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How to Execute your Daily Business Planning Like a Boss

Do you know what it feels like to wake up and have your daily activities mapped out from start to finish? Or are your plans just as scattered as the sticky notes you use to keep up with them?

Even if you have your whole life planned to a tee on your Trello Board, you need a go-to manual and a hard copy backup.

Our next podcast guest, Ashley Crenshaw, will tell you all about the benefits of planning and the one planning tool you shouldn’t run your business without.

Get ready to be in the know about:

  • How entrepreneurs can use planning to stay organized and productive.
  • The benefits of using a physical business planner in the digital age.
  • How a newbie can get started on the path to planning.

Ashley is CEO of Boss Made Planners, LLC, a YouTuber, and an avid planner. She also has a Business Management degree from the University of South Alabama.

Ashley loves connecting with fellow #plannerbaes, so find her on social media at the links below:

Danielle Towner | Entrepreneur + Digital Creative Resources


Danielle Towner (31s): “A dream written down with a date becomes a goal. A goal broken down into steps becomes a plan. A plan backed by action makes your dreams come true.” That’s a quote by Greg Reed, and it’s also a quote on our next guest website that sums up the whole mission for her business. 

Ashley Crenshaw of Boss Made Planners LLC dreamed, planned, and executed her business with one mission in mind—to bring simple goal planning to everyone. You’ll learn more about her business journey and also her planning products on this next episode. Stick around and keep listening for more. 

Welcome back for another episode of Dreamer’s Den Podcast. I’m your host, Danielle Towner. If you haven’t met me already, I help entrepreneurs build their online presence and brand awareness through website design, social media marketing, and digital products. 

Danielle Towner (1m 6s): Today, I have a special guest with us on. In the past, I’ve talked a lot about planning—marketing, planning, business planning, all that good stuff, and how it’s critical to the success of your business. We have with us today, Ashley Crenshaw of Boss Made Planners, and she’s going to talk all about business planning for the small business and the product that she provides to help you do just that. Thank you for coming to Dreamer’s Den. 

Danielle Towner (1m 36s): Welcome, Ashley. Ashley (1m 38s): Hi, thank you so much for having me 

Danielle Towner (1m 40s): Awesome. I’m excited to dive in and learn about what you have going on. We’re going to get started with you telling us about your business, Boss Made Planners, and what made you get into the planner business? 

Ashley (1m 56s): Boss Made Planners is an offshoot of a previous craft that I had before this. It started when I was doing a craft. I had started crafting where I would take old furniture and slip it and make it new. I’ll buy something from the flea market or from the Goodwill and then bring it home, set it down, painted it up, and then resell it at a higher price. 

Ashley (3m 2s): When I started to get a pretty good amount of momentum with that, I wanted to be able to track it in a way that would benefit me. I would look around to find planners that could help me stay organized and also help me manage my resources and funds, and there just wasn’t anything like that anywhere on the market. I decided it would be much easier, instead of just hoping and praying or building something that other people were making, to just make one of my own, and that’s what I did. 

Danielle Towner (3m 3s): It took me a year and some change to actually make the planner, to design it. Then it took several more months to have the planner printed, but once I got it done, it was exactly what I needed. I figured I needed to go ahead and share that with other people like me; other crafters, other entrepreneurs, other small business owners who pretty much don’t know where to start and just need something to help and guide them. That’s how it started. 

Danielle Towner (3m 35s): That’s awesome. I used to watch Shabby Chic back in the day. I hope I’m not telling my age too much, but I think that’s cool to take something and have this vision for it and recreate another piece out of it. I think that’s cool. I’m not really crafty with my hands like that, but it’s cool. I used to love to watch the process. That’s cool. Another point that you hit on is the financial piece with managing the finances, and that’s another very critical thing throughout any stage of a business, but especially in the beginning phase when you may not have a lot. 

Danielle Towner (4m 22s): You may be working with not a lot and you need to manage every penny. There wasn’t a lot out there to help do that. I think having that planner with all of those components in it, that’s exactly what’s needed in the marketplace. They say when you can’t find exactly what you’re looking for, that’s what a lot of these dreams and these businesses, that’s what they’re born from. That’s exactly what you did. 

Ashley (4m 50s): Yeah. That’s exactly what it became because I was doing these things and then I realized that I didn’t really have a means to keep up with how much I was investing into these products. When you’re making something by hand and then turning that into a service, it’s way harder to quantify the price of a service than it is to quantify an actual physical product. You already know how much that physical product cost you, you can just tax it. 

Ashley (5m 22s): You can mark it up and then that can be your revenue. When your product is your time and your energy, how do you charge that? How do you make an income from charging for a service? No matter what I could do, no matter what I did, I never could find anything that would help me out as far as making sure that I wasn’t going over my budget, making sure that I had the items that I needed for certain things. 

Ashley (5m 51s): When you’re making something by hand, it’s super easy to get distracted or add something that you never intended to add, and that’ll run the price up on something. Then you’re like, “Oh, wait. I didn’t have another $20 to add to that. Why did I do that?” It just helps me personally to stay focused when I can write it down and then go back to it and look at it and say, “Okay, Ashley. 

Ashley (6m 24s): You wrote it down here. You said you were going to use this item from this store. It costs this much and you’re not spending more than that.” That benefited me in the long run. 

Danielle Towner (7m 11s): It’s easy to get carried away as a creative. I know exactly what you’re talking about. You can compare that to a grocery list. If you go into the store without your list, then you’re just grabbing everything you think that you want or you just imagine that you want, but if you have your list, you can go back and say, “Hey, this is not on my list. This is not in the budget today. Let me put that back.” That’s a good way to look at it, and that’s already some of the benefits of your planner. What are some of your other benefits compared to other planners out there? 

Ashley (7m 17s): Well, to begin with, there really isn’t a planner like this on the market. There are different little workbooks I’ve seen that may have a page or two that are similar to what I have, or there may be an Etsy shop that sells a page that you can print and then save it on your own. 

There isn’t a physical planner that has all of these components together that I personally have seen that has the options that my planner gives you. As far as a business planner, in the sense of what it is, it gives you everything down from your calendar, to how much your monthly budget is, to your sales tracker, to your inventory, to just things that you need to buy that you’re low on stock on. 

Ashley (8m 6s): That’s just the stuff that you get per month, and that’s only about half of the planner. We haven’t even talked about the goal-setting portion. We haven’t talked about the client’s portion. There’s a place for marketing. There’s a place for you to review at the end of the year and keep up with your progress and track how much you’ve grown and how much didn’t grow because all of that stuff is important. 

Danielle Towner (8m 34s): Absolutely. It’s a lot to keep track of in a business. It’s good to have something, a resource, to put it all in one place. In my field, I’m all about business and marketing plans. You have a planner customized for small business owners. You touched on that a little bit, but how exactly does it help them to stay organized, to stay productive and to stay on top of their business? 

Ashley (9m 9s): Well, the way that it’s set up it has different components that are broken down into steps. Especially in the goal setting portion, that is the very first thing that you see when you come into this planner. You will see that the first thing I’m saying is, “Your year starts whenever you decide.” By the way, the planner is an undated planner, so you can start it whenever you get it. It doesn’t have to start in January or even in March. It can start whenever you want it to start. In the beginning of the planner, there’s a section for you to plan out your goals for the year and each action for you to achieve that goal. 

Ashley (9m 50s): Each month, there should be a goal achieved based on your action steps. The way that the planner is set up, it allows you to refer back to your goals and see your progress every single month. One of the ways that I personally use my planner is for my social media growth. Every single month, I have a dashboard that is blank. It’s different compartments, different cubes, different places for you to add whatever you want there. 

Ashley (10m 24s): I choose to use one of those squares to see where my Facebook following is, my Instagram following is, my YouTube following is each month and then project where I want it to be for the next month. When I go back to that, I can look at my planner and be like, “Maybe I haven’t quite reached my goal for this month,” and I can put some energy into making sure that I reach that particular goal for that month. You can do the same thing with your sales.

Ashley (10m 54s): There’s places for you to have a goal for sales each month. There’s a place for you to have a goal for your debt each month. I know not every business owner has that, but a lot of us do, especially if you are in a field that requires a large investment. It’s a good idea to always keep track of how much you’ve paid down on your debt and what kind of goal you have for the end of the year, end of each month. Every single month has a goal setting option for you guys so that you can keep track of everything that you want to do and everything you want to achieve. 

Danielle Towner (11m 34s): That’s awesome. You have a lot packed into this calendar and that’s one of the things that aligns with what I tell my audience when they’re doing sales and marketing plan, you have to work your way backwards from the goal. Like you said, break down your steps to monthly, to weekly, to daily, and even hourly if that’s the way that you work. It sounds like you have everything that they need to set up those goals. 

Ashley (12m 7s): Well, I tried to be as universal as possible. There will definitely be things that I couldn’t put in the planner, and there were things that I had to take out just for the size of it. It’s a 350-page planner. I couldn’t get it any bigger. Otherwise, it wouldn’t have been functional at that point. The idea is for it to not only be functional, but to also make you want to use it. You can have a planner that’s amazing, but if it’s too bulky you don’t want to carry it. 

Ashley (12m 38s): You don’t want to pick it up. If you don’t like looking at it, you might not think about it anymore. You need something that is not only functional, but makes you want to use it. That’s what I was trying to focus on, function and aesthetic. The aesthetic is makes people want to gravitate to it. 

Danielle Towner (13m 2s): That’s another point that I was going to come to; speaking of carrying it around. Many people and even companies are switching to using digital resources for planning. What would you say is still the advantage of using a physical planner versus switching to digital? 

Ashley (14m 2s): There are benefits to both. Digital planning is becoming a big market as of late because people like to be able to use their tablet to decorated it and you can set an alarm for things. For a lot of people, it works better for them that way, but there are a lot more people who generally just prefer to write it down and then see it. 

I know that, at least for me, writing something down and then breaking it down only really works when I’m using pen to paper. You understand what I’m saying. It takes a  different kind of person, in my personal opinion, to only rely on the digital of it because everybody at some point is going to want at least a notebook with just some paper and a pen to jot down ideas. You’re right. 

Ashley (14m 51s): At the very least, people gravitate towards that. For those people who absolutely just refuse to pick up a planner for various different things because there are those people who just absolutely cannot deal with it, I think a lot of that is due to just the stigma of it a little bit. The planning community has gotten to a point where it’s making people feel like if it’s not this kind of way, then it’s wrong, or if you don’t use 1,000 stickers every single month in you planner then it’s not going to work for you. 

Danielle Towner (-): You’re not doing anything. 

Ashley (14m 60s): That’s just not true. My planner is minimal. It doesn’t have a lot of color. It’s that way so that you can add as much color as you want. If you don’t like color, you don’t have to deal with color because there are plenty of people who don’t want that. As far as the benefits of doing physical versus digital, there’s always that worry that your items would disappear on a digital flat platform. I’ve heard so many horror stories of, “I planned my whole week on my phone and then it cracked.” 

Ashley (15m 38s): Or, “Everything I had was on my tablet and then I dropped it, and it’s gone.” If you don’t have a way to back that up, at the very least, have an external drive somewhere or just have it written down somewhere where you can easily get to it. It’s a hassle. It’s a pain. Then you lose more than what it’s worth in my personal opinion. I would say to anybody, it’s a good idea to have both. There are certain things that your digital planning can help you with, like keeping track of appointments, especially if you’re one of those people who isn’t good with time, like I am. 

Ashley (16m 19s): A good alarm makes everything go around. It’s a good idea to have your digital planning for that, and it’s a good idea to have physical planning for things that you absolutely need to pick up and see immediately. It’s way easier to pick up your planner and flip to a page and see something, versus logging into a computer or a tablet and then downloading this app, then opening that app, then searching and swipe it, then finally finding it. 

Ashley (16m 50s): If you’re like me, once again, I like to keep everything in my email. So trying to remember what was the name of the email that I sent to myself three months ago that told me this information, it’s way easier, in my personal opinion, to just write it all down. It’s also a good idea to have multiple. You should never be afraid to have two or even three forms of planning because people need that in order to keep track of certain things. 

Danielle Towner (17m 55s): All right. I want to share a little secret with you guys. When I was first getting started with Dreamer’s Den Podcast, I had to research to answer a lot of questions. Like how do I record an episode? How do I get my show into all the apps that people like to listen to? Of course, how do I make money from my podcast? The answer to every one of these questions is simple. Anchor. 

Anchor is a one-stop-shop for recording, hosting, and distributing your podcast. The best thing of all is that it’s 100% free and ridiculously easy to use. Now, Anchor can match you with great sponsors who want to advertise on your podcast. That means you can get paid to podcasts right away. 

One thing that I also liked about it is that it reduced the workflow so that you didn’t have to do a lot of the legwork and I could focus on getting guests and start interviewing and recording immediately. If you’ve always wanted to start a podcast and make money doing it, go to to join me and a diverse community of podcasters already using Anchor. That’s I can’t wait to hear your podcast. 

Danielle Towner (18m 60s): All right. A little side note: if you follow me on Instagram or Facebook, you probably saw a story from me recently where I shared a photo of me completing my application for my absentee ballot. I’m staying home as much as possible and keeping and mine safe, but I do understand that my vote and my voice matters, especially at critical times like these. 

Now, if you share some of the same concerns that I do, just know that voting isn’t just going to the polls on the election day anymore. Options like early voting, mail-in voting, and ballot drop boxes are available to more voters and are growing in popularity. 

How to Vote, a tool created by Democracy Works, breaks down the options your state offers for casting a ballot, empowering you to decide when and where to vote. With the How to Vote voter tool, you can sign up for election reminders, see what’s on your ballot, get step-by-step assistance requesting your mail ballot, explore your options for returning your vote at mail ballot, check your voter registration status, find your polling site, and make sure you have the appropriate ID. 

Decide when and where you vote this year at There are three things that happened to me that caused me to be somebody who uses a combination of both. Number one, I had a baby, so my flawless memory is now all over the place sometimes, and sometimes I just can’t keep up with two people’s whole agenda at the same time. That incorporated the reminders, as you said. 

Danielle Towner (19m 32s): Number two, I’ve broken a couple of laptops and number three, I’ve broken about three phones. 

Danielle Towner (20m 17s): I know exactly what you’re talking about with planning out your whole life and losing it with the drop of a laptop or a mobile device. I’m a believer of doing both. When I worked started working with a business consultant and she was like, “Okay. Pull out your paper.” I’m like, “Paper? What do you mean paper?” It helps. You can do so many more things and draw diagrams and map things out like you said. 

Ashley (20m 19s): To visualize. 

Danielle Towner (20m 19s): If you decide to go in a different direction, you can go back and you can adjust it, and it’s different from just typing on a device. Your point is well taken. Now, for someone who is not used to planning out their day on, one of the newbies that you talked about or the person who you said just never did it, what advice would you give them to get started? How can they get into the habit of using a planner? 

Ashley (20m 56s): Well, there’s no one-size-fits-all answer for that because different strokes for different folks. To just begin with, I would tell people to start off with your just normal, regular Walmart planner. Get a pen that you like to use to write with, and just start off by doing simple things like writing down an appointment that you have two months away or writing down a date with a friend or something. 

Ashley (21m 28s): Write down maybe a list of things that you want to remember and just keep that item, that planner with you. That way you can grab it and periodically use it whenever you need to use it. Over time, as your life gets busier, you’ll start to see where you can incorporate your planner more. Then it’ll become more of an extension of your arm versus external thing to do on a regular basis. 

Ashley (21m 60s): You’ll definitely want to use it just because you feel the need to, versus using it because you just think you should, if you understand what I’m saying. 

Danielle Towner (22m 14s): Right. The goal of it is to make your life easier or make the flow more fluid versus being a task or something that you just feel like you have to do. 

Ashley (22m 29s): Exactly. The last thing that you want to do is incorporate another task to your planning. The planner isn’t meant to be a task, it’s meant to help you with your task. I noticed that a lot of people, like I said before, the planner community is really, really hyped. Sometimes they have people thinking that you have to do this a certain way or have all of these things in order to plan correctly, but there is no one correct way to plan. 

Ashley (22m 60s): There are so many different ways to plan your day, to plan your week, to plan your month, to plan your goals. That’s why there are so many different kinds of planners. You need to work on figuring out what works best for you because not every single kind of planner is going to be your bae. 

Danielle Towner (23m 20s): Now, when you say community, do you mean there are groups and different forums dedicated to planning? 

Ashley (23m 31s): Yes, ma’am. There are forums, there are groups, there are Facebook pages, there are all kinds of social media, YouTube. There is everything you could possibly imagine, and that’s also a good way to get into planning as well. If you watch YouTube, look up a planner review and it will put you down a gigantic hole of everything. You’ll just be like, “Oh. All of this is happening?” 

Ashley (24m 36s): You’re just going to can take the world up, and then you’re going to see all the stuff that they’re doing. You’re going to be like, “Oh. That might help me do this and that. I didn’t even know you could use a planner in that way.” It will really enlighten you. There’s definitely plenty of resources out there for you to definitely get into the planning community. You don’t even have to be in the planning community. 

I say that because that’s what it’s called technically, but just be a planner or a person who watches people plan. That’s how I learned what people were wanting in their planner while I was building mine; just watching them on YouTube and hearing what people had to say on Facebook and getting that feedback because, like I said, not everybody wants the same thing in their planner. 

The best thing to do is just find a group of like-minded people and just make a connection with those people. They will also help to motivate you so you won’t feel like you’re just in a rudder, struggling to do something. 

Ashley (25m 11s): It’ll just be organic. It’ll be fun. It will become something that you do for relaxation. It’ll give you a different outlook on the planning as a whole. 

Danielle Towner (25m 25s): You’ve definitely given me a different outlook on it and I’m intrigued by it. I’m intrigued by your product as well. 

Ashley (25m 35s): Thank you. That’s the goal. We just want people to be into it because it’s not the pain that people like to make it seem. I know that also people just don’t think about it. People just don’t think about writing stuff down sometimes, and then they forget, then they don’t know why they can’t remember such things. When you have a super busy life, most of us have really busy lives, it’s hard to just remember things off the coast. You need to write things down sometimes. 

Ashley (26m 27s): Another way that I like to use my planner is just to go back and reminisce on things. I have a planner from college that I look at every once in a while, and be like, “Wow. I was really stressed this day.” I was like, “Ashley from 2010 was not feeling it.” 

Danielle Towner (26m 31s): It’s almost like a diary. 

Ashley (26m 31s): It is. When you go back and look at all the stuff, all those assignments, and I was one of those people who liked to make little comments or make little faces around events. Then I would color code these depending on how important it was to me. I would know this thing was really important and I was really upset about something because I made this emoji right here. It’s fun. It really is a good therapeutic way to really release your whole day. 

Ashley (27m 5s): People take off certain days just to plan their week and I support that wholeheartedly. It’s also a good way of self-care, in my personal opinion, to just really take a moment for yourself, put down on paper something you need to focus on, then throughout the days, just achieve those goals. I know, if you’re like me, it feels so good when you can check off a goal. You’re like, “Oh my God, I did it.” Then you’re ready to do the next one. 

Danielle Towner (27m 45s): That’s all it takes, is to get started and that’s something I try to do too. I’ve seen people say, “Well, I take a Sunday or I take a Monday, and I plan out all of my posts for the week or all of my writing for the week,” or whatever it is that they have to do to get things accomplished, then they break it down into those bite-sized goals. That is a good pointabout self-care because that’s something that we all need especially, right now with so much going on. 

Ashley (28m 18s): It is for sure. 

Danielle Towner (28m 21s): Definitely. Now, how can our audience reach out to you to collaborate or to make a purchase? 

Ashley (28m 51s): You can see me personally on Facebook. My name is Ashley Crenshaw. You can check out our Facebook page at Boss Made Planners. We’re also @bossmadeplanners on Instagram and you can check out our website at, and that is planners with an S. 

Danielle Towner (-): Okay. Awesome. Ashley 

(29m 9s): If you want to collabo with us, shoot me a DM, and I will definitely get back to you. I’m always down to collab with anybody. I’m a really friendly person so don’t be scared, and especially if you make your own planner. I would love to meet other planner baes. I’m super excited for that.

 Danielle Towner (-): Cool. 

Danielle Towner (29m 21s): Cool. It seems like you’re excited about it, and it’s a difference when you’re passionate about what you’re doing. That’s really cool. Now, you’ve heard everything from her and how to reach Ashley Crenshaw of Boss Made Planners, and how to grab one of those planners for yourself. If you have any questions for either one of us, if you’re listening from the Anchor platform, just press that record button and record your question and we’ll get back to you. Or you can reach out to Ashley, you can reach out to me or post a comment on my website with your question and we’ll get back to you. 

Danielle Towner (29m 51s): Thank you, guys, for listening, and as I always end my episode, dream until your dreams come true.

How to Execute your Daily Planning Like a Boss

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As owner of Dream Work Creatives, LLC, Danielle has the opportunity to use her gifts of business development and creative expression. She has a passion for helping solo entrepreneurs and small businesses make their dreams work through marketing and creative strategy. Danielle’s digital marketing services have helped countless businesses build their brand awareness and online presence using social media marketing, website design and content marketing. Her blog features business and lifestyle growth tips and “Dreamer’s Den Podcast: Entrepreneurs Making the Dream Work”. During her free time, she enjoys travel, movies, books and the endless joy of her little one.