this business.
00:24:50.201 --> 00:24:52.292
So that's what I'm going to do.
00:24:52.292 --> 00:24:58.744
Also, this Friday I will be DJing the disco night.
00:24:58.744 --> 00:25:00.276
It's a disco costume night.
00:25:00.276 --> 00:25:13.883
I'll be there Friday night and then in July it is the redneck night, is the mullet and Daisy Duke night, and I will announce that that will be the last DJ gig I take at the saloon.
00:25:16.174 --> 00:25:18.585
I'm trying to do different for my family.
00:25:18.585 --> 00:25:37.726
You know I don't have any business being in a bar DJing till 12, one o'clock in the morning with my little girl at home, and in the summertime I shouldn't be saying yes to bar gigs instead of saying yes to fairs and festivals and rallies and events for my brand.
00:25:37.726 --> 00:25:50.622
So it's one of these things that I heard this saying many years ago in the motorcycle business that said you know that guy over there, he'll step over a dollar to pick up a dime.
00:25:50.622 --> 00:26:14.395
And I started to think that maybe that's me that I'm stepping over a dollar to pick up a dime because I'm taking an event that I know pays me money that I guarantee I can DJ and I can look at my schedule and say this many Fridays a year I'm going to get that guaranteed cash in my pocket and I can spend the night at home and I say yes to it.
00:26:14.395 --> 00:26:17.521
But am I stepping over a dollar to pick up that dime?
00:26:17.521 --> 00:26:18.523
Maybe I am.
00:26:19.289 --> 00:26:36.884
So for me, I'm starting to realize that I'm living too much in my comfort zone, even though I'm fearful of all the things that I have on my list that are unknown, but I subconsciously built a safety net and a safety blanket that I didn't really think about.
00:26:36.884 --> 00:26:42.923
So I'm asking all of you are there things for you that are holding you back?
00:26:42.923 --> 00:26:48.001
Are there things in your life that have now become a sense of boredom or a lack of excitement?
00:26:48.001 --> 00:26:52.501
When your daily routines begin to feel monotonous, they lack any spark.
00:26:52.501 --> 00:26:56.770
It's a sign that you've stayed in that comfort zone for too long.
00:26:56.770 --> 00:26:58.536
Do you have stagnation?
00:26:58.536 --> 00:27:03.134
Are you feeling like you're not learning anything new, developing new skills, making progress towards your goals?
00:27:03.134 --> 00:27:05.278
It's time to challenge yourself.
00:27:05.278 --> 00:27:07.932
Are you fearful of new things?
00:27:07.932 --> 00:27:19.900
If you find yourself consistently constantly avoiding new situations, activities, interactions, if you have a fear of the discomfort, you might be limiting your own growth and potential.
00:27:19.900 --> 00:27:26.135
Maybe your comfort zones are actually beginning to feel uneasy or anxious, even though it's familiar.
00:27:26.135 --> 00:27:29.740
Sometimes what was once comfortable can start to feel stifling.
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