Gathered Here

Last week, Kelsey shared a simple thought that stopped me in my tracks:

What if I fail?

And then, just as quickly:
Then I'll start something new.

In this Quick Chat, I'm reflecting on why those words hit so close to home. From selling The Bradford and navigating one of the hardest seasons of my life to taking the leap into owning two new venues, I've spent a lot of time wrestling with fear, uncertainty, and the pressure to get it right.

But somewhere along the way, I realized something important: my success was never tied to a building, a business, or a specific path. It was tied to what I had learned, what I had built, and who I had become.

We talk a lot about success in entrepreneurship, but we don't talk nearly enough about the fear of failure—or the freedom that comes when failure stops having the final say.

If you've ever found yourself lying awake wondering if you're making the right decision, questioning your next step, or feeling stuck between playing it safe and taking the leap, this conversation is for you.

Because sometimes the question isn't What if I fail?
Sometimes the better question is: What if I'll be okay either way?

Thank you to our amazing sponsors!

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Interested in learning more about The Venue Masterclass?

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What is Gathered Here?

The stories from the places where people gather.

Dana Kadwell (01:29)
Hello, hello and welcome back. I am so excited to be here today. Today we're going to be doing a quick chat. We're going to be talking about the interview I had with Kelsey from last week. If you haven't heard the episode, make sure you go and check it out. It is a really good one. One, I just love Kelsey's energy. I met her a few years ago at the masterclass. She was at the very first one and I met her and I was like, ⁓ I, we, we should be friends because she just has such an amazing.

positive vibe about her and just being around her, like just her confidence just radiates into you. And I just, I just loved so much of her story. So make sure you go check it out. it was really great. It was really inspiring. It really made me think through a lot of things. I could find a lot of similarities between me and her and just this idea of like trusting your gut and, ⁓ taking risks and whatnot. ⁓ I probably, I say this every single interview, so this is not a shocker. I probably could have like a thousand quick shots, but, ⁓

Today, I wanna talk about this thing that she said.

It was when she was talking about kind of, we were talking a little bit about failure and like that fear of failure, like, did I make a bad choice? Like, was this a good risk? Like those, all of those are questions that we ask ourselves. Like every single entrepreneur at some point in their life, and I can say, especially if you're a venue owner, but entrepreneur in general, at some point in your life, you laid in bed and you questioned your life choices and you said, what in the actual fuck did I get myself into? Like,

why am I doing this? And then you could start listing all the ways that this could fail. ⁓ And I think that's, I think it's super natural. And there's no shame in that either. I remember somebody, was talking to somebody and they were like saying, like, that's such negative thinking. like, I don't want to paint this as being a human is negative because being a human is questioning the decisions you've made. Being a human is asking yourself, did I make the right choice? Right? And she said this.

And she said that she was laying in bed that night and she thought, what if I fail? What if I fail? And then in the next breath she said, well, then I'll start something new. And I like just got goosebumps when she said that because it just so resonated with me, especially like at this new stage of my life and, you know, selling the Bradford and opening these two new venues.

there was a lot of, and there still is days where I'm like, my God, like what if this fails? Like what if I, what if I invested in the wrong thing? Like what if I, I didn't negotiate that price down enough? Like can I make this mortgage payment? Like what if, what if this bar program I can't get off the ground? Like there is like a slew of what ifs. And, and I think what's hard too is, ⁓ and I can just speak from my own personal experience here is, ⁓ I am very excited about it. Like I don't want to confuse this. Like I'm super excited about it. I feel very confident in the past that I'm,

and that I'm walking down, right? But already the path that I thought I was gonna go down with both of these venues is already kind of shifted and turned and I've had to pivot here and pivot there. And I think that there is this like never ending conversation about how the path that we thought we were gonna be on, it might not be the path that we're on anymore, right?

And I think for me, it really hit close to home because I think that's a lot of how I've been feeling is like truly like when the Bradford was when we had to sell the Bradford, there was this overwhelming sense of failure that like, okay, like I not failure in the sense of the business fail, but failure in the sense that like I no longer can be a a venue owner. Right. And there was this very crippling fear of what am I going to do now? Like, what can I do now?

And I remember I was sitting in my office and ⁓ just that year of going through selling was just soul crushing. ⁓ I talk about it a little bit, like where I gave myself a lot of grace because it was so emotionally hard, like everything about it was hard, like because the business and the personal got intermixed so intensely. And I was super depressed and just not in a great place. And so I gave myself a ton of grace that year where

If I needed to go take a nap, would go take a nap. I needed just to like sleep the rest of the day, I just did it. I just, got through it the best way that I could get through it. And so this is one day I had just like, I couldn't handle life anymore. I snuggled the dog and I took a nap and I came back up here and I remember I was sitting in my desk and I just felt this, ⁓ I can tell you, felt like ashamed. Like why am I over here wallowing and crying about this? Like,

who says that this is the end? And then I just got really angry. I think that's so true. I got so mad and I wasn't mad at a single solitary person. I was just mad at myself that I believed for so long that the only time I could be successful is if I was in a partnership, if I was tied to somebody else. And I remember sitting there thinking like, I'm just gonna start something new. I'm just gonna start something different. so I literally went on, what's it called? Loopnet.

loopnet.com and I started searching for buildings and I was like, if I can't own it, I'll just lease it and I'll create an operations and I'll get some money and then I'll have enough to buy some land and do this. And I, I went and saw a couple of pieces of land. I interviewed with a, another space and none of them felt quite right, but I felt for the first time, like I can start something new. I can do something new. Like I don't have to be stuck in this place anymore. And just taking those actions and taking those steps just felt

so cathartic and so good. And so when she said that, was just like, I really, really, really, really resonated with me

Dana Kadwell (07:27)
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Dana Kadwell (08:14)
I think that when we talk a lot about ⁓ entrepreneurship and you hear, and especially on this podcast, you hear a lot of successes. There's a lot of people that were super successful and granted there's minor failures along the way and we aren't afraid to talk about failures on this podcast and the things, the mistakes that we made, but none of the failures led to the point where the business had to shut down.

None the failures led to the point where you're like, my God, like I have to sell this or I have to walk away. And so there hasn't been a lot of conversations about true and real failure. And ⁓ I say this

Cause it really hasn't been a lot of conversation about people saying the what if, right? And granted Kelsey is super successful, granted ⁓ I was super successful, but I think it's really important to talk about the what if. And with one of my venues that I bought, ⁓ I was really more intrigued because the real estate was such a good deal. And it was very much, there was a lot of green flags. There's a couple of red flags with it. Like the operations were kind of dead in the ground. So I knew I was going to be rehabbing it. And I think it was like a couple of months in, I was like, this is really hard.

like, and I'm not afraid of hard work, but it felt a little bit like I couldn't overcome it. And there were lots of reasons for that. The main reason was because I was still dealing with the Bradford Closing and there was still that kind of just emotional turmoil, emotional weight, mental load. Every day was a landmine. Every day was a battlefield. Every day of my life from probably January of 2025.

Well, I guess I could probably really say until since like October 2024 until the day we closed was a freaking battlefield. And it was just like that sinking in your stomach anytime you saw an email. Right. And just it just everything was so heavy. And so I felt like my efficiency was super crappy, super low. And so so now that I'm in this space and I I love the new venue, I love what I'm doing, But it felt really hard and because everything else in my life felt so much harder.

And I remember talking to Sam about it and he's like, well, what happens if you can't, he's like, what happens if you can't get this going? Like what, what's our, what's our exit plan? how are we going to get out of this basically and still be solvent? And I said, I'm so glad that you asked because I have an answer to that question. And I walked into that investment knowing what is my way out. If for some reason I couldn't, ⁓ I couldn't make it work. Like I couldn't turn it around.

what would I do? And I had a plan in place to do it. And I said, and he goes, okay, so when are you going to pull that trigger? was like, when this happens, right? And so I felt like it was a lesson that I learned in this process with the Bradford of like recognizing that it's okay to fail. It's okay to feel like you fail. It's okay to, to take a risk. But I always wanted to go back to how can I get out of this if something happens?

And then the realization that it's not gonna be the end of the world. Like it's not gonna be the end of the world if it all fails and I can just start something new. And I think that that is where I had to get to with the Bradford closing is it's not the end of the world. And I say that I went through a long time of like therapy and I'm not gonna sit here and tell you it was an easy realization to get to, but.

It's what I, it's really what I needed to understand to move on. And the question I had to ask myself is, am I in love with the land? Am I in love with the building or am I in love with the people? Am I in love with the, the idea of business? And so when I could take a step back and say, what am I going to miss? Right? What's the thing that's going to like, that makes my heart hurt the most. And ultimately it was,

really not having something of my own, right? Like something that I, like this pride of building something and growing it. It was, you know, there's definitely pieces of it, like the clients, the team, the community, all that stuff, but really what it came down to, it was feeling like my career got taken away. And it was in that moment I realized, well, I could just do it again. Like if my success isn't tied to a piece of grass,

If my success isn't tied to this building, if my success is tied on like what I've created, who I am, what I can do, then I could just go do that again. And so I think it really made me so much more bold to be able to do the things that I wanted to do. now, so now when I was like this, one of the venues came up and I was like, yeah, I could totally do this. Like why not? My success had nothing to do with XYZ, everything to do with what I've built and who I am and how I can.

you know, what I know about the industry now. And then this other venue came up and I was like, hell yeah, you know, I'm not saying I don't recommend buying two venues at the exact same time. Like it has been a wild ride, but at the same time it has been one of the most affirming things ⁓ I've ever done. And I'm not afraid to fail at them. I really am not afraid to fail at it. I'm not afraid to look at it and say, okay, if for some reason this doesn't pan out to exactly how I want it to be, then.

here's how I'm gonna move forward and I'm just gonna try something new. I'm just gonna do something else. Like, all right, that didn't work, stick a pin in it and go on to the next thing. ⁓ it's one of the biggest pieces of growth I've ever had in my life because I am not a quitter. ⁓ I am somebody who is terrified of failure, like terrified of failure, so afraid to ⁓ not be successful that this...

new Dana where she's like, okay, yeah, let's try it. Let's take this risk. Like, let's not be cavalier about it. Let's not make, you know, fucking stupid choices, but like, yeah, let's, let's try it. Let's see what happens. Let's see how we can get this to pan out. And if it doesn't, well, you know what, let's move on to the next thing. ⁓ I think there's a lot of, a lot of freedom in that. And I think it allows me actually to have more discernment and I'm not making a decision out of an emotion, out of fear, out of scarcity. It's really out of, okay, like,

going back to that of that gut instinct of like, is this a good decision? Yeah, I gutturally feel like this is good. And that's what I had to say, go back to that venue that I was talking about, you know, after Sam had asked me that question, I looked at him, said, but gutturally, Sam, I know I can make this work. Like gutturally, I know this will take off. I just need some more time. And ⁓ I'm already seeing it. We're already seeing it start to move, start to do what it needs to do.

start to be successful because I trusted in that ⁓ Yeah so I like just there are so many things that Kelsey said that just really resonated with this where I where I am at this point in my life ⁓ and

so grateful for Kelsey and sharing her story. ⁓ was really affirming in a lot of ways for me ⁓ coming off the heels the week that this is like when I'm recording it right now, has just been, it's been a tough one. There's been a lot of like, a lot of decisions that had to be made, ⁓ a lot of direction that I like choosing a lane, choosing a path. And so much of my nighttime conversations with Sam have been filled with this, am I going down the right one?

Am I taking the right step? And there's this kind of like hesitancy in some ways of taking that step. And I told actually literally just last night we were talking about it and I said, you know what babe? I was like, either I'm gonna like, you know, keep asking these questions or, like kind of be in it, but, or I'm just gonna do it. And I'm just gonna do it. I'm just gonna do it. And he looked at me, he's like, you just need to do it. He's like, you know the answer. Like you just need to do it.

just do it. And I think it wasn't until I was talking to Kelsey that I realized the reason why that I was kind of hitting that roadblock was, I was afraid to fail. was afraid that if I took the wrong path, that it would lead to this ultimate demise. And, and I think, you know, and she said it that she said it as well, ⁓ that the path we think we're supposed to take might not be the path, but it doesn't mean it's the wrong one. And I have said that so many times, like I have preached that, that

literal statement like sometimes you're on the right path you have to get off the one you're on but it just didn't really hit home until she said it and realizing that's what's that is what's holding me back is this fear of not going down this path that i think i'm supposed to go down and not doing the things that i think i'm supposed to do as opposed to going down this path because it's what i want to and she said this and i love this she said i can do this and i like it

And it's so true. I can do this and I like it. What a bonus. Like what an amazing thing to say that like, yes, I can build this business and also I freaking love it. Like, and that is just what I keep, that's just what's keeping me going today. anyways, thanks so for joining me today with the quick chat. Next week we're going to be talking, have a little, another little quick chat for you about Kelsey's.

interview If you haven't listened to Kelsey's interview, make sure you go check it out. It is such a good one.

Dana Kadwell (17:31)
Thank you so much for joining us for Gathered Here. To learn more about my new properties, be sure to follow us at McAlser Leftwich and at the Graham Mill. If you want to stay in the loop for all things Hustle and Gather, the venue masterclass, or our mastermind group, be sure to follow us on Instagram at Hustle and Gather. And for updates to the podcast and see all the fun things we're going to be doing this year, be sure to follow at Gathered Here Podcast. I'm your host, Dana Cadwell. Join us next time on Gathered Here.