Jennifer Dawn | How to Optimize for Profit in 2019

What makes for a successful business? Coach, author, and speaker Jennifer Dawn says too many entrepreneurs need to change their idea of what success really means, as well as the mindset and practical strategies they’ll use to achieve it.

Jennifer has built two multimillion-dollar companies (with a third on the way) and even had tremendous success in a corporate position (although the experience still soured her from ever going back to that world).

Her passion is helping entrepreneurs find the same level of success without sacrificing what’s most important. One essential element is something Jennifer says 80% of entrepreneurs don’t do. We take a deep dive into that, as well as…

  • How to use bad experiences to bounce back
  • Making your own rules as an entrepreneur
  • Why you can’t hold yourself truly accountable – and who to turn to
  • The wrong way to set goals (that you think is right)
  • And more…

Episode Timeline:

00:11 Today Steve speaks with Jennifer Dawn. Jennifer is a serial entrepreneur who has built two multi-million dollar businesses, is the owner of Jennifer Dawn Coaching and the founder of Best Planner Ever.

01:18 Jennifer tells us about her backstory where she had her first business at the age of 8!

08:12 Jennifer explains how she got into amusement park software development.

11:00 Jennifer tells us about how mindset determines the amount of success you achieve. She had to move from surviving to thriving.

15:10 Steve and Jennifer talk about the confidence and power they took from overcoming tough situations.

17:51 Steve talks about negative analysis and why you should change the rules of the game.

19:39 Jennifer explains why she hired a life coach.

23:27 Jennifer tells us the secret to achieving your goals.

27:12 Steve talks about accountability and capability.

28:47 Jennifer talks about how it all starts with having a vision.

32:19 Jennifer talks about her “grocery store” analogy in strategizing your business.

35:27 Jennifer talks about thinking everything though.

37:22 Jennifer talks about delegation and her upcoming workshops.

41:35 Jennifer tells us how best to get in contact with her and gives the UCEO listeners a great bonus resource!

Mentioned in this Episode:


Welcome to the Unstoppable CEO Podcast. I’m your host, Steve Gordon.

Today we’ve got an exciting interview for you. We’re talking with Jennifer Dawn. Jennifer is a serial entrepreneur. She’s built two multi-million dollar businesses. She’s working really hard on her third right now. She’s a published author and an accomplished speaker. She is the owner of Jennifer Dawn Coaching and the founder of the Best Planner Ever. As I confessed to her at the beginning, before we started recording, I’m a little bit of a planner geek, so I own them all. Now I’ve got another I’ve got to go get.

Jennifer serves entrepreneurs, and she does that through her coaching and through two-day deep dive intensive workshops. She is an absolute master at setting and achieving goals, problem solving, and going in and finding cash flow for your business.

Jennifer, welcome to the Unstoppable CEO. Really happy to have you here.

All right, Steve. Thank you so much. I’m so excited to be here.

This is going to be fun. We’ve got a lot to cover. Before we dive into that, I would love for you to give everybody a little bit of context so they know where you’re coming from, what got you to this stage of your career.

Yeah, absolutely. I would love to say that it was a beautiful journey with rose petals along the way, but it was not. It was hard-fought, blood, sweat and tears.

But I started my first company. I think I was really born with the entrepreneurial bug. I started my first company when I was eight. Not official company. My first business, I should say, when I was eight. I decided that I wanted to have an apple stand. My grandfather was a chiropractor and he had his office attached to his home. There was a steady stream of patients coming in, and there get an apple tree in his front yard, and those apples were just going to waste. I started an apple stand. I thought that a lemonade stand was so yesterday, all kids did that. I’m like, “Let me do something different here.”

Now looking back, I realized, when you talk about a perfect business, that was the perfect business. My inventory was free, I had a steady stream of clients I didn’t have to do anything for. I’m a cute kid. All I had to do was smile, and you’re the best salesperson ever. I got to keep all my profits. I can still remember holding those shiny quarters in my handing and being like, “I’m rich. I’m the richest person in the world.” It was just such a great feeling.

I went on to start my first official real company. It was a software company when I was 23, had no idea what the heck I was doing. I just knew I could do it better than what the competition was doing. I designed a software system that was for water parks, amusement parks. It was a point of sale system. Any kind of a family entertainment sort of place, when you go in and buy a ticket, it was my system that was at the front that sold the ticket, and turned the turnstile open, and did all of that good stuff.

I grew that company from nothing to seven figures. That’s the company that was the hard-fought, really trial and error. Back then, there were no business coaches everywhere. I actually remember I had hired a business coach briefly, and it was so unheard of in my industry. They did an article on me in a trade publication because they had never heard of a coach, like, “What is this crazy thing she’s doing?”

It was a great, great experience. I became a little disillusioned with software. I wanted to do something else, and so I had sold my company. I turned around, I bought a log home company of all things. I did it the same year the real estate market completely bottomed out, and I ended up having to shut my doors within a year. It was a huge catastrophic failure. Now looking back, I’m grateful for the experience. But then, it was no fun whatsoever. I became a little disillusioned with the entrepreneurial journey.

From there, I took a position in corporate. I became the software division president for a big $52 million manufacturing firm. They had five divisions. I was the software division president. They had bought a software company. They had no idea what to do with it. I had come from software. It was still point of sale, just a different industry. For me, it was a piece of cake because I walk into this big company and they have a human resources department, and a marketing department, an IT department. I’m like, “Holy cow, I was all those departments. Wow, this is fantastic.”

While I was there, I grew their sales. They were at about 300 thousand when I took over, and we took it to 2.2 million in just under two years. It was definitely much faster, but when you have all these resources at your hands, you can definitely do a lot. Plus I had learned a lot with my first company.

The Hazards of the Corporate World

But while I was there, I found that the corporate mentality didn’t really sit well. I had discovered some problems in their software. They didn’t want to fix them. I had come from a world where if I had a problem I fixed it. They didn’t want to fix it. It started to be out of alignment when I knew the customers were going to be using this software that was going to blow up eventually because they weren’t doing what they needed to do. It really caused a conflict with my core values, and I really didn’t like it.

I was the president of the company. They started blaming me for the problems. I’m like, “Wait a second, I found the problems. You guys bought this company before I was even here. How could this be my fault?” But sometimes they want somebody to point a finger at. My corporate career really started to sour after a couple of years. I just was like, “I can’t be this person. We could fix it, we could do the right thing,” they didn’t want to do the right thing. I was just stuck in the middle.

I decided to go out on my own. It was funny, when I first went out on my own, I was just doing some consulting work, and I was doing some writing, I was doing some marketing. It such a funny story when I look back now because one of my first clients, she was an intuitive, like a psychic-type person. She had hired me to rewrite some of her marketing copy. We’re talking about it and we’re on the phone one day. She just impromptu stops and she says, “Jennifer, you should immediately rebrand yourself as a business coach. I see big money in it for you.” I’m like, “What? Who wants to be a business coach?” I’m like, “Who wants to listen to me? What the heck would I do that for?” I was just like, “That’s just crazy.”

I kept on doing my consulting, and then I eventually relocated to upstate New York. When I got here, there was a national network of women entrepreneurs, and they asked me to come in and lead their masterminding and accountability circles, and they eventually made me the president of the company. Actually while I was there, I tripled their revenue, so I had a lot of fun doing this for all these different places. But while I’m helping all these women entrepreneurs, I’m starting to discover this love of mentoring, and coaching, and helping. It started to dawn on me, like, “Duh, you’ve built your own business. You took it to seven figures. You’ve done it in corporate. You’ve been doing this and now you’re helping other people. Why not go out on your own and do this for yourself?” That’s really what gave me the courage to coach, was helping this national network of entrepreneurial women.

There you go. I stepped out on my own and started coaching. I’ve been going strong for several years. Love my clients, love the work. I look back, I’m like, “Wow, maybe if I had rebranded myself a little sooner, I might have done some extra fun things there,” but we’re all where we are. I wasn’t quite ready to take that leap back then, but now I’m absolutely loving the work. There you go. There’s the not so short version of how I ended up where I am today.

Yeah, you’re right. We all are where we are. We can only act from that point and move forward.

I want to take you all the way back to the beginning, because I’m really curious about this. Why a software company in the family entertainment and amusement park industry? I’m seeing, as you’re describing it, I’m thinking, “How would I have ever even put two and two together that that was an opportunity?” I always love to hear those little discovery points.

You know what, I worked for one of their competitors, and so one of my future competitors. I worked for a company that did that, and it was something that I had never even heard of either. They hired me in, and part of my job was to go out and travel to all of these different locations, and install software systems. That’s what I did. While I worked for them, they actually purchased three of their competitors. The whole thing became just a giant disaster as they continued to buy competitor after competitor. But for me, I got exposure to four different systems, and I could see what they were all doing. I was the person out at the client side, I was the person trying to help the customer get their crappy software to work. It wasn’t really my original idea at all, it was really after my time out in the field and just seeing the struggles.

The amusement industry, they’re just such nice people. They were really fun to work with. They’re in the business of fun, and just seeing the struggles that they were going through, I’m like, “You know what, I was never a developer but I could do everything else. I could design the software, I could install it, I could train on it, I could troubleshoot it, I could do some database work. Just some stuff.” Not anymore, because I’m not in that world anymore. But when I was in it, I could do the basics. Really just found a programmer and was able to kick it off like that. That’s really where the idea came from, was just really wanting to help this industry have a much better solution.

That’s interesting. But you had some background.

I did.

I always run across people that are in these really off the wall … Maybe that’s not the right term, but just these really small, little, you wouldn’t have even believed that there’s a specific niche for that. There they are, and it’s a great business, and they’re doing really well. I always go, “How did they think of that?” Thanks for sharing that. That’s interesting.

But now, you’re working with businesses, and you’re working with business owners in particular, and helping them achieve their goals. I know probably both with the clients that you’re dealing with, and clearly with what you’ve shared in your own journey, it’s not always a straight line between here I am today, and there’s my goal, and I’m going to go get it. What are some of the things that you’ve put into your own practice to push through when things get tough? Whether it’s a mindset, or a habit, or just a way of approaching things. Maybe on top of that, when your clients run into those situations, how do you coach them through that?

Yeah, absolutely. You know what, it really … Mindset, I believe, is really what it all comes down to because it’s so powerful, and it’s really going to … In my opinion, it’s really going to determine … Your mindset is going to determine if you succeed or if you fail, or what level of success you’re going to have. What a great question about what I’m doing in my own practice. I would say I’m doing definitely two things.

Do You Have to Choose Between Career and Family?

I had a big shift a couple of years back because I had built my first company, I had built the second company, but there was a lot of personal turmoil and sacrifice that went into it. I went through a divorce, actually went through two divorces. I’m happily married now. I’m not a nut, but I am happily married now, thank goodness. But the personal side of my life really took a big hit in growing these businesses.

It sounds wonderful to be like, “Hey, I grew a seven figure business,” but I also went through a divorce, which was just terrible. Really suffered personally as a result of it. There have been a couple of times where I’ve been in … One in particular, when I was in corporate, I went through about six months where I really felt like I was in a functional depression. It was just so hard being in the environment. I have three children, I had hired a nanny. The nanny was seeing my children more than me while at that time I was a single mom with the three kids, and trying to pay for everything myself. Really, it was the kids that kept me going, but just this almost functional depression of tricking myself to get out of bed every day, it just go to be so bad.

I’ve had these really difficult times. It’s funny because I remember there was a shift where one day I was so angry at everything, and I said, “You know what,” I was screaming at the universe and I’m like, “Look, I don’t really care what you send me. You’ve sent me this, and this, and this. You’ve sent me all these things and I have survived it. I will survive anything that you send my way. Screw you.” I don’t know if I can say that on your podcast, Steve, but that’s the light version. That’s the PG version of what I was saying to the universe. I’m just like, “You bring it, I will survive it. I am a survivor.”

It sounded good and it sounded inspiring, but when I had the shift I started to realize, I’m like, “Wait a second, I’m getting a lot of things to survive, and this isn’t good. Building a business is hard.” I was feeling like I’m going to survive this business, I’m going to survive this business. When I had the shift, I realized, I was like, “Wait a second, I’ve got to shift myself to thriving, not surviving.” For me, again mindset. It was my own mindset. Even though many people are like, “That sounds really inspiring that you were like bring it, I’ll survive it.”

I love those songs that are about, “I was down on my knees, but I got back up again.” I love those things, but there was a point for me where I realized, this isn’t really inspiring. I think I’m bringing some of this stuff in. I’m making it harder than it needs to be. I don’t have to sacrifice my soul to have a successful business. I can do it differently.

After that shift, the business that I’m running right now, I run it a lot different than I did my first two. I don’t kill myself, I don’t work 80 hour weeks, I do take vacations. When I start feeling like my batteries are low, I make an effort to do things in my life so that I can keep my batteries charged up.

When you talk about the things that you’ve done in business, I think that mindset shift for me was the hugest one where I decided this business was going to be different, that it wasn’t going to kill me. I was going to have a personal life, I was going to have a happy marriage, I was going to see my children, we are going to take trips. These are the things that are important to me.

Daily, I have lots of tools that I use. You’re a planner geek, which I love. I have a planner and I use it. It was a planner I create, and it’s got the mindset pieces in it that I needed to remind me every day, so I didn’t fall back into some of those old unhealthy habits and patterns.

It’s so interesting. I can relate so much to what you just shared. You shared a number of important things. I want to unpack them a little bit. I think back to, for me, that time period in ’08, ’09 was not a fun time in business. I went through a divorce about that same time as well, or just after that. It took a little while, but looking back on it, kind of like what you said, you look back on it and you’re like, “Well hey, I’m still standing after all of that.” You know.

I probably had a little bit of that bring it attitude, but the point of that is that when you go through some of those things and you come out the other side okay, the confidence that at least I got, I don’t know if you had that experience, but it’s like, “Okay, I’ve been through that, and that was as bad as I thought it could possibly get, and things are okay now. Really, if it happens again, it’s not going to be as difficult. It’s not going to last as long. I’m going to know how to get out, how to escape all of those situations in the future, and build the business back up.” That’s what I took out of it, was just this great sense of confidence and power, that, “Keep throwing it at me, I got it.”

Do you get that sense, that confidence as well from that experience?

The Power of the Bring It On Attitude

Yeah, absolutely. Absolutely. Because it’s like, “Wait a second, I’ve been to hell and back a few times and I’m still here.” I think that’s such a great point, Steve, to make is absolutely, it gives you confidence when you’ve survived, and you’re still here, and you’ve been through these things. Without a doubt, you start to almost feel like, “You know what, I can handle it. Whatever comes at me, I can handle.”

I think that the difference for me is that I’ve taken that confidence and I’ve actually now shifted it into … Anytime anything bad happens, I’m like, “Wait a second, I’ve been through worse than this, this is a no-brainer. I can handle it.” You know what? I’m even going to set my intention to say, “Even though it feels like it could be bad, I’m going to set my intention to be, it worked out a lot better than I was expecting, or everything worked out fine.”

I think that confidence now that I’m trusting that everything is actually, even if it seems like it might be bad at the time, I’m like, “Nope, it’s fine. It’s just the next step.” I think that’s part of that confidence. It’s given me that confidence to be able to just set my intention now to say, “It’s going to all work out great, and in fact it’s going to work out better than I am expecting.”

What’s so interesting about taking that approach is that it’s all just a story. Your analysis of a set of circumstances is separate and distinct from the circumstances themselves. I think this is where a lot of business owners struggle sometimes, when things get tough. I think they also probably give themselves too much credit when things are going really well, is that when times are tough and we attach all of this negative analysis to it, none of that is real. That’s just what your mind made up about it. If you can rewrite the story like you just described, it now gives you an ability to act, and to move. That’s really what gets you out of the circumstance.

I’ll tell you, the other thing that I think is really valuable in what you said is that in this new business, you’re doing it differently. I think that’s really hard for people sometimes because particularly in an entrepreneurial business, we don’t realize often that we get to make the rules of the game. That’s the gig. Fundamentally we get to make the rules of the game. If you’re coming from another background, it’s like, “Wait a second, who’s going to tell me what I have to do?” For places sometimes for guidance to tell me what to do, but at the end of the day, you make the rules. If you want to work an 80 hour week and that’s the way you want to build your business, you can. If you want to work a 20 hour week and that’s the way you want to build your business, you can. I bet you and I could both point to examples of each of those and find people who are being successful doing it each way. It doesn’t matter.

Exactly. But you make such a great point because sometimes it’s almost like it’s there, but you don’t know it. It’s hard to see it when you’re in it.

I had a coach once tell me it’s hard to see the picture when you’re in the picture. I think that outside perspective can be important. When I transition from corporate back out onto my own, I had hired a life coach. She was so instrumental in helping me just figure it all out because when you’re so caught up in it, and if you’re somebody who’s working an 80 hour week and you want to be the person working a 20 hour week, but you’re so maxed out, it’s hard to see that bigger picture. Sometimes it’s hard to find that confidence to shift the mindset, and you’re so bombarded that you just don’t even have the time to figure out how to get out of it.

As I’ve gone along my journey, I haven’t been alone. That’s one of the key things I think is so important with mindset. It’s easy to sit here and go, “I just shifted my mindset.” Now I do it so much and I work with other people on it so much, it’s become a habit, it’s become pretty easy for me, but it wasn’t always the case at all. It was hard to shift my own mindset at times of my life, and it was these other people that I brought in, or groups I was part of that really gave me that outside perspective, but that was really was the kicker to help that mindset shift.

Yeah, I know that when I went through that, it probably took three, maybe even almost five years before I got to a point where I could almost immediately remove myself from any interpretation of circumstance. In other words, I would get that impulse to judge something negatively, and I’d immediately stop it. But it took a long time to get to that point. It is very easy to sit here and just say it. For those who are going through it, you’re not going to experience it that way. But you have to be present, and mindful, and aware of your thinking, and do things like you did. You created a planner that has the mindsets built into it, so that we see them every day. You’ve got to do things for yourself that give you those triggers.

I want to pause right here Jennifer. I want to come back after the break. I want to talk about goals because I know that one of the things that you’re really masterful at is getting entrepreneurs to set and then actually achieve goals. I think that’d be really beneficial for everybody listening. We’re going to be right back with more from Jennifer Dawn.

Welcome back, everybody. This is Steve Gordon, and I’m talking with Jennifer Dawn. Jennifer, we left off on the idea of goal setting and goals. There’s so much written about this today. You can’t go on the internet and not see, “10 ways to achieve your goals,” and it’s about to get worse. We’re recording this in November. We’re all about to get the onslaught of New Year’s goals, and all that stuff. Help straighten us out. What’s the secret? We expect nothing less than the secret to all of our goals.

How 80% of Entrepreneurs Sabotage Their Success

Okay, here’s the secret. The secret is to keep it simple and get some help. That’s it. It’s keep it simple and get help because … It’s so funny, I just read a stat the other day that said 80% of business owners don’t track their goals, 80%. To me, that’s so sad when you think about how many people are in business, and how many things they’re out there trying to achieve, and 80% of them are not keeping track of their goals.

There’s also another statistic that says 93% of people are not going to meet their New Year’s resolutions, 93%. They even have a name for … Have you heard of Blue Monday?

No. Never heard of Blue Monday.

Blue Monday, right. I actually am working on an article about this right now of how to avoid Blue Monday. Blue Monday is the third Monday in January. Statistically, it’s the unhappiest day of the year because at this point, people have already started to fail on their New Year’s resolutions, usually the weather is crap, especially for those of us who live up north. The weather is bad, it’s cold, we’re in debt from the holidays, we’ve already started failing on our diet, and statistically Blue Monday is the saddest day of the year. I know right. It’s terrible because it doesn’t have to be that way.

You’re right, there are so many goals systems and goal strategies, and all of this out there. My motto is, “Don’t fix it if it isn’t broken.” If a certain system or certain strategy is working for you, fantastic. Keep using it.

I never want to do anything with any of my clients or even in my own goals that’s so rigid that it sets me up to fail. I’m probably the least rigid goal person because when it comes down to achieving the goals, sometimes a goal literally is a day, it’s today, it’s in this five minutes I’m going to make a different choice, and that’s my goal is to make a different choice today. Then it’s going to be to make a different choice tomorrow. Sometimes the goal is that minute and that small, and sometimes the goal is going to be a 90-day goal, or it could be a year-long goal. If you’re looking at health and wellness stuff that’s often just an ongoing, long-term, permanent lifestyle change that you’ve got to look at making. When it comes to especially business owners and meeting the goals, keep it simple. That’s the first thing, as simple as it can possibly be, but also get help.

Accountability. People talk about it, we know it, but it’s literally the secret weapon of the most successful people in the world. They have somebody hold accountable. It can’t just be a best friend who will let you off the hook, it’s got to be a mastermind group, a coach, a mentor, an accountability partner. It’s got to be somebody who’s invested. If you’re paying them, even better because now you’ve got money on the line, you’ve got skin the game. But having that accountability person who helps you through it is absolutely the biggest most simple secret. It’s not really a secret, it’s the most simple thing because we all start with good intentions, but it’s that accountability that will keep you going when you want to stop, and when you’re stuck. All of that, it’s that accountability piece that will get you to the end.

I’m a big finisher. I like to finish stuff. You’re a planning geek, you like to cross it off the list. Well with a goal, you can’t cross it off a list unless you finish it. I think that’s probably why I love this work because my clients, they come to me, and it’s fun and exciting to get started, but it’s the middle and the end that are so tough. That’s where we work on the mindset, and that’s when it’s like, “We’re finishing, we’re finishing, we’re finishing.” That’s where you’re going to see the results.

Yeah, you said something important, accountability. I think we’re all probably at this stage, with all that’s talked about, mindset and the need for accountability in the entrepreneurial world right now. I think we’re all probably keenly aware of that, but I think there’s a component that goes with that, that a lot of entrepreneurs just want to take it all on themselves. Yeah, they go get accountability, but they still take the execution of the goal all on their own shoulders.

I think the thing that really is forgotten is capability. You need accountability to the goal, which you as the entrepreneur have, because ultimately you got to make sure it gets delivered on. But man, go get yourself some capabilities to help. Go get some people that can help you get to that goal, whether it’s just a coach, or whether it’s somebody with a specific expertise who can do a specific task.

I see people load themselves up with this long list of goals. A lot of times there’s this pressure out there that particularly when it comes to the number of figures that are in your annual revenue, whether it’s I’m going to be a six-figure, or a seven-figure, or an eight-figure, or whatever. To me, yeah they’re good goals to have I guess, but they’re really hard to actually execute on.

Mm-hmm (affirmative). They are.

How do you take people and get them more focused in a practical way on something they can actually do?

Yeah, absolutely. Great question. You’re right. I will take a profitable business over a high sales business. This is from the person who works with … I’ve had multi-million dollar companies come to me that are really struggling to make payroll. Okay, great. So you do 12 million a year in sales, but you don’t pay yourself, and you’re a million dollars in debt, and you can’t make your payroll. There’s a problem here, people.

I tend to not really care as much about what top line revenue is. Not that we don’t want to grow our businesses and drive sales. I’m not saying not to do that. Yes, it’s important, but it’s that bottom line that really matters to me. Because at the end of the day, when you’re paying yourself and you can take vacations, that’s really what makes a business a joy. A joy to own, not like a soul sucking, cash sucking monster. We don’t want those.

But to your original question of, how do we do this? The first thing that I want to start with is vision. Maybe the company has a vision statement. Often, probably 80% of the clients I work with, they don’t have any vision statement whatsoever. If they have one, it’s so bland and generic. It puts you to sleep. The first thing that we start working on is vision. What do you really want the business to look like? Who do you want to work with? Who’s your ideal client? All of this stuff to a picture of what do you want this to actually look like because vision is the direction. That’s direction that we’re heading in. Sometimes if you’re just spinning your wheels and you haven’t done any work figuring out what do you really want it to be, that can be part of the problem.

We always start with vision. We take the vision and we break it down into specific and measurable goals. From there we prioritize, which sounds simple but you’d be surprised when you talk about the people with the huge long list of goals. They haven’t prioritized any of them. They just made this huge list of goals because they’re trying to keep up with Joe Blow next door, and they haven’t prioritized. Now you’re stretched thin, you’re overwhelmed, and you’re making little teeny-weeny bit of progress in a million directions instead of laser focusing on your top one or two priorities, and making significant progress in a direction.

Once we have specific measurable goals, we prioritize, then we do the strategy work. The strategy is what most people just skip right over. They just, “This is what I’m going to do,” and they go get busy doing it. We slow that process down a big, we work on the strategy, and we really think through, we create the plan. What’s the Eisenhower quote? “Plans are nothing, planning is everything.” That planning is the strategy. We do the strategy piece and then we executive.

When we get to the point of executing, yes, it’s a little slower before we get started, but then once we start executing, it falls out so much faster, so much easier. The business owner is over the top like, “Holy cow, I didn’t know it could be easy,” and it is, and it starts to be fun. Now we get forward momentum going. Once we have forward momentum going, then we just rinse and repeat, and do it again. Goals achieved, do it again. Goals achieved, do it again. In a nutshell, that’s what we’re doing.

So simple. It’s amazing.


Talk a little bit about strategy. You said that’s the missing piece for most people, that they skip from the goal to the execution. I’d love if you could make that practical. What does a good strategy look like for an entrepreneur trying to implement something?

How Your Business Is Like Grocery Shopping

Yeah, so one of the analogies I like to use is going to grocery store. Everybody can pretty much relate to this. You can sit here right now today and go, “I’m going to go to the grocery store. I need to go to the store, I need food.” Okay, great. That’s a plan. That’s, “Okay, here’s what I’m going to go do.” But if you want the trip to the grocery store to really be successful, you need the strategy. The strategy’s going to be planning our meals for the week because you’re on a certain diet, and you want to make sure that you’re eating the right foods, and so you’re planning the meals for the week, and you’re getting your coupons, and you’re getting your reusable grocery bags, and you’re making your list, and you’re writing it down, and you’re figuring out the time that you want to go because if you go at 5:00 in the morning, they’re restocking all the shelves, and they’re going to be out of half of what you want.

That’s the strategy piece. It’s the thinking through. Anybody can go to the store, but you may have to go back to the store again because you just went and you didn’t have your list, and you didn’t have your meal plan for the week, you’re going to buy too much food or not enough food, or have to go back multiple times. That’s what happens in our goals, because we aren’t doing that strategy piece, so it’s just like having to keep going to store over and over instead of one trip that you get everything you need, you spend the right amount of money, you took your bags, you didn’t pollute the environment. It’s a win-win for everybody. That’s the strategy piece.

When we start to look at the goals and we’re like, “Yes, are they specific? Are they measurable?” Yes we’ve got that piece. Now we start to ask, do I need skills that I don’t have? Do I need to hire somebody with the right skills? Do I need to fire somebody who is on my staff right now who doesn’t have the skills, and that’s why we’re not succeeding and rehire somebody new? Do I need more education? Do I need accountability? Do I have accountability? Do I have my person? Look at the ways you’re going to fail. Really, look objectively at what are the things that are going to stop us? What are the blockers going to be? What are our challenges going to be? Let’s figure out how to overcome those before we even get started. That’s really the strategy piece.

I’ve got to tell you, I was sweating a little bit as you talked about the grocery store. Have you talked to my wife? Because you just described how I go to the grocery store. There’s not even a plan. It’s just I happen to show up and some food comes out with me.

I love the way that you broke that down because it’s a huge missing piece for people. It’s really easy to write down, “Here’s what I want to do.” Maybe you go the next step and here are a few of the things that I’m going to do to get there. But what you’re talking about is going really a layer deeper and looking at what are the obstacles in the way? What could blow this up that I ought to account for ahead of time? What do I need that I don’t have, skill wise, or people wise, or whatever?

You’re really taking this to a level where at the end of it, it sounds like you end up with something that’s a whole lot easier to execute because you’ve answered all of the unknowns.

That’s exactly what it is. It’s very hard. Even before I started doing this, because I was the business owner that would just be like, “Of course I’ve got a goal. Of course, I’ve got a list.” Every day I’d get up and I just go, go, go, go, go because I want to cross things off that list. I never really thought it through.

Now, I think everything through. I’ve gotten so good at it that I now realize I’m not starting any major project until I’ve really thought through it because it will fall out so much easier. That’s the key right there. When it starts to be easy, then it starts to be fun. Then you start to see results, and then you get motivated by your business instead of drained by your business. It becomes this really predictable, repeatable process, and it actually starts to then be easy and fun, when you’re doing that strategy work.

When you just skip it, you’re just going to stay stuck in the having to redo things, and, “Wait, now I have this new information,” or we talked about mindset, or my mindset got in the way. Because I didn’t have a plan for how I was going to get into the right mindset, then I failed again. With that strategy piece, we think through as much of it as possible so it really does, it falls out easy.

Yeah. It’s so interesting thinking about the times that I’ve actually gone through something similar to the steps that you’ve outlined. It actually makes it easier to get the work done. Because I’ve thought through everything ahead of time, I can get other people involved in it. Then I skip that step, I can’t get anybody to help me because I haven’t thought through everything enough that I can give them any of it. It’s still in my head. Really what you’re telling us, there’s not only good reasons to do this, but really it’s probably a vehicle for getting more off your plate.

Without any doubt, whatsoever. If you’ve thought it through, then when you go to delegate, that person knows what their next step is, and it’s not this big mess of nobody knows what they’re supposed to be doing, and nobody’s executing at all. Now you can actually get your team involved in this process as well. This is part of, where if you can bring the team into the strategy and planning work too, they’re now pre-thinking it out. Whatever individual goals they have, they’ve got more clarity there so when they go to execute, it also is easier on them. It starts to really become something that the whole company can participate in, not just the owner.

If you do it well, and I think if you do it repeatedly, you begin to get this momentum. All of these goals that you start stacking on top of one another really become powerful. I think it makes you unstoppable at a certain point.

We could probably talk about this forever, because as I’ve said, I’m a little bit of a planner geek. I think about goals a lot, and love this topic, but I know we’re about out of time. I know you got a program coming up that actually you’ll help take people through this process. I’d love for you talk a little bit about that, and some of the other things you have going on, and let people know where they can connect with you.

Yeah, absolutely. I have new workshops that I’m going to be starting in January where it’s a one-day planning workshop. Now I also do this for companies as well, where I will go into the company. It’s a two-day deep dive, work with the management, work with the … Usually it’s the upper management and the owner of the business, but work with them as well. With the workshops, this is what I’m doing. I actually go in and we do the visioning, we do the measurable goals, we prioritize, we strategize, and then we make a plan to execute.

One of the things that I am able to do is use my planner, which is the tool. That’s why I created it. I created it for my own business because my desk was just a mess. It’s a funny story, when I was working at the women’s networking group, they had their own planner. I was president of the company, I was expected to use it and I hated it. It was awful. I just didn’t like it at all.

When I went out on my own, I’ve got all these things on my desk and I was like, “I need to consolidate all of this. I’m growing a business, I have three kids, a family, I’ve got too much going on here, I’m goal-oriented, I need something that’s going to put it all together,” and I put that together for me. Then I started using it with my clients, and they started getting great results.

One day, I told my husband, I was like, “Honey, this is the best planner ever.” He’s like, “It is.” I’m like, “Yeah, it is.” I was like, “You know what, I think I’m going to call it that.” He’s like, “You are?” I’m like, “Yeah, I am.” Then I looked it up for the domain and nobody had it. I was like, “How does nobody not have bestplannerever? That’s so obvious? How does nobody have it?” They didn’t. Ding-a-ling it was done. I was like, “That’s it, that’s the name.” I’m not an egomaniac, it was just that’s how the name came about.

But the thing is, it’s a tool. It doesn’t matter what planner you use. You’re a planner geek, I see the sticky notes on your wall behind you, Steve. It’s like, “Right on. This is my kind of guy here,” because I love sticky notes. There’s room in my planner to put sticky notes. There’s space in there for your sticky notes. It doesn’t matter what planner you use, but find one that really, really works for you. Do your thinking on paper.

When we talk about these workshops that I’m working on, that’s probably the biggest part, is that when you walk out of there, whether I’ve come to your company or you’ve come to a workshop, you’re going to have a tool in your hands with a daily plan of here it all is. It’s all broken down, it’s prioritized, we’ve pre-thought out everything, and now you have a tool in your hand to be able to implement and execute, that will keep you on track. Whatever it is, that’s part of the key too, is just making sure you have the tool to keep you focused, and keep you on it.

Absolutely. I think it’s so important. Where can folks find out more about your workshops, about the planner? I guess, you said that. But all of the rest of the things that you’re working on.

Yeah, absolutely. They can find me at, spelled the normal Jennifer way, J-E-N-N-I-F-E-R, Dawn, D-A-W-N, We’ve actually set up a custom landing page. If you go to, I’ve got some free goodies on there, some downloads for you. Just some fun stuff to check out. That’s where you would find me.

Awesome. Thanks for sharing all that stuff with the audience. We’ll link all that up in the show notes. If you’re looking for those links and didn’t write them down, if you’re driving or running, or whatever you’re doing, just go over to this episode on our website, and we’ll have all that linked up there.

Jennifer, thanks so much for investing a little bit of time with me this afternoon. This has been so much fun. I appreciate everything that you shared.

You’re welcome, Steve. Thanks so much for having me.

Leave a Comment

There are many ways to build your authority in business, but the very best way is by authoring a book.

If you've had "write a book" on your bucket list for too long, why not join the next "Write Your Million Dollar Book"
Free 5-Day Accelerator
for entrepreneurs?