3 Things To Do If YOU Had To Start Over

But I think the biggest sales job we have to do before we learn how to sell other people is we have to sell ourselves. Okay.

One of the number one questions we get asked all the time is, if we were starting over, what would we do? Because think about it. So many people are in the space of just starting or they've never started. And so looking back, I mean, you have 30 years of experience. I'm edging up to a decade edging. There's a lot of things we do differently. And so let's kind of place ourselves into the lives of what we imagine. Maybe people listening are kind of at, like, what if we didn't have the resources or the connections or the knowledge or the personal development to be where we are today? So let's just point blank, just, like, we're starting over. And, Jenna, we are beginning.

So I think, first off, I try, even though it's impossible not to. I try not to forget that feeling of starting over, because that was such a driver. Like, sometimes I. And you know, and same with you. I'm a hustler. I'm hungry. I'm hungry. Like, I'm broke. Like, literally, like, I hustle. Like, somebody's gonna take it away from me. Yes, I really do. But. But that. That. That drive to want more, you can't replicate that when you really are desperate for a change. So I would say a couple of things. If you're just starting and you're saying, how would you guys start over? Because you don't know where to begin. You want more, you see it. You might be a little envious of other people that are getting it. Cause we all had that. I don't know if you did. I was envious of people like, how's that girl got all of her shit together? And I don't. Right. But I would say, don't be envious of the drive you have. Like, when I look back, I wouldn't change one bit of my burning desire. Like, I didn't need to set goals back then. I wasn't into personal growth when I first started. I didn't know how to manifest. I didn't have a structured goal list. I didn't know where I was, where I want to go. All the cool stuff I write about now, that stuff I learned through the years, all I knew when I started was is, this sucks, and I don't want to be here anymore, and that looks a lot better, and I want to go there. So I think I would keep the drive. But I think the biggest thing I would Love to. Like, there's two different ways we could talk about this, right, Jenna? We could talk about, like, should we go? Like, I would know marketing before anything else. Like, I wouldn't build the product. I'd learn marketing. So let's get to tactical later.

Yeah, yeah, yeah.

But. But if I was talking about a mindset, because at this age, you shared how old you were. I'm 50 this year. Like, I look back now in my 20s, I probably thought, like, 80% was give me the magic tool, and 20% is the right mindset. And as I've gone through 30 years of being an entrepreneur, now I know it's 90% if my mind's not right. You could. Like, you could sell $20 bills for 10 bucks. It still won't work, Right? So I would say if I was starting over, I would love to approach it as if. Who gives a crap if you fail? Like, I was so afraid. Like, I wanted it and I desired it, and I had this passion, and I knew I hated my life the way it was here, and I wanted this different life, but still there was this always. But what if it doesn't work? But I had nothing to lose. It's like. It's like, I look at it now, it's so. I don't know. It's like, I don't want. I don't want to dismiss it.

I love you as much as you can yourself.

Thank you. Like, who was I gonna let down? Like, the squirrels, the birds? Like my parents who always thought I was gonna. Thought I was gonna fail anyway? Like, so I would say one thing would be. Is keep the drive I had. Second thing, I wouldn't give a crap about what anybody thought. Like, zero. And I know that's easier said than. But I've got too many years of being in business. I've already lost a whole group of friends along the way. I've gained new, amazing people in my life. I. The people who I thought mattered aren't there, and the people I didn't know were going to matter are the closest people in my life.

Right?

So I wouldn't care about what anybody thought. I would keep that drive, and I would go at it as if you have nothing to lose, because you don't. And the last thing. And this is just the philosophy side, and I want to hear your side of it, is I would keep. And this sounds maybe morbid, but I would always keep the conversation of If I was 95 and I looked back in my life, if I don't do this, if I just go status quo. If I just stay in the corner office that had no window, if I just stay in this relationship that kills me a little bit every day, if I don't speak up for myself, if I don't finally say no or yes, I'm going to be free. If I don't do that at 95, looking back, like, what are you going to regret? You're not going to regret staying in the office. You're not going to regret saying, I played small because it was what my parents thought was safe. I, again, in my 20s or 30s, if somebody said that, like, oh, that's morbid. I'm not going to be old for a thousand years.

Yeah.

Maybe I'm looking through different glasses because I'm 50, but right now, I don't want to. I don't want to mess with that. Like, I want to. I'd much rather be at the end of my life going, I tried all that stuff and I failed. But, man, I went after it.

Right.

Rather than saying, I played it safe and, you know, everything was good and my parents died and they were happy with the job I had. Like, screw that. Yeah. So I know we can get more tactical, but I think that would be the foundation. What about you?

Well, I think women approach this a little differently because I think mindset is more of a journey than a destination for women. And I think we'll talk about this.

Yeah, that's a really good point.

I just feel like the voices never get quieter for women. I think they only get louder. And so when I look at starting over again, I think the two biggest objections are time and money. I mean, that's the biggest objections for anything. So I don't have time and I don't have money. So, one, we all have the same amount of time in the day as Beyonce, right?

Yeah, exactly.

We all have the same amount. So if we can do what Beyonce can do, I mean, she has a whole team of people, but really we have time for what we care about. We make time. If working out is important, if Netflix is important, if. Whatever that is.

So.

So when I look back at the beginning, I think there are two options. So you can start your passion or your business or pursuing the life of your dreams as a side hustle. And I often think that side hustles get a lot of flack. Like, they make people feel less than. Whereas I think if you are. You're in this lane of life and you have this lane that you want to go on, there is no shame in, like, taking Whatever margin you have left over and putting it towards this bigger dream. So for me, like, I worked the corporate job. I use that to fund my entrepreneur, like, same here. Life. Yeah. Like, it's like, I didn't. I didn't win the lottery. I had student loans and all this stuff. The other thing, though, is, like, if we're looking at this, I think it's just a lot of, who am I to. Who am I to become a photographer? Who am I to sell real estate? Who am I to. It's like, who are you?

Do you feel like. Did you feel like you maybe need yourself?

You have to legitimize yourself or you.

Need permission from somebody?

Yeah, yeah.

And it's like, I never looked at it through those lenses. Like, you're waiting for someone to say, oh, Jenna, you'd be amazing at photographer. It's time to quit that job, honey. Here's the signs. We're going to cheer you on and.

Look at it like corporate life. Like, you have, like, quarterly reports. You sit down, you get feedback. But if you're going out into this entrepreneur space, it's the first time in life that you really don't have direct feedback. Like, results are the only feedback. For a lot of people, that's scary because they need someone to say, like.

You did good, or, like, you need a score.

Yeah. So mindset. Absolutely. But I think that mindset for a lot of people is something that you said. It's, like, learned over time, the importance of it. So when I think about starting over, it's like, use for me. I would say, use what gifts you have right now to fund wherever you're headed.

Gotcha. You know what? This is really great. This is why I'm going to love these conversations. No, because it's a different perspective. Like, looking at. I never. Because I've been an entrepreneur so long, I forgot that I'm like, we give ourself the line in the sand. And we know. We know if we reached a plateau of success. We kind of know if we give ourselves a blue ribbon or like a flogging on our back for messing up. You know what I mean? And there's no one else to tell us. But it's also like, I think I wanted people to say. I wanted my dad to say, I think you can do this. Or my mom to say, you're not crazy. Or my sister to be like my sister. When I decided to go in the infomercial business to create a. Well, I went in the knowledge industry, right? Like, I created a course and back then, when I started the only way, like I bought Tony Robbins course. So I'm like, oh, I bought his off an infomercial. I need to do an infomercial. So I took every dollar I had. Like, when I say that, Jenna, it's like now it's like, it's like this thing. It's part of the story. Like, I took every. No, when I say I took every dollar, it was every dollar I had. I got nine different credit cards. I applied for them all at once. And I had $70,000 worth of credit cards. Because I applied all at once. They didn't know that I was doing that. I used 100%, I used 100% of that 90 grand on credit cards. I borrowed money from two people I knew and I was doing okay in my car business and real estate business, right? But I was using real estate. Like, I used the car. I use the firewood business to get in the car business. I use the car business to get in the real estate business. I use the real estate business to get in direct response self education business. I use that business to write books. I use the book industry to get into live events. Right? Like, so everything you're saying, I never just said, oh, like, I used one to go to the other, right? But I say that because as you mentioned it, I was looking for someone at one point to just say, hey, I believe in you. You got this. And some people are going to have that, but most don't. Like, what I was saying is when I decided to go in the infomercial business to sell my direct, my self education, my course, my sister drove from Virginia eight hours to have an intervention with me and said, enough is enough. Dean, you didn't go to high school. Now, I had a collision shop and I owned 1322 apartments. 13 houses, 22 apartments. I was building houses, I was subdividing land. I was probably making 250 grand a year at 26, coming from nothing. Like, more than anyone in my family had ever made. So I had already made it. And now I was going to be the fool who went to another level. And I remember thinking, so, yeah, anyway, it made me look through that lens is we have to become our own cheerleader. And I think the biggest, and I want to talk about tactical a little bit more in a minute, but I think the biggest sales job we have to do before we learn how to sell other people is we have to sell ourselves, whatever that means. Like looking at your goals every single day or looking at what like Some people need to look at what they don't want. Like, we're all designed different. Some people can look at and go, I want the house. I want the car. I want the wife. I want the kids. I want the girlfriend. You know, I want that. And some people got to go. I don't want the corporate office. I don't want the window. I don't want an asshole man telling me how to run my. Like, whatever that is, just figure out what that is, but sell yourself. Like, I think we need to find a way that, like, I would suggest everybody listening. And again, if I was going back and start over, yeah, I would. I would literally read my goals of what I didn't want and what I wanted every single morning. Like, every single morning. So you become Teflon when they tell you you can't, when you don't get the nod when things go wrong, you're like, no, but I'm sold.

Yeah, well, and I think, when I think about this, I think the lie that Instagram and the culture we're in that is being painted is that entrepreneurship for women, maybe for men, is, like, sitting at a beautiful latte in Paris with a computer and a peony and a latte, and that's the life of an entrepreneur. And we've changed this narrative of, like, pursue your passions. Well, yeah, pursue your passions, but, like, you've got to fund that dream.

You got to pay the bills.

And so I feel like there's this, like, weird juxtaposition, this shift going on in the world of entrepreneurship where we're selling a lie because we're. We're putting out the Instagram version of. Of the hard work that's happening behind the scenes. And so I think what's confusing for people that see these lives and they're like, I want what she has, or, I want that next level. They're only seeing, like, the pretty version of the next level, like, that 1%, and they're not seeing, like, the 99% of the things that are happening behind the scenes or what happened. It's exactly why people like you and I aren't afraid to teach every single step of the process, because I could give away every single thing that I've done, and I don't believe anyone would do it, because it was a lot of work.

Yeah. You know, true story.

So when I think about starting over, I feel like there's just too much messaging these days of, like, chase your dreams, pursue your passions. Like, quit and daydream about life. And it's like, no, we work to fund the dream. You sometimes have to do jobs you don't want to do solely because you can collect money and invest into the dream. And it's like choosing to invest into the dream over and over and over again until you're finally living it.

No, I love that. And here's what I'd say, too. So looking back, I would do more of what I did. Meaning this is if you're listening or watching and you're in a job or a company that you currently have and you hate it. And I've said this before, so I don't want to be. So I don't want to be too cliche. But how we do one thing is how we do everything. And now looking back, I realize that more than ever is. I hated Jenna, hated working on cars. So I didn't go past high school. I decided to work with my dad in his collision shop. But my dad never made over 30 grand a year, but worked hard. So we had a collision shop. So picture a collision shop with one little window, and all day in there was painting. You know, like, there's primer, and then there's actual paint, and there's Bondo. The stuff they put on dents and everything in a collision shop stinks like chemicals, right? And I would get headaches. And because I was overachiever, I became a good painter by the time I was 19. So I painted the cars in the spray booth, and it didn't have great ventilation, and I hated what I did, massively. But somehow I knew I was gonna do more. And again, this is only in retrospect, looking back, I hated it. My hands were dirty. Every day, I'd scrub them because I was embarrassed. All my friends were going to college, and I had the dirty nails, right? I was the blue collar. I was the epitome of the blue collar guy, right? I drove a tow truck at night. Like, literally. The most embarrassing thing is a buddy of mine got pulled over for drinking. And I was on the town roster. I lived in a little town, so if someone got pulled over, got in an accident, my pager would go off. This is a pager for a cell phone. And I'd have to. I'd get the page. I'd call the police department. They go, 1, 2, 3, Main Street. There's somebody there. And in the middle of the night, my buddies are all having fun, and I go there, and I'm picking them up in a tow truck. I'm in, like, mechanic blues. I got a. I got coveralls on. And I'm like, but here's what I. I look back and again, if I was starting over is you need to find a way to love what you currently do. I know that's really hard for people to say, like, oh, really love my crap ass job that I have, but you have to, because I gotta tell you a story. Like, I found a way to know that being in the collision business was just the stepping stone. I don't know how I'd love to say I had a mentor. Like, I look back and I'm sure someone gave it to me. I didn't figure it out on my own, but something like, I knew there was more. I just didn't know it. I was trying all these different things. I was trying weekends, I was going to the city, I took acting classes for a while. I ra. I was trying to raise money, I was trying to do all these different things. But I worked on my collision shop and I had a guy come in, I did his car and I was just in a great space. I was really happy. And he's like, God, you're so happy. You must love doing what you do. I'm like, no, I actually don't. And I was trying to get into real estate.

Yeah.

And that guy lent me $90,000 cash after. Make a long story short, after like two, he just brought me, literally brought me 90,000 bucks and said, go for it, make me a partner and we'll do it. And that was my first. That was the biggest real estate deal I'd ever done up to that point. And that real estate deal ended up bringing in a million dollars. Right. Because he came and he saw an enthusiastic, energetic guy that looked like, I love my job. I hated it, but I knew somehow I tricked myself. So anyway, I don't mean to go deep on, but I think that's a key component because how you do one thing, if you're like saying, well, I'm do this shit ass job, I don't care, you're miserable. But someday I'll do that. That someday I'll never come. It just won't. If you weren't. Listen, you got a camera and I'd love to hear more. You got a camera, you booked 20 something your first year so you could get out of that corporate job. I bet you knew that you weren't happy just doing 20 weddings a year, right?

Yeah.

But you found a way. I bet you if you interviewed the people, the brides, and said, how did Jenna do? Like, oh my God, she hung my thing up in a tree. And she did this. And she showed up. She had this huge smile. She was so full of life. But you weren't saying, hey, I want to do. I want to make 40, 50 grand a year doing weddings for the rest of my life. You knew there was more. So how important do you think that is?

Well, I just think that, you know, one thing that I think is really compelling and I challenge people to do this is if you scrolled all the way back. I have over 4,000 Instagram posts. I was talking about the same things I talk about today. I've not deleted a single post. I mean, there are like, yeah, yeah. It was when Instagram was just an editing software. And what I think is so interesting and what you said that caught my attention is like, people think like, well, when I get there, then I'll start, you know, living this life or living this mission. It's like, no, you start talking about it before the people are there. Because what makes you think that when the people are there, when the eyes are on you, you can keep talking about it. And, you know, I look back and it's like, Yeah, I shot 25 weddings and then 27 weddings and 30 weddings. And I thought that more work was more success, but I was really just glorifying busy. Because in a business, that means you're doing well, Right. But really, I got anxiety and I was anxious, and there was something more. I just didn't know what. I've never known what was next. I think that's like, the beauty is, like, stepping into it, showing up how you expect other people to show up and saying, I'm open. I'm open. So, I mean, I like you. I never forget what it was like to start out. But what I think is so important for people that are just starting out is they think, like, you take the first step, the staircase is right there for you. And it's like, no, we're just stepping in confidence, and we're falling and we're stumbling and we're going backwards, but we're still walking. So, I mean, I just. When you think about this, like, really think about, like, remove all of this.

Yeah.

Like, strip it down. Like, what would you do first if you were like, I hate where I'm at, and there's gotta be something more, and I just don't know what it is. And I don't know if I'm qualified.

Really. Great question. I think, again, like, legit, from what I know now, I would write down, if I don't do anything different, what Is my life going to look like in five years from today? Like, that's. That would be the first thing I do. And I would write down, I'm still in this corner office. I got a 20% raise in all those years. I'm miserable. I'm in a relationship I don't like because I don't like myself. I'm not healthy because I don't like myself. Like me, I would write down the painful future. I would, because I'm really motivated by making my own decisions. Like, I don't want anybody to tell me how to dress, how to parent, where to live, when to take vacations, how to speak. I don't like rules at all. This is just me. So I would write down a really crappy future if I didn't do anything different. You took all my money away. It's like I'm starting. I'm like, oh, my God, if I don't do anything, I'm going to be working for somebody else. The future thought of working for someone else for me. Right. So I would load pain. Yeah, that's me.

I'm opposite.

Okay. I would load pain. And then when I felt absolutely horrible about where that could go, I would sit down and write my compelling future. Like, okay, I lost everything. But in three years, I'm going to be back where I was. I learned I'm going to be smarter, I'm going to be able to play. So I would paint, and then I'd do a compelling future. And then for me, again, I have experience. But if I was starting over and didn't have the experience, I. I used to always try to come up with the idea. Like, what's the book, what's the course, what's the training, what's the widget? I remember I wanted to start a sauce club. I wanted to do a club where every month, every month you got a different sauce from different parts of the world. You got one from Northern Italy, then Spain, then you got. Yeah, I think so. Right. So that was one then. Then 20 years ago, I owned etherapy.com. i wanted to do chat therapy where people could just, like, have counseling online. Yeah, right. So that was. That was something I want to do. So I always had these ideas. What I would do now is know that if I don't understand marketing and sales, I can have the best idea in the world, but nobody will come. It's that, you know, if you build it, they will come. They won't come.

Yeah.

So I would. I would write my crappy future, my compelling Future. And I would obsess on sales and marketing and then I would figure what vehicle I want to get to other people.

Okay, So I would take a different route. So I'm the opposite. And well, I can't be motivated by negativity and not negativity for some reason. It's just like the vision has to be so pure that I'm moving. But what I would do is, and what I feel like is what helped me was taking a step back and defining what enough is. And so for me at my job, it wasn't picking up extra hours. It wasn't like I didn't need more money doing that dead end job. I needed more time. Got it. And so what I think happens is that people get these endorphins from being busy. And when you ask someone like, hey, how are you? And they're like, busy, me too. And you feel like I'm so important. And so I feel like if I were going to go backwards, I would say, what is the bare minimum? What do I need to make this month to make ends meet? So, you know, we were living in a little condo, whatever, and I would only work that amount and then I would invest my time, whatever's left into that dream. And I feel like people look at.

It, that's you, the planning person. I'm the jump out of the plane, grow wings on the way down. I am. And that's why this back and forth is going to be amazing. Because the thought of that, I'm like, oh, I'm just going to do it. I don't want to, I don't want to think about that. Yeah.

I feel like people don't. They use the time and money, of course, so then they fill their time with making more money. More money. But what they're doing in that time to make that money, they don't even have time to enjoy, spend or dream with it.

True story. And the other thing is, right, we know there's emotional and logical buyers, decision makers, emotional decision maker, logical decision makers. So I think the cool thing, especially with this dynamic is just figure out what works best for you. Like I'm the type to go, go, go. And one day it's like I made a decision. Yeah, I'm pulling the shoe, I'm exploding something. Like for me to have a breakthrough, I have to break something.

Yeah.

Like immediately. Like smash it on the floor. It's in a million pieces. I can't glue it back together. I have to now I have to find another way. Like I don't like this boat, poke a hole in it, let it sink. I'll have to find a new bowl. Right. Where someone else might need to say, okay, I'm going to stay on this boat for a year and then I'm going to find. Like, just figure, like, I love that approach. And you could do that with money as well as time, right?

Yes.

Like if I. One of the biggest misconceptions, and this could be a whole nother podcast with us is people are afraid to invest in a business. Like, people have a job, they want something different, but they feel they got to take 10 or 15% and put it in a 401k that they don't even know how much they're getting. They don't. If it's speculative, it could go up, it could go down. And one thing again, not pie in the sky, not overnight riches, but a lot of times that extra revenue can go into your own thing and nothing could give you a bigger ROI than that. And that's just something to think about. Again, I'm not talking about getting rich overnight. Don't risk your savings. But I had a great friend that was a few years older than me years ago when I was in my 20s and every dollar he had actually put into a 401k. 401k. And then there was the bust in the 90s and he had this horrible, like I met him at that time and then he built it all back up and then like in 2007, he lost it all again. And I remember seeing him after all these years, he goes, just to get it back and it's all gone. And he sacrificed his whole life to put it in this thing that wasn't an extension of him. He was relying on other people. So just a different way to look at different things.

Yeah. And I mean I never, I've never had credit cards. I never took out. So it was like $100. Get a domain. Yeah, $100 buy, you know, like get a website. Like, and so mine is just like this slow grow. But I also think, you know, if you were to use the example, like if I were to want to start a bakery, I'd have to like buy a storefront, get an oven, get the ingredients, you know, the price, the cash register. And I feel like people look at modern day businesses and they don't want to pay to have a domain or to have an email service, writer or any of those like logistical things. And it's like if you wanted to launch any business, you would understand that before the doors open You've got to invest. And I feel like nowadays people want to start these things just by showing pretty pictures or writing whimsical captions. And it's like, there's a lot that goes into it and you have to be willing to do what it takes to get there.

The sacrifice is real, the time is real. What is it Bill Gates says? We all overestimate what we can do in a year and underestimate what we can do in five. Five years are gonna go by anyway. You might as well start now. And then. The last thing I'd say, and maybe this is a misconception because you deal with women every day, but when I'm with Lisa or Lisa's friends, and they're all like, you know, Lisa's a badass entrepreneur. She does great for herself. Voted best hairstylist 10 years in a row. But every time I sit with Lisa, we're talking about expanding her business right now and franchising and her friends, who are all strong businesswomen. Every time I sit with them, the conversation always leads to colors, style, how girls will feel when they come. And when I try to bring up sales and marketing, they're like, oh, no, we're just going to make it so beautiful. People are going to flood in. And you and I had a training on that. But I'd love to have a discussion more on people feel because I think I've insulted her friends in a nice way when I say, but why are they gonna come to you? Right? And I ask really hard questions and I see that. And I think that's one thing I'd say starting over. Spend as much time. If you wanna do colors and style and all this, that's great. The feel, the style. I mean, I love the way all your stuff looks. It's beautiful, it's gorgeous. But if you don't have a real company behind it with an email marketing system and own a URL and have a market, and if you don't sell anything, if you don't impact lives, you can't afford to do all that stuff. Exactly right. So just spend as much time on the marketing and sales as you are, as the design and creation.

Oh, yeah. And I mean, really, branding is not just what things look like. And that's a whole thing that people are getting twisted. It's about, like, why you? Why you every. We could do the same things. Why do people choose Dean? Why do people choose Jen?

Yeah. Two great restaurants.

Yeah.

Food's almost the same, one you can't get into. And when you can't get that one, you go to the other one because it's the. And the food's just as good. Why are they over there? Yeah, right. Marketing, sales. So with this, we were all over the place, which is awesome. Which. I love this.

I love it.

But if there was three tips that you give before we go, what are three things? If you were starting over today, what are three most important?

I'd say define what is enough for you and free up your time. Because time is going to be your biggest asset and time is the most required thing in pursuing your dreams. Two, take the first step. You don't have to have the full vision, the whole staircase figured out, but what is the more that you're in pursuit of? And then three, start sharing your message now. Don't wait until the masses come. Start it. Whether you have 10 people or a hundred or a thousand, you are an influencer. So start acting like one because that is going to translate as you grow, because you will grow.

I love it.

What about you?

I would say for me, define either like, for me, it's like, if I don't do this, what kind of pain is my life going to be? So whatever moves you, whether it's pain or pleasure, what moves everybody in the world? If it's pain, stack the pain. If it's pleasure, stack the pleasure. Because that gets. I just want. I can decide all this other stuff, but if I don't move, it doesn't matter. I could design it, I could build it, but if I'm not going to move. So one is either pleasure, pain, stack it. Number two, sell yourself on that dream every day. And number three, because you said some good stuff so you can take all six, is focus on marketing and sales. I'd love to. I'm going to start by saying as much, but the truth is it should be 80%. Once you know what you want to do, learn how to market and sell. So you could be the full restaurant, not the empty one.

Yeah, I think that's it.

I think that's it.

I think people just have to start.

Just do it. What's up? What's up? Hey, before you go, you need to watch these next few videos. They're absolute game changers. Hurry up and click right over here and watch them and I'll see you there.