Jennifer Dawn | How To Set Goals To Achieve Happiness, Fulfillment, and Satisfaction In Your Business

Adam LeanPodcast

In this episode of P is for Profit, we talk to a serial entrepreneur about how business owners can master their goals, achieve a mindset for success, and build remarkable businesses and lives— with very special guest Jennifer Dawn.

Jennifer has grown several multi-million dollar businesses and is a successful speaker and author. Jennifer spends her time working with clients to help them reach their goals.

We’ll chat with Jennifer about the biggest mistake most people are making in running their businesses, what separates successful business owners from those who struggle, as well as… 

  • Why mindset matters
  • What makes a healthy business
  • How to set goals to help you achieve happiness, satisfaction, and fulfillment in your business
  • The one piece of advice Jennifer has for entrepreneurs
  • And more

Listen now…

Mentioned in this episode:


Adam Lean: In this episode, we’re going to talk about how to grow profitable, healthy, and truly exceptional businesses. We’re going to talk to a serial entrepreneur about how business owners can master their goals, achieve a mindset for success, and build remarkable businesses and lives. This is P is for Profit. 

Adam: Welcome to P is for Profit. My name is Adam Lean and I, along with the rest of the team at The CFO Project, are passionate about helping business owners improve the profitability of their business. My guest today is Jennifer Dawn. Jennifer is a serial entrepreneur who has grown several multi-million dollar businesses and is a successful speaker and author. Jennifer, welcome to the show.

Jennifer Dawn: Thank you so much, Adam. I’m really excited to be here.

Adam: Yeah, excited to have you, and you know, I have so many questions for you, but uh, but tell us your background and how you got into this?

Jennifer: Oh, gosh, that’s a great question. And honestly, you know, it’s funny, getting started in business was one of those things that I don’t know if I really had a choice in it. To be honest, it was just so intriguing to me, and the idea of, you know, having a thought or an idea for something and then being able to turn it into money, I was just irresistibly drawn to the idea. 

So I really got started at an early age, when I was eight, was my first official business. I had a lemonade stand because… No, I didn’t, I’m sorry. I had an apple stand because I thought a lemonade stand was, like, totally old school, and like, who wanted to do that anymore? 

So I had an apple stand with my grandfather, and he had a chiropractic office, and patients would come in and out of the office all day. It was attached to their home, and we would spend summers with them. And there was an apple tree in the front yard, and I was like, “You know what, I could sell apples to those patients.” And my grandfather was like, “Go for it.” And all the money I made, I got to keep. And my inventory was free. And I was like, the best company ever. 

Adam: Yeah, the best kind of business.

Jennifer: Yeah, that was the best, I should say, the best business ever. And then, from there, I went on to start my first software company when I was twenty-three. I guess that was really an official company, like a real business. That was my first software company. 

I went on to actually have another software company through corporate. I was hired as their software division manager of their software division for a big fifty-four million dollar manufacturing firm. And then, let’s see, from there, I went on to lead a national network of women entrepreneurs, and it was really from there that I discovered a love of coaching and went out on my own, and that’s the business that I have today. 

Adam: Got it. Okay. So, in your experience working with business owners, what’s the biggest mistake that most people make, most business owners or entrepreneurs, make in running their business?

Jennifer: Oh my goodness, that we could talk about, like, all day. So, you know, it’s interesting, like I’ve had several companies, and I made so many mistakes along the way. And I think that, in itself, is one of the mistakes we make is by thinking that we’re going to go into it, we’re going to figure it out the first time, it’s all gonna work great. And then when it doesn’t, we kind of, like, fall completely apart. 

So I’m going to say that one of the biggest mistakes I certainly made was going into it thinking that I wouldn’t make so many mistakes, because it wasn’t true at all. And if you’re really going to be successful in business today, or anytime, really, you’ve got to go into it thinking that, “I’m going to make mistakes. It’s okay. And I’m willing to make those mistakes and I’m willing to fail. I’m willing to feel whatever I need to feel that goes along with all of that. And that is okay.” 

And that’s what I would say is one of the biggest mistakes I see, that I made, and I see so many entrepreneurs making, is they’re just like, oh, they think it’s going to be so easy. And when it isn’t easy it’s like a ton of bricks, you know, falling down on them. And it just, it’s way harder than it needs to be because they’re not really going into it with the right kind of thinking.

Adam: So, let me ask you this. You know, you mentioned that you started your first business when you’re, you know, eight with the apples. And you started another business when you’re, you know, very young at twenty-three. 

Are business owners, like yourself, that somehow are just born to be an entrepreneur or business owner, are they more resilient when it comes to making mistakes? In other words, is the glass always half-full? And so it’s easier to sort of fail because you know this is your path? Does that make sense?

Jennifer: Yeah, absolutely. So, I don’t know if business owners are more resilient than, say, somebody climbing, you know, the corporate ladder. I grew two businesses. My first software company was on my own and the second one was part of a very large corporation. And so would I be more resilient, one or another? I would say, no, I think you do need resiliency no matter what. 

I think if you’re going to be a successful entrepreneur and in it for the long haul, then being resilient is actually going to serve us so much better than somebody who isn’t willing to fail, doesn’t want to have to keep getting back up, doesn’t want to keep having to try again. So yes, I mean, resiliency is absolutely going to serve you well. 

But you know, I think that, you know, even if your career, you know, in a corporation, you’re still going to need resiliency to be successful. I think people who are not willing to, you know, try and fail, try and fail, and try and fail, that’s really where they don’t get to where they want to be. Because they’re not willing to kind of put themselves out there.

Adam: I mean, would you say, though, that business owners that are willing to do that and put themselves out there, they’re going to succeed, eventually, just everybody fails at some point or the other?

Jennifer: Yeah.

Why Mindset Is Crucial

Adam: So, let me ask you this. What separates successful business owners from those that always seem to struggle, though?

Jennifer: Oh, that’s a great question. And I’m going to say, mindset is really what separates them. Because if you go into your business and your thinking is, “This is really hard, you know, this is not any fun.” You know, you look at your team, you’re like, “Everybody’s an idiot. Nobody can do it better than me. I never make any money. I always have to work so hard.” Like all of this stuff that you’re thinking, when you go into it, that’s exactly what you’re going to get. 

Now, that doesn’t mean that you can’t grow a successful business. You can. I did. My first company, I grew from nothing to seven figures. And I thought that I had to work hard. And as I started growing my first team, I remember thinking, “God, nobody can do it better than me. You know, my team are idiots.” Right? That was my thinking. And that’s what I got. 

And even though I was still successful, technically, you know, I achieved my goal. I grew a seven-figure business. I did those things. It wasn’t very fun. I worked way harder than I needed to work. And it was this constant, like, struggle to be like “Let me get the business to one hundred grand, and let me get it to a quarter of a million, and let me get it to five hundred.” 

And I just kept thinking, “Oh, when I get to this next level, then, you know, all my problems will be solved, and then I’ll be happy, and then it’ll all work.” And it was that kind of thinking that really kind of kept me in this loop that just really wasn’t that fun. And it wasn’t easy. And it was really, really, really hard to do. 

But when you shift that mindset, and you shift that thinking, and you show up in your business, and you’re just like, “This is going to be fun. And I’m going to set my intention that I want to grow this business, and I want it to be spectacular fun each day.” It changes your thinking, it changes how you show up, and it makes that whole process, even when you do fail, it’s not that big of a deal because it’s just, you know, sort of part of that process. 

And so I’m going to say that, you know, and for myself, too, like I know how much I struggled in my first businesses, and I know how much I don’t struggle in my current business. And the only thing that changed was my mindset and how I looked at it, how I think, how I go about doing things, how I show up each day. That’s really the piece that is the big difference between whether I’m going to struggle in my day or not.

Adam: So let’s explore that a little bit more. If mindset is the biggest differentiator between somebody that struggles or not, what are some tangible things that a business owner listening today, who questions whether or not they have the right mindset, what can they do today? 

Jennifer: Yeah, yeah, that’s so great. The first thing is, if they’re questioning their mindset, that’s great. That’s a good sign. Because if you’re questioning your mindset, to me that says, especially as a coach, to me that says you’re willing to look at other options. People who are so closed in their mindset and unwilling to learn, unwilling to hear something different, unwilling to change, right? 

Change can be tough, you just think, “Oh, I’m just right. And I’m gonna create all this story and stuff to prove myself right.” Those people are going to have a much harder time changing their mindset, but if you start to question your mindset and go, “Hey, wait a second, Jennifer is talking about, you know, showing up in her business and having spectacular fun and not struggling. And I’m showing up in my business and I feel like it’s a huge struggle every day. What the heck, like, what’s going on here?” Right? 

So I think questioning that mindset and going, “Well, how do I get myself into a better mindset?” is really the first step in the process, being willing to consider that whatever you’re doing maybe could stand for a little improvement. There’s room to grow there. There’s room to change and being willing to change that mindset. 

So I would say that’s really the first part of the process is looking at it and asking, you know, “How am I showing up in my business every day? And is that serving me? Is that serving my business? Is it serving my team, my clients, my vendors? Is it serving all of these, you know, connected pieces with the mindset that I’m showing up in every day? 

And if the answer to that question is, “Yes,” fantastic. If the answer to that question is, “No, not so much…” Then from there, there’s so many, you know, different tools and things out there that you can use to start improving your mindset.

Profit Is More Than Money 

Adam: Okay, got it. So let me ask you this: how do you define a healthy business?

Jennifer: A healthy business to me is a business that is fun to own. It is providing a great-quality, high-quality service or product, and it’s profitable. Yeah. And profitable, guys, you know, profitable isn’t just money. Money is important. But when we look at profit, I like to look at all the ways of businesses profiting. 

So as an owner, if you’re showing up in your business and you love what you do, you’re profiting from that. You’re generating happiness. You’re generating satisfaction and fulfillment for yourself. You’re gonna then take that home to your family, and it’s going to spill over on them. If your employees love, you know, working with you, they’re profiting from the experience of, you know, working in your business, and they’re going to take that home. 

And it just starts to become this beautiful expanding thing, where profit, you know, it comes in many, many forms. And so when I say that the business is profitable, it’s, of course, at the bottom line, of course, it’s generating money, but also that it’s generating happiness and good stuff out into the world.

Adam: Yeah. That makes sense. I agree.

Jennifer: Yeah. That’s my definition. That’s how I would define a successful business out in this world. And, you know, you see businesses where they have products that, you know, they harm the environment or businesses where their product isn’t really necessary. A lot of scammy type stuff or they’re just selling stuff people don’t really need, you know. That, to me, is not necessarily a successful business. 

But one where, you know, it’s a high-quality product or service, it’s, I’m gonna say, fueled by love. I know this is a business podcast, but I’m gonna get a little emotional here. Like where it’s really being fueled by love of helping people, love of providing, you know, high quality, love of creating a company that brings, you know, in employees that love working there. That, to me, that would be the definition of a really successful business.

The Truth About Goals

Adam: Yeah, that makes sense. So you have a product that is essentially a goal-setting planner?

Jennifer: I do, it’s called “Best Planner Ever.”

Adam: Yeah, it looks very nice. So let’s talk about goal setting. Everybody, I think, understands, conceptually, why goal setting’s important, but what specifically is goal setting? Because I don’t think a lot of people do it correctly.

Jennifer: You’re absolutely right. Most people don’t do it correctly. I didn’t do it correctly for years because we’re taught how to do it incorrectly. And so, often, what happens is people are taught to set their goals because when they meet that goal, then they’ll be happy. It’s kind of like that “if-then” model of happiness. “Well, if I meet, you know, if I get my business to, if I’m brand new, one hundred grand a year, well, then I’m going to be happy.” 

And then you get to one hundred grand, and you’re like, “Oh, wow, I have a whole different set of challenges. I’m not really happy. Let me get it to a quarter of a million.” And you kind of get stuck in this process of “Let me set that next goal because, when I get there, well, then I’ll be happy when I attain that goal.” And it’s baloney. 

And guys, and here’s the thing, like we’re not really taught the right way to set goals. And if you look at all the marketing that’s out there today, like, some of the smartest people in the world are working on ways to separate you from your money. 

And guys, as business owners, we do this, right? We look at our marketing, and we’re like, “How can I get people to buy more of my product?” And one of the ways that we get them to do that is by promising that if you get my product, you get my service, well, then you’re going to be happy. 

So it starts to sort of, like, feed this whole machine of, you know, if we do this, then we’ll be happy. So when we set our goals, though, we really don’t want to set goals where we’re attaching our happiness to them. And I think this is probably one of the biggest mistakes so many people make, entrepreneurs make, I certainly made. 

And instead, focus on being happy in the becoming, the becoming a business owner, the becoming of whatever you’re working to, you know, working towards to become. And then when you do that, your goal is just kind of like a benchmark. It’s really just an indicator if you’re on track or you’re off track. That’s really what it kind of becomes. Less like, “Oh, I’ve got to hit this goal or I can’t be happy.” 

So, I mean, we could talk about goals all day long. I love this topic so, so much. But you know, this is one of the things I see with entrepreneurs is we set these goals in our businesses and then we achieve them and we’re happy for five seconds and then we’re off to that next goal because we really didn’t achieve happiness, we really didn’t achieve satisfaction and fulfillment. 

But if you can focus on having those things, wherever you are in your business, and being okay with, “This is where I’m at today, and it’s okay.” And bringing that happiness in, then setting the goal just kind of becomes, like, the next thing that we want to do that’s kind of fun to be like, “Hey, let me see if I can get out there and really achieve my potential,” and it starts to almost become like a game and not this necessity we have to get to, if that makes any sense at all.

Adam: Yeah, no definitely. So essentially, you should set goals to help you achieve this happiness, satisfaction, fulfillment, and living up to your potential in your business. So how does somebody go about doing that?

Jennifer: That’s a great question. So here’s the way that I do it. I first get clear on the experiences that I want to have, and an experience is going to be different than just setting a goal. So here’s, one of my personal ones is, the experience I want to have in my business is I want to have spectacular fun in my business every day. 

That essentially is my goal, but it’s an experience that I want to have. It’s a way that I want to feel. And so a goal might be, “Alright, well, how do I get my business revenues to the next place, but do it in a way where I get to have spectacular fun?” And it’s just a different way of thinking about it. 

So instead of saying, “Oh, I want to get my business revenues to one hundred thousand dollars a month.” Okay, fine, you can get your business revenues to one hundred thousand dollars a month, but you might lose your soul and sanity in the process. And you might have to work way harder than you need to work, and because the logical mind is going to figure out how to do that, it might not be in a way that really makes us feel good. 

But if you say, “Hey, I want to get my business revenue to one hundred grand a month, and I want to do it in a way that’s spectacular fun,” that sort of changes everything, and it changes the experience that you have on your road to getting your business revenues to one hundred thousand dollars a month. 

Adam: Yeah, that makes sense. 

Jennifer: So that’s how I do it. I kind of focus on, well, what’s the experience I want to have? And then, based on that experience, how do I have to grow as a person in order to have that experience? So if I want to get my business revenues to one hundred grand a month in a way that’s spectacular fun, well, who do I need to become to do that? 

I might need to go and I might need to learn how to do some things. I might need to hire a coach. I might need to, you know, work with some people, or get a mentor, or join a group, or I might need to do some of these things so I can learn what I need to learn so that I can do this. I might need to go learn how to set goals in a different way. Because maybe, you know, the way I’m setting my goals is just a whole lot of struggle and not any fun at all. 

So yeah, that’s how you can kind of shift it as well. Who do I need to become to now have this experience? And it’s just a different mindset shift, it doesn’t mean that you’re not going to still do some of the things, the actual tangible actions that you’re taking in your business. It’s not that you won’t be doing those things. 

But it’s kind of a difference between being pulled by this vision and this experience that you want to have, versus forcing yourself to do these things every day. So you can get to this goal that, you know, may or may not make you happy.

The 3 Types of Action–and How to Work Less

Adam: Yeah, absolutely. So if you could go back in time to when you started your first business, let’s say the software company in 2013, what’s one piece of advice you’d give your younger you?

Jennifer: Oh my goodness, I would tell my younger me so many things, so many things. I would say to younger me: learn the difference–

Adam: Find an apple tree?

Jennifer: Yeah, exactly. Keep that first business because it was, you know, it was the best one. No, I would say to younger me, or I would teach younger me about the different kinds of action that we take. Because I didn’t understand action. I just thought as long as I got busy and I got working really hard that I would be successful. And yes, I was successful in business and on paper and my business made a lot of money. 

Okay, fine, but I wasn’t as successful in life as I really wanted to be. And I didn’t feel satisfied. I didn’t feel fulfilled. I didn’t feel happiness. Every single day, I always felt driven and pressured and under the gun to get to that next place because I thought that’s what would make me happy. 

And so I didn’t really understand the different kinds of action and so, if I went back, I would be like, “Hey Jennifer, know the difference in the kinds of action that you’re taking.” And I like to think of action as three different kinds of action I can be taking. 

So the first action is massive action. Massive action is, “I’m going to figure it out, and I’m going to keep taking action until I get the result I want.” It’s not, “I tried it once, I tried it twice, I failed, I gave up, and woe is me.” Okay, so massive action is: decide that you’re going to figure it out and keep going until you do. 

Versus passive action, which is that time, and it’s… And passive action is good, too. Passive action is, “I’m learning, I’m taking a course, I’m reading a book, I’m, you know, listening to this podcast, right, I’m expanding my skill set. I’m learning. I’m growing.” That’s passive action. And it’s fantastic. I love passive action. But listening and learning, it’s important, but it’s not going to get us to where we want. 

There’s that point where we have to actually start doing and taking massive action. If you’ve ever worked with a client who’s like, yeah, they can list off all the coaching programs they’ve been in, and they’re still not getting the results. Why? Because they’re just stuck in this loop of passive action–of always learning, always growing, but never actually putting their butts out there and doing. And that’s why they’re not getting the results. 

And so you need that balance between the learning and the growth and the actually getting out there and doing and taking that action. So massive, passive, and then you’ve also got reactive action. That’s what I was in for years and years and years. Where you’re reacting to something, and often, it could be an unpleasant emotion, or we’re distracting ourselves from something we don’t want to deal with or driven by fear or worry or things like this. 

And this is where you’re just, like, doing things. Almost like, just like, crazy, madwoman, like just action, action, action. Because I’m trying to find my happiness or, you know, my personal relationship isn’t going well. And so instead of dealing with the relationship, I’m just going to go work harder. Or padding the ego, like, you know, look at me, I’m so important because I’m so busy, blah, blah, blah. 

And then I ended up doing so many more things than were necessary, but not always getting the results I wanted. So often, when you’re stuck in that reactive action, you’re crazy busy, but you’re often not really getting the results that you want. And that reactive action is what kind of tends to lead to the burnout and the depression and the exhaustion. 

So this is something I really, for years, I guess that’s why would go back and tell younger Jennifer, “Hey, Ding-a-ling, know the difference between these kinds of actions.” Because I worked way harder than I needed to work. And I often was in a state of just exhaustion when I didn’t really have to be because I was really taking too much action. 

So that’s what I would teach myself is the difference between the different kinds of actions so that I could be more aware as I go through the day, you know, what kind of action am I really taking today? I work a lot less, a lot less, than I ever worked in my other companies, and I get way better results, and I’m super, super happy. Like, if I could go back to younger Jennifer, I think I’d save her a whole lot of time so she could take more vacations.

Adam: Wow. Yeah, no, that makes a lot of sense. You know, Jennifer, one last question for you. Where can people learn more about this and about you? And if they, you know, would like your help in exploring working together? Where can they go?

Jennifer: Yeah, you can visit either of my websites. So is my coaching website. Or we mentioned the planner, is my planner site.

Adam: Excellent. Yeah. So we’ll put those two links in the show notes. Jennifer, thank you so much for being with us today.

Jennifer: Adam, you’re so welcome. And thank you so much for having me.

Adam: If anybody listening would like to see if Jennifer can help you with your business, feel free to reach out, and I’ll put those two links in the show notes. But thank you so much for listening. And remember, the goal of your business should be to make more profit than last year and turn that profit into cash that you get to keep. Thanks for listening.