Hack Your Online Business Logo


What does it take to build not one, but two, wildly successful companies? We grow as we learn from the best, which is why today's episode is extra special as I invite Jennifer Dawn on the show.

Jennifer Dawn is a successful business coach, founder of Best Planner Ever, published author, and accomplished speaker. A master at setting and achieving goals, she is dedicated to creating positive change in the lives of entrepreneurs globally. 

She uses heart-centered and authentic principles around profitability and cash flow to guide business owners in building financially solid companies.

Don't forget to subscribe to the show and leave a review on iTunes. It greatly helps the show with Apple's algorithm!

"I use a simple system. ABCDE. A is a high priority, like it's gotta be done and something you might procrastinate and be as important. C is when you're able, D is delegate ease, E is eliminate. So we just use a simple ABCDE system when you're looking at, okay, this is my big goal, this is my quarterly, this is my monthly focus, these are my projects."

Hack Your Online Business Free Guide

Click The Button Below To Receive The Top 9 Online Business Tips From Successful Online Entrepreneurs. I'll Send It Straight To Your Facebook Messenger.

Subscribe To Hack Your Online Business

Topics Discussed In This Episode:

  • How Jennifer went from working at a POS software company to becoming a serial entrepreneur
  • The challenges of starting her first software company at age 23
  • The turning point of her first POS software business
  • What she has always done that really worked in growing her business and getting more clients
  • Why she started her third business, Jennifer Dawn Coaching
  • The story behind launching The Best Planner Ever
  • How Jennifer plans the business strategy for her past and present businesses
  • Jennifer's advice on planning your business strategy
  • The #1 mistake business owners make over and over again

Resources Discussed In This Episode:

Full Transcript

Chrystabelle: On today's episode, my guest has built two multimillion dollar businesses. She's a successful business coach, founder of best planner ever, published author and accomplished speaker. So a master at setting and achieving goals. She's dedicated to creating positive change in the lives of entrepreneurs globally.

She uses heart-centered and authentic principles around profitability and cashflow to guide business owners in building financially solid companies. So here's my guest, Jennifer Dawn, Jennifer, I want to thank you so much for jumping on this episode with me today.

Jennifer: Oh, I'm so excited and you're so welcome.

Chrystabelle: Jennifer, like I was saying, I've been following you on LinkedIn. I've been seeing the stuff you've been doing. Two multimillion dollar businesses, you've done a lot with this life.

Jennifer: That's the idea, right? We have one life, so we got to get out there and we got to like do something with it.

Chrystabelle: Exactly. And you're an inspiration, at least for myself. So I want you to inspire my audience today. Jennifer, you are a serial entrepreneur. You've had tremendous success. You've built two multimillion dollar businesses. So tell us more about who you are and your backstory.

Jennifer: Yeah, absolutely. My backstory. So I think that I was born really with the entrepreneurial bug because my very, very first company was when I was eight years old and I decided that I was going to have an Apple stand outside my grandparents, a chiropractic office, because I thought a lemonade stand was so yesterday. I didn't want to do that.

And so that's really, I remember though as a little kid and my inventory was free, I just had to pick it off the tree and I had a steady stream of clients coming into my grandfather's office. And here I am, this little kid and like, hey buy my apples. And people did. And I remember just standing there holding, I can still see the shiny quarters cause I think I would sell two apples for a quarter or something.

And I remember holding those shiny quarters in my hand and just feeling like this is the coolest feeling ever that I provided something that people really enjoy and I got paid to do it.

And I don't know, there was just something about it that was like magic for me. Plus the summers that I spent with my grandparents were just the best memories I ever had as a kid. And my grandfather had his chiropractic office attached to his home, so he worked from home, had the office there.

And so I guess that really just kind of stuck with me, that whole model of really being able to control your schedule, control your time still at home in your space, but excelling in a career and he was a healer. And so I love the high idea of healing. I just do a different version of it through coaching instead of I'm not a chiropractor.

Chrystabelle: I love it. My mom works for a chiropractic clinic for the past, I think 35 years. So I grew up in that clinic. I've gotten free chiropractic treatments since I was a baby. And so it's so funny because as a kid I used to sell football cards because I would do that to earn extra cash as well. Do you think that being so entrepreneur as a young age kind of shaped who you became as an adult?

Jennifer: Yeah, absolutely it did. Because even like in high school, I created a cake decorating business. I did have regular jobs as a high school student and through college and stuff. But I remember just like, Hey, I'm going to start a business. And there was like no fear around that for me.

And then that's really what kind of started my first company, my first software company was just that idea that I could do something better and I didn't have to go work for somebody. I was working for a company that was providing point of sale software and they were just doing a terrible job of it and they didn't take care of their clients.

And I hated that. I hated it. So much of the not taking care of people. And so I really do believe that that entrepreneurial spirit along with just stubborn determination and the idea that I could do something better is really what then started to launch me for real into having my own businesses.

Chrystabelle: Let's talk about that. So you were 25, you were working for this company that does POS system company and you were like, you're not doing a good job. What made you decide to go from I'm working for them, they're not doing a good job, I'm going to start my own stuff. It's so different.

Cause when you're working for a company, they've got a regular stream of clients coming in, you're not worried about paying your employees. So what made you decide like I'm just going to go gung ho, I'm going to start my own stuff right now. I'm going to compete against them.

Jennifer: Yeah, because I was actually 23 when I started it. And I'll tell you the thing that was the most important thing was that I had no idea. I had no clue what it meant to have payroll and what it meant to pay for a building and what it meant to deal with taxes and insurance and all this stuff. Like I had no idea.

And truthfully, when they say ignorance is bliss, ignorance is total bliss. When you're just like, I have an idea and I'm going to go do it and I know I can do this better. And so that truly was, I just didn't know those early years in the company. They were not easy. Like I tell everybody, I'm super transparent about this. Like building up my first million dollar business was a lot of hard work. I mean, when I say a lot of hard work, like some people say they work hard.

No, like I really like was burning the midnight oil. When I say we pulled all nighters, like we pulled all nighters where we worked through the night, we would drive to trade shows and be driving through the night. I would be like pregnant with my first two children, seven months pregnant, sitting on a red eye flight across Canada and a middle seat, feeling like I'm going to die if I don't do something different here.

But that's really what it took to get it that off the ground and get it to a seven figure level was that kind of dedication and commitment. But I loved what I was doing. I love my industry. I love my software. I loved what I was doing and so that's really where a lot of that determination came from. If it was just a job that I hated, I probably would never have stuck with it.

Chrystabelle: What made you decide to focus on the amusement park industry? Was it because you wanted free tickets for your kids?

Jennifer: That's a great perk. It really ended up being that, but no, the first company that I worked for, that's what they did. They did software for the amusement industry. And so that's how I got introduced to it. And then while I was with them, they had purchased two of their competitors.

And so I got this huge education cause my job was to go out on site and install some version of software because now they had multiple versions of software at these customer sites. And of course it was a giant mess and it didn't work. But I really got inundated into the industry and that's really where the idea came from. It was not an original idea. It was just like I was working in the industry and seeing that there were just so many opportunities to do it a lot better.

And this was a while ago. So our point of sale software was actually the first point of sale system for the amusement park industry to use a touchscreen. And when you think about it, like you see touchscreens everywhere. My laptop I'm working on right now is a freaking touchscreen.

And so back then though, this was like groundbreaking that we used windows, we use a touch screen interface and it really kind of launched our product because we wanted to make it super user friendly on the users.

Chrystabelle: You had a different product from your former employers, right? And you were really young, so you would go to all these places and you would pitch your stuff. I am sure your age would have been an obstacle or a factor for them.

And they're looking at you and you look a little bit too young to be selling me a POS system right now and I'm already using this product from your former company. So why should I want to change and use yours? So what did you do back then to convince them to like, hey, drop those guys, use my stuff instead.

Jennifer: Yeah, oh, that's such a great question. So it's so funny. The first company that I worked for then I ended up leaving... quick little funny story. So they hired me to be in this position to go out all across the country and be installing their software systems and they didn't know how old I was. And so once I actually got hired, the CFO of the company, I later found out was very upset. She's like, when I started working for them, I was like 21 and she thought I was much older.

Chrystabelle: Were you insulted, were you like, did you just call me old?

Jennifer: No, it was really funny when I found out that she had no idea because I came in like gangbusters. I started changing things. And eventually, obviously the respect came with that. But she actually thought I was much older and so had she even known my age, I may not have ever got that first job.

But one of the things that I learned very quickly is I took on the sales for my company because there was just nobody else to do it. And I learned very quickly to listen. That was like the number one thing is that when I went out to these sites and I would talk to customers, I would ask them like, what is the pain point? What are the problems, what are the challenges? And then I would shut up and I would listen.

And then what the things that were their biggest pain points, I would really focus on those. And so age kind of like didn't matter. When they could tell that I knew my stuff and I knew what I was talking about and I listened to them and nobody else had been listening to them. And so it really set me apart and it almost got to a point where they just didn't care how old I was.

They trusted me. And then I came in and I delivered a product that actually worked and I would say to them, it does this, it doesn't do this. And that honesty and that transparency just went so far with my customers. And that's an important part of how I built that business was because I ended up getting a lot of referrals because it's a small industry.

They all know each other. And so if you do a good job for them, they're going to talk and tell everybody. Just like if you do a bad job, they're going to talk and tell everybody.

Chrystabelle: Like your former employers. So what happened next? So you build it up from zero to seven figure, did you sell the company? What did you do with it?

Jennifer: Yeah, so I ended up, I went through a divorce and an amicable divorce, but a divorce nonetheless. I decided that I didn't want to do software anymore. And so I bought a construction company, which sounded like a good idea at the time, but it was the same year the real estate market completely crashed.

So I ended up closing my doors within a year. It was a horrible but good fail fast lesson. I learned a lot from that. Looking back now, I'm glad it happened, but while I was going through it, it sucked and I hated it.

But then I took a job in corporate, so I took a job with a big $54 million manufacturing firm and they had bought a software company, again, point of sale, but a different industry, not in the family amusement industry. So they bought a software company and they had no idea what to do with it. And so I did, I took a job in corporate and grew their company from about 300,000 when I took it over to 2.2 million in just under two years.

So that was again, another lots and lots of good lessons there. And while I grew the company and there was a lot of success on paper, I just didn't like the corporate mentality. There was definitely conflict in core values. I found I wasn't really, again, seeing my children, I didn't have that flexibility. I was just gone 11 hours a day.

And so that part of it just didn't work for me, but that's what actually caused me to kind of go back out on my own again and be like, okay, there's something that I can do here. I'm just not quite sure what it is.

Chrystabelle: I'm just wondering what's it like to go back and work in a corporate career again, once you've built a huge business, it's done so well and now you're back working for someone else? I'm wondering what's the experience like?

Jennifer: You know, it's funny because the beginning, the first year was really amazing. Like I would show up for me it felt like kind of like a cakewalk job. I'd grown my own company, this is a 50 plus million dollar company. So they have an HR department, they have a marketing department. Our marketing budget was $1 million.

Like, okay, I'll take that. They had an IT department, if there was a problem, you had all this support. And so that part of it was so good because it was as an entrepreneur, I was used to basically just doing everything myself. And so you came in, you had all these resources, you had huge marketing budget, you had these things, which were really, really good.

And so for that first year I was loving it. And if you've been an entrepreneur and you're like, you're responsible for your own paycheck and then your check just shows up every week, this company paid weekly. So every week it was like ding money, ding money. I'm like, Oh my God. Like that was a gift that was such a gift. And full benefits package. I was at the executive level, so I had all the benefits that go along with it, several weeks of vacation.

So yeah, it was awesome to say that part of it was really good. Not having to worry about where my paycheck was coming from, but the flip side of it, not seeing my family, I had found some problems in their software, they didn't want to fix it.

Those kind of conflicts where I had a problem with my software, I would fix it and they didn't want to do that. And that for me was the hardest thing. That's what caused me to lose, lose sleep at night, is those, those kinds of decisions that made all those perks and benefits not worth it. The good news is, I mean, I'm out on my own now and I've more than doubled.

So there's definitely a good happy ending to that story. But when you step away from that after you've been used to it for a few years, it's definitely scary to kind of go back out on your own and venture back out into the entrepreneurial world and be like, where's my money coming from? Like there's definitely some fear involved there.

Chrystabelle: I think that's one of the most common fears that entrepreneurs face right when they leave the corporate career and they're like, Oh my God, I don't have the regular paycheck coming in anymore.

Jennifer: Absolutely. No, I mean, I had a huge severance package when I left, so I walked away with a bunch of money. But which was wonderful. So it gave me some time and some space to figure it out. But like for those of you who are transitioning out of a corporate career, I'm like get the money figured out a little bit.

Like build up your resources because the last thing you want is to try to grow a business and not be able to pay your rent or your mortgage and have that additional stress on you while you're trying to get a business off the ground. So this is one of the things like when I work with entrepreneurs who are in that struggle, I'm like stick it out a little longer if you have to just to fill up the resources, get some income coming in.

Cause trust me, you don't want the stress of I can't pay any of my bills and I'm trying to grow this business based on all your years of experience starting and running multimillion dollar businesses.

Chrystabelle: Can you share what you've always done that has really worked in growing your business and getting more clients?

Jennifer: Ooh, that's a great question. And so it's interesting because what I've done has actually changed over the years as technology has changed and just everything has changed.

And so, like with my planner company, I used to get a lot of my sales off Facebook and now Facebook ads just don't really seem to be doing it like they used to do. It's very saturated. People are so bombarded. It's been much, much harder for coaching. I used to get, again, leads and stuff on Facebook as well, but now really all my traffic comes off of Google of people just sitting down and typing, I need a business coach, whatever.

And that's where most of my stuff has come from when I very first started. And I still do get a lot of referrals. So referrals are always really important and I love referrals so much, but it's hard to build a business on referrals cause it's, it's like building a business on hope. I really hope somebody says something nice about me today.

But if they don't, you're kind of screwed. And so I always want at least three sources of lead generation at all times going on. So podcast interviews, if I'm out networking, I do speaking, I'm doing paid traffic. So advertising on Facebook, Google, got the whole social media thing going so that we're out on social media.

So definitely putting it out there on the channels that where my people are. But if you do have to kind of change with it with the times, and like I said, like I wasn't using Google really at all probably two years ago for my coaching practice and now I'm moving just about everything over to Google because that's where the qualified people are coming from.

I've decided that in my business is I really want to make myself as easy to find as possible for the warm people who were looking for what I sell instead of slamming myself in front of everybody and kind of fishing and hoping somebody will bite.

So for me it's been a little a change in my strategy. I don't want to be, all those blasted ads everywhere. I really kind of just want to be as available as I can be for the people who are looking and ready.

Chrystabelle: Let's talk about your coaching business. This is your third business, right? Your third business, Jennifer Dawn Coaching. Tell us more about it. Who do you serve?

Jennifer: Yeah, so I serve entrepreneurs. I'm not specific to an industry. I believe that if you're in an industry and you need to be specific to it, you absolutely should do that. But for me, when I started my coaching practice, it was just really important for me to help whoever I needed to help. And so I serve entrepreneurs across the board.

I work with a lot of business owners who have I actually have four different packages. So I have one package, which is women only for more startup or beginning businesses revenues under like 250,000. My primary private coaching generally am working with entrepreneurs who have businesses from 500,000 to 5 million.

I do a lot of mindset work. I do profit first. We get your finances and your business financially, just really lined out help with goals, mapping out strategies and then any challenges that come up while you're executing the strategy. I'm there to help you work through, so that's ultimately my coaching practice.

Chrystabelle: You mentioned profit first coaching, right? So tell us more about that. What is Profit first coaching?

Jennifer: Yeah, so profit first is actually, it's a book. It was written by a gentleman, Mike Michalowicz and then he created an organization around it which certifies bookkeepers, accountants and coaches. Mike actually asked me to lead his first mastery group when he was getting it off the ground as I did that for him for two years.

And so I was helping his bookkeepers and accountants implement the profit first system in their businesses and also helping them with their client's businesses. And so it's something that I've always done with my clients as well, but it's basically a cash management system so it does not replace your accounting system or the love of, having like you have to have an accounting system, don't get rid of it.

But the cash management system kind of sits on top of it. So we're really looking at the cash coming into a business. We're earmarking it in different envelopes or counts. Kinda like the envelope system with Dave Ramsey, only sort of an electronic version with your business.

So as money comes in, you're earmarking it. So when you look at your bank account balances, these are my operating expenses, this is my hard costs. This is my owners pay. So you're really spending much more wisely in your business.

And we could do this with small companies, large companies any size company. It also helps us to get companies out of debt. It helps us to turn things around as far as their bottom line.

There's just, there's so many good things from it. One of the things I recommend really for all business owners is to get on something like profit first for your business.

Chrystabelle: What is your strategy on growing Jennifer Dawn Coaching to your next multimillion dollar business?

Jennifer: Oh my goodness. What a question. So it's interesting because coaching, private coaching isn't really scalable and as a coach, I know this like it's not really scalable, but it's work I love, I just love it so much.

And so I know that it's not scalable, but I don't really care. I'm going to do it anyway. I do have some groups and those groups are definitely more scalable, but really it's my planner company that's the one that's scalable and so I'm growing both of them with the full intention that someday, I don't know what's going to happen with the coaching practice.

Maybe I would sell it, maybe I wouldn't. But the planner company, that's the one that is scalable, that's the one where the passive income comes from. That's the one that really, I'm more concerned about getting that to the seven figure level, which I'm on track to do, which is very exciting.

And then maybe one day who knows, sell it to a bigger company, sell it to somebody else. That's really my strategy is with the planner company for now with coaching, just want to help the right people.

I don't want to overwhelm myself, I want to show up and be a hundred percent present. So I do limit the number of clients I take on. I'm very blessed because I'm generally full, just a real gift. So really that's my strategy.

Coaching, I'm just going to keep doing it cause I love it. I've built some programs and things like that, but it's the planner. It's Best Planner Ever. That is my retirement plan.

Chrystabelle: Tell me more about this planner. So what gave you the idea to create a planner? What did you do to sell it? Did you launch it? Tell me all about it.

Jennifer: Yes, yes, yes. So the planner actually came about because I was sitting looking at my desk and it was a disaster and I'm in between corporate and going out on my own. I had been asked by a national network of women entrepreneurs to come in and lead their accountability and masterminding circles. And they had a planner that they use.

And because I was at the top of the company and they eventually made me the president, like I was supposed to use this planner that they had and I hated it. I didn't like it. I was like, Oh, I don't like this planner. I never said that, but inside I was like, this thing does not work for me.

And so after I stepped away from them, went out on coaching on my own, I was looking at my desk and I'm just like, this is a disaster and nothing. I can't find anything that would work. And that's really where it came from.

So I created it and I started using it and I told my husband one day, I was like, Oh my gosh, this is the best planner ever.

He's like, really? I'm like, yes. I'm going to call it that. He's like, you're crazy. I'm like, I know. And, but then the domain was free. And I'm like, how is this domain not taken best planner ever? And so I grabbed it and that's where it started. And I started using it with my coaching clients. And then from there I took it out to the world.

And now we sell, I don't know exactly how many, 3000 planners a year. We're helping people like really take control of their productivity. And so that's the best planner ever from there. This year I released the best journal ever. I didn't really want to do just a regular journal.

So I did a different take on journaling, which is an amazing exercise I use in my coaching practice. And so I turned that into a journal and we've got some great online courses around it and this January I'm coming out with my book, which is, it'll be out next month, it's called the joy guide, finding your joy in a world of crap.

And so that's when the evolution from there and honestly just the whole planning productivity, time management as an entrepreneur, it's so important. Like if you're not managing your time, you're not going anywhere. You're not building a big business if you can't manage your time well. And so it's just such an important thing for me and my clients that that's really where it, where it came from.

Chrystabelle: Before we talk about your book, I want to ask you this question. So we know there are a lot of business planners and journals out there, right? So when you had this idea and you were going to go market it out to the world, what did you do to differentiate yourself from the rest?

Jennifer: Yes, a great question because you're right, especially these days, I don't know what it is about planners, but like everybody in their brother seems to have one.

Chrystabelle: It's Pinterest.

Jennifer: Yeah. Like, Oh my God. Like there's so many and competition is tough and I'm going to be straight up honest. Like there's so many planners out there that unless you're doing a high volume, it's a hard thing to make money at like good money. Because it is such a competitive competitive market.

But I do it obviously cause I love it, but how did I set myself apart? And so I really just started focusing on, I'm one of the very few business coaches who created a planner and that really for me kind of felt like I set it apart, but I'm a business coach but I also bring in mindset some law of attraction, some woo woo stuff with the business and you don't see that very often.

You see like the woo spiritual stuff over here and you see the business, anal retentive data analysis numbers over here in time blocking, get it all lined out.

And so I really kind of bringing those two together because I felt like in my life to get balanced in my life, I needed some of that little more anal time blocking. But I also needed the spiritual mindset, stay in the right mindset and alignment.

And the other thing I did, which is not in most planners is I created vision pages because that was the one thing that I saw that was really missing. Nobody was taking any time to get clear on the vision of your life, where you want to go, what you, where you want to end up, what you want it to look like. So before I ever even start to plan my day, I align with my vision. I'm like, well let me get clear on where I want to go before I get busy today doing stuff. And I didn't see that.

And I still don't really see that any planners today, like on my daily planning page, it actually has a reminder to read your vision statement, align with it, see yourself succeeding before you start getting busy. So there were some of those things that I just wasn't finding anywhere and I use those to kind of set myself apart.

And then of course like every other entrepreneur spend a lot of time and energy and money on marketing and ads and all of that branding and messaging and all that stuff. To kind of get that dialed in and it's worked. It's worked.

Chrystabelle: All right. Now quickly tell us about your new book. So it's a very interesting title. Tell us more about it.

Jennifer: The joy guide. It's funny, why I'm a coach, right? And so I, I had to do something to just help people because this has happened to me too.

I go out and I read a book and I get super inspired and I'm like, Ooh, I'm going to go do all this. And then it's like, it just sort of fizzles. Or it's like, I don't really know where to go. I don't really know where to start. Or you watch a documentary and you're like, Oh, I'm going to go do this.

And then you're like, yeah, I don't know what to do. And you just sort of get back to my crappy life as normal. And so I wanted to write a book that would help people know like, well, what do I do? Like what am I do to actually bring more joy into my life?

And so that's what this is. It's literally chapter by chapter of these are the things like if you want to shift your mindset, here's some tools of how you shift your mindset.

If your mindset is not shifting, here's a tool to help you figure out how and why your mindset isn't shifting. And so that's really what the joy guide is. It's about finding your joy with all this stuff going on in the world. I don't care. It's about not making excuses. If you want more joy in your life, you can have it. But I wanted to teach like practical, tangible tools of how to actually do the work to get there.

Chrystabelle: And where can people get this book?

Jennifer: Well, they'll be able to find them on Amazon or my best planner ever sites. Officially November 15.

Chrystabelle: Awesome. All right, now before we go on, today's show is sponsored by my messenger marketing agency, Chrys Media. We work with our clients to help them get more leads and increase engagement and sales with messenger marketing. Now, if you're interested to learn more about messenger marketing and how it can help your business, then go check out my free online training at hackyouronlinebusiness.com/messenger after today's show.

Jennifer, I want to talk about business strategy. How do you plan or how have you planned the business strategy for your past and present businesses?

Jennifer: Oh, awesome question. So in my past businesses, I didn't plan anything. I just literally was like, Hey, we need to make more money. So let me get busy selling more stuff. And then we sold more stuff and then we needed to hire more people and then it was like, Oh my God, payroll is going to kill me. I'd better go sell some more stuff.

And that was really the cycle that I was in in my earlier businesses and there really wasn't much planning or strategy to it. In this business, I spend a lot more time on planning and strategy and a lot less time on execution. And in a nutshell, this is actually a course I teach and I do this with my private clients where I help them through the process.

So it's going to sound easy, but there's like, if you try it and you're like, this isn't easy at all. It's like, no. Some of my clients, it's so funny, I had one in particular who we were doing all this planning and strategy work and she's like, this is a lot of work.

Like, yeah, it really is. It's going to take some work to do your planning and your strategy, but if you could do that pre-thinking ahead of time, then when you go to execute it's way easy and things just fall out so much easier and faster.

But in a nutshell part one is the vision. Get really clear, where do you really want to end up in a year, three years, five years? What does it look like? What does your business look like? What role are you're playing? What does your team look like?

Like start to really get clear on where you want to go first. And then from there we kind of reverse engineer it. So we back it and we go, okay, so what would this year, if we were to end this year, what would that look like? Then we break that into quarters and then for each quarter I try to have a monthly focus goal. So it's like, alright, so like right now we're coming in, we're in fourth quarter, so I have an October and November and a December focus goal.

So based on that focus for the month, we'll break that down into projects. And then from the projects we do a little strategy work. So it's like, Hey, what's going to stop me? Ask that question ahead of time. What's going to stop you from succeeding? Because if you can figure out your blockers ahead of time, then when you go to do it you're going to be like, Oh, I figured that out already.

And off I go. So we do some strategy questions. Are there skills I need? Are there people I need to hire? What do I really need to do to accomplish this? And then from there we break it down into daily tasks and your daily tasks. 

I use a simple system. ABCDE. A is a high priority, like it's gotta be done and something you might procrastinate and be as important. C is when you're able, D is delegate ease, E is eliminate. So we just use a simple ABCDE system when you're looking at, okay, this is my big goal, this is my quarterly, this is my monthly focus, these are my projects.

So what am I going to do today to move that forward? And the A task, we'd like to break those down into maybe like 10 minute tasks. So you could literally sit down every day and do one or two things to move your business forward.

Then you can get on with all the important stuff that you're going to do anyway. But it's really about pushing every single day, getting out of your comfort zone, opening doors, like really pushing, pushing, pushing, pushing and pushing that envelope a little bit and not procrastinating.

I know entrepreneurs see this all the time on their sales. They're just too busy to sell and it kills your sales. So we have to kind of get rid of some of that busy work and re-prioritize or the times going each day. So that's a nutshell what we do.

Chrystabelle: Should we be ambitious with our goals or do we want to be more realistic with our goals?

Jennifer: For me, I of course have a big goal that's definitely ambitious. A vision, I should say that. My vision is ambitious, but when I'm setting my goals, I like to set, I like to lower the bar a little bit and set myself up for success. In today's world, we are bombarded with just so much stuff that I've found.

If you set the bar too high, it just becomes so easy to get overwhelmed, to give up, to feel like a failure that kills your mindset. The whole thing just sort of unravels. So I'm definitely ambitious in the vision, but when it comes to the goals, I scale it back and I ended up telling a lot of my clients and myself to lower the bar or lower the bar and lower the bar. And just as long as you're going forward.

Chrystabelle: What is the number one mistake that people make when they're planning their business strategy?

Jennifer: Not having a vision really in truly not having a vision because they don't spend any time whatsoever on where they want to end up and they just start making goals and getting busy and nobody spends any time on vision and nobody spends any time on strategy.

And being rich is not a vision you can have in your vision. Like, I'm wealthy, my bank accounts are flowing. Absolutely. But then it's the goals that we want to now set the tangible benchmarks. And so being rich might mean that you got to get all your debt paid off and now you've got to fix your company so you're not relying on debt to keep the doors open.

And then you've got to set up your own line of credit, which is funded with your own cash. That's the strategy piece of you want to be rich. Okay, great. But now let's get down to the brass tacks of how we're actually going to make that happen. And it's probably going to mean that you're going to change your mindset, change some bad habits, change your patterns, change your routines, be willing to change in order for any of that stuff to happen.

Chrystabelle: Can you share one secret hack or tip or strategy that you normally only share with your private clients when it comes to building your strategy?

Jennifer: This is a good one. Well I have a list of strategy questions that I go through with my clients that are just questions that we ask to make sure we're sort of covering all of the bases. And so some of those questions would be, oh, this is a good one.

So what toxic things are going to stop you from achieving this goal? And it could be your own toxic mindset. It could be bad habits. It could be people that you're hanging out with. It could be places that you are frequenting. It could be crap that you're watching. It's killing your mindset.

And so that's one of my favorite strategy questions are what toxic elements do you need to eliminate so that you can set yourself up to be successful in this goal that you set for yourself in your business.

Chrystabelle: Now before we end this episode, I'll like you to share what is the biggest lesson that you've learned as an entrepreneur?

Jennifer: Oh my goodness. Check your ego and get help. No, I'm serious. Like for my first software company, I was like, look at me. I'm so important. I'm the president of a software company. I didn't need any help and I was making mistakes for left and right. And so when I learned to check my ego and just be like, you know what, Jennifer, leave that outside. You need help. Ask for it. Like that changed everything for me.

And even with my clients, they come into coaching and they get the help that they need and it shortens their curve and it makes the whole thing more fun. I'm trying to just like solve the world's problems all by yourself because you're so important and nobody else can do it as good as you. I would say that's probably the best lesson I've learned is check the ego and get help.

Chrystabelle: All right guys, go check out JenniferDawncoaching.com after today's show. I want to thank you guys so much for spending time with me and Jennifer. Head on over to hackyouronlinebusiness.com, you can find the show notes, the links and everything that we just talked about today. Thank you so much Jennifer. I want to appreciate you for coming on the show today.

Jennifer: You're so welcome. Thank you for having me.

Thanks For Listening, My Friend!

To help out the show:

  • Please leave a review on iTunes. Your ratings and reviews will help the show to rank and it will also help me create a better podcast show for you!
  • Subscribe to the show on iTunes.
  • logo


    Hack Your Online Business Free Guide

    Click The Button Below To Receive The Top 9 Online Business Tips From Successful Online Entrepreneurs. I'll Send It Straight To Your Facebook Messenger.

    Copyright © 2021 Chrys Media